All of Our Fun Day Trips Near Boston

All of our Boston area tours and activities below are in partnership with local businesses and guides. Support the local tourism industry by getting out of Boston and discovering everything Massachusetts has to offer!

Want to learn more? Read How It Works and please get in touch if you have any questions. Otherwise, what’s stopping you from planning your next fun day trip from Boston?

Explore Our Sightseeing Tours From Boston

Trillium VIP Brewery/Distillery Tour & Tasting

From$105
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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A Day at Louisa May Alcott’s Orchard House

From$65
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!
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Guided Maple Syrup Making Experience

From$72
Join us at Natick Community Farm for a maple sugaring adventure! Learn to identify trees, explore Native and Colonial sugaring methods, watch sap boil into syrup, and grab fresh syrup and produce at the farm shack!
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From Hive to Glass: Local Meadery Tour & Wine Tasting

From$69
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!
(1 Review)
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White owl in the snow
Seasonal Tour | Currently Unavailable

Crane Beach Snowy Owl Trek: A Coastal Wildlife Adventure

From$75
Join us for a 4-mile trek through Castle Neck’s dunes, maritime forest, and coastal trails in search of Snowy Owls. Explore diverse ecosystems, spot wildlife, and enjoy stunning views in this unique winter adventure!
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Hidden Gems of Castle Hill: Hike the Seashores, Gardens, and Scenic Trails

From$65
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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Guided Wildlife Nature Walk at the Dunes of Castle Neck Beach

From$75
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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Hammond Castle exterior view
Seasonal | Tours begin April 2025

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

From$64
Deck the halls Holiday Event Nov 14- Dec 29! 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)
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Winter Castle Hills exterior covered in snow
Seasonal | Tours begin April 2025

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

From$75
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)
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Explore The New England Botanic Garden at Tower Hill from Boston

From$70
A botanical adventure awaits you at the top-rated New England Botanic Garden at Tower Hill! Join our self-guided tour for a captivating journey through lush flora. Then, unwind at our charming coffee shop amidst nature's tranquility and explore on your own.
(1 Review)
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Seasonal Tour | Currently Unavailable

Classic New England Oyster Farm Tour & Tasting

From$215
Your tour starts where the oysters do: in our hatchery! See how we recreate the ideal conditions for oysters to reproduce, and learn the stages of growing algae (oyster food).
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Seasonal Tour | Currently Unavailable

Explore New England: Exclusive Cranberry Farm Tour

From$63
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.
(3 Reviews)
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Seasonal Tour | Currently Unavailable

Fall Farm Day at Sauchuk Farm: From Boston with Transportation

From$63
Explore Massachusetts' largest corn maze at Sauchuk Farm, celebrating 100 years of the Boston Bruins! Enjoy world-class maze designs, farm games, delicious treats, and pick apples or pumpkins this Fall.
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Seasonal Tour | Currently Unavailable

Plymouth Haunted History Tour

From$65
Join us this Halloween for a spine-chilling journey through the darker side of Plymouth's rich history. With over 400 years of stories, Plymouth is a city where the past lingers, leaving behind an indelible imprint.
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Seasonal Tour | Currently Unavailable

Become a Cranberry Bogger: Experience a Day on the Farm

From$199
Become a Cranberry Bogger for a Day at Benson’s Pond in Middleboro, MA! Join our small-group tours to experience a hands-on New England cranberry harvest.
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Seasonal Tour | Currently Unavailable

Bogs, Brews, and Views: Harvest Photo Op Experience

From$132
Immerse in the magic of cranberry harvest with our In the Bog Photo Op Experience. Suit up in chest waders and enjoy 30 minutes wading through vibrant cranberries. Afterward, relax with food, brews, live music, and sunset views.
(2 Reviews)
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Seasonal Tour | Currently Unavailable

Day Trip from Boston: Cape Cod Kayak Tour at Lawrence Pond

From$150
Join us for a delightful summer day at Lawrence Pond on Cape Cod! Pack a delicious picnic lunch and come along for an adventure-filled day of guided kayaking exploration and time on your own to unwind and enjoy the natural splendor of Cape Cod.
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Seasonal Tour | Currently Unavailable

Kayak Popponesset Bay on Cape Cod: Day Trip from Boston

From$150
Escape the Cape Cod traffic and join our all-inclusive kayaking adventure, featuring secluded beaches, stunning real estate, and diverse wildlife. Guided by ACA certified experts, you'll explore the best routes and discover ocean critters at the "Spit" while enjoying breathtaking scenery.
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Seasonal Tour | Currently Unavailable

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

From$95
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)
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Seasonal Tour | Currently Unavailable

Guided Plymouth Walking Tour: Explore History and Enjoy a Scavenger Hunt

From$65
Embark on a captivating walking tour of historic Plymouth, Massachusetts with local guide Vicki. Click to read more…
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Seasonal Tour | Currently Unavailable

Pick-Your-Own Tulips Adventure

From$62
Jump into spring with a tulip-picking adventure at Wards Berry Farm in Sharon, MA. Join us on the farm where you can wander through vibrant fields of blooming tulips, hand-select your favorite blossoms, and create a personalized bouquet in a mason jar to take home.
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Our tours and day trips outside Boston are set to launch at the end of April 2024. 

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