New York Itinerary: 5 Days in New York City

It’s easy to take it for granted that I live within 4 hours of one of the best cities in the USA. I can’t count the number of times I’ve dropped in for a day trip or the number of times I’ve stayed for the weekend. It’s the city that always has something fresh to visit, restaurants to try and coffee to taste. There are new shops and foodie places popping up weekly and while it’s hard to keep up with all of them, the sheer variety makes visiting the city that much more fun.

This New York itinerary travel guide is a conglomeration of visits throughout the years and is constantly being updated; it’s a guide for how to plan a New York itinerary no matter which season you decide to visit and what mistakes to avoid while planning for your trip. Wintertime can make New York sightseeing a little difficult but as long as you dress warmly, you should be able to do most of the attractions on this list.

I’ve developed 3 types of New York itineraries for the visitor: weekend, 4 days and 5 days in New York City each with their own unique set of things to do.

Transportation in New York City – If you decided to brave the crazy driving in the city and you brought your car with you, you’ll want to book your parking in advance. This is a smart strategy if you want to save money on overnight parking but even still, parking will run between $60-$100 per day. If you’re visiting for longer than a weekend, I would highly recommend not bringing your car into the city.

Transportation within the city is easy. You can opt for Uber (they’re available everywhere) or you can take the Metro. You’ll have to purchase a Metro card (I believe the price is $1 per card) and you’ll load it with fares when you want to use the metro. The transport system offers package deals where you can get unlimited rides for 7 days, etc. This is a great option if you’re staying for more than a weekend.

New York Itinerary: Hotels

Trying to find a hotel in NYC can get overwhelming at times. And if you’re not familiar with the city, it’s difficult to figure out which locations make the most sense for your visit. A few tips to keep in mind as you’re looking for a hotel:

1. Pick a central area to your activities
When we visited NYC the very first time, we made the mistake of booking a hotel in Upper East Side because we found a hotel/room that would fit us all. It was a big mistake as it was so far out of the way, that it took us forever to get to all the places we wanted to see.

Even though it doesn’t look it on the map, there is quite a difference between staying in upper Manhattan and lower Manhattan. Public transportation is readily available but regardless, it does take time (up to 45 minutes from upper to lower) and that might not be something you can afford to lose if you’re only staying for a few days. So choose your location wisely even if that means you have to pay a little more.

2. Look for bed bugs
I hate to even mention this nasty issue but it needs to be said. Many hotels in NYC, including luxury hotels, have been plagued with bed bugs. It’s all a part of being located in a large city that sees millions of worldwide visitors. So what can you do as a visitor to prevent this?

Research your hotel and make sure it doesn’t have a history of bed bugs. And exercise caution when you’re actually in your hotel room; don’t leave your suitcase on the floor or use dressers/drawers. Try to keep everything sealed in your suitcase. I have never had an issue yet but it is something worth noting as NYC is notorious for them.

3. Rooms are small
NYC rooms are TINY; this is not just an exaggeration or something that’s specific to certain hotels. Overall, your typical king bedroom in NYC has enough walking room around the bed, a small place to put your luggage and a mini bathroom. It’s not an issue but is something to keep in mind when you’re setting your expectations.

Sometimes you walk in and are pleasantly surprised and other times, you discover that the wide angle photography on the hotel’s website really oversold the place. Just know that most rooms are small and your hotel isn’t the hotel touting miniature rooms.

4. Book in advance
Generally speaking, if you want to find good rates and availability at your top choice hotel, then you would want to book several weeks in advance of your visit. If you decide to book last minute (within 1 week or less) of your planned trip, then use Hotel Tonight. The app does a great job of finding deals as long as you aren’t attached to any one hotel. You can zero in on your preferred location and it’ll bring up the available hotels for you to choose from. Since this is NYC, expect prices to be upwards of $200 and anything less, a deal.

MIDTOWN MANHATTAN HOTELS
1. Shelburne NYC in Midtown
The Shelburne NYC is a classic boutique hotel located in Midtown. It has the perfect location for a visit with friends – it’s close enough to Times Square that you can walk to if someone in your group is dying to visit the main hub but far enough away that you don’t feel congested and claustrophobic.

