23/07/2024

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The Ultimate New York City Itinerary (3, 4 or 5 Days)

39 min read
The Ultimate New York City Itinerary (3, 4 or 5 Days)
The Ultimate New York City Itinerary (3, 4 or 5 Days)

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Wandering around Central Park on a sunny day. Cruising past the Statue of Liberty on a boat tour. Gazing at a million twinkling lights from the top of the city. New York City is as iconic as the United States, combining the background for countless TV shows and movies with the very real place nearly 8.5 million people call home. If you’re visiting the city for the first time, or looking for a way to get to know the Big Apple a little more intimately, this New York City itinerary will allow you to see the city from above, below, afar, and intimately inside. 

Growing up in Kentucky, I was no stranger to NYC, since my parents grew up in New Jersey 45 minutes away from “the city” (as locals call it). My aunt took my brother and me to many Broadway shows growing up, and I was lucky to see performers like Kristin Chenoweth play Glinda in Wicked and Sutton Foster in Little Women.

But aside from my stint as a Broadway-loving child, I felt like I never really knew who she (NYC) was. Sure, she was busy, overwhelming, and had top-notch entertainment, but what was the magic throughline that permeated every inch of this bustling concrete jungle? And maybe more importantly, what should I do outside of Times Square and the theatre district?

Luckily I have recently dove head-first into exploring the city with help from local friends, exploring the must-do things for first-time visitors as well as some unique things you may have never heard of. So let’s get into the Ultimate New York City Itinerary!

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manhattan skyline from governos island new york city-2
The Manhattan skyline looks incredible from Governors Island, which is on this itinerary!

Things To Know About Visiting New York City

Below are some answers to some commonly asked things when it comes to visiting NYC, like how do I get there, when should I come, and how do I get around?

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How to get to NYC

There are several ways of getting to NYC, including by train, plane, or automobile. Here are some options for getting here by those means:

By Train

If you’re close enough to get to NYC by Amtrak, congratulations! You can travel to NYC from cities like Boston, Chicago, DC, and Philadelphia, in a matter of hours ending up at Moynihan Train Hall at Penn Station, which is in midtown and close to where you’ll be staying. It’s an easy, cheap way to get to the city. Just check the Amtrak website for all the available cities, times, and costs.

By Plane

Flying into NYC will largely depend on where the airline flies into, which includes Newark Airport, LaGuardia Airport, and JFK Airport. The two times I flew into NYC recently didn’t seem to give me the option – one time it was LaGuardia, and the other was Newark. 

Here is some general advice on how to navigate getting to midtown from where you land, and remember Google or Apple Maps are your friends when using public transport. You could use a ride share, but it’s the difference between a couple of dollars for public transport and about $80 for a ride:

  • Newark Airport – Located in the New Jersey city of Newark, this airport is approximately an hour’s trip from the airport to midtown. Once you land, you’ll follow signs to the AirTrain Newark to board the NJ Transit to NYC. To avoid a line at the NJ Transit ticket machines, download the NJ Transit App beforehand and purchase a ticket from Newark Airport to Pennsylvania Station (the one in NY, not NJ). For way more detailed information, check out this Newark Airport guide.
  • LaGuardia Airport – Located in the Queens borough of NYC, LaGuardia is also about an hour from midtown. The fastest way to get to midtown is to take the free Q70 “Laguardia Link” bus to the subway, and then take the subway to the closest stop to your hotel.
  • JFK Airport – JFK Airport is also located in Queens (but the lower part), and is too about an hour from Manhattan. You will take the AirTrain JFK (or the temporary bus if the train is closed) to Howard Beach Subway station and take the A train to lower Manhattan.
manhattan bridge from the east river in new york city-2
The Manhattan Bridge from the waters of the East River.

By Car

So it’s more convenient for you to drive, huh? Well, this is where we get a little bit in the weeds because parking is going to be the central part of this battle! 

Your best bet is probably parking at Port Imperial in Weehawken, NJ. For just over $20 a day, you can park in this covered garage in Weehawken, NJ. It’s right across the street from the Port Imperial / Weehawken ferry line, and you can hop on the ferry to 39th Street Midtown. From there you can hop on one of the port buses or the subway to get to your hotel.

This is always how my family got into the city from NJ (for the day) and it’s a fun way to see the skyline, especially if you’re visiting for the first time!

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Taking the Subway

If you’ve been to NYC before, you know that the Subway is pretty easy to take, especially when using Google or Apple Maps. It will give you the station name, timetable, and any transfers you need to take. And if you miss a train, never fear, another one is usually coming very soon. But here are some tips and tricks for taking the subway, and you should definitely check out NYC Subway Guide for a super complete guide:

  • If you’ve used the MetroCard in the past, the bad news is that it’s being phased out by 2024. The Good news is that it’s being replaced by the OMNY, which has its upside. While you can buy an OMNY card in stores, you can actually use any contactless card you have (debit or credit) or your phone with pay set up and just tap the turnstiles on the way in! Also, after 12 rides between Monday and Sunday, the rest are free, meaning you will only spend a total of $33 to ride the subway on any given week.
  • Something that always slightly confused me, even using maps, is what side of the street to enter the subway to go in the right direction. And honestly, the best way I’ve found is to use the compass on maps to see which way you’re going and then enter on the right side of the street in that direction. Meaning basically, we drive on the right side of the road and the subways will also be going in that direction. 
  • Keep in mind that the subway can be dirty, overwhelming, and hot and smelly in the summer (not all train cars have AC). You need to be wary while riding with other people and where you fit into the flow of the subway experience (i.e. pay attention and try to stay out of the way). Here is more great information about miscellaneous things you need to know about the subway.
a couple in new york city central park
Lovers in Central Park on a gorgeous June day.

