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I will always remember my first trip to NYC: the honking horns, the glowing lights of Times Square, and the towering buildings. Nothing beats the view from the Empire State Building or seeing the Statue of Liberty up close. Yes these famous landmarks are touristy, but they are a must to visit. If it is your first time visiting use my 4 day NYC itinerary to make sure you see all the iconic sights.

There is so much more to NYC than Times Square. Whenever someone says they don’t like New York and it is too crowded for them I ask, “Did you leave Manhattan”? New York City is comprised of 5 boroughs: Manhattan, Brooklyn, the Bronx, Staten Island and Queens. Within each borough there are numerous neighborhoods. Most of the well-known sights are located in Manhattan so the majority of visitors to NYC hardly leave Times Square, much less Manhattan.

This 5 day New York City itinerary takes you to all five of NYC’s boroughs. Use this itinerary and spend one day discovering each borough. This itinerary doesn’t even make a dent in what there is to do in each borough, but hopefully it will give you a good introduction to each one. Combine these 5 days in NYC with my 4 day NYC itinerary for first time visitors and you will have 9 days in New York all planned out!

Getting Around NYC

Before you begin your 5 days in New York you need to know how to navigate the city. Here is a quick transportation guide to help you know how to get around and how not to get around the city.

Renting a Car

Do not rent a car! I once read a NYC guide where someone recommended doing this. I’m not sure if that person had ever been to New York before. When you rent a car you will of course be paying for the cost of renting and gas. In addition you will usually pay at least $20 a night for parking at your hotel and about the same for everywhere you go. Times Square will be more expensive and some places in the outer boroughs will be less. Let’s not forget you actually have to drive the streets of the city that never sleeps (or stops honking) and find parking spots as well!

Taxis

If you don’t mind the cost, then you might as well take taxis and not worry about parking or driving. Lyft is my go to app in the US.

MTA: Subway & Buses

The Metropolitan Transportation Authority (MTA) of NYC isn’t always talked about too fondly by New Yorkers. Complaining about the MTA is one of our favorite pastimes and quite the bonding experience. After living in the city I can never be on time to save my life, because I got so used to the MTA always being delayed and that was a perfectly excusable reason to be late. One of my co-workers was late on his interview and even got the job!

It may seem contradictory for me to now say that the subways and buses of the MTA are the best way to get around New York…..but they are! It costs $2.75 for one trip on the subway/bus. For $33 you can travel as much as you want for one week. If you are planning on taking the subway or bus 12 or more times within one week it is worth it to buy the week pass. Here are a few basic steps to riding the subway in NYC.

1. Buy a subway card at a vending machine in any station or from a station booth in some stations.
2. Swipe your ticket to enter.
3. Follow the signs to the line you need to take (a color with either a number or a letter)
4. Once you find your line you need to make sure you are going in the correct direction. For some lines you go down the same stairs and wait on the same platform for both directions. One side goes in one direction and the other side goes in the opposite direction. For other lines you need to go down different staircases depending on which way you want to go.
5. Get off at your correct stop and follow the signs to exit. You don’t need to swipe your ticket to exit.

For buses you can use the exact same card as you use for the subway. Simply insert your card in the slot when you enter the bus. It will pop back out for you to continue using. When your stop is next, remember to pull the cord by your seat so the driver knows to stop. If there isn’t anyone waiting at the bus stop, the bus will only stop if a passenger requests a stop.

You can reach everywhere in this NYC 5 day itinerary by bus or subway. I provided some simple directions on how to get to each place on this itinerary. Use google maps for exact directions and times.

5 Day NYC Itinerary: Day 1 – Manhattan

There are so many interesting neighborhoods in Manhattan. One of my favorite neighborhoods to spend a day in is the Lower East Side (LES). There is a great deal of history in this neighborhood and a lot of tasty places to eat. It’s known for being a diverse neighborhood full of musicians, artists and people from all walks of life. The LES is one of the best places to see the old, gritty side of Manhattan alongside the newer, trendier side.

After arriving in the LES you shouldn’t need any transportation other than your own two feet! The neighborhood is great for wandering around and stumbling upon interesting places. This day involves a little bit of everything, history, food, art, shopping and nightlife!

Tenement Museum

Begin your day learning about the history of the neighborhood. At the Tenement Museum you can walk through one of the many buildings where the first immigrants to New York used to live! On the guided tours you get a glimpse into what life was like as an immigrant new to the city and living in a crowded building on the LES.

