City Break: Manhattan

By Amanda Wowk

June 29, 2021

City break (noun): a short holiday spent in a city, such as when on business travel.

Before there was bleisure travel, there was the city break—the short space of leisure time that grants you access to the cultural and culinary amenities that big cities offer. In this series from TripIt, we explore some of the world’s best cities for planning a quick getaway or extending a work trip. 

Here are our tips for making the most of your city break in Manhattan.

Where to fly in

The New York metro area is served by three major airports: John F. Kennedy International Airport (JFK), Newark Liberty International Airport (EWR), and LaGuardia International Airport (LGA). When determining which airport is the best to fly into, you should consider two factors: flight price, final destination in the city, and ground transportation options. 

As for your ground transportation options, cabs and ride shares are available upon arrival at all airports, but they also incur the highest cost—especially from JFK and EWR. As an alternative from JFK, you can take the AirTrain, which runs 24 hours a day, to the subway. Depending on your final destination, you can catch the A, E, J and Z trains. From EWR, you can take the AirTrain and transfer to New Jersey Transit’s Northeast Corridor or North Jersey Coast Line trains at Newark Penn Station. Visit NJ Transit’s site for more detailed information. Finally, from LGA, your public transportation options are limited to bus routes. Grabbing a cab or a ride share is often your most convenient and time-saving option to the city.

Where to stay during your city break

city break Manhattan

Despite being dubbed “The City That Never Sleeps,” Manhattan alone offers more than 450 hotels from which to choose. 

With so many iconic and unique hotels to choose from, it can be both challenging and exciting to pick where to stay. Here are a few to consider:

  • Looking for a boutique hotel? After finding success in Chicago, Miami, and LA, the trendy Freehand Hotel New York calls the Flatiron neighborhood home. Then, you’re just walking distance to the area’s iconic sites and dining destinations (more on where to eat, below).
  • If a hotel in a prime Manhattan location is what you’re after, look no further than the Hotel Sofitel New York. Conveniently located in Midtown West, the Sofitel is walking distance to Rockefeller Center. After work, you’re just a block from the designer stores on Fifth Avenue and the Theater District.
  • The Bentley Hotel is an ideal spot if you’re attending an event at Guastavino’s but want to avoid Manhattan’s busier neighborhoods. From the hotel, you can easily walk to Midtown or hop in a cab to take the FDR elsewhere.

How to get around

city break

Getting around the city requires prioritizing two of the following: time, money, or convenience. Taking the subway, for example, is your least expensive option. You can pay one MetroCard swipe and traverse all five boroughs. While taking the subway is often faster than grabbing a cab to your destination (when traffic is considered), this is not always the case. Track fires, sick passengers, and other unforeseen events all delay train travel. But you’ll definitely spend the least amount of money, if that’s a priority to you.

Your MetroCard also gives you access to the city’s bus system. However, while buses sometimes run more frequently up and down the avenues, throw time out the window. Even with dedicated lanes, buses are probably your slowest option for getting around.

Also available above ground: the iconic Yellow Cab. Hail one, call out your cross-streets to the driver, and away you go. Grabbing a cab is typically convenient, but cost can greatly fluctuate based on your destination—especially if you’re heading to or from the airport, or incurring tolls by traveling over bridges or through tunnels. Ride shares like Uber, Lyft, and Via are also available throughout the five boroughs and to all the major airports. 

Pro tip: Use TripIt’s Navigator feature to search transportation options available to you. It will show you the estimated costs and travel times for each option, so you can decide which works best. You can find Navigator within your flight, hotel and rental car details screens. Plus, if you add a restaurant reservation to your itinerary (more on where to eat later), Navigator also helps you find the best transportation options for getting to your table.

Convenience aside, let’s talk about the cost of riding in a cab versus a ride share. Considering factors such as your starting location and final destination, time of day, traffic, demand for rides (hello, surge pricing), and other factors—Uber is typically cheaper when traveling long distances, like from your Manhattan hotel to JFK airport. Meanwhile, on shorter trips through congested streets, a taxi is often the more economical choice.

Finally, you might want to consider Citi Bike, NYC’s official bike-share program. Riders can access bikes in the Lyft or Citi Bike apps. Single rides in the app start at $3.99/trip. Lime bikes and electric scooters are also available to help you get around on two wheels.

Where to eat

city break Manhattan

From street carts to Michelin stars, Manhattan has it all. For a quick bite, head to Urbanspace—a food hall with rotating concepts and a variety of cuisine options to choose from. There are two permanent locations: Urbanspace @ 570 Lex in Midtown East and Urbanspace @ Vanderbilt, located just north of Grand Central Station. Other seasonal locations pop up throughout the year as well, so check out their website to see if any coincide with your travel dates.

Craving Italian? Maybe some wine and cheese? Head to perennial favorite Eataly—now with two NYC locations, Eataly Flatiron and Eataly Downtown.

If you’re after a ramen fix, you’ve come to the right city—this side of the Pacific, that is. Take your pick from authentic to fusion at popular spots like Ivan Ramen, Ippudo, Nakamura, Totto Ramen and more.

And finally, let’s talk pizza. Keeping with a home base of Manhattan, here are some of the best places to grab a New York slice: Joe’s Pizza, Prince Street Pizza, and Rubirosa. Of course if you want to venture further afield to say, Brooklyn for Di Fara, or to Staten Island for Joe & Pat’s, we would not blame you. (Also, can you bring us back a slice?)

What to do on your city break

city break Manhattan

After last night’s pizza-crawl, you may want to start your day with a workout. Good news—you have plenty of options in Manhattan. 

Runners, head to Central Park for a six-mile loop of car-free running. Make sure to stay in the pedestrian lane and keep a careful eye out for those tourists biking out of their dedicated lane, too. Runners can also head to the West Side Highway for an uninterrupted trail along the Hudson River. 

If you prefer a studio workout, an app like ClassPass can orient you to all of the indoor running, spin, yoga, HIIT, Crossfit, etc. classes available in your neighborhood and across the city.

The city’s green spaces also offer an ideal place to host a walk-and-talk meeting, people-watch, or catch a free class or performance. Many of Manhattan’s parks, like Bryant Park, Madison Square Park, Union Square Park, and Washington Square Park, host free events throughout the year. Plus, you’ll almost always be treated to an unorganized event, too, like a busking musician or a friendly game of chess. If you have some downtime, pass through a park in your neighborhood and soak in the essence of everyday New Yorkers just doing their thing.

If you catch a rainy day, head to one of the city’s world-class museums. The Metropolitan Museum of Art and the Guggenheim Museum are located on the Upper East Side—just a few minutes’ walk away from one another, too. There’s also the Museum of Modern Art in Midtown, the Whitney in the Meatpacking district, and the American Museum of Natural History on the Upper West Side. Lesser-known museums worth a visit include the Tenement Museum, the Museum of the City of New York, and El Museo del Barrio—just to name a few.

Rain or shine, be sure to also pay a visit to the iconic (and independent) Strand Bookstore—the last of the surviving bookstores in what was formerly known as “Book Row” along Fourth Avenue. The Strand boasts 18 miles of new, used, and rare books. Pop in to pick up that personal development book you’ve been meaning to read or grab a leisure read—both for a fraction of the price of a last-minute purchase at the airport.

Note: As cities reopen around the world, be sure to consult and adhere to all local guidelines and travel restrictions, as they vary widely and will continue to change. One way to stay on top of changing guidelines is to consult the COVID-19 travel guidance feature in the TripIt app for destination-specific information, including current infection rates, quarantine rules upon arrival, testing requirements, and other information you need to know before visiting the area.