We easily fit 4 people in our room. as the rooms at the Shelburne are large by NYC standards. The best aspect of this hotel is the rooftop which gives you sweeping views of the city and during the warmer season, a rooftop bar where you can hang until all hours of the night.

2. Arlo Nomad in Korea Town
The Arlo actually has two locations: one in NoMad (aka North of Madison Square Park) and one in Soho. Here we are specifically referring to the one in NoMad. This hotel is known for beautiful rooms with city skyline views. These rooms tend to also be the most expensive that Arlo has to offer but they’re worth it. The city view rooms are amazing as well so don’t be afraid to go with the cheaper alternative if you don’t want to splurge.

And no matter what room you choose, you can still have access to the scenic rooftop. During winter, it’s decked with cute igloos that are furnished with comfortable chairs, pillows and blankets. Summertime brings warm breezes and you can sit and enjoy a drink at the bar. I also loved exploring the restaurant downstairs; it has cute artwork on the walls and is decorated nicely.

3. Lotte NY Palace in Midtown
This hotel is pure luxury in Midtown Manhattan. Opt for a cathedral view or skyline view room to make your stay even more beautiful. The interior is lavishly and elegantly decorated and there is even a spa on-site for those wanting to pamper themselves during their stay.

LOWER MANHATTAN HOTELS 
1. NOMO Soho Hotel in SoHo (aka South of Houston)
NOMO is a cute boutique hotel located in Soho, a charming, artsy neighborhood on the lower Manhattan side. It’s dog-friendly so if you’re considering traveling with your pet, they only charge an additional $100 fee. NOMO has amazing views over the city and features a few Instagram-worthy photo spots.

2. CitizenM NY Bowery Hotel in Lower East Side
This hotel boasts a beautiful rooftop bar and an eclectic interior. If you’re looking for easy access to Brooklyn, then this hotel should be at the top of your list!

3. SIXTY SoHo Hotel in Soho
SIXTY offers well-decorated rooms and a colorful rooftop with plenty of seating. The common areas are classically designed as well. This is modern day luxury if you’re looking for it.

TIMES SQUARE HOTELS
1. Refinery Hotel
Sometimes you travel to New York and want the full touristy experience, Times Square and all. If this is what you’re looking for, then you can opt for the Refinery Hotel which is a block away from the center of Times Square. The Refinery Hotel has the most amazing rooftop restaurant/bar so even if you don’t stay here, you should check it out. Rooms here are simple, plain. The dining areas (Parker & Quinn especially) are fun photogenic spots.

2. Knickerbocker Hotel
Luxury smack dab in the middle of Times Square, the Knickerbocker Hotel offers one of the best rooftops overlooking Times Square. Rooms are simple but very modern.

New York Itinerary: Restaurants

If you thought the number of choices for hotels was overwhelming, then prepare to feel pretty lost when it comes to dining in NYC. There are so many options which can be great if you’re picky but also tough if you have a hard time making decisions. Because NYC is such a great melting pot, you’ll find every type of food under the sun: Indian, Thai, Greek, Pakistani, literally everything. A few tips to keep in mind when you’re planning your dining experience:

1. Don’t forget to make reservations
We’ve run into this issue on more than one occasion while traveling in NYC. Either we forget to call ahead and make a reservation or we decide to make last minute plans. When you’re traveling in a group, it’s crucial to either have a plan B/C or to call ahead and reserve a table. Dining during the weekends is especially difficult as sometimes places will book for the entire night.

2. Call ahead and confirm opening hours
It’s NYC and many places cater special events. This means that your favorite breakfast shop might not actually be open the Saturday you’re visiting. Before making the trek out to wherever you’ve planned for, just make sure you make a quick call to confirm that they’re open. One time we were en route to Clinton Street (known for the best pancakes) when I decided to give them a call. It turns out they were closed for a special event they were hosting.

3. Expect wait times
If your restaurant does not take reservations, you will be expected to wait. Thankfully, you can use the Yelp app to minimize your wait times. You sign in and then select your restaurant (if available). You can then ask to be added to the waitlist (the app will also tell you approximate wait times).

