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Boston Guided City Tours

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Our Boston Guided City Tours make for truly unique gifts they're sure to remember forever.

Cloud 9 Living's experience gifts are the perfect solution for anyone on your list and are guaranteed to bring a smile to your gift recipient's face.

Create a memory. Give the gift of experience!

Wine Tour in Boston
Boston Wine Tour
Avg. Rating of 5
(21 Reviews)

Sip 'n' stroll your way through the vibrant neighborhoods of one of America's most beloved cities, enjoying VIP treatment on the Boston Wine Tour.
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Region: Boston
From: $70
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Boston South End Walking Food Tour in Boston
South End Food Tasting and Walking Tour
Avg. Rating of 4-half
(8 Reviews)

Taste your way through Boston's historic South End neighborhood on this delicious and informative walking food tour.
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Region: Boston
From: $66
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Boston Chocolate Tour
Boston Chocolate Walking Tour
Avg. Rating of 4
(7 Reviews)

With this one-of-a-kind Chocolate Walking Tour of Boston, you're in for a treat - lots of them!
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Region: Boston
From: $48
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Draft Beers during History and Tavern Tour in Boston
Boston History and Tavern Tour
Avg. Rating of 5
(7 Reviews)

Walk the Freedom Trail and learn fun, historical facts while enjoying the best brews in town on the Boston History and Tavern Tour!
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Region: Boston
From: $58
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Dessert tour in Boston
Boston Cupcake Crawl

Visit the finest of bakeries in town on the deliciously fun Boston Cupcake Crawl!
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Region: Boston
From: $55
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North End Photo Tour of Boston
Photo Tour of Boston
Avg. Rating of 5
(2 Reviews)

Explore the city through a lens on this Photo Tour of Boston!
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Region: Boston
From: $40
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Cambridge BBQ Kayak Tour
Cambridge BBQ Kayak Tour
Avg. Rating of 5
(3 Reviews)

Departing from Cambridge, enjoy an evening kayaking one of the most scenic sections of the Charles River, followed by some of the best BBQ the area has to offer.
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Region: Boston
From: $79
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Boston Bike Tour
Boston Bike Tour
Avg. Rating of 5
(2 Reviews)

Soak up the sights and sounds of Boston as your guide shows you the best of the city by bike on this Boston Bike Tour!
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Region: Boston
From: $58
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Boston Bikes at Night
Boston Bikes at Night

During one of the most unique bike tours in Boston, you will enjoy the beautiful waterfront as the sun sets and explore some of the city's best sights as the night begins to fall!
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Region: Boston
From: $42
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Walking Tour of Boston
Walking Tour of Boston (for 2+)

Choose from 4 different neighborhoods to explore in the city on a unique Walking Tour of Boston!
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Region: Boston
From: $50
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From: $50
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Explore the very best of Beantown with Boston guided city tours from Cloud 9 Living!

From history to modern hot spots, Boston sightseeing to sweet tooth satisfying — discover one of the east coast's most famous cities in brand new ways.

Let your taste buds lead the way! Navigate the city streets via Boston food tours, featuring some of the city's finest ways to eat and drink. Learn fascinating facts about different neighborhoods and enjoy VIP treatment on the Boston Wine Tour. Or stroll down memory lane —aka the Freedom Trail— on a sought-after tavern tour. Sample beers from 10 different watering holes, once frequented by famous Massachusetts locals like Paul Revere, Samuel Adams and John F. Kennedy. Or indulge in dessert, making your way along a mouthwatering Boston cupcake crawl or chocolate walking tour.

And if the hankering for good eats and historical treats isn't stopping there, then check out the Boston guided city tours that take you along beautiful, bow-front Victorian houses, specialty shops, and markets — all deliciously paired with tantalizing local eats. A tried and true foodie favorite, the South End Walking Food Tour features sandwiches, baked goods, pizza, ethnic fare, and much more!

And what better way to explore "America's Walking City" than taking in Boston attractions via Cloud 9 Living's (very appropriately named) Walking Tour of Boston! Enjoy a fascinating immersion into the city's history, architecture, cultural influences, and charm on this two-hour outing. And best yet — you can choose which neighborhoods you'd like your Boston sightseeing to include, for a nearly-customized experience: downtown, Back Bay, Beacon Hill, the Waterfront, North End, Harvard Square, Cambridge, and more!

And for Boston guided city tours that put an ultra-unique spin on sightseeing, don't miss excursions like urban photo safaris, bike rides by day and night, Cambridge kayak tours, and more!