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Outdoor Adventures & Tours in and near Brookline, MA


Boston Freedom Trail Scavenger Hunt Adventure
Boston Freedom Trail Scavenger Hunt Adventure

Turn Boston into a giant game board with this fun scavenger hunt adventure! This challenge combines the excitement of the Amazing Race with a 3-hour city walking tour. Using your smart phone to guide you, make your way through Boston among well-known and overlooked gems of the city, solving clues and completing challenges while learning local history. Great for families, friends and those ready to have fun while seeing the city!

1 Beacon Street, Boston 3.6 mi
3.0
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1 Ratings
$20.52
Boston Freedom Trail Scavenger Hunt Adventure
Go Boston Pass to 40+ Things to Do - Six Flags, Aquarium, Museums, Whale Watching Cruise, Zipline & Tours
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Go Boston Pass to 40+ Things to Do - Six Flags, Aquarium, Museums, Whale Watching Cruise, Zipline & Tours

Go Boston Pass: Things to do, Kids Activities, Fenway Park, Cruises, Museum of Science, Foxwoods, New England Aquarium, and Whale Watching

26 Locations 1.2 mi
$44.00
1-Day Go Boston Pass for 1 Child
430+ bought
Boston Explorer Pass: Access to Things to Do from 20+ Museums, Aquarium, Cruise, Zoo, Bike Rental & More
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Boston Explorer Pass: Access to Things to Do from 20+ Museums, Aquarium, Cruise, Zoo, Bike Rental & More

Pass to 20+ Things to Do - Boston: New England Aquarium, Boston Duck Tour, Hop-On Hop-Off Trolley, Museum of Science

15 Locations 1.2 mi
$35.15
Two-Attraction Go Boston Explorer Pass for One Child (Ages 3–12)
730+ bought
Boston City view Bicycle Tour
Boston City view Bicycle Tour

Discover Boston’s famous sites and hidden treasures on this 2.5 to 3-hour guided bike tour – a perfect way to explore the city! Start at Little Italy in Boston’s North End and pass sites like Copley Square, Fenway Park and the Faneuil Hall marketplace. Cruise through Beacon Hill and admire the diverse neighborhoods as your knowledgeable guide provides insightful commentary on Boston’s unique history. You may also choose to do this tour on an e-bike (select e-bike option at checkout, but note: you must be 16 or older to select the E-bike option).

4 Yawkey Way, Boston 1.5 mi
5.0
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129 Ratings
$68.00
Boston City view Bicycle Tour
Boston Chocolate Tours w/ Private Tour Option
Boston Chocolate Tours w/ Private Tour Option

Boston is a city known for its significant role in shaping American history and its contribution during the American Revolution. Alongside this historical significance, Boston has long been known as one of the leaders in the chocolate movement. In fact, the first chocolate shop in the colonies opened in 1740 in the North End of Boston with a "drinking chocolate". And we didn't stop there! Boston takes pride in the creation of several iconic desserts that we'll sample during our chocolate-filled journey through the city!

Tremont Street, Boston 2.5 mi
$206.58
Boston Chocolate Tours w/ Private Tour Option
1 bought
Boston's Beacon Hill Guided Photography Walking (Small Group)
Boston's Beacon Hill Guided Photography Walking (Small Group)

Walking along the picturesque streets of Beacon Hill is an immersion into a 19th-century English-inspired neighborhood that's rich in history and charm. 

Learn how to compose amazing pictures of Beacon Hill’s diverse architecture, antique gas lamps lining the brick sidewalks, colorful flowers spilling out of the window boxes, the most photographed street in Boston as well as an exclusive enclave and other surprises hidden in unexpected places. 

Fascinating commentary on Beacon Hill's historical sites along the itinerary is also provided throughout the tour.

Tremont Street, Boston 2.5 mi
4.7
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12 Ratings
$42.67
Boston's Beacon Hill Guided Photography Walking (Small Group)
Pro-Photoshoot in Historic Boston or Cambridge, Massachusetts
Pro-Photoshoot in Historic Boston or Cambridge, Massachusetts

An urban style photoshoot in historic Boston! Let me take you to my favorite locations: -Copley Square -Newbury St. -Public Gardens -Beacon Hill We will walk through this historic landmarks and we will explore the area while I take the best photos of your trip. We will walk a lot, so make sure to bring comfortable shoes. In about 48 hours after the end of the photo session​,​ you will get an email with a link to your digital gallery with your edited images so you can download them on your computer or laptop and share your memories with friends and family. You can also print your photos in your preferred​ printing shop and showcase the images of your vacation in Boston in your living room, your office or just post them on your social media!!!!​ Note: if you have a special request related to a specific time of day, location and or a big group, please do not hesitate to write me and let me know about it, I will work with you to have your photo-needs happen.

