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Boston Tours & Sightseeing

Explore a selection of top-rated Tours & Sightseeing experiences across the United States. Bike, ride, walk & sample your way around food, art, tourist attractions & more. Our top-rated guided tours & sightseeing experiences make for a great experience gift, or a fun way to explore with your friends and family!

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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!