What’s the best time of the year to visit NYC?

New York City is a bit like the perfect date in Miss Congeniality: You want it to not be too hot, not be too cold, and all you’ll need is a light jacket. That’s why I recommend going in April-June, or September-November

NYC in the summer is a hot, sticky, asphalt jungle mess, with sweltering subway trains making it feel like you’re on the express train to hell. It’s also high tourist season (locals who can flee the city) which means that everything is more expensive. Basically, you’ll pay more to be miserable – but not you, because you’re reading this guide!

New York City in Winter is also a great time to visit if you don’t mind the cold and potential snow, and you’ll see way fewer crowds after the holiday season. But for all intents and purposes, this guide is for your warm-weather excursion.

new york city street scape
A New York City streetscape.

How this Ultimate New York City Itinerary Works

This itinerary can be used for 3, 4, or 5 days, depending on your preference and the days can really be used in any order, depending on the weather / when things are open. For example, strolling through Central Park on a rainy day may not be your cup of tea (but still magical in its own way!), Broadway shows don’t play on Mondays, and the MET is closed Wednesdays.

To keep it simple, the itinerary should work perfectly Wednesday – Sunday, just be sure to check that business hours and days open haven’t changed. Some of the restaurants, shows, and tours will require reservations as well, so make sure to make those ahead of your arrival.

To make the most of this itinerary, you will be based in or around midtown (the where to stay options are at the end of this article). New York City is a large place, and staying centrally will ensure you are able to start and end your day in a place where it won’t take you too long to get back to your home base. But don’t worry, I have scoped out some really budget-friendly options in the heart of NYC.

For most days I have not suggested a place to eat breakfast, but I suggest finding a bodega that serves breakfast sandwiches and the like close to where you’re staying and stopping by in the morning. Some of the hotels suggested have breakfast options as well. It’s an inexpensive and easy way to get a filling meal without having to sit down and eat!

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statue of liberty in new york city
She’s beauty and she’s grace, she’s Miss United States.

New York City Itinerary: Day 1

  • Today you’ll be taking a food tour in Hell’s Kitchen, learning all about the city from the Hudson River, and gazing at the skyline from the Top of the Rock!

Day one in New York City! You can basically hear Liza Minelli singing “New York, New York” already, can’t you? Your first activity of the day isn’t until noon, so you can take your time getting up and grabbing breakfast at a bodega or your hotel.

cheese boat new york city
Are you ready to try the pure magic that is a Georgian cheese boat?

Take a Food Walking Tour of Hell’s Kitchen

What’s the best way to learn the history of a city? Well, one is food, and the other is walking around it. So voilà, a walking food tour!

The Hell’s Kitchen Food Tour by Manhattan Food Tours takes you through the neighborhood of Hell’s Kitchen, located on the west side of Midtown. What was once filled with Irish tenement housing and gangs is now a trendy, expensive, food-focused neighborhood.

On this two-hour tour which begins at noon, you’ll explore the modern-day eateries of one of NYC’s most food-centric hoods while learning about the riots, gangs, and notorious Irishmen who ran the streets. Basically, you’ll be learning about the gangs of New York over meatballs – how authentic!

You’ll try some famous cookies, Japanese BBQ, a Georgian “cheese boat”, and so much more! If there is one thing you can guarantee about this tour is that you won’t be leaving hungry.

See The City From the Water on a Boat Tour

Now that you know about the gangs of NYC it’s time to learn more about the city itself! But don’t worry, this 1.5-hour Landmarks Circleline Cruise (book the 3pm tour) is seated so you can relax as you are entertained and educated!

The boat tour starts at Pier 83, which is a 1.2-mile walk or short subway ride from where the walking food tour ends.

On this ride along the Hudson River around the tip of Manhattan to the East River, you’ll see landmarks like One World Trade Center’s Freedom Tower, the Empire State Building, the Statue of Liberty and Ellis Island, the Brooklyn Bridge and many more! It’s one of the best ways to see the city because you’re not *in* the city but getting to view it from the water in all its vastness!

Besides the stunning views (which are worth the cruise alone), it is the most comprehensive and fun way to learn about the city from one of the fabulous commentators. The day I went Andy was absolutely hysterical and taught us things like how Manhattan means “land of many hills” in the Lenape language, how Wall Street used to have a literal wall built by the Dutch to keep the English out, and that Brooklyn is almost the size of Chicago.

As you cruise, you can also get beer, wine, and cocktails as you learn about the city! 

After all these tours, now is a good time to pop back to your hotel and rest for a little while before your evening begins!

los tacos no. 1 in new york city
The Adobada tacos from Los Tacos No. 1 are my favorite tacos ever!

Get a Relaxed Dinner at Los Tacos No. 1

Now that you’ve had some time to freshen up, let me introduce you to one of my favorite places to grab a fast and cheap meal in the city, Los Tacos No. 1!  This Taqueria is a colorful, quick-service restaurant that has a limited menu that is all fantastic.

You’ll want to check out the Times Square location on 43rd St., which is normally bustling, but they get you through the line quickly!

All the tacos are divine but the Adobada pork tacos with pineapple on top is the best taco I’ve ever had in my life, hands down. Get some other tacos (or just the Adobada) and chips and guac to share and you have a meal!

new york city skyline fromt he top of the rock
Seeing the NYC skyline at night will truly take your breath away!

See the City from the Top of The Rock

Now that you’ve seen the city from below and from the water, it’s time to take in the city from up above! Take a short 13-minute walk to your next destination.

While there are plenty of observation platforms in the city, Top of the Rock has one of the best views of Central Park and the Empire State Building. It’s nestled right in Midtown and has sweeping, 360-degree views from 850ft over Manhattan. It may not be the highest platform in the city, but it has less crowds, a cheaper admission ticket, a great location and gorgeous Art Deco architecture to make up for it.

