All of Our Fun Day Trips Near Boston

How Our Tours Work:

Each tour includes a Weekend Commuter Rail Pass, private transportation to and from the train station, and a uniquely curated experience. After booking, you’ll receive step-by-step instructions on which train to take and everything you need to know. To learn more about how our tours work, visit the HOW IT WORKS page.

What’s stopping you from planning your next epic day trip from Boston? We can’t wait to welcome you on tour!

Explore Our Adventures from Boston

Guest of the Cranes Guided Tour of Castle Hill on the Crane Estate

From$78

Upcoming Availability:
Saturday, Oct 25th
Sunday, Nov 9th
Saturday, Nov 15th
Saturday, Dec 6th ( Holiday Tour)

Visit Castle Hill at the Crane Estate and experience the grandeur of a seaside estate, its marvelously landscaped grounds, restored Grand Allée, gardens, and Casino complex.

(4 Reviews)

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A Day at Louisa May Alcott’s Orchard House

From$69

Upcoming Availability:
Sunday, Oct 26th
Sunday, Nov 9th

Step into the world of “Little Women” with a guided tour of Louisa May Alcott’s Orchard House! Includes round-trip rail, private shuttle, and time to explore historic Concord. Perfect for fans of history, literature, and adventure!

(1 Review)

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Explore New England: Exclusive Cranberry Farm Tour

From$75

Upcoming Availability:

Saturday, November 8th

Discover the magic of cranberry farming at Benson’s Pond in Middleboro, MA! Join our guided walking tour of a third-generation family-owned farm.

(4 Reviews)

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Historic Guided Walking Tour Featuring the North Bridge in Concord, MA

From$55

Upcoming Availability:
Sunday, Oct 26th
Sunday, Nov 9th

Step back in time on our North Bridge & Beyond Walking Tour! Explore the site of the “shot heard ’round the world,” see the Minute Man Statue, and an exclusive visit to historic Wright Tavern. Walk in the footsteps of revolutionaries!

(3 Reviews)

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Castle Hill Uncovered: Guided Nature Walk of Hidden Shores, Gardens & Trails

From$78

Upcoming Availability:
Saturday, Oct 25th ( Fall Foliage!)
Saturday Nov 15th ( Fall Foliage!)

Discover the hidden gems of Castle Hill! Enjoy stunning views from the Grand Allée, explore the peaceful Steep Hill Beach, hike through scenic dunes, and visit the newly restored gardens. This hike has it all!

(1 Review)

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Explore New Bedford: Food Tour & Whaling Museum Experience

From$165

Upcoming Availability:
Saturday, Nov 8th

Discover New Bedford’s rich history and flavors on this full-day trip! Enjoy a diverse food experience with local eats, explore the renowned Whaling Museum, and stroll through historic downtown. Includes round-trip transportation from the Commuter Rail.

(2 Reviews)

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Guided Nature Walk Through the Dunes of Castle Neck Beach

From$75

Upcoming Availability:
Sunday Nov 2nd
Sunday Nov 9th
Sunday Nov 16th

While just about everybody on the North Shore has probably been to Crane Beach, the dunes of Castle Neck are a much less explored world unto themselves. Offering one of the most accessible dune ecosystems north of Cape Cod, Castle Neck has.

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Traveler Favorite!

Day Trip from Boston: Explore The New England Botanic Gardens at Tower Hill

From$75

Upcoming Availability:
Sunday, Oct 12th 2025
Monday, Oct 13th 2025

Experience the New England Botanic Gardens and enjoy the beauty of floral blooms on a self-guided tour. Take your time exploring the gardens at your own pace, all while enjoying a scenic, all-inclusive day trip from Boston.

(5 Reviews)

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Day Trip from Boston: Self-Guided Tour of Hammond Castle Museum

From$72

Upcoming Availability:
Sunday, Nov 2nd

Nestled on a bluff overlooking the Atlantic Ocean explore the enchanting European-style Hammond Castle Museum at your own pace with a self-guided tour through its stunning galleries.

(4 Reviews)

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Hidden History at The Fruitlands: Utopian Dreams & Timeless Art

From$69

Uncover New England’s hidden past at Fruitlands Museum—a scenic hilltop retreat blending utopian dreams, Shaker heritage, Native American culture, and American art. Explore historic exhibits, tranquil trails, and breathtaking views on this self-guided day trip from Boston. Weekend Commuter Rail Pass and shuttle from the Ayer Station included.

(1 Review)

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From Hive to Glass: Local Meadery Tour & Wine Tasting

From$72

Upcoming Availability:
Saturday, Nov 8th 2025
Saturday, Dec 13th 2025

Discover Honeybound Meadery in Tyngsboro! Tour The Colony, explore mead-making, and enjoy tastings paired with charcuterie. Includes $10 weekend rail pass + private transport. Sip tradition, savor flavor—no car needed!

(2 Reviews)

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