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New York City and Boston for Outdoor Enthusiasts

6 to 9+ Nights from $674*
* Sample price: priced within the past 7 days for a 1/6/2026 arrival, departing Miami MIA (FL), US. Choose departure city, cabin and dates.

Customize and Book

Add Outbound & Return Flights

This 6 night sample itinerary includes:

  • Flight into New York City and out of Boston
  • Hotel for 3 nights in New York City
  • Flight from New York City to Boston
  • Hotel for 3 nights in Boston

    Sample of Included Tours:
  • Central Park Guided Bike Tour in New York City
  • Sightseeing Cruise Experience in New York City
  • Freedom Trail Walking Experience in Boston
  • Harbor Cruise Experience in Boston

    Your price will only include confirmed available tours; some tours may collect for entrance fees or attraction tickets on site. If an included tour becomes unavailable, alternate options may be available at an additional cost.

New York and Massachusetts favorite cities to enjoy outdoors!. Bike through Central Park and see the epic skylines of New York City (one of the world's largest entertainment and culture capitals, with stunning urban views) and Boston (home of the Boston Red Soxs and New England Patriots) by boat. If you want to do more than just meander around town, this might be a great vacation package for you to try!.

What Makes Tripmasters Vacation Packages Different?
Unique, fully custom approach to vacation planning
Choose your preferred flight cabin class
Select up to 14 nights in each city during your stay
Pick from a wide selection of accommodation types (hotels, apartments, B&Bs, Guesthouses, and more)
Add transfers, activities and experiences, and more services to enhance your vacation
Live phone and chat support

Flexible Itinerary

  • New York City, NY

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  • Boston, MA

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USA

Customer Reviews

Trip Summary

  • New York City, NY
    New York City, NY

    New York City, the Big Apple, is the USA's largest city. Founded as New Amsterdam, the capital of New Netherland, it became the most important city in the English colonies, and the USA`s first capital. New York City is the world capital of finance, media, and culture, and is perhaps the world`s most diverse city, where over 800 languages are spoken. There are so many layers to the city that never sleeps...you'll have to come back again and again to experience all of them.

    Visit and vibe with the Central Park, Statue of Liberty, Empire State Building, Times Square, Museum of Modern Art (MoMA), Metropolitan Museum of Art, Brooklyn Bridge, Rockefeller Center, The High Line, Grand Central Station, One World Trade Center, Fifth Avenue, Broadway, and so much more!

  • Boston, MA
    Boston, MA

    Whether you are looking to take in the skyline or enjoy art, visit a museum or spend the day getting pampered, you will find what you want in Boston. Laced with parks, and pathways you can easily take in the skyline, while enjoying walking the Greenway, Harborwalk, Esplanade or Freedom Trail.

    Explore The Freedom Trail, the Museum of Fine Arts, the Faneuil Hall Marketplace, the Boston Tea Party Ships & Museums, the Boston Public Garden and so much more!

  • You can now

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