If you can, try to arrive a little while before sunset (also keep in mind it takes about 20-30 minutes to actually get up on the deck). This way you can see the city during golden hour and then watch the city light up all around you. There is something so magical about seeing millions of twinkling city lights that feels so NYC.

Plan to spend about 45 minutes to an hour on the observation deck. There are also several more stairs up to higher platforms than the level you enter from the elevator, so don’t miss out! Get your admission ticket in advance here.

Get a Nightcap at Lillie’s Victorian Establishment

Lillie’s Victorian Establishment on West 49th Street is like stepping back into a… well, a Victorian establishment. And luckily it’s just an 8-minute walk away!

Gilded mirrors and red leather chairs line the bar, stained glass windows are illuminated alongside portraits of old-timey people, and there’s a general feeling in the air that Charles Dickens may walk in with a top hat and cane at any second.

This is the ultimate place to grab a nightcap (or dessert), and they have plenty of handcrafted cocktails on the menu, many named for Old Hollywood celebrities (but no Victorians…). Try the Fly Me To The Moon honoring Tony Bennett with Gin Laine 1751 Violette, Fresh Lemon, Pomegranate Puree, Rhubarb Bitters, & a Splash of Soda, or the James Dean which is “cinnamon smoked” with Templeton 4yr Rye, Amaro Nonino, Giffard Peche, & Angostura bitters.

If you want to round out your evening with dessert, they have a decadent Tiramisu or Creme Brulee

Once you feel properly toasty and Victorian, it’s time to head back to your room to rest up for another day!

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New York City Itinerary: Day 2

  • Today you’ll be traipsing through Central Park, exploring the Metropolitan Museum of Art, and enjoying dinner and a Broadway show!

Today is the iconic NYC day! Central Park, the MET… and Broadway!

Bethesda Fountain in central park new york city
The Angel of the Waters Statue in the Bethesda Fountain in Central Park.

Take a Stroll Through Central Park

What’s a more iconic way to start your NYC adventure than strolling through Central Park? Something about wandering under tall trees surrounded by skyscrapers with people rush this way and that feels like the most New York morning ever.

The park itself is about 843 acres, but you’ll only be seeing some of the park as you start at the southern end and work your way halfway up towards the Metropolitan Museum of Art

Following this route, you’ll talk an easy 1.4-mile walk through the park, which should only take 30-45 minutes depending on how slowly you stroll. The good thing is that the MET doesn’t open until 10:30am, so you can take your time and don’t need to start too early!

You’ll enter the park by the iconic golden General William Tecumseh Sherman Monument, passing the adorable Central Park Zoo, taking you towards one of the most quintessential Central Park areas: The Mall & Literary Walk

Down this gorgeous stretch of American Elms, you can see statues like those of William Shakespeare and the newest statue celebrating Women’s Rights Pioneers, along with many others. At the end of the mall, you’ll reach the Bethesda Terrace, with the Angel of the Waters statue shining in the sun above the Bethesda Fountain.

The rest of your stroll will take you past the status of Little Mermaid author Hans Christian Anderson, the model boat pond, and the whimsical statue of Alice in Wonderland

By this point, you’ll be close to the MET, but feel free to wander and explore if you have more time!

the met msueum in new york city
The front of the MET is a bustling place.

The Metropolitan Museum of Art 

The Metropolitan Museum of Art is an institution almost as famous as NYC itself, exhibiting some of the most famous works of art over a tremendous 2 million square feet. This museum is the most visited in the United States, with more than 5 million visitors each year. So the real question is, how do you make the best of your visit to one of the busiest and largest museums?

Your first expectation is that you are not going to see it all in one day, let alone a few hours! It’s also a good idea to take a peek at the visitor guidelines before you enter the museum as well. One thing to note is that they do have a free coat check, but will not hold electronics for you.

Here are some of my personal favorite things to see, but if something tickles your fancy on the map, head there:

  • The French rooms of the Hôtel de Varengeville – If you’ve ever wanted to step into highly ornate rooms from mid-1700s France, the easiest way is to wander through the maze of reconstructed rooms from the Hôtel de Varengeville. Originally from one of the private residences of eighteenth-century Paris, you’ll see gilded oak paneling richly embellished with C-scrolls, S-scrolls, sprigs of flowers, and rocaille motifs in fully decorated rooms with dramatic lighting and a serene, almost eerie, ambiance.
  • The Greek and Roman Sculpture Court – Something about seeing sculpture really transports me to another place, they are 3D, imminent, and tactile – you can almost feel them being carved. The Greek and Roman sculpture court is filled with statues larger than life, like Perseus with the head of Medusa, Venus Italica, and Ugolino And His Sons.
  • The Temple of Dendur – This Egyptian temple from 10 B.C. stands inside the MET in a grand room with window-covered walls and water features all around. While it’s not a huge temple, it’s certainly stunning, depicting some of the most important gods of Egypt like Isis, Osiris, and their son Horus. In the same room, there are also huge and evocative statues of the lion-headed goddess Sehkmet, the goddess of war and healing.

For more things to see at the MET, check out this excellent 20 Things to See at the MET guide. You can even download free audio tours while you are there, like The Highlights Tour, or even book a two-hour guided tour of the highlights that starts at 11am!

Grab a NYC Lunch at Pastrami Queen

I don’t know about you, but walking through centuries of art makes me hungry. Luckily there is a place to grab a sandwich that is the true NYC experience just about a 10-minute walk away!

Pastrami Queen is the real Kosher NYC sandwich experience, even Anthony Bourdain was a fan! The lunch special I believe is the way to go, with half a super-stacked pastrami sandwich and Matzoh Ball Soup, though you can choose any soup and sandwich you like.