Admission: The only way to visit is through a guided tour. Tours can sell out in advance, so buy your tickets ahead of time.

Transportation: Take the J or Z trains to the Bowery stop or the B or D to the Grand St. stop.

Lower East Side Food Tour

I love going on food tours in NYC. With Free Tours by Foot you only need to pay for what you decide to buy. I have taken several tours with this company and the Lower East Side food tour is one of my favorites. It’s a great way to learn about a new neighborhood, while trying out the best foods. There are so many great places to eat in the city that you can eat somewhere different everyday and still not try everything. It’s so helpful to have a guide taking you to the best spots! Also more so than any neighborhood in the city, food really shaped the LES.

Admission: Free Tours by Foot require advanced reservations, but are tip-based. You pay for all the food during the tour. If the tour isn’t offered when you are visiting you can take a paid LES food tour. On the paid tour all the food is included in the price. Numerous other LES food and walking tours are available as well so you are sure to find one that fits your schedule!

Transportation: The tour begins at Yonah Schimmel’s Kinsh Bakery, which is less than a 10 minute walk from the Tenement Museum.

Essex Street Market

It would be unlikely that you need more to eat after the tour, but if you do or aren’t able to take the tour, visit Essex Street Market. If you are a foodie you don’t even need to be hungry to enjoy looking at all the food vendors and prepared food merchants in the market. The public market has been around for over 100 years. Taking a tour of the market is also available.

It’s also a good place to visit if you need a bathroom break!

Admission: Market tour

Art: New Museum or Art Galleries

With so many artists living in the neighborhood there is bound to be a lot of opportunties to see art. The New Museum is a contemporary art museum with art from around the world.

The LES is also packed full of art galleries. It’s also probably no surprise that the neighborhood is full of street art. See what you can find on your own or take a guided street art tour.

Admission: Tickets to the museum are $18 or free with the New York Pass. The Alternative New York Street Art Tour is $37 or free with the NY Pass.

Shopping

NYC is known to be a shopper’s paradise. Different neighborhoods will give you different experiences shopping-wise. Within the LES you will find a wide variety of stores ranging from trendy boutiques to mom & pop shops. Bluestockings is known as a “radical” bookshop that focuses on alternative literature topics. You will find a lot of shops on Orchard St.

Dinner

If you have seen When Harry Met Sally you will want to head to Katz’s Delicatessen for dinner. The Jewish Deli is well-known thanks to the classic scene from the movie and it’s renowned pastrami sandwiches. Whatever sandwich you get you may want to share. You will thank me later for that tip!

You can find almost any cuisine you are looking for within a few blocks. It’s hard to even begin recommending restaurants. The Boil is a fun cajun style seafood place. Spaghetti Incident is a trendy place to go for Italian. The MasalaWala serves both classic Indian food and inventive South Asian street food in a colorful ambience. For a cozy wine bar with French food head to Jadis. 

Nightlife

There is a big nightlife scene in the LES. It’s where the locals go whether they want a night at a dive bar or want to spice up their usual routine somewhere more upscale. Use this NYC Go Guide to help you plan your evening based on what type of activity you are looking for.

5 Day NYC Itinerary: Day 2 – Brooklyn

I had a really hard time deciding what to include for your day in Brooklyn. I lived in Brooklyn for four years so needless to say I have a lot of great things to recommend to do and see in this borough.

Brooklyn Bridge

Start your day bright and early by walking across the Brooklyn Bridge from the financial district of Manhattan.

Transportation: Take the subway to the Fulton St station in Manhattan and then walk to the start of the bridge.

Brooklyn Bridge Park

Brooklyn Bridge Park offers some of the best views of Manhattan. You can simply walk along the riverfront, take a rest at one of the many benches or make use of the many sporting areas. In the summer the park provides free kayaking a couple days a week.

Transportation: The park basically begins under the bridge on the Brooklyn side.  

Brooklyn Transit Museum or Brooklyn Historical Society

These are two great museums in the downtown Brooklyn area. The Brooklyn Transit Museum is housed in a 1936 subway station. The museum takes you through the history of transportation in NYC and provides interactive exhibits for all the important events that are related to the subway station. One of the best parts is the old-fashioned subway cars that you can walk through.

The Brooklyn Historical Society covers Brooklyn’s 400 year old history. The exhibitions change frequently and focus on specific people or events. When I visited there was an exhibit on the history of slavery in Brooklyn. We hear about the history of slavery in the south so often, but it is rare that it’s role in the north is mentioned.

Admission: Adult admission to both museums is $10 each. The Brooklyn Transit Museum is included with the New York Pass.

