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NYC in Summertime: How to Spend 5 Days

Updated: Aug 12

NYC birds eye street intersection

Looking for beach alternatives this summer? New York City is a great place to visit, with so much to do and see. You’ll find yourself planning return visits before you’ve left for home. One of the best parts of visiting the city is that it stays the same just as much as it evolves, meaning there are classics to revisit and new things to do all the time.

Below are a few ideas and recommendations to get you started on a beautiful trip to the big apple!

Trip Expectations:

The first time I visited the city from suburban America, I was exhausted without having done a thing. Something not often talked about is the sensory overload you can experience on your first day or two in the city. The din of sounds from traffic and the buzz of more than 26,000 people per square mile can overwhelm the senses, but then that’s also part of the notorious and intrinsic energy of New York City.

NYC Summer Packing List:

One of my favorite things about going to New York is the stylistic freedom. There are so many unique styles and people visiting every day from all over the world that you’re bound to see a lot of different looks.

So, pack comfortably for the days sightseeing, and maybe a few nice outfits for going out to dinner or shows, but really anything goes. If you’re ever in doubt, check the places you’re planning to visit that day for any notes about the dress code. Even in fine-dining restaurants, attire hardly seems to matter these days.

My other recommendation would be to dress in layers. It will be hot walking around the city, but the AC is sure to be cranked inside. Having a light jacket or sweater will keep you from getting too chilled. With that being said, make sure to plan outfits for each day with a few extra pieces as it might be challenging to re-ware any items.

Finally, choose your accessories wisely. You are in the city, after all. It’s not to say that New York City is a horribly dangerous place. It's about keeping the odds in your favor and being conscious of the fact that you’re in unfamiliar territory.

Pick comfortable shoes and purses that are not easily swiped. It would also be wise to keep your jewelry on the modest side. Not just for fear of thieves but the chance of knocking off an earring getting in or out of a cab, or breaking a necklace caught while taking off a jacket or purse.

What to do:

Five days might feel like a long time when you're working your 9-5, but in NYC, time has a way of flying by. There is so much to do that filling your days will be the least of your concerns. Below are some favorite options to consider.

Live Shows:

NYC Broadway Theater

On Broadway, Off-Broadway, and so much more. Getting tickets to shows is probably one of the first things you should do when planning a trip to the city. Shows can sometimes sell out years in advance, so knowing you have secured tickets to that one show you’ve been wanting to see will really set the tone for the rest of your planning.

Don’t forget about the Lincoln Center or the Metropolitan Opera House for additional performances. Summertime also brings all types of outdoor concerts in Central, Bryant, and other parks around the city, so make sure to check those out too.

Or maybe you need a good laugh and would enjoy sitting in the audience for an episode of your favorite late-night show. If you thought the competition for Broadway tickets was tough, you may be surprised to hear that some coveted late-night shows like Saturday Night Live don’t even sell tickets. In order to score a pair, you have to win them through a lottery process. But what an incredible experience if you’re able to win tickets!

Whatever type of cultural experience you decide on, it’s going to be incredible.

NYC Museums:

The MET, the MoMA, the Guggenheim, Natural History, and so much more. Though slightly less competitive than some of the performance arts, demand for entry can get crowded at times, so double-check if there are advanced tickets to purchase before visiting. Purchasing advanced tickets for special exhibits is almost always required, as many have timed entries.

Pro Tip:

Though many people don’t enjoy the planning aspect of travel, I think it can be quite freeing. When everything is set, it’s much easier to be present and enjoy the action at hand. So don’t worry if you’re feeling a little boxed in. Try scaling back the number of activities you have planned, and remember, once the planning is over, the fun can start.

Talking with friends and family during the weeks leading up to the trip is all part of the travel fun. You’ll get so many additional ideas and tips from them that will continue to build your excitement for the trip.

Sightseeing Around NYC:

The list goes on and on. There is so much to see all over the city that it's really best to group your activities by district. This way, you can walk from one attraction to the next. Though it saves a lot of time and energy to use public transport, walking around the city is a great way to really take in the sights and get a sense of the different neighborhoods.

From walking through Little Italy and Chinatown to the Upper East Side, or hitting the High Line for a break from traffic. There is so much to see that makes New York City unique, and doesn’t cost a thing. Below are the big highlights that may or may not already be on your list of to-dos. Get that camera and insta-worthy fit ready.

NYC Radio City Music Hall
  • Statue of Liberty

  • Wallstreet Bull

  • Brooklyn Bridge

  • World Trade Center Memorial Site

  • Central Park

  • Time Square

  • The New York Public Library

  • Central Station

  • Bryant Park

  • Rockefeller Center

  • Radio City Music Hall

  • The Chrysler Building

  • The Flatiron Building


Though I love to shop, Big City shopping isn’t typically my thing. Unless I know of a few specialty boutiques or stores that aren’t accessible locally, I find it overwhelming. You’ve got to love the hunt and the act of looking, whether that be at vintage shops, boutiques, or Flagship Retail stores.

The stores in NYC for typical brands can sometimes be the size of a mall themselves. You could spend hours in the Zara flagship store, not to mention the flagship department stores like Macy’s or Bloomingdales.

NYC evening view of Chrysler Building

Spending a whole day in one store could be great, but you might also be spending a whole day in a shop you could visit online from home. So, it’s a bit of a trade-off and a matter of priority, I suppose.

If you’re looking for some exciting finds, check out the Nolita District near SoHo and the Chelsea neighborhood. Though the city is bubbling over with unique things, it’s also huge.