Also in typical NYC fashion, this place is tiny – 6 tables tiny! So if you’re unable to procure a table, I suggested moseying back to Central Park by the MET and having lunch on a picnic bench, like a real New Yorker. 

After lunch, I suggest walking through the park some more, checking out more in the MET (you can re-enter) or just heading back to your hotel before your dinner and a show!

pizza from Capizzi in new york city
The Hot Honey pepperoni pizza from Capizzi is absolutely divine.

Grab Neopolitan-Style Pizza at Capizzi

Now that you’re rested, dressed up, and ready to hit a night on the town, it’s time to grab dinner before you go out and see a show!

Capizzi is a pizzeria born out of the owner working in his own father’s pizzeria as a child, so this is some ancestral pizza action. The restaurant is intimate and decorated in a cozy, Italian way, with a wood-burning pizza oven which is the sign you’ll be getting some incredible pizza.

Start with their Arancini Spinaci which are spinach, garlic & cheese rice balls, that are crispy and so decadent. For your pizza order, I highly recommend the Hot Honey pepperoni pizza if they currently have it on the menu (it seems to rotate), if not the Loaded Pizza with provolone, pepperoni, sausage, mushrooms, onions, roasted peppers & whole roasted garlic should do the trick.

Capizzi is located in Hell’s Kitchen on 9th Ave and 40th Street, making it just steps from the Theatre District without being in Times Square itself. This is good for so many reasons – it’s not as pricey, not as crowded, and most importantly, the food is actually good.

kimberly akimbo playbill new york city broadway
I saw this Tony Winner before it won, just sayin’!

See a Broadway Show

Now that you’ve been fed, it’s time to head over to the Theatre District, Broadway, the Great White Way – whatever you want to call it!

Broadway is the catch-all name for the 41 theaters in the area that have 500 seats or more, and it’s where you’re going to see the biggest, most spectacular shows on the planet. Even if show-stopping musicals aren’t your thing, they usually have non-musical plays with some of the best actors in the country treading the floorboards.

Broadway shows come and go, but some will be here forever, like Phantom of the Opera and Cats! Oh wait – they’ve closed?! Well, a good thing can’t last forever. 

Keep in mind during September there is also Broadway Week, where you can get discounted tickets for Broadway shows. And if you really don’t care what you see and are willing to line up, you can get tickets for cheap at TKTS in the middle of Times Square the night of the show (here’s a how-to guide for TKTS).

Below are some of the best shows on Broadway right now, and remember you can view all the shows on the Broadway website:

  • Kimberly Akimbo – The Tony Award Winner for Best Musical 2023 is Kimberly Akimbo, the story of a 16-year-old girl who looks like an old woman due to a rare disease. This show has no huge, show-stopping production numbers. But it is smart, funny, and relatable – perfectly encapsulating the human experience.
  • Wicked – Since opening in 2003, Wicked has remained one of the most well-attended shows on Broadway, and for good reason. It has spectacle, humor and pathos, and looks at the story of the Wizard of Oz from Elphaba’s, the Wicked Witch’s, side!
  • Sweeny Todd – Sondheim has produced some of the best American musicals, and the darkly macabre Sweeny Todd turns the happy Broadway musical on its head. Never has the story of one man’s murderous, revenge rampage been so beautifully operatic.
juniors cheesecake new york city
Getting Juniors Cheesecake is a rite of passage. And oh, it’s good!

Grab Some Cheesecake at Junior’s Cheesecake

If you need a little post-show snack, Junior’s Cheesecake has two locations at Broadway and 45th / 49th Streets. 

This place is always bustlin’ and is totally worth visiting because the cheesecake is really that good. It’s not too dense and has that little bit of tartness to it which really screams New York Style Cheesecake to me!

They have a plethora of flavors, from S’mores to Peanut Butter Chocolate Banana to Red Velvet and so many more. But if you ask me, the Plain Cheesecake is *chef’s kiss* perfect.

Time to hit the hay and get ready for another day of NYC adventuring!

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New York City Itinerary: Day 3

  • Today you’ll be walking along the Highline and Little Island, getting lunch at Chelsea Market, grabbing an early dinner at Left Bank, and experiencing a theatrical experience like no other.

Your journey today is going to be very walk-heavy, so be sure to wear your walking shoes (here are some of our favorite travel shoes for men & women)! 

highline park mural new york city_
The High Line has plenty of art and nature to enjoy, Nina Chanel Abney’s mural “NYC LOVE.”

Stroll Down the High Line 

Grab some breakfast at your favorite bodega by your hotel (or wherever), and head to the High Line, a historic elevated rail line that has been transformed into a park in the sky, allowing you to walk past native plants and trees, sit on benches, admire huge murals, sculptures, and performance art, and see NYC from an entirely different point of view. 

The High Line is 1.45 miles long and makes for a great stroll for about an hour. You’ll see city streets from above at the observation deck, kinetic sculptures, and plenty of flowers blooming along the trail. 

For this itinerary, start at the 30th St. Entrance (which is the northernmost entrance) and head south so you can walk the entirety of the park. Since it was once a train line, it’s easy to follow (and not get lost) and you’ll see some of the old rail tracks now being taken over by nature.

little island in new york city

Explore Little Island

Little Island is hard to miss, it looks like little white floating clouds on the Hudson River with a lush, green park on top!

To get to Little Island, exit the High Line at the 14th Street ramp (almost at the end of the park anyway) and cross 11th Avenue. 

Little Island is a public park floating over the Hudson River, and feels very much like an extension of the High Line. It’s beautifully manicured with flowers and grasses, filled with art installations, and has beautiful overviews of the river and city. 

