April 21, 2022

New York City – 5 Day Itinerary

I’ve spent a lot of time in New York City, from living there to visiting as a tourist, so I thought it’d be easy to come up with the perfect itinerary for first-timers. But as I started writing things down, there are so many things to do you’d probably need 40 hours in a day to get through them all! And let’s not even get started on the list of restaurants that you MUST go to. It’s about a mile long! This is part of the reason I decided to come up with the perfect itinerary for first time visitors that includes a wonderful mix of tourist sights and local favorites and makes sure you aren’t spending wasted hours going back and forth across the city.

If you’re a first-timer to the Big Apple, this itinerary and travel guide will help you check off the boxes for all of your must-see activities. If this is your second or even 25th visit, you’ll find great recommendations for restaurants, activities, and local favorites that will help you to pretend you’re a New Yorker (even for just a little while!).

Day 1

8AM – Grab a quick breakfast at your hotel or a nearby coffee shop (PDF pg. 25 for recommendations) and head to Battery Park to catch a ferry to the Statue of Liberty & Ellis Island (get there early to avoid crowds). For a free option, hop on the Staten Island Ferry (you can’t get off at the Statue of Liberty, but you will get a nice view).

12PM – Lunch near the Village (Recommendations: Jack’s Wife Freda or Buvette).

1:30PM – Wander through the Village’s winding streets and neighborhoods. If you get hungry, grab a slice from Joe’s pizza at Bleeker and Carmine (the best slice in the city!).

3PM – Visit boutiques in SoHo to get your shopping fix and enjoy walking through the cobblestone streets.
5PM – Head back to your hotel to rest and get ready for dinner.
7PM – Dinner Recommendations: OTTO Enoteca, Waverly Inn, Lombardi’s, The Spotted Pig, or Alta
9PM – Tonight you are in store for laughter at the Comedy Cellar (You must order tickets several weeks ahead of time).
11PM – Pop into a nearby bar for a drink or head back to your hotel for zzz’s.

Day 2

8AM – Grab a New York Bagel (try lox and cream cheese for a true NY experience (Recommendations: Black Seed Bagel (Nolita), Absolute Bagels and Zabars (UWS), Murrays (West Village), Ess-a-bagel (Midtown)).
9AM – Central Park – You could spend hours wandering through the park, so pick a few spots you’d like to check-out ahead of time (see NYC’s Central Park – What to See).
12PM – No trip is complete without lunch at Shake Shack. Head to the original in Madison Square park.
2PM – Visit Top of the Rock or the Empire State Building (Top of the Rock is less expensive and you’ll have views of the Empire State Building in your photos, but the Empire State Building is a classic sight to visit. Both options will provide you with a great view!).
4PM – Pop into Grand Central Station and look for the whispering gallery. Head back to your hotel to rest and get ready for dinner.
6PM – Book an early dinner since you’ll be going to a show (New York City Restaurant Guide)
8PM – Tonight you’re going to see a Broadway show. Post show – Walk through Times Square (Keep your eye out for the “Naked Cowboy”). There are plenty of nearby bars and rooftops for after-show drinks.

Day 3

9AM – Do as New Yorker’s do and enjoy a leisurely Brunch (New York City Restaurant Guide)
10AM – Make your way down the island and stop at the 9/11 Memorial & Museum (a perfect time to break from Manhattan’s madness, catch perspective, and honor those who gave all). The Wall Street Charging Bull, New York Stock Exchange, and Trinity Church are also nearby.

12PM – Walk or bike across the Brooklyn Bridge (Note: there are no bathrooms on the bridge).
1:30PM – Stop for lunch at a Brooklyn style coal-fired pizza joint (Juliana’s or Grimaldi’s are two of the best).
2:30PM – Explore DUMBO and Brooklyn Heights’ shops and cafes.
4PM – Take the East River Ferry back to Manhattan.
7PM – Dinner in Chinatown at Joe’s Shanghai for soup dumplings (New York City Restaurant Guide)
9PM – Order a fun cocktail at the speakeasy “Please Don’t Tell” – call ahead in the afternoon to make reservations.

Day 4

8AM – Grab a coffee and pastry in Chelsea Market and window shop through the stores. Finish the morning with a walk on the High Line, an urban 1.5 mile walking path on an elevated rail trail.
Noon – Lunch at Katz’s Deli – famous Meg Ryan scene from “When Harry Met Sally” was at this restaurant 1:30PM – New York has so many great museums to visit. For your first-time visit we recommend the MoMA, The Met, the Guggenheim or the American Museum of Natural History (great if you’re traveling with kids).
4:30PM – Stop for a treat at Levain bakery (the cookies are amazing) or Milk Bar (famous for cereal flavored milk, cookies, and cakes) and head back to your hotel to rest before dinner .
6/7PM – Dinner in the Lower East Side if you’re going to United Citizens Brigade or an early dinner if you’re seeing a Broadway show.
9PM – United Citizens Brigade comedy show or another Broadway show.

Day 5

7AM – If you’re an early bird, get up to say hello to Savannah and Hoda at the Today Show and explore Rockefeller Center.
9AM – Brunch at Sarabeths
10:30AM – Window shop through 5th Ave and Madison Ave. Take a look at diamonds in Tiffany’s flagship store and famous department stores like Bergdorf’s and Bloomingdales.

12PM – Lunch at Eataly for a vibrant Italian marketplace experience, check out nearby Fish’s Eddy for whimsical homewares.
1:30PM – Visit another museum, do more shopping, visit the Brooklyn or Bronx Zoo, check out the New York Botanical Garden, or head out to Coney Island.
7PM – Dinner (New York City Restaurant Guide)
Evening – Get tickets to a New York sporting event (Yankees, Mets, Brooklyn Islanders), see a show, or head to a rooftop for a farewell cocktail.