So don’t expect to just stumble upon amazing things constantly. You could literally be around the corner, or a block away from an incredible store and not even know it. Finding out after the fact is always a bummer, but also a new reason to revisit.

Special Experiences:

Picnic in Central Park

NYC skyline from Central Park

I can hardly think of a more enjoyable way to spend a sunny summer afternoon than picnicking somewhere in Central Park.

You can either pick up your picnic goods on your way, have a basket prepared for you in advance or make it a luxury experience where all you have to do is show up!

Check out Perfect Picnic or Al Fresco Picnics for options ranging from affordable to indulgent.

Take a Peloton Class

I bet if you’re a fan, it’s already somewhere on your list of to-do’s. What a great way to have a fun experience and stay active on vacation. From their landmark cycling classes to yoga, running, strength, and more. There is a variety of different disciplines to experience live while in the city.

At the time of publishing, classes are booking out a month in advance. However, it's worth checking back closer to for any cancelations or waitlist opportunities.

Book your Peloton Studio Experience here

NYC Farmers Market Flowers

Hit a Farmer’s Market

Of course, Union Square Greenmarket is the quintessential NYC farmers market, but I also love the Tucker Square market a block off Central Park on the upper west side. If you’re planning your picnic for a weekend day, you could build your picnic at the farmers market and head right over.

For a complete list of markets around the city and Burroughs, check here.

Where to Stay:

Depends on the type of trip, what your priorities are, and if you feel comfortable using public transportation.

NYC Skyscrapers

Hopefully, you’ve got your tickets in hand and a rough idea of your remaining priorities while you’re in the city. At this point, lodging will come down to two things, the remaining budget, and commute.

Are most of your activities centered around the theater district? Finding a place between midtown and the upper west side will make an excellent base for an easy walk to most of your activities. Then you could use taxis or subways to get to other parts of town.

If you don’t mind commuting and want to save some money, you could look at staying outside the city in either New Jersey or one of the Burrows and taking the subway or ferry into the city for various activities.

When Booking your Lodging, Always Remember To:

Look for deals through your credit cards and consider renting an apartment or condo for your real city experience. Sometimes these can be more affordable than hotels depending on the area of town.

If you’re flying, some airlines have flight and hotel deals that can be very reasonable. Make sure to check these out too.

Below we have a brief summary of a few main parts of town so you can ensure you’re well-rested for each packed day of activity.

Midtown Manhattan:

NYC at night: Midtown

This bustling neighborhood is home to iconic landmarks such as Times Square, Rockefeller Center, and the Empire State Building.

It's known for its vibrant energy, numerous Broadway theaters, and high-end shopping on Fifth Avenue.

Lodging options in Midtown Manhattan range from luxury hotels like The Plaza and The Peninsula to more affordable options like boutique hotels and chain accommodations.

Upper East Side:

This upscale residential area is known for its elegant townhouses, luxurious boutiques, and the renowned Museum Mile, featuring prestigious institutions such as the Metropolitan Museum of Art and the Guggenheim Museum. The Upper East Side offers a mix of upscale hotels like The Mark and The Carlyle, as well as a few mid-range options.

NYC Central Park Upper West Side Skyline

Upper West Side:

Located west of Central Park, the Upper West Side is characterized by its leafy streets, charming brownstones, and cultural institutions like the Lincoln Center. This family-friendly neighborhood offers a range of lodging options, including boutique hotels, bed and breakfasts, and some larger chain hotels.

Greenwich Village:

Known for its bohemian atmosphere and historic charm, Greenwich Village is a neighborhood with tree-lined streets, historic townhouses, and an eclectic mix of restaurants, bars, and independent shops. Lodging options here are mostly boutique hotels, inns, and guesthouses that capture the neighborhood's unique character.

NYC Fountain


Short for "South of Houston Street," SoHo is famous for its cast-iron architecture, art galleries, high-end boutiques, and trendy dining scene.

The neighborhood offers a variety of accommodations, including boutique hotels and stylish loft-style apartments that cater to the artistic and fashion-forward crowd.


Located on Manhattan’s west side is a vibrant neighborhood known for its thriving art scene, trendy restaurants, and architectural charm. It offers a diverse range of lodging options to suit different preferences and budgets. Visitors can choose from boutique hotels with stylish designs and personalized service, as well as larger chain hotels offering modern amenities, all within easy reach of Chelsea's art galleries, dining establishments, and shopping opportunities. Don’t forget to hit the high line for a beautiful stroll above the city streets.

NYC Charging Wall Street Bull

Lower Manhattan/

Financial District:

The southernmost tip of Manhattan is home to the Financial District, where Wall Street and the iconic Charging Bull sculpture can be found.

This area also includes the poignant 9/11 Memorial and One World Trade Center. Accommodations in the Financial District range from business-oriented hotels to stylish boutique establishments.


Located in the northern part of Manhattan, Harlem is renowned for its rich African American cultural heritage, historic jazz clubs, and the Apollo Theater. Accommodations in Harlem include a mix of bed and breakfasts, budget hotels, and a few boutique hotels.

These are just a few examples of the diverse neighborhoods in Manhattan, each with its own unique characteristics and lodging options. When considering accommodations, it's essential to research specific hotels, read reviews, and consider factors like location, amenities, and budget to find the best fit for your stay.

Bon Voyage

If there is anything we love as much as visiting NYC, it's sharing the experience with others. Did you find some helpful tips here or take ideas for your next trip? We sure hope so! But with so much to do and see, we would love to hear from you too. Share your favorite insights for visiting the Big City below or message us on IG at for a chance to have your tip featured in future article updates.

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