4. Don’t be tempted by the food trucks
I know everyone has a different opinion on this matter but I would highly recommend NOT eating from the hundreds of food trucks parked along the streets. While theoretically they are inspected, it’s not a good idea try your luck with it. My friend is an expert in food safety and practices and he’s mentioned on multiple occasions how risky it is to be eating food from one of these food trucks. Save your food truck cravings for a different city. NYC has too many amazing dining options that it just isn’t necessary to possibly ruin your trip over a hotdog or two.

Coffee:
Happy Bones in SoHo, Lower Manhattan
Happy Bones is fun if you’re looking for unique coffee shop with a hipster vibe. The coffee wasn’t my favorite, though I have friends who say it’s their favorite. Their baristas are latte art experts so if you’re looking for the perfect photo op, you’ll find it here. They have a handful of croissants you can buy if you’re hungry but be warned, there are about 5 seats and maybe 2 tables in the entire shop. It is TINY. So be prepared to grab and go.

Remi Flower & Coffee in Midtown East
Remi’s has the best lavender lattes in all of NYC. They also happen to be the prettiest lattes you’ve ever seen. Seating is limited here as well so you may have to wait for a table or take your coffee to go. They have a few croissants and pastries if you find yourself slightly hungry.

Urban Backyard in SoHo, Lower Manhattan
This cute coffee shop offers unique lattes (lavender and rose) as well as flowery teas. It’s a tiny little shop but adorable on the inside. Urban Backyard does a great job with their seasonal decorations as well.

Bibble & Sip in Midtown
This tiny cafe serves the best quiche around. Coffee is also delicious so while you may not want to visit if you’re super hungry, this is a wonderful place to grab a quick coffee and quiche before you start your day.

Breakfast & Brunch:
Wild Son in Chelsea
The pancakes are to die for in this small, cozy restaurant. They come topped with berries as well as a delicious syrup. If you’re craving something salty, try the grain bowl topped with eggs. Equally delicious and not sweet.

MamanNYC in SoHo, Lower Manhattan
This company has several locations scattered throughout NYC. The easiest one to get to if you’re staying midtown is Marché Maman on Centre Street. This cute breakfast spot is a part of a beautiful home decor store. Attached to the store/restaurant is the original Maman coffee shop. If you find yourself here, you need to try the lavender hot chocolate, lavender waffles and quiche.

Clinton St Baking Co in East Village, Lower Manhattan
This famous breakfast spot is said to have the best pancakes in NYC so make sure you add this to your New York itinerary if you’re a pancake connoisseur!

Lunch & Dinner:
Scotty’s Diner in Midtown East
I’ve never been a diner fan but after recently trying one in Denver and now Scotty’s in NYC, I think I have an easier time giving them a chance. Scotty’s had a very laid-back NYC vibe – portions are huge and food is delicious. I would highly recommend their desserts (which you can preview as soon as you walk in the door) and their omelettes for breakfast. Scotty’s is about 3 blocks from the Shelburne (a huge convenience).

La Nonna in Little Italy, Lower Manhattan
Originally we were planning on trying out Cafe Habana but since we were in Little Italy anyhow and all of us (me included) were craving Italian, we decided to give this place a shot. We loved the fresh homemade pastas and the service was impeccable. *UPDATED 2019: Pelligrino’s Ristorante is closed; their menu is now being served at La Nonna’s.

La Gioconda in Midtown East
If you’re staying in Midtown, I’d highly recommend the Italian restaurant called Gioconda’s. They have a fantastic selection of fresh pasta and homemade dishes and a very cozy interior.

Tasty Dumplings in Chinatown, Lower Manhattan
Located in a nondescript hole-in-the-wall in Chinatown, this Asian restaurant serves the cheapest and most delicious dumplings you may find in the city. $1.25 for 5 piping hot, crispy dumplings. Let’s be real – it doesn’t get cheaper than that.

Spice Symphony in Midtown East
One of the best Indian food restaurants around, Spice Symphony has a great variety of authentic Indian food for you to choose from. Though it doesn’t look it from the outside, the interior is modern and clean. You really can’t go wrong with anything on the menu but make sure you try the paneer, masala and tandoori.

ABA Turkish Restaurant in Hell’s Kitchen (Midtown Upper)
Turkish food is delicious and ABA does a great job of serving unique and amazing dishes. Recommendations: stuffed grape leaves, lebni, and manti as a main dish.