Transportation: The museums are located in Brooklyn Heights/downtown Brooklyn and about 20 – 30 minutes away on foot from the park.

Lunch in Brooklyn Heights or Downtown Brooklyn

Montague Street in Brooklyn Heights has a wide variety of independent restaurants to choose from. If you want some Thai food try Lantern. Bijan’s a Mediterranean restaurant in downtown Brooklyn has the most delicious fries! If you are a foodie you will love all the choices at Dekalb Market Hall at CityPoint. 

Grand Army Plaza

Grand Army Plaza is the name of the large oval entrance to Prospect Park and the name of the subway station that provides convenient access to many interesting places. Check out one or more of these places during your afternoon in Brooklyn.

Brooklyn Museum

The Brooklyn Museum is a large art museum with a huge collection of pieces from different cultures and of different mediums.

Admission: Adult admission is $16. For $28 you can visit both the museum and the Botanical Gardens. 

Brooklyn Botanical Gardens

While the Brooklyn Botanical Gardens are great to visit year-round, spring is extra beautiful because of the cherry blossoms. Be aware that it is crowded during this time of year though. There are a wide variety of gardens and indoor conservatories to explore.

Admission: Adult admission is $18. For $28 you can visit both the garden and the Brooklyn Museum. Admission is included with the NY Pass. 

Prospect Park

Central Park is very well known, but did you know Prospect Park was designed by the same man? For more of a leisurely afternoon discover one of Brooklyn’s largest parks.

Transportation: Take the 2 or 3 subway to Grand Army Plaza and walk to any of the following activities in the Prospect Park and Crown Heights neighborhoods.

Dinner on Franklin Avenue

Franklin Ave between Eastern Pkwy and Atlantic Ave in the neighborhood of Crowne Heights is full of interesting restaurants. While the neighborhood has went through quite a bit of gentrification in the last 10 years, it is still far from the usual tourist trail. Most tourists who come to Brooklyn don’t get this far into the borough!

There is Chavelas for your Mexican fix. Cent’Anni if your go to is Italian. There is a large Caribbean population in this part of Brooklyn, so get some great authentic Jamaican dishes at Island CZ. Berg’n food hall, off of Franklin Ave, is great if your group all wants something different. Barboncino has delicious pizzas. For drinks and/or dessert go to Butter & Scotch.

The Chocolate Room 

I couldn’t omit one of my very favorite places in Brooklyn. The Chocolate Room has two locations in Brooklyn, one in Park Slope and one in Cobble Hill. I recommend picking the one that makes it easiest to get back to your accommodation afterwards. Although it involves some extra transportation, the all chocolate menu is definitely worth it! There are so many delectable items behind the counter, but the chocolate layer cake is so good that I can’t help but order it every-time.

Transportation: Park Slope –  Take the 2/3 to Bergen St., Cobble Hill – Take the 2/3 to Borough Hall 

5 Day NYC Itinerary: Day 3 – The Bronx

The Bronx holds one of the worst reputations out of the five boroughs, but in reality it is seriously underrated. If possible visit the Bronx on a Wednesday when both the gardens and zoo are free.

New York Botanical Gardens

The New York Botanical Gardens in the Bronx is my favorite botanical gardens in the city. It’s the biggest, but also the priciest garden to visit. There are very few places in the city where you can get away from all the people. The Thain Family Forest is one of the many areas of the gardens that you might not see another person! It’s a great place to walk around, but there is also a tram that goes around the grounds. All the outdoor paths and gardens are the highlights for me, but there are several indoor spaces as well.

There are a couple different cafes where you can eat lunch.

Admission: Adult tickets are $23 – $30, depending on the day of the week. If you are a NY resident you can buy a grounds only ticket for $15. Grounds admission is free for everyone on Saturdays from 9 – 10am and on Wednesdays. Free with the New York Pass. 

Transportation: Take the B, D or 4 train to the Bedford Park Blvd Station. Then walk about 20 minutes to the gardens or take the Bx26 bus. You can also take the 2 train to the Allerton Ave Station and walk to the gardens.

Bronx Zoo

The Bronx Zoo is one of the best zoos I have ever been to. The animals have more room to roam and their spaces are designed to resemble their natural habitats. The baboons were one of my favorite animals the last time I visited. I don’t know if they are always so energetic, but they were putting on quite the show. Try to catch one of the daily sea lion feedings too!

The zoo has several options for lunch and snacks. During the winter many of the places are closed.