 There are also scenic overlooks that give you beautiful views of the river and city, and a great place to snap a shot of you with the city in the background.

Get Lunch at Chelsea Market

Chelsea Market is one of the most bustling, exciting, and delicious indoor markets in the world, and is absolutely worth the visit to grab some excellent food and do some shopping if you like. 

Chelsea Market is just about a 6-minute walk from Little Island, and is situated across from the Google Corporate Office and the Starbucks Reserve Roastery and has a decidedly fancy and upscale atmosphere (Chelsea is one of the trendiest neighborhoods after all). But that doesn’t mean you shouldn’t just wander in off the street, it’s a big tourist spot!

There are all kinds of food options in this 1.2 million sq feet building, with 40,500 sq feet alone being dedicated to food vendors! I hope you’re hungry, because some of the best food vendors include:

  • Miznon – If you are an Israeli food lover, this is the place for you. While you can get a falafel burger in a pita, you can also get more “American” eats like the “Folded Cheese Burger in a Pita”, which is just what it sounds like! Definitely try “The Original World-Famous Baby Cauliflower” which is a whole cauliflower roasted to perfection.
  • Very Fresh Noodles – If you’re a nood kinda dude, check out Very Fresh Noodles, which has just that! Try the La Mei Taiwanese beef noodle soup, with slow braised beef shanks in a tomato, beefy broth, or the Tingly & Spicy cumin lamb that you can get “dry” (just with a sauce) or as a soup!
  • Lobster Place – Though you’re not quite in Maine, you can still pick up a killer lobster roll in NYC! The lobster roll features claw and tail meat in a buttery brioche, or you can find other fish fare like a crab cake sandwich or salmon burger!
  • Friedmans – This place has some seriously stellar American favorites. We’re talking hand-cut pastrami sandwiches, fried chicken and with cheddar waffle, burgers, soup and so much more!
  • Takumi Taco – Can’t decide between Mexican and Japanese food? Why not have both! Here you can try tacos with the best of both worlds, like the spicy tuna taco with Sashimi Grade Big Eye Tuna and a Crispy Gyoza Shell or the Japanese Curry Beef with Medium Spiced Japanese Style Curry and Cotija Cheese.
drinks from dante new york city
The Espresso Martini and the With A Twist Martini!

Head to Dante for a Drink

Now this is the time of the day to get off your feet and relax! If you’re not a drinker (though they have mocktails as well!), or need a *proper* rest, skip this activity and head back to the hotel for nap.

Now if you are up for some fun, Dante West Village is a half-mile walk south and was named the world’s best bar in 2019, which is definitely a title it still lives up to to this day. Dante (the first location a bit south on MacDougal St) opened in 1915 and is now a registered historic landmark, and famous faces like Al Pacino, Alec Baldwin, Whoopi Goldberg, Jerry Seinfeld, and Bob Dylan have stopped in for a drink or two.

The bar itself feels like something you’d find in Paris – mint green and white accents color the establishment, with soft lighting and plenty of ambiance. Sitting at the bar is a great choice, and live music is usually floating in the background (The Bailsmen were playing live jazz when we visited).

Their bar is famous for Martinis and aperitivo, and from 3 to 5 pm you can enjoy $10 martinis during “martini hour”. The With A Twist martini includes absolut citron, beefeater, alessio bianco, essence of grapefruit, lemon and lime, and in the words of my friend Mario, is the “‘most perfect martini I’ve had in a long time”.

If martinis aren’t your thing, they have an extensive list of signature cocktails, including the Negroni Bianco with Brooklyn gin, quinquina, alessio bianco, carpano dry, lemon bitters, verjus, and garnished with little white flowers. Basically, no matter what you get, you know you’re gonna get an excellent drink!

pasta from left bank new york city
For happy hour we are having capricci cacio e pepe and wine!

Dinner at Left Bank

If you have had a couple of drinks and are feeling a little toasty, you’re in luck because Left Bank is only two doors down from Dante!

Left Bank features farm-to-table, simple food that leans into the American / Italian fare. The best part is that from 5-7pm Monday-Friday and 4-6pm Saturday & Sunday you can order from their happy hour menu, which is truly a great deal!

Highlights from the happy hour menu include pasta and a glass of wine, a burger and beer, and two appetizers at a fixed price, which really makes the price of your meal much more affordable!

For your apps, I recommend the half dozen east coast oysters on the half shell and the shaved brussel salads, and for your entree the capricci cacio e pepe, which is tender and delicious (with your choice of wine, of course). Their parmesan fries are also on the happy hour menu, which makes a great additional app if you want something truly decadent.

Once you’re done with dinner, you’ll head to your evening entertainment!

glass of champagne and woman singing at sleep no more new york city
Picture from the post-show jazz concert… no photos allowed in Sleep No More!

See a Show like No Other at Sleep No More

To get to your super exciting, life-changing show (more on that in a second), take the subway about 16 minutes to the McKittrick Hotel, a hotel with a collection of mysterious guests you’ll get to know better.

Sleep No More is an immersive theatrical experience that tells the story of Macbeth as you wander around different rooms and sets, encountering different characters and their stories. You may find Macbeth in the graveyard, Lady Macbeth in the bedroom, and a whole slew of tortured spirits in the ballroom.

Sleep No More is like wandering through a dream and a nightmare at once – think the most gorgeous, intricate haunted house you’ve ever been to – without the jump scares. It’s eerie, dark, and stunningly beautiful at once. The story is mostly told through dance and music which lilts from every corner of the expansive, several-story warehouse, and it’s easy to get lost. Characters run from this room to the next, and at any point, you can follow whatever character you like.