Wondee Siam in Hell’s Kitchen in Midtown
This is one of the smallest restaurants in NYC so prepare yourself for a very cozy experience. The Thai food here is amazing with panang curry being one of the best.

Desserts:
Dough Doughnuts in Times Square, Midtown
The doughnuts here are great but they’re not your typical ultra-sweet donut. These lightly sweetened donuts are more of a cake-y, dough-y donut. Try the dulce de leche and coconut flavors! The interior of the shop is adorable and there is plenty of seating.

Milk & Cream Cereal Bar in SoHo, Lower Manhattan
This popular shop dips their soft serve in cereal but fair warning, the ice cream is pretty sweet so don’t order more than you can handle! Try Cookie Crisp Carnival flavor off the specials menu.

Junior’s in Times Square, Midtown
A popular Times Square spot, Junior’s is the place to go if you’re craving cheesecake. They served huge slices of classic NY style cheesecake in every flavor you could ever hope for. The place is bright and colorful (think crazy headache-inducing lights) so if you are sensitive at all to flashy lights, take your cheesecake to go. Otherwise, sit and enjoy some awesome people watching. Junior’s tends to have a wait time.

Eileen’s Special Cheesecake in SoHo, Lower Manhattan
This small little shop has gourmet cheesecakes in unique flavors and round vs slice shape. Portion sizes are much more modest than Junior’s but the quality and taste are both fantastic. I’d recommend taking your cheesecake to go and sitting in the little park across the street. There is limited seating indoors.

Schmakary’s in Times Square, Midtown
If you’re craving cookies and hot chocolate, then this Times Square cookie shop will make you smile. They have delicious cookies and baked goods but they’re busy so be prepared to wait in line for a few moments!

New York Itinerary: Things to do

What are the best things to do in New York City?

There’s something for everyone in NYC. You’ll find a ton of things to do and places to see. I’ve broken up these New York attractions into different sections of the city so it’s easier to plan your time in New York City.

New York Pass – You may have heard of the New York Pass. This pass gets you into Top of the Rock Observation Deck (OR Guggenheim Museum), Empire State Building, the American Museum of Natural History, The Metropolitan Museum of Art, Ferry Access to the Statue of Liberty and Ellis Island (OR Circle Line Sightseeing Cruises), and the 9/11 Memorial & Museum (OR Intrepid Sea, Air & Space Museum).

It costs $133 starting March 2019. It’ll be up to you and your individualized itinerary to decide if the pass is worth it to you. Breaking it down, this is how much each individual ticket costs based on adult pricing (*estimated prices):

$20 advance ticket; $33 at the door; $54 with bonus entry Empire State Building*
$28 American Museum of Natural History**
$40 Top of the Rock OR $25 Guggenheim Museum
$25 Metropolitan Museum of Art
$18 Statue of Liberty OR $37 cruise
$33 Air & Space Museum OR $26 9/11 Museum

*According to the City Pass website, the 102nd floor observatory will be closed to the public for renovations December 17, 2018 through July 29, 2019.
*The City Pass website lists this cost as $54 because they are giving you a bonus same-night entry. $20 is the typical admission rate assuming you book in advance.
**The American Museum of Natural History actually operates on a pay-what-you-wish system assuming you get your ticket at the ticket counter. So while advance ticket price is $28, you can actually pay as little as $1 at the door. However, please note that you cannot get access to any special exhibits.

LOWER MANHATTAN
Little Italy and Chinatown: These sections of the city are small but pack in a bundle for the visitor. So many restaurants line the streets of each area and street vendors can be found selling cannolis (Little Italy), fish and fruit (Chinatown) and chachkas galore. Lots of fantastic restaurants are located within each area.

Wall Street: This area houses the financial district as well as the One World Trade Center area: 9/11 Memorial and Museum, One World Observatory as well as the Oculus and Battery Park (where boats depart for the Statue of Liberty).

Oculus: Located in the World Trade Center area, the Oculus was built to replace the train station that was destroyed in 9/11. It’s a masterpiece of architecture and I think it deserves a visit. The inside is also a retail mall so if you’re craving some shopping, you can stop in and browse the shops that line the inside.

Brooklyn Bridge: Brooklyn Bridge is not only iconic but it provides passage between Manhattan and Brooklyn. I’d recommend waking up early (before 7am) to walk the bridge as it fills up with A LOT of people throughout the day.