Admission: Adult tickets are currently $29.95. Admission is free on Wednesdays.

Transportation: The botanical gardens and zoo are right next to each other. Exit through the East Gate (Waring Avenue and Bronx Park East) at the gardens and walk about 12 minutes to the zoo’s Bronx River Gate entrance on the Bronx River Parkway.

Arthur Avenue – Little Italy

When someone mentions Little Italy in NYC they are usually talking about the one in lower Manhattan. Did you know that the Bronx also has a Little Italy? They claim to be “the real Little Italy”! It’s located along Arthur Avenue. Stroll along the street and find somewhere that looks appealing for a nice Italian dinner. There are a lot of great options, but I enjoyed Enzo’s. Save some room for an Italian pastry after dinner too!

Transportation: Walk about 10 minutes from the zoo.

Yankees Game

The Bronx is probably most known for being home to Yankee Stadium. If you visit during baseball season try to snag some tickets to one of the most well known baseball teams in the country. This is something I haven’t gotten a chance to do yet, but would really like to. Stadium tours are also available during the daytime.

Admission: Yankee game ticket prices vary. Stadium tours are $20 when purchased online and are included in the New York Pass. 

Transportation: From Arthur Avenue you can either walk about 15/20 minutes to the D train to the stadium or you can take a bus to the D train. These neighborhoods aren’t necessarily dangerous, but they also aren’t the safest. Be aware of your surroundings everywhere, but especially in these areas.

5 Day NYC Itinerary: Day 4 – Queens

Queens within Queens county is one of the most diverse areas of the USA! It’s also the biggest borough in NYC, size-wise. That means that there is a lot to see, but it takes a long time to get from one place to another.

Museum of the Moving Image

I found the Museum of the Moving Image to be a really cool museum. It’s different than your typical history or art museum. From time to time as I am watching a movie I am still reminded of little details I learned about the movie making process from this museum.

Admission: Adult tickets are $15. Admission is free Friday nights from 4 – 8pm.

Transportation: Take the R or M to Steinway Street or the N or W to 36th Ave.

Lunch in Astoria 

Astoria is known for its wide selection of dining options. For an indulgent brunch Queens Comfort always delivers.

Flushing Meadows Corona Park

Flushing Meadows Corona Park was once home to two World’s Fairs and still hosts the US Tennis open. It is now one of the city’s biggest parks. The 140-foot steel globe that was built for the world’s fair is known to be the centerpiece of the park. With scenic trails and lots of sporting activities there is a lot to do within the park. On Meadow Lake you can rent kayaks and paddle-boats. You can also visit one of the many museums or cultural centers within the park.

Queens Museum

The Queens museum is an art museum with many exhibits focusing on the World’s Fairs. The panorama of the city of New York is the most impressive part of the museum. It was one of the most successful attractions from the 1964 World’s Fair. The model takes up 9,335 square feet. You can walk around it from all sides.

Admission: Suggested adult admission of $8. 

Queens Botanical Garden

The Queens Botanical Garden isn’t quite as sprawling as the one in the Bronx, but it is a little lesser known so it provides a nice oasis in nature away from other people. All the small gardens make it an ideal place to relax.

Admission: N/A 

New York Hall of Science 

This interactive science museum is fun for the whole family. If it is nice weather there are some great outdoor exhibits too.

Admission: Adults are $16. Included with the New York Pass. Every Friday (2 – 5 pm) and every Sunday (10 – 11 am) the museum is free. 

Queens Zoo

The Bronx once again gets all the attention for it’s huge zoo. The Queens zoo is much smaller, but has some nice animal exhibits as well.

Admission: Adults tickets are $9.95. 

Transportation: From Astoria go to the 30th Ave subway station and take the N to Queensboro Plaza. Then take the 7 to 111th St Station.

Downtown Flushing 

There are nine different chinatowns within the 5 boroughs of NYC! The most well known is in lower Manhattan. Flushing is home to the 2nd largest in the city. Unlike the one in Manhattan you won’t find very many tourists. To me downtown Flushing feels like the Times Square of Queens as it is a pretty bustling area. I’m usually not one for food courts, but the one at the New World Mall is one of my favorites. Forget McDonalds, Burger King, Taco Bell and all the other typical food court staples. This one is full of different Asian cuisines.

Now that I no longer live in the city I always stay at the Grandview Hotel in Flushing when I come to visit. It’s a nice hotel with much more reasonable prices than you will find elsewhere.

Transportation: Take the 7 from 111 St. Station to Main St. 