When you arrive your phone is locked away and you are given a creepy mask to wear, making everyone in the “audience” anonymous. What stories will you find on your journey? Well, it’s really up to you. Here are some general tips for exploring Sleep No More (not spoilers per se, but skip if you want to know nothing at all):

  • Try to get the earliest ticket time you can (for this itinerary, the 7pm show). The show doesn’t actually happen once but three times, giving you the chance to explore different character tracks over the same story (hence why you want to start early). This also means at certain times characters may “reset” the set, so if you see the maid putting pillows back on the bed that may not be the main “story”.
  • This experience is meant to be a solo one, and you will be told that exploring on your own will bring the most unique experiences (plus you can compare journeys later). Fortune favors the bold.
  • If you get lost and no one is around, try to find where the crowds are. Crowds mean something is happening (i.e. a character is doing something somewhere). If you’re alone the story isn’t happening there. When in doubt try to listen to where the music is coming from as well.

Sleep No More was a show that was on my bucket list for many years and it did not disappoint. It may be one of the best hidden gems in all of New York (and I never use that phrase).

If you feel a post-show drink is in order, head up to the rooftop of the McKittrick Hotel to Gallow Green, their lush, jungle-like rooftop bar!

Head back to your hotel and get some rest, because day 4 is imminent!

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New York City Itinerary: Day 4

  • Today you’ll be exploring Governor’s Island, one of the most unique (and free!) things to do in NYC, as well as taking a food tour of Chinatown and Little Italy. Let’s go!

You’ll be seeing NYC today from a perspective most New Yorkers have never seen before, so let’s keep this our little secret, okay?

view from the overlook on governors island new york city-2
Governors Island is a park like no other!

Take the Ferry to Governors Island

Governors Island is a 172-acre island in the heart of New York Harbor that is only 800 yards from Lower Manhattan, so it’s just a short ferry ride away. And since it’s only been completed for a few years, most NYC residents haven’t even visited yet!

To get to Govenor’s Island, you will need to book a ferry ticket that is free before noon on Saturday and Sunday, and is just $4 any other time of thew week and departs from a gorgeous old Victorian ferry station. Before you catch your ferry, grab a breakfast sandwich from the Garden City Deli a couple of blocks away.

As the ferry pulls from the station, you’ll see the Battery and the NYC skyline in all her glory, and as you approach Governors Island, the views only get better!

Explore Governors Island

Governors Island has lived many lives, from the Lenape Native Americans who used the island as a seasonal fishing camp in the 1500s, to the British Govenor’s residence in 1699, to eventually turning into a fort against the British (Fort Jay) in the late 1700s. Let’s just say this little island has seen a lot of action.

Today, the remnants of Fort Jay still exist, and the rest of the island has been developed into a gorgeous, sweeping park complete with food trucks, slides, and the most stunning view of the Statue of Liberty you can get without going to Ellis Island. 

The best way to learn about the history, and actually get to see most of the island in a structured way, is to take one of their free walking tours. The first tour starts at 10:45am Wednesday – Sunday and lasts about 1.5 hours, and meets at the visitors center on your left when you disembark the ferry.

Along the way, you’ll be taught the history of Fort Jay, and learn about how the island is now home to artist residencies in the old buildings that were housing for the coast guards (which moved off the island in 1995). You’ll see permanent art installations, such as The Field Sta­tion of the Melan­choly Marine Biol­o­gist, Moving Chains, and plenty of other evocative artwork.

The tour ends at the “park” side of the island, so make sure to check out the hammock grove, slide hill (which has a three-story slide!), and outlook hill on the lower left side of the island, which gives you stunning views of the Statue of Liberty!

drinks from gitano on governors island new york city
Governors Island’s hottest new club is Gitano Island – it has everything! Disco balls, amazing drinks, and drag shows!

Grab Lunch on Governors Island

Luckily for you, you don’t even have to leave the island to grab a bite to eat! 

The main place to grab a bite to eat is the Liggett Terrace, where you will find all the food trucks lined up and plenty of spaces to sit and enjoy a lovely outdoor meal and a drink if you like. Some of the food trucks include:

  • Little Eva’s – This place has delicious summer drinks and all the classic American fares like hamburgers, fish and chips, sandwiches, baked goods, etc!
  • Taco Vista – Just what you expect! Tacos, nachos, chips and salsa, Mexican burgers and more!
  • Pizza Yard – Pizza! Pizza Yard has Neapolitan pizzas because you can never have too much pizza.

If you want to try a more sit-down experience, there are also some restaurants on the island. A couple of those include:

  • Island Oyster –  This seafood restaurant is right by where the ferry comes in on the water and has sweeping views of Manhattan! The menu is limited but contains high-quality seafood like oysters, fish & chips, lobster rolls, and a whole bunch of other freshly caught fare.
  • Gitano Island – Gitano Island is like stepping into a lush jungle, transporting you into an island oasis you didn’t know could exist in NYC! The menu consists of modern Mexican food like lobster tostadas, duck carnitas huarache, and watermelon & tomato salad. If nothing else, stop by here for a drink like the Jungle Fever with del maguey vida mezcal, chile, lime, and cilantro. There is plenty of comfy seating all around (perfect for cuddling), good music playing, and even a giant disco ball in the center! 

After lunch, explore more of the island until it’s time for your evening activity!

Take a Food Tour of Little Italy and Chinatown

A 17-minute subway ride from the ferry station will take you to your next destination, a Little Italy and Chinatown food tour!

This two-hour Little Italy and Chinatown Walking Food Tour takes you through the colorful neighborhoods of Chinatown and Little Italy, and though they are neighbors, feel worlds apart. Along the way, you’ll try light-than-air spongecake, try Dim Sum Dumplings, pizza, cannolis, and more. 

You’ll learn about the mafia, the origin of Chinatown, walk underneath a pegasus made of noodles (just wait), and learn all kinds of customs and traditions associated with Chiantown and Little Italy.