Staten Island & Ellis Island: While the actual Staten Island ferry ride to Staten Island is free, you have to pay to access that Statue of Liberty. Tickets also give you access to Ellis Island.

DUMBO – This area is a neighborhood located in Brooklyn and stands for Down Under the Manhattan Bridge Overpass. You can see Manhattan Bridge in the distance in the below photo. DUMBO is a great mix of Brooklyn and Manhattan; popular places to visit here include Jane’s Carousel and Brooklyn Bridge Park.

UPPER EAST SIDE
Metropolitan Museum of Art: Though not a museum lover typically, I LOVE the Met. It’s probably my favorite museum and once you enter it, you’ll quickly realize why. There is something for everyone and the museum is so enormous that it’s nearly impossible to see everything in one visit.

This is why I recommend allotting a specific number of hours beforehand for walking through the museum. It will help you plan your visit better and make sure you don’t miss exhibits/galleries that are at the top of your list. I made the mistake of not planning well once and regretted it as we ran out of time to see some of our favorite galleries.

Central Park: The most famous of all the parks in NYC, Central Park is beautiful to visit year-round. It’s a huge park with over 800 acres of land. This is where you’ll run into talented street performers, people seeking solitude, dog walkers and more. It’s definitely worth stopping by for a few hours to enjoy, especially if it’s a beautiful day. It’s unexpected calm amidst a hustling and bustling city.

MIDTOWN
Times Square: The number 1 destination for first time visitors to NYC. Times Square is a rather chaotic mass of people visiting NYC for their first, second, tenth time. This is where you can find A LOT of shops, restaurants and the big billboards that are so infamous.

Broadway: If you’re even remotely a Broadway fan, I’d highly recommend reserving a night before you visit. Our friends advise to book the show a few days before you arrive in NYC to ensure good seats at a great show or you can wait in line the day of for last minute tickets to shows that haven’t sold out yet. Broadway shows are not cheap so expect to spend at least $100 and possibly several hundred depending on the show and seat assignment.

MoMa: Art lovers will enjoy the The Museum of Modern Art, a famous art museum in NYC. If you visit Friday nights between 4-8pm, admission is free; otherwise, it’s $25.

Rockefeller Center: If you’re in NYC during Christmastime, be sure to wander the Rockefeller Center. You’ll see the beautiful ice skating rink as well as the famous Christmas tree that the city always puts up in the middle. This is the area where you’ll see crazy shops like the big Lego store and the M&M store.

Grand Central Terminal Station: Once you enter this station, you’ll feel like you stepped into a different world. This is basically Times Square in a smaller area but with even more crowds, pushing and things to make your head spin. It’s a beautiful place, full of amazing architecture and if you’re not using it as a means of transport to and from the city, then at least stop by for a quick peek. The station also has restaurants and shops just in case you didn’t get your fill outside.

New York Public Library: This library is stunning, another amazing study of architecture in NY. Even if you don’t want to read, stop in and admire the ceilings and artwork.

High Line: The High Line is a 1.5 mile elevated walkway that was built on the location of a historic railway. It looks out over the city and is filled with greenery and interesting artwork.

Flatiron Building: If you’re looking for that classic NYC shot, then walk over to the Flatiron Building. This is the iconic skinny building that you see everywhere and it’s worth a quick photo snap if you’re Midtown.

NEW YORK CITY VIEWPOINTS
Empire State Building: One of the oldest views over the city, the Empire State Building looks out over NYC with the One World Observatory in the far distance.

Top of the Rock: Another great viewpoint in NYC, Top of the Rock is located in Rockefeller Center. Elevators take you up to the Observation Deck and while you can grab a few photos from inside, the best views are outside located on two different levels. You can catch views of the Empire State Building in the distance.

One World Observatory: This tall building was originally called the Freedom Tower and is located in the World Trade Center area. For $34 you can gain access to the top and enjoy dramatic & stunning views over NYC. You can view Manhattan in the distance.

Which view is best: Top of the Rock vs Empire State Building vs One World Observatory? Some will argue that the view from the Empire State Building isn’t quite as stunning as Top of the Rock or One World but it all comes down to personal preference. If you have the city pass, go to both and decide for yourself. If not, I don’t think you can really go wrong with whichever viewpoint you decided to go with.

