A Multigenerational Tour of Manhattan: 5 Days in NYC

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Advisor - Sara Shelley
Curated By

Sara Shelley

  • Family Travel

  • Accessible Travel

  • City Travel

  • New York City

  • Downtown

Advisor - A Multigenerational Tour of Manhattan: 5 Days in NYC
Curator’s statement

New York City is one of my favorite cities on this planet, and I had the opportunity recently to take my family to the city. My stepson and mom came with us, so there were many different tastes and needs to accommodate on this trip. My stepson has a communication disorder, and my mom recently had her hip replaced, so with this in mind, I was able to plan a trip with activities that all were able to enjoy and that met everyone’s needs.

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Day 1: Arrive in NYC & explore Times Square

Times Square, Manhattan

Day one was primarily a travel day, so we opted to stay in Midtown for its proximity to many classic NYC attractions. The Dream Hotel NYC offered the perfect location—just outside the chaos of Times Square but close enough to walk.

After taking in the energy of Times Square for the experience, we strolled over to Angelo’s Pizza, near the Ed Sullivan Theater. The pizza was excellent, and the location gave us a break from the crowds—plus, we’ve never had trouble getting a table.

Day 2: Take in NYC's sights by cruise

View of The Battery from our tour boat

Day two was packed with activities! Since one member of our group was visiting NYC for the first time, we wanted to fit in plenty of sightseeing, while still being mindful of how much walking we could manage. Enter Circle Line Cruises and their 2.5-hour “Best of NYC” tour. It was the perfect solution. We circled the entire island of Manhattan by boat and took in all the iconic sights we hoped to see—effortlessly. A perfect way to experience the city!

Day 3: Join an architecture tour & catch a Broadway show

Lena Horne Theater in Manhattan

Day three was all about historic landmarks and Broadway magic. For architecture lovers, the Walks Tour of Grand Central Terminal is a must—offering exclusive access to behind-the-scenes areas and fascinating insights into the history of this iconic space.

Later, we took in a Broadway show and saw the pop phenomenon Six. At just 80 minutes, it’s an energetic, fast-paced performance that’s perfect for all ages, including those with sensory sensitivities.

Day 4: Visit the Empire State Building

Views from the top of the Empire State Building

Day four brought us to the iconic Empire State Building, followed by a bit of shopping at Macy’s in Herald Square.

After several days of nonstop sightseeing, we took a much-needed afternoon break to rest and recharge.

That evening, we honored a special request from my stepson and dined at the original Benihana—a fun and memorable way to wrap up the day.

Day 5: Travel home

Day five was our travel day home, so while there wasn’t time for additional activities, I wanted to share a few of our favorite restaurant finds from the trip.

For a classic NYC breakfast, Applejack Diner delivers that authentic New York diner vibe. Dutch Fred’s quickly became my go-to spot for creative cocktails in Hell’s Kitchen. And for a cozy evening of pasta and wine, Gnoccheria in the East Village was a standout—absolutely delicious and worth the visit.

Need to know

Be sure to pack your walking shoes and your sense of adventure whenever you visit Manhattan. One thing I was thrilled to see was that the subway now takes contactless payment, so as long as you have a credit card stored on your phone, you can easily get on the subway without a ticket.

Advisor - Sara Shelley

Travel Advisor

Sara Shelley

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