Since the tour is only two hours, you don’t walk too far, but you will definitely get plenty to eat!

drink from ophelia lounge in nyc
The Purple Tuxedo drink under a star-filled sky!

Grab a Drink at Ophelia Lounge

I know it’s been a long day, but if you have one more stop in you head to Ophelia Lounge which is about a 30-minute venture back uptown to Midtown East (you’ll have to go up this way toward your hotel anyway!).

Ophelia Lounge is a stunning sky lounge in a 1928 Art Deco building that has sweeping views of the Hudson River and is a great place to take in the city from above at night. You can even see the old Pepsi-Cola neon sign blazing across the river – now that’s nostalgia!

With twinkling star lights hanging from the ceiling, navy blue walls, and a black and white checker floor you’ll feel like you’ve truly stepped into a magical, heavenly space between the earth and sky. And the drinks are great, too!

Check out the purple tuxedo, with gin, absinthe, plum bitters, and more which makes it purple, sweet and refreshing as well as the Beekman classic palo santo martini, a gin martini with a smokey twist.

Once you’ve had a drink (or two), head back to your hotel for your final day!

people walking across the brooklyn bridge nyc
The Brooklyn Bridge is a rite of passage, and worth the trip!

New York City Itinerary: Day 5

  • Today you’ll be exploring the Dumbo neighborhood in Brooklyn, where you’ll take in the iconic view of the Manhattan Bridge, walk the Brooklyn Bridge, and end at the Tenement Museum to learn about NYC’s earliest residents.

Today is your last day, and what better way than to take in a bit of the Brooklyn Dumbo neighborhood and walk the Brooklyn Bridge, which is one the of most beautiful ways to experience the city and the East River.

Grab Breakfast at Bread and Spread in Brooklyn

If you need to break up with monotony of bodega breakfast, try Bread & Spread at 151 Front St in Brooklyn. 

Here you can get an awesome breakfast sandwich starting at $5 with two large brown eggs, arugula, tomato, a choice of spread and you can add bacon or cheese for $2. Now that’s a NYC deal!

They also have pricier roasted and toasted sandwiches like the porchetta, cast-iron chicken caprese, beef short rib and more if you are completely over breakfast sandwiches (I get it).

The best thing about this place is that it’s right by your first stop of the day: the Manhattan Bridge view!

manhattan bridge from the dumbo new york city
The view is totally iconic! What is cropped out: other people taking photos and food trucks.

Take a Photo with the iconic Manhattan Bridge

Just a three-minute walk away from Bread & Spread, you will find the Manhattan Bridge view! And if you happen to be here on the weekend, check out the Brooklyn Flea for antiques and thrift goods located under a Manhattan Bridge overpass on your way.

The Dumbo area is named such because “DUMBO” is an acronym that means “down under the Manhattan Bridge overpass”, and no, I am not making this up!

This is one of the most fabulous places to get that “NYC photo”, just you, the cobblestone stress, the red brick buildings, and the blue Manhattan Bridge against the sky! 

It’s worth mentioning that it is usually a pretty busy area for photos, so getting here early, or even as sunrise, is worth it especially with the sky painted in oranges and pink as the sun comes up (sunset is also great for this!). 

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Strolling along the Brooklyn Bridge.

Walk the Brooklyn Bridge

It’s kind of a rite of passage to walk to Brooklyn Bridge, and it is also one of the most glorious ways to take in Manhattan. The wind coming in off the East River, the neo-Gothic stonework, passing by tourists and locals on the wooden path.

The Brooklyn Bridge is about a 12-minute walk from the Manhattan Bridge view, and will take you up along a long paved boulevard to the bridge. 

Since lunch will be in Brooklyn, the goal isn’t to necessarily go all the way across the Brooklyn Bridge – in fact, I wouldn’t recommend it. 

The closer you get to the Manhattan side the busier it gets, with not only people walking (and dangerously and illegally climbing the bridge) but vendors, spinning picture platforms, music, pandemonium, etc! Literally, my friends and I were like “Awwww Empire State of Mind is the best!” and by the end of walking the bridge we had heard it so many times it became ridiculous.

So if you don’t want to be in stand-still crowds on the Manhattan side of the bridge, stick to the out-and-back method! You’ll have much more room to take your own pictures and have a much nicer experience.

randolph beer in brooklyn new york
Cheers! At Randolph Beer!

Grab Lunch at Randolph Beer

Once you’ve had a nice bridge walk, head to Randolph Beer which is about 8 mins from the start of the bridge

Now that you’ve had views from the Brooklyn Bridge, it’s time to enjoy rooftop views of Manhattan from Randolph Beer’s Rooftop patio. It’s one of the most fabulous places to grab Sunday brunch, a beer, and a view!

Randolph Beer is known for its super fun game room (downstairs) and is only one of 5 places in the country with Belgian feather bowling, but the real star is the view of Manhattan, the bridges, and the beer!

For Sunday brunch you can snag breakfast tacos or challah french toast, or skip straight to brunch with nachos, burgers, and pretzels. Of course, a lunch beer is naturally in order, and they have over 20 beers on tap including such delightful flavors as the Orange You Lovely IPA and the Left On Red Wheat Beer.

If beer isn’t your thing, they also have some excellent cocktails like the smokey yet refreshing  EL Pepino Fresco with mezcal, St. Germain, lime, cucumber, and Peychaud’s.

Do keep in mind the rooftop is weather permitting, so if it’s really nasty out you may be better off having an afternoon playing games instead!

tenement museum in new york city
Inside a recreation of a 1933 tenement!

Learn about Life in NYC’s Past at the Tenement Museum

To get to the Tenement Museum, take a 10-minute subway ride back to Manhattan.

