The 12 Best Boston Boat Experiences to Enjoy in Summer 2025

Summer is a short season in Boston so locals love to enjoy it to the fullest – and that means getting out onto the water. Whether you’re an expert sailor or still trying to find your sea legs, there’s a relaxing waterbound option for everyone.  by Celina Colby 1) <a href="https://joyraft.com/event/community-boating-boston-rentals-boston-419856">Kayak or Paddleboard on the Charles River</a> When: April 1 - October 31 Where: The Charles River &amp; Esplanade Lagoon Cost: $40 for two hours Info: There’s almost nothing more relaxing on a warm day than lazily drifting down the Charles River and the Esplanade Lagoon in a kayak or on a paddleboard. Community Boating has downtown Boston on lock, for boating in Brighton, Cambridge, Medford, Somerville, and other locations surrounding Boston check out <a href="https://joyraft.com/event/paddle-boston-canoe-kayak-paddleboard-rentals-cambridge-348555">Paddle Boston</a>. 2) <a href="https://joyraft.com/event/boating-on-jamaica-pond-jamaica-plain-458903">Sail on Jamaica Pond</a> When: April 21 - October 31 Where: Jamaica Pond Cost: $70 for two hours Info: Fulfill childhood dreams of adventure by taking a sailboat out for a spin on Jamaica Pond. If that seems a little too ambitious, you can also rent paddleboards, kayaks, and row boats here. If you’re up for some athletic fun, join a paddleboard yoga class.  3) <a href="https://joyraft.com/event/boston-harbor-sightseeing-cruise-boston-450752">Boston Harbor Sightseeing Cruise</a> When: May 15 - July 26 Where: Boston Harbor Cost: $46+ Info: For a scenic boat trip that’s also educational, this sightseeing cruise will bring you around the harbor while pointing out notable historic and cultural spots. Grab a drink from the bar, snag a seat in the outdoor upper deck or the comfy inside seats, and learn more about Boston.  4) <a href="https://joyraft.com/event/cycleboat-boston-charlestown-458905">Cycleboat Boston</a> When: April 17 - October 26 Where: Boston Harbor Cost: $45.95+ Info: Pedal your way around the Boston Harbor (or just relax) on this unique boat concept that’s powered by its riders. Choose from different kinds of tours, including a mimosa tour, sunset cruise, harbor cruise, and others.  5) <a href="https://joyraft.com/event/the-tall-ship-boston-floating-oyster-bar-waterfront-experience-live-music-food-trucks-popups-more-east-boston-385284">The Tall Ship Oyster Bar &amp; Waterfront Experience</a> When: April 19 - Late September Where: East Boston Cost: Cost of food and beverage Info: If you want to be on the water but not necessarily moving, this is a great option. The Tall Ship is an oyster bar, live music venue, and nightlife hotspot on a large ship docked in the East Boston end of the Boston Harbor. There’s no motion sickness, but you’ll definitely feel sailing vibes. 6) <a href="https://joyraft.com/event/rent-a-boat-on-boston-harbor-with-boston-electric-boats-boston-379741">Rent a Boat on Boston Harbor with Boston Electric Boats</a> When: April 13 - October 7 Where: Boston Harbor Cost: $439+ for two hours Info: If you prefer to be the captain of your own destiny (and ship), get a group of friends together and rent an electric boat to tour the harbor with. You drive the boat and a group of up to five friends can capture the experience in photos and command the in-boat playlist. 7) <a href="https://joyraft.com/event/boston-harbor-sunset-sail-on-a-tall-ship-boston-456373">Sunset Sail of Boston Harbor on a Tall Ship</a> When: May 17 - September 28 Where: Boston Harbor  Cost: $68 Info: Explore the Boston Harbor at sunset in a classic tall ship. While you sip cocktails and take in the sights, the crew will sail around the harbor in the magical hours of sunset. You can also enjoy the fireworks from this boat around the Fourth of July.  8) <a href="https://joyraft.com/event/free-water-taxis-ferries-around-boston-harbor-summer-2023-boston-426893">Take a Ferry or Water Taxi</a> When: April 17 - September 30 Where: Boston Harbor Cost: Varies, some are free Info: For a low cost boat ride, check out the shuttle run by Boston Launch Company that connects all of their restaurants Reel House Seaport, The Tall Ship, Reel House East Boston, and Pier 6 Charlestown. Riders with a dinner reservation get on for free, everyone else pays just $4. Encore also runs a free luxury boat shuttle from Lovejoy Wharf to the casino.  9) <a href="https://www.bostonharborislands.org/">Explore the Boston Harbor Islands </a> When: May 16 - October 13 Where: Boston Harbor Cost: $15-25 Info: The Boston Harbor Islands are a beautiful natural piece of the city that often go unexplored. You can enjoy the beach on Spectacle Island, go hiking, explore Fort Warren on Georges Island, and much more. Pro Tip: on May 17 and 18 you can get <a href="https://joyraft.com/event/free-ferry-day-boston-418033">free ferry tickets</a>! ONE-TIME EVENTS:  10) <a href="https://joyraft.com/event/free-ferry-weekend--2-boston-1017537">Free Ferry Weekend</a> When: Saturday May 17 - Sunday May 18 Where: Boston Harbor Cost: Free Info: Enjoy free ferry service to Georges Island in the Boston Harbor for free all weekend. There you can explore historic Fort Warren, listen to live music, engage in children and adult friendly activities, and enjoy the Boston skyline from the water. 11) <a href="https://joyraft.com/event/neponset-day--2-dorchester-1018077">Canoe &amp; Kayak for Free at Neponset Day </a> When: Saturday August 23 Where: Dorchester Cost: FREE Info: During this annual family-friendly celebration of the Neponset River and the Greenway Trail you can canoe and kayak on the river for free as well as enjoy live music, food trucks and ice cream, a spray deck, and environmental exhibits.  12) <a href="https://joyraft.com/event/sunset-paddleboarding-on-the-boston-harbor-boston-456357">Sunset Paddleboarding</a> When: Fridays starting June 6 - August 29 Where: Boston Harbor Cost: $37 Info: Take in golden hour while drifting down Fort Point Channel admiring the city skyline. This hour-long session takes you to the Boston Harbor in a slow, easy-to-follow paddle.

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Our top picks: outdoor dining, free events, spring festivals, best bars, upcoming concerts, museum parties - the latest in and around Boston.  Slug: joyraft-top-picks-best-things-to-do-boston-ma

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S28: calendar experiences

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The 12 Best Boston Boat Experiences to Enjoy in Summer 2025

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