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Historic Northeast Cities (Philadelphia - New York City - Boston - Portland)

10 to 15+ Nights from $1,995*
* Sample price: priced within the past 7 days for a 9/14/2025 arrival, departing Miami MIA (FL), US. Choose departure city, cabin and dates.

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Add Outbound & Return Flights

This 10 night sample itinerary includes:

  • Flight into Philadelphia and out of Portland
  • Hotel for 3 nights in Philadelphia
  • Train from Philadelphia to New York City
  • Hotel for 3 nights in New York City
  • Train from New York City to Boston
  • Hotel for 2 nights in Boston
  • Train from Boston to Portland
  • Hotel for 2 nights in Portland

    Sample of Included Tours:
  • 911 Memorial and Statue of Liberty Combo in New York City
  • Gilded Age Mansions Tour in New York City
  • Freedom Trail Walking 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.

Discover the endless wonders, treasures and History of these Northeast Cities!. Start in Philadelphia (notable for its rich history, where the Declaration of Independence and Constitution were signed) after that, is New York City (one of the world's largest entertainment and culture capitals) where enjoy Guided Tours to New York 911 Memorial, Statue of Liberty and Age Mansions. Next, in Boston (home of the Boston Red Soxs and New England Patriots and famous for the Boston Tea Party) have a Freedom Trail Walking Tour. Lastly, have a pleasant stay in Portland (small vibrant city with narrow cobblestone streets and redbrick warehouse buildings).

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

  • Philadelphia, PA

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  • New York City, NY

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  • Boston, MA

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  • Portland, ME

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USA

Customer Reviews

Trip Summary

  • Philadelphia, PA
    Philadelphia, PA

    Philadelphia,`The City of Brotherly Love`, is one of the most historic cities in the U.S. It houses Independence Hall, where the country was born, and the Liberty Bell, commemorating its principles. It's a lively and modern city situated on the Delaware River, with skyscrapers rising above green areas and old residential neighborhoods. Also iconic are the steps of the Philadelphia Museum of Art, immortalized by Sylvester Stallone’s triumphant run in ``Rocky``, one of the greatest sports movies ever made.

    Explore the Liberty Bell, Philadelphia Museum of Art, Independence National Historical Park, Barnes Foundation, Philadelphia Zoo, Reading Terminal Market and much more.

  • 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!

  • Portland, ME
    Portland, ME

    Portland is set on a peninsula extending into Casco Bay. This charming city will enchant you from ornate mansions to ocean views. Visit the Portland Head Light, which dates back to 1791, and is the oldest lighthouse still in continuous use in the U.S. The Old Port district is known for its 19th-century architecture and nightlife.

    Explore The Portland Head Lighthouse, the Old Port, the Fort Williams Park, the Portland Museum of Art, the Casco Bay, the Peaks Island, the Victoria Mansion, the Portland Observatory and so much more!

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