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.

Looking to gift a tour this holiday season? buy one of our gift cards so your loved ones can choose their own adventure!

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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

Deck the Halls of Hammond Castle Museum: Self-Guided Exploration from Boston

From$72

Upcoming Availability:
Sunday, Nov 16th
Friday, Nov 28th
Saturday, Nov 29
Sunday, Nov 30th
Saturday, Dec 6th
Sunday, Dec 7th
Sunday, Dec 14th
Saturday, Dec 20th

Nestled on a bluff overlooking the Atlantic Ocean explore the enchanting European-style Hammond Castle Museum decked out for the holidays at your own pace with a self-guided tour through its stunning galleries and beautiful holiday decor.

(4 Reviews)

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Guided Nature Walk Through the Dunes of Castle Neck Beach

From$75

Upcoming Availability:
Sunday Nov 16th
Friday, Nov 28th
Sunday, Nov 30th
Sunday, Dec 7th
Sunday, Dec 14th

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

From$78

Upcoming Availability:
Saturday, Nov 29th

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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From Hive to Glass: Local Meadery Tour & Wine Tasting

From$72

Upcoming Availability:
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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Christmas at Castle Hill on the Crane Estate

From$78

Upcoming Availability:
Sunday, Nov 16th
Saturday, Dec 6th
Sunday, Dec 7th
Sunday Dec 14th
Saturday, Dec 20th

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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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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