The 9 Best Boston Boat Experiences to Enjoy in Summer 2026

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/save-the-harbor-spectacle-sundays-cruises-boston-1039154">Free Boston Harbor Cruise</a> When: Select Sundays through September Where: Boston Harbor Cost: FREE Info: Explore Boston Harbor’s Spectacle Island for FREE from 10 am - 2 pm! These cruises are rain or shine so be prepared for any weather conditions.  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: Free - $7 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 $7. 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.

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S22: conversations

Wondering what to do in Boston? Places to eat? Free activities? Good for a group? Date night spot? Girls night out? The best things to do? Ask Joyraft!

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S4: top picks

The most fun, cool and unique things to do in Boston. Can’t miss events, shows and experiences. Concerts, restaurants, bars, free things in Boston and beyond.

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S11: happening this weekend

What to do in Boston this weekend? From festivals, concerts, performances, free events, screenings and more, Joyraft has the best things to do in Boston.

25+ things to do in Boston/Cambridge/Somerville this weekend

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S21: roundups

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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S20: c+d experiences

Discover new, unique events and experiences happening in and around Boston. Perfect for date night, good for a group or with a friend. Be the first to know.

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S16: editor picks

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Unique and Can’t Miss Things to Do in Boston

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S2 (A): top experiences

The most popular things to do on Joyraft. Concerts, restaurants, bars, events, parties, openings, kid friendly, date ideas, free things in Boston and beyond.

Top 20 things to do in Boston

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S3 (A): trending experiences

Discover can’t miss events and things to do in Boston. The most fun, unique and cool events coming to the Boston area this spring and summer.

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S19: interest based

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S18: interest based

Where to eat and drink in Boston? Joyraft has Boston’s newest bars, restaurants and specials. Drinks and pre fixe dinner menus. Cambridge & Somerville too.

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The 9 Best Boston Boat Experiences to Enjoy in Summer 2026

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