OTHER
Helicopter Tour over NYC: And for those who want a completely unique experience, several companies in NYC offer helicopter tours over the city.

*Other museums: Guggenheim Museum (art museum), American Museum of Natural History, Air & Space Museum, 9/11 Museum (all of these are included with the city pass as mentioned above)

Related New York travel guide: Day trip from NYC

5 Days in New York City

Where to stay: Midtown or Lower Manhattan; since you’re spending about 2 days in Lower Manhattan, you can afford to stay in this area
*Depending on how much you enjoy museums, you may want to get the city pass (see above). You also might want to consider the 7 day metro ticket for unlimited rides as you’ll be traveling pretty extensively during your stay

Day 1 Check in. Start your 5 days in New York City with a Broadway show and Times Square exploration.

Day 2 Midtown: Visit architectural landmarks like the Flatiron Building, Grand Central Terminal & the public library & Rockefeller Center. Go up Top of the Rock or the Empire State Building and watch the sun set over the city. This is the day to visit the Intrepid Sea Air & Space Museum and MoMa.

If MoMa or the Intrepid Sea isn’t your thing, then opt to explore Little Italy and Chinatown for the evening instead.

Day 3 Upper East side: If you’re staying in SoHo or Lower Manhattan, note that it will take close to 40 minutes to travel to the Upper East side. Start your day off with the Metropolitan Museum of Art (depending on your love of art, you can spend the entire day here; however, your ticket allows you to break up your visit into several days) & Central Park. If you want to visit the Guggenheim Museum or the American Museum of Natural History, this is the day to do so.

Day 4 Lower Manhattan: Get an early start to your day and visit Brooklyn Bridge before it becomes crowded. Make your way over to the One World Trade Center and visit the 9/11 Museum and go inside the Oculus. Take the ferry out to Staten Island.

Day 5 Lower Manhattan: Take a helicopter ride and enjoy your morning in Battery Park or DUMBO. If you’re not staying in Lower Manhattan and you don’t care to explore this area again, you can visit the Met again.

4 Days in New York City

Where to stay: Midtown because of its close proximity to most things
*Depending on how much you enjoy museums, you may want to get the city pass (see above). You also might want to consider the 7 day metro ticket for unlimited rides as you’ll be traveling pretty extensively during your stay.

You may want to follow the above itinerary for your 4 days in New York City though you will have to eliminate one day. If you really want to do a helicopter tour, then I would recommend replacing the ferry ride to Staten Island with the heli tour. You might still have time to take the ferry ride (and it’s free!) but you just won’t have time to actually enter the island and climb the Statue of Liberty.

What is a must do weekend itinerary in New York for a first timer?

You can’t accomplish everything in a weekend but you can definitely see your fair share of the city.

Where to stay: If you’re only in NYC for a weekend and it’s your first time, then I would recommend staying in Times Square. This is because Times Square is a central location and if you’re planning to see any Broadway shows, you’ll be glad you’re close to your hotel late in the evening. The Knickerbocker Hotel is a great luxury option as well as the Refinery Hotel. If you prefer chain hotels, there are plenty of options in this area including Marriotts, Hiltons and Hampton Inns.

Friday: Check in to your hotel. Take the metro down to Lower Manhattan, You will have just enough time to do ONE of the following: Little Italy & Chinatown with dinner, Brooklyn Bridge and Dumbo, the World Trade Center (Oculus and the 9/11 Museum) or Battery Park and Staten Island Ferry & Statue of Liberty.

Saturday: Walk in Times Square and see it during daylight, maybe grab a cheesecake from Junior’s or a cookie from Schmakary’s. Stop in Grand Central and the public library for a quick look. Have lunch in Hells Kitchen then go visit MoMa.

Make your way over to Rockefeller Center towards evening, visit the Lego and M&M stores if you are obsessed with either and then prepare to go UP. Reserve a ticket in advance for Top of the Rock or Empire State Building and watch the sun set over the city. Enjoy dinner in Midtown. Or you can opt to watch a Broadway show instead of Top of the Rock. You can do both if you do Top of the Rock early enough in the day (no sunset).

Sunday: Spend your day at the MET or visit Central Park until it’s time to leave.

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