The Tenement Museum explores the lives of immigrant and migrant families through tours of reconstructed family tenement apartments. You can learn about how Italian, Jewish, and Irish families lived and worked in NYC and the oftentimes cramped and difficult living conditions they were subjected to.

Each hour-long tour focuses on one working-class family and time period, and shows you an apartment that has been refurbished to be what it would have been like in the period. The buildings you tour were actually tenement residences from 1863-1935 and once closed, weren’t touched until 1988, leaving a time capsule of relics and a huge window into the past.

There are plenty of tours exploring apartments from 1869 to the 1960s, and I explored the 1933 Tenement. Our excellent guide Jill took us through the lives of the Baldizzi family, the trials of immigrating from Italy and the Great Depression, and the everyday realities of a family in a tenement.

This is a great way to really see NYC from a new perspective, and learn about the actual people who helped build the city, and a fabulous way to end your time in NYC!

Where to Stay in New York City

As mentioned in the introduction, the best way to make use of this itinerary is to stay in the Midtown area. All activities are easily reached from this area so you won’t need to worry about traveling too much to get any of your days started!

Here are some great places to stay in New York City that won’t break the budget:

  • citizenM Time Square – The citizenM located near Time Square has everything you need – three outdoor terraces, a rooftop bar, and hot & cold breakfast buffet! Not to mention the hotel itself is super stylish with comfortable rooms where you can control all aspects of the room with an iPad. You’ll be super close to the action and the subway, so this is the perfect place to base yourself!
  • Pod Times Square – These “pod” rooms may be on the smaller side, but are inexpensive and don’t leave out the luxury of staying in a hotel! The hotel itself is modern and cool with a bar, and they even have double bunk rooms, which is a great option if traveling with a friend. It’s a couple blocks away from Times Square and close to the High Line, so super convenient!
  • The Standard, High Line – Now if you truly want to stay right on top of the High Line with some truly stunning views of the Hudson River, check out the Standard. This hotel screams luxury without the price tag of full-blown luxury, with white and wooden accents, and each room features floor-to-ceiling windows and a city or river view. Watch the sunrise or check out the sunset from their rooftop nightclub or biergarten!

About The Author: Richie Goff is a Louisville, Kentucky native with a great love of the outdoors. When he is not growing flowers for fun, he is the Editor-in-Chief of Practical Wanderlust and Let’s Go Louisville. He has been a friend of Lia’s since high school, and they have taken plenty of their own disaster-prone adventures together!


Which activities in this New York City Itinerary are you most excited about? What questions can we answer? Let us know below!

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Wandering around Central Park on a sunny day. Cruising past the Statue of Liberty on a boat tour. Gazing at a million twinkling lights from the top of the city. If you’re visiting the city for the first time, or looking for a way to get to know the Big Apple a little more intimately, this New York City itinerary will allow you to see the city from above, below, afar, and intimately inside.

Our Top Travel Tips & Resources

Here are our favorite travel tips & resources for saving money and planning travel logistics! For more tips, check out our travel tips resource page or our guide to planning a trip.

  • Booking Flights: To score flight deals, search on Google Flights or Kayak. Money-saving tips: fly mid-week or on the weekend; fly carry-on only on a budget airline; and take red-eyes or early morning flights.
  • Accommodations: We usually stay in budget-friendly vacation rentals, boutique hotels or private rooms in hostels. We use Booking.com to book hotels (we love their flexible cancellation policy) and Hostelworld to book hostels (low deposit, easy change/cancellation, and excellent reviews). For vacation rentals, we prefer to book using VRBO because they’ve got lower fees and better support than Airbnb, and we’re not fans of Airbnb’s unethical track record. You can also book vacation rentals on Expedia and Hotels.com. We also use TrustedHousesitters as both hosts (for our home and our fur-child) and travelers!
  • Travel Insurance: We always, always, ALWAYS buy travel insurance for international trips, and we STRONGLY suggest it – visit our Travel Insurance Guide to find out why. We recommend either World Nomads or SafetyWing for international travel insurance. SafetyWing is one of the few policies that covers Covid-19, and they have excellent monthly policies that are perfect for Digital Nomads and long term travelers!
  • Travel Credit Card: We book all of our trips on our favorite travel credit card. Not only do we earn cash back that we can spend on more travel, but the card offers fantastic travel perks like travel insurance, trip delay and cancellation coverage, lost baggage reimbursement, and rental car coverage, which helps protect us on our travels. Learn more here.
  • Vaccines & Meds: We use the travel guides on the CDC website to research recommended medications and vaccines for international trips. We always recommend getting every vaccine recommended by the CDC! You can get them at your primary care doctor’s office or a walk-in pharmacy.
  • Tours: We love booking guided tours, especially food tours and walking tours, to get a local’s perspective and a history lesson while sight-seeing! We book our tours using Viator and GetYourGuide.
  • Transportation: We use Rome2Rio to figure out how to get from place to place, and book local transportation online using Bookaway wherever we can. When we book a rental car, we use DiscoverCars to compare rental companies and find the best deal.
  • Luggage Storage: Whenever we’re checking out early or taking advantage of a long layover, we use LuggageHero to safely store our luggage while we’re running around. Use the code PRACTICALW for 2 hours of free luggage storage on us.
  • VPN Service: A VPN keeps your digital information (like website login details, bank info, etc) safe, even when you’re connected to an unsecured network while traveling. Plus, it lets you use Netflix & other streaming sites abroad! We use NordVPN. Use the code WANDERLUSTPROMO when you sign up!
  • What to Pack: Here are the travel essentials that we bring on every trip. We also have packing lists for hot weather, cold weather, and many more. Take a look at all of our packing guides!

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