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

Day Trip from Boston: Kayak Castle Neck River at Crane Estate

From$115

Upcoming Departures:
Sunday, June 1st 2025
Saturday, June 7th 2025
Sunday, June 22nd 2025

Experience the beauty of MA's North Shore with a guided kayak tour through the waters of the Great Marsh. Explore the Castle Neck River & discover the diverse wildlife of New England’s largest salt marsh.

(1 Review)

Baker Island Boat & Lighthouse Tour in Salem

From$98

Upcoming Availability:
Sunday, June 22nd 2025
Sunday, July 20th 2025

Escape the city and set sail for a one-of-a-kind coastal adventure! This guided tour takes you from Boston to Salem by train, followed by a scenic boat ride to the historic Bakers Island Lighthouse, a hidden gem in Massachusetts Bay.

Kayak & Hike Adventure to Historic Thacher Island

From$130

Upcoming Availability:
Saturday, May 31st 2025
Saturday, June 21st 2025
Saturday, June 28th 2025

Paddle 2.5 miles to Thacher Island for an unforgettable adventure! Explore scenic trails, historic twin lighthouses, and vibrant bird habitats. Discover the life of a lightkeeper while soaking in stunning coastal views.

Crane Estate

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

From$78

Upcoming Availability:
Sunday, May 25th 2025
Monday, May 26th 2025
Saturday, June 7th 2025

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.

(1 Review)

Hammond Castle exterior view

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

From$72

Upcoming Availability:
Saturday, May 31st 2025
Sunday, June 1st 2025
Sunday, June 8th 2025

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.

(2 Reviews)

SPECIAL EVENT *Early Bird Pricing through 7/6*

Special Event Shuttle & Meal Voucher: New Bedford Feast of the Blessed Sacrament August 2-3 2025

From$40

Feast Dates:
Saturday, August 2nd 2025
Sunday, August 3rd 2025

Skip the traffic and ride in comfort to the largest Portuguese festival in New England! Our Special Event Shuttle includes a Weekend Commuter Rail Pass, shuttle service, and a $20 Food & Beverage voucher — no parking hassles, no stress. Just book, ride, and feast! **Early bird pricing available through July 6, 2025!**

A Day at Louisa May Alcott’s Orchard House

From$73

Upcoming Availability:
Saturday, June 7th 2025
Sunday, June 8th 2025
Saturday, June 21st 2025

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)

Hidden History at The Fruitlands: Utopian Dreams & Timeless Art

From$72

Upcoming Availability:
Saturday, May 24th 2025
Monday, May 26th 2025
Saturday, June 7th 2025

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.

Exclusive Guided North Bridge Walking Tour in Concord, MA

From$72

Upcoming Availability:
Sunday, June 22nd 2025
Saturday, July 19th 2025

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!

(1 Review)

Lights, Camera, Castle Hill: A Hollywood & History Tour

From$85

Upcoming Availability:
Saturday, June 14th 2025
Saturday, July 12th 2025
Saturday, August 9th 2025

Step onto the grand estate where Hollywood magic and history collide! This exclusive tour takes you through Castle Hill at the Crane Estate, the breathtaking filming location of the acclaimed 2019 movie Little Women.

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

From$78

Upcoming Availability:
Saturday, May 31st 2025
Sunday, June 15th 2025
Sunday, June 29th 2025

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)

Rockport Guided Coastal Kayak or Stand-Up Paddleboarding Excursion

From$108

Upcoming Availability:
Sunday, June 15th 2025
Saturday, June 28th 2025
Saturday, July 5th 2025

Paddle through the scenic shores of Rockport on a guided coastal kayak or SUP adventure! Perfect for all skill levels, this tour offers stunning ocean views, local wildlife, and expert instruction. A refreshing, unforgettable New England experience—Book now!

Gloucester Harbor & Annisquam River Kayak Tour

From$120

Upcoming Availability:
Sunday, June 8th 2025
Saturday, June 14th 2025
Saturday, July 5th 2025

Paddle through Gloucester Harbor and, tide permitting, the serene Annisquam River on this guided kayak tour. Discover sea glass on Ten Pound Island, spot Wicked Tuna boats, and enjoy skyline views from Dog Bar. Weekend Commuter Rail Pass and shuttle from the Gloucester Station.

Traveler Favorite!

Explore The New England Botanic Garden at Tower Hill from Boston

From$75

Upcoming Availability:
Sunday, June 8th 2025
Saturday, July 19th 2025

Experience the New England Botanic Gardens and enjoy the beauty of spring 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.

(2 Reviews)

Explore New Bedford: Food Tour & Whaling Museum Experience

From$185

Upcoming Availability:
Saturday, June 7th 2025
Saturday, July 19th 2025
Saturday, August 16th 2025

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.

Trillium VIP Brewery/Distillery Tour & Tasting

From$75

Upcoming Availability:
Sunday, June 15th 2025

Discover Trillium Brewing on an exclusive tour! Explore their history, craft, and innovation with a behind-the-scenes look at brewing and distilling. Enjoy guided tastings of their finest creations.

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