Long Island City

Long Island City (LIC) is the perfect neighborhood to end your day in Queens. There are a lot of trendy restaurants and bars that have a fun evening atmosphere. As LIC is along the river, you can find rooftop bars with great views of Manhattan. Walk along Vernon Blvd and you will see restaurant after restaurant. Sweet Chick is good if you want some classic or inventive chicken & waffles!

Transportation: Take the 7 from Main St in Flushing to Vernon Boulevard-Jackson Avenue in LIC. It will take about 30 minutes. 

5 Day NYC Itinerary: Day 5 – Staten Island

My first visit to NYC I did what many people do, I hopped on the Staten Island ferry, arrived at Staten Island and immediately got on the next ferry back to Manhattan. Other than this quick turnaround visit, Staten Island is the least visited borough. Contrary to popular belief that doesn’t mean there isn’t anything to do on the island!

Staten Island Museum

The Staten Island museum is a general interest museum with permanent and rotating exhibits on a variety of topics. While many of the exhibits focus on different aspects of the history of Staten Island, other exhibits are on art, natural science, or cultural topics from around the world.

Admission: Suggested admission is $8. You can receive free admission with the New York Pass.

Transportation: Take the free Staten Island Ferry from the Whitehall ferry terminal in the financial district (Manhattan) to St. George ferry terminal on Staten Island. Then take the S40 bus to the Richmond Ter/Snug Harbor Rd stop or the S44 bus to Henderson Av/Westbury Av stop. You can also reach Staten Island by bus from Brooklyn.

Snug Harbor Cultural Center & Botanical Garden

Snug Harbor was originally a community for retired sailors. Today it hosts cultural programs and the grounds are full of beautiful botanical gardens to explore.

Snug Harbor has a cafe if you would like to eat lunch there.

Admission: The main grounds are free to visit. Three of the attractions, the Newhouse Center for Contemporary Art, the New York Chinese Scholar’s Garden, and the Connie Gretz Secret Garden require admission. You receive free admission to the gardens with the New York Pass.

Transportation: The Staten Island Museum is within Snug Harbor so you are already in the same area!

Historic Richmond Town

Historic Richmond Town is compromised of four different sites. The main one is an open-air museum that is set up to resemble an authentic town and farm. The town showcases American life through various periods in history. The original town of Richmond is from the 17th century. The site is so different than anything else you will find in NYC.

Admission: Tickets are $8 for adults. On Wednesdays the admission is suggested. 

Transportation: To reach Historic Richmond Town you will need to take a couple of buses for 40 – 60mins. Use google maps to plan your journey and see what buses to take depending on the time of day.

Dinner on Staten Island

Head back towards St. George’s Ferry terminal for dinner. After dinner you can walk back to the ferry terminal for a convenient journey back to Manhattan or wherever you are staying in the city. Beso is a cozy Spanish restaurant with many of my favorite dishes that I savored while studying abroad in Spain.

Enoteca Maria is a restaurant on Staten Island that I have not had the chance to try yet. The restaurant’s claim to fame is that it is run by grandmothers, nonnas, who cook the cuisine of their ancestors. The restaurant began with only Italian nonnas, but now has an Italian nonna running the downstairs kitchen while a grandmother from a different background leads the cooking in the upstairs kitchen. It sounds like a really cool concept! Who needs a professional chef when you can eat grandma’s cooking!

*You can also visit the Staten Island Zoo, Staten Island Children’s Museum or attend a Staten Island Yankees game, which are all included with the New York Pass.

In this NYC 5 Day itinerary which borough caught your attention the most? I hope you agree with me that it is worth it to get out of the most visited neighborhoods of Manhattan and explore more of the city. 

Not quite what you are looking for? Don’t worry, I can help! Through my Personal Travel Planning service I can plan the perfect 5 day trip to New York to meet your travel needs…or any other place you dream of visiting!

More About NYC

BOOKS

• Historical Fiction Books Set in NYC
• Chick Lit Set in New York City
• Children’s Books about NYC

BROADWAY

• How to Get Discount Broadway Tickets

CHRISTMAS

• The Best Things to Do in New York in December

ITINERARIES

• 4 Days for First Time Visitors

LIFE IN NYC

• Moving to NYC Alone
• How to Save Money Living in NYC

MUSEUMS

• NYC Museums by Category
• New York Historical Society
• Museum of the City of New York

TOURS

• The Best NYC Tours

WHERE TO STAY

• Grandview Hotel (Queens)
• Where to Stay in Brooklyn

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