560 Boylston Street, Boston 2.6 mi
$163.47
Pro-Photoshoot in Historic Boston or Cambridge, Massachusetts
1 bought
Boston CityPASS Tickets for Adult or Child
Boston CityPASS Tickets for Adult or Child

Discover Boston’s best attractions at great savings and enjoy instant delivery with convenient mobile tickets.

4 Locations 2.6 mi
5.0
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1 Ratings
$64.00
Boston CityPASS
Tour of MIT for Two or Four People
Tour of MIT for Two or Four People

MIT students steer groups to notable landmarks while imparting college factoids

300 Main Street, Cambridge 2.7 mi
4.8
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48 Ratings
$26.58 $18.00$16.00
 Sale Ends 4/12
Tour of MIT for Four People
$22.49 for Team Scavenger Hunt Tour for Up to 12 People from Puzzling Adventures  ($49.99 Value)
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$22.49 for Team Scavenger Hunt Tour for Up to 12 People from Puzzling Adventures ($49.99 Value)

Players explore the city via an adventure combining the fun of a scavenger hunt with the information of a self-guided tour

179 Locations 2.8 mi
4.1
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1,667 Ratings
$49.99 $24.99$22.49
 Sale Ends 4/12
One Team Scavenger Hunt Tour for Up to 12
Harvard University Campus Guided Walking Tour
Harvard University Campus Guided Walking Tour

What better way to see Harvard than through the eyes of a student! This tour is a 70-minute student-led walking tour of America's oldest university, designed to be a funny and educational journey through Harvard's campus. After meeting your tour guide, an enthusiastic Harvard student, in the heart of Harvard Square, you'll be led into historic Harvard Yard. Enjoy the sights while your guide entertains and inspires with tales of Harvard history and personal experience at the university they call home. You'll get an up-close look at major Harvard landmarks including Johnston Gate, the John Harvard Statue, Memorial Hall, and Widener Library. You'll even become privy to a few Harvard secrets along the way! Whether you're a student visiting colleges or a family on vacation, the Hahvahd Tour is undoubtedly the top way to see Harvard.

1350 Massachusetts Avenue, Cambridge 2.8 mi
5.0
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35 Ratings
$19.50
Harvard University Campus Guided Walking Tour
Self-Guided Boston Scavenger Hunt for Two, Four, or Six from ScavengerHunt.com (Up to 54% Off)
Self-Guided Boston Scavenger Hunt for Two, Four, or Six from ScavengerHunt.com (Up to 54% Off)

Participants gear up and launch the ScavengerHunt.com app to start their own adventure, racing against the clock at a time of their choosing

2 Locations 2.9 mi
3.9
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3,672 Ratings
$60.00 $34.50$32.78
 Sale Ends 4/12
Boston Scavenger Hunt for Two People
$14.99 for One Augmented Reality Detective Game from YouSleuth ($35 Value)
$14.99 for One Augmented Reality Detective Game from YouSleuth ($35 Value)

Augmented Reality Game users can play detectives in their neighborhood using a real-world map on their smartphones

313 Locations 3.0 mi
$35.00 $14.99
57% discount_off
One Augmented Reality Detective Game
300+ bought
Walking Tour for Two, Four, or Six from Showbiz Boston (Up to 50% Off)
Walking Tour for Two, Four, or Six from Showbiz Boston (Up to 50% Off)

Tour-goers explore Boston’s colorful history through its grand theaters and scandalous celebrities

139 Tremont St., Boston 3.3 mi
4.0
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3 Ratings
$40.00 $25.00$23.75
 Sale Ends 4/12
Walking Tour for Two People, valid Saturday or Sunday
$27.55 for Two-Hour Self-Guided Boston Freedom Trail Tour from Go Trivia ($47 Value)
$27.55 for Two-Hour Self-Guided Boston Freedom Trail Tour from Go Trivia ($47 Value)

