Paddle Boston - Waltham

Boating in Boston at Spot Pond

Boating in Boston features gorgeous boathouses all across the greater Boston area waiting to launch you on your next kayaking, canoeing, sailing or paddleboarding adventure. The story actually starts in 2002, in our small New England hometown of Hopkinton, Massachusetts. That’s where a charismatic man named Barry began the boating vision by opening Outdoor Recreation of Hopkinton, a kayak rental concession in Hopkinton State Park. The word started getting around and the business grew and grew, bringing forth a community of water lovers. And soon Barry was introducing sailing and summer camps and boating season passes to the park.

Paddle Boston - Allston/Brighton

Charles River Recreation is dedicated to providing affordable and accessible outdoor recreational opportunities in the Boston, Massachusetts metropolitan area. Today we operate Charles River Canoe & Kayak (offering canoe, kayak and paddleboard sales, classes, guided trips, and multiple rental locations), Weston Ski Track (located at the Leo J. Martin Golf Course in Weston and offering cross-country skiing and instruction on groomed, lighted trails), and Kendall Square Community Ice Skating (a refrigerated, Zamboni-maintained ice skating rink in Kendall Square, Cambridge).

Boston Belle Charters

Boston Belle Charters is one of Boston's oldest Boat Charter Service. You'll get spectacular views of the Boston skyline and Atlantic horizon as you sail through the historic Boston Harbor. We're happy to accommodate a full boat, or even an intimate tour of the Harbor for you and your lover, or other special occasions. You can customize your experience, right down to the food, music, decoration and drinks. We look forward to sailing with you! Whether you want to join one of our unique tours or book a private event for your team, our professional crew can handle every detail.

Cycleboat Boston

Our 1.5 hour tour starts in the Navy Yard in Boston and opens directly into the incredible Boston Harbor. From the Cycleboat, you’ll see some amazing views of Boston and American History including the Boston Tea Party Ship, the Downtown Boston Waterfront, Bunker Hill and the Charlestown Navy Yard with the USS Constitution and WWII destroyer Cassin Young. We have three boats with capacities of 16, 24 or 26. Each boat has 10-12 pedal seats around the bar with comfortable lounge seating at the bow. Our crew will assist in rotating pedaling seats during the tour so everyone that wants to pedal has the opportunity.

Charles River Canoe & Kayak : Allston Brighton

Rent a Canoe, Paddleboard and Kayak in Boston and enjoy one of the most scenic sections of urban river in the country. Boating on the Charles River from our Boston location in Allston/Brighton is a wonderful respite from the surrounding city, with parkland on both shores and rowers plying the waters. Paddle downstream towards Boston to see local colleges (Harvard, M.I.T., and B.U.) the Esplanade, and Boston skyline. Make sure to stop for a picnic

Paddle Boston - Newton

Classic Harbor Line Boston

At Classic Harbor Line, we are dedicated to providing the most impeccably luxurious and hospitable sailing experience in Boston. Our guests can look forward to the privilege of being escorted on a breathtaking excursion aboard the most elegant sailing vessel in Boston Harbor, the schooner Adirondack III or a relaxing cruise aboard the motor vessel Northern Lights If you are a first time visitor or a seasoned local, an excursion aboard one of Classic Harbor Line’s yachts will provide you with a new perspective on the city of Boston. While aboard our stylish boats, you will be treated to views of the spectacular Boston skyline, historical sites, harbor islands, and perhaps a glimpse of some of our elusive wildlife, such as: the harbor seal. So, come on out and experience the best sightseeing adventure in Boston! And please, kick up your feet because we’ll do all the heavy lifting (and drink pouring)!

Boston Sailing Center

Our facilities are unique - a Louisiana Riverboat berthed at Lewis Wharf on Boston Harbor. Just a short walk north of Faneuil Hall Marketplace, our floating classroom and clubhouse is an excellent venue for parties and other functions. We're also close to a wide variety of historical sites, restaurants and nighttime entertainment spots. Public parking is available nearby. From the Riverboat, we enjoy unrestricted sailing along Boston's historic waterfront and beyond, including day sails among the beautiful Boston Harbor islands, overnight trips to Marblehead and longer sails to destinations like Provincetown, Martha's Vineyard and Newport.

Paddle Boston - Stoneham