Patrons can enjoy a self-guided tour with elements of scavenger hunt and trivia and learn more about Boston

24 Beacon Street, Boston 3.5 mi
$47.00 $29.00$27.55
 Sale Ends 4/12
Two-Hour Self-Guided Boston Freedom Trail Tour for up to Five
2.5-Hour Walking Tour of Boston for One or Two from Roger's Wicked Fun Tours (Up to 33% Off)
2.5-Hour Walking Tour of Boston for One or Two from Roger's Wicked Fun Tours (Up to 33% Off)

Focusing on the evolution of Boston, this tour highlights Boston’s rise from colonial era’s port city to today’s global metropolis

24 Beacon Street, Boston 3.5 mi
$35.00 $25.00
28% discount_off
2.5-Hour Walking Tour of Boston for One
2 bought
Guided Walking Tour of the Freedom Trail in Downtown Boston
Guided Walking Tour of the Freedom Trail in Downtown Boston

Dive into early American history and architecture as you explore the Freedom Trail in Downtown Boston. On a 70-minute walking tour, admire the architecture, and learn about the history and culture of the city as you pass attractions and landmarks like Faneuil Hall, King's Chapel, and Boston Common.

101 Tremont Street, Boston 3.5 mi
4.9
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30 Ratings
$20.00
Guided Walking Tour of the Freedom Trail in Downtown Boston
Private Boston Movie Mile Walking Tour
Private Boston Movie Mile Walking Tour

Tour the Boston Common and Beacon Hill areas and visit more than 30 movie locations on this captivating private movie and TV walking tour! This tour is a must for film buffs, and is also a great way to explore Boston and its many attractions. On this Boston walking tour, your guide, a local actor, will provide a unique sightseeing tour with an entertaining twist!

1 Beacon Street, Boston 3.6 mi
4.2
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5 Ratings
$43.75
Private Boston Movie Mile Walking Tour
Boston Freedom Trail Day Trip from New York City
Boston Freedom Trail Day Trip from New York City

See the historical sights and famous universities of the Boston area on this full-day trip from New York City. After a scenic drive through Connecticut, arrive in Boston, Massachusetts. See top Boston attractions including Harvard University, Trinity Church and the site of the Boston Tea Party. Follow the red-brick Freedom Trail, which leads to important historical locations. You'll learn all about the rich and colorful history of Boston from your informative and engaging guide.

1 Beacon Street, Boston 3.6 mi
5.0
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192 Ratings
$169.00
Boston Freedom Trail Day Trip from New York City
$14.70 for Scavenger Hunt Adventure for One Team at ZeeTours ($50 Value)
$14.70 for Scavenger Hunt Adventure for One Team at ZeeTours ($50 Value)

During the scavenger hunt teams answer trivia questions, follow clues scattered around the city, and complete photo and compass challenges

130 Congress Street, Boston 3.7 mi
4.1
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82 Ratings
$50.00 $19.00$14.70
 Sale Ends 4/12
Scavenger Hunt Adventure for One Team
General-Admission Ticket for One Child or Adult at Boston Tea Party Ships & Museum
General-Admission Ticket for One Child or Adult at Boston Tea Party Ships & Museum

The Boston Tea Party comes to life with immersive exhibits, tea-ship replicas, and one of the original tea chests from December 16, 1773

306 Congress Street, Boston 3.8 mi
4.8
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812 Ratings
$21.95
General-Admission Ticket
Self-Guided Walking Adventure for One, Two, Four, or Six from Crazy Dash (Up to 57% Off)
Self-Guided Walking Adventure for One, Two, Four, or Six from Crazy Dash (Up to 57% Off)

Performing silly tasks and hunting for checkpoints around the city, digital walking tour brings adventure and family-friendly fun

77 Locations 3.9 mi
4.1
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214 Ratings
$20.00 $10.00$9.00
 Sale Ends 4/12
Crazy Dash Walking Adventure for One
Adventure Scavenger Hunt Walking Tour for One, Two, Four, or Six from Wacky Walks (Up to 57% Off)
Adventure Scavenger Hunt Walking Tour for One, Two, Four, or Six from Wacky Walks (Up to 57% Off)

Players set out on scavenger hunt walking tour challenge through city answering questions and performing family-friendly tasks

73 Locations 3.9 mi
4.1
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298 Ratings
$20.00 $10.00$9.00
 Sale Ends 4/12
Adventure Walk for One
90-Minute Sunset Cruise for One, Two, or Four from Massachusetts Bay Lines (Up to 50% Off)
90-Minute Sunset Cruise for One, Two, or Four from Massachusetts Bay Lines (Up to 50% Off)

On sunset cruises, passengers watch the evening overtake Boston’s skyline and get a glimpse of the historic USS Constitution

60 Rowes Wharf, Boston 4.0 mi
4.5
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1,458 Ratings
$28.05 $19.00$15.65
 Sale Ends 4/12
90-Minute Sunset Cruise for One
Boston Harbor Sightseeing Cruise
Boston Harbor Sightseeing Cruise

Enjoy this 1.5 hour cruise around Boston Harbor on classic 1920s-style Yacht Northern Lights, which is 115-feet in length, features 6 bathrooms and provides comfortable seating through the boat. Some notable sites include great views of Boston's skyline, Old North Church, Bunker Hill Monument, USS Cassin Young, and the USS Constitution along with Boston's Harbor Islands. Bring your camera! Grab a beverage from the bar (available for purchase by credit card) and relax in the climate controlled main observation cabin or from the open top deck. Small bites available for purchase onboard as well.

60 Rowes Wharf, Boston 4.0 mi
3.0
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1 Ratings
$34.14
Boston Harbor Sightseeing Cruise
Trolley Tour for One, Two, or Four at CityView Trolley Tours (Up to 56% Off)
Trolley Tour for One, Two, or Four at CityView Trolley Tours (Up to 56% Off)

Historical sites headline a trolley tour that affords sweeping views of the city

Atlantic Avenue alongside 255 State St., Boston 4.0 mi
4.6
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11,349 Ratings
$41.00 $25.00$23.75
 Sale Ends 4/12
Hop-On/Hop-Off Historic Trolley Tour for One
Boston Tours from Urban Adventures (Up to 32% Off). Two Options Available.
Boston Tours from Urban Adventures (Up to 32% Off). Two Options Available.

Boston tour guides provide historical insights and visit many of the city’s most sightseeing worthy landmarks

222 State Street, Boston 4.0 mi
5.0
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6 Ratings
$46.00 $35.00$33.00
 Sale Ends 4/12
Boston History and Highlights
Adult or Child City Tour Admission from Old Town Trolley Tours of Boston
Adult or Child City Tour Admission from Old Town Trolley Tours of Boston

One can explore Boston during this sightseeing experience visiting such iconic spots as Faneuil Hall or Boston Common

200 Atlantic Avenue, Boston 4.0 mi
4.7
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55 Ratings
$26.25
Boston Old Town Trolley City Tour
Tours at Ghosts and Gravestones of Boston (Up to 24% Off).
Tours at Ghosts and Gravestones of Boston (Up to 24% Off).

Participants can discover old burying grounds and hear tales of the tortures, punishments, and executions that took place in Boston

200 Atlantic Avenue, Boston 4.1 mi
$41.95 $31.50
24% discount_off
Ghosts and Gravestones Tour
130+ bought
Boston's North End "Little Italy" Pizza, Cannoli, and History Walking Food Tour
Boston's North End "Little Italy" Pizza, Cannoli, and History Walking Food Tour

Treat yourself to some of the best pizza in Boston on this North End History & Pizza Walking Tour through Boston's "Little Italy". See the sights as you walk in the footsteps of Revolutionary Patriots like Paul Revere, Samuel Adams and George Washington. During this fun history walk you’ll see FIVE Freedom Trail sites, plus enjoy THREE different slices from some of Boston’s very best Pizzerias. Pizzerias on tour can rotate from day to day, and may include – a slice named in the “Top 25 Best” in America by a Famous Food Critic, a slice from Boston’s oldest Pizzeria with a brick oven from 1883, a “Secret Underground” spot for grilled flat-bread Pizza, or from a restaurant named one of the “Top 10 Best” Italian Restaurants in the World! Bonus Stop at Modern Pastry to finish with a FREE cannoli! See top Boston sites including Paul Revere House, the Skinny House, Bunker Hill Monument, USS Constitution, and Copp's Hill Cemetery.

19 North Square, Boston 4.1 mi
5.0
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108 Ratings
$49.00
Boston's North End "Little Italy" Pizza, Cannoli, and History Walking Food Tour