The 9 Best Boston Boat Experiences to Enjoy in Summer 2026
When:
Wednesday, Apr 01, 2026 10:00a -
Saturday, Oct 31, 2026 8:30p
Wednesday, Apr 01, 2026 10:00a -
Saturday, Oct 31, 2026 8:30p
Where:
Boston
Surrounding areas
Boston, MA
Admission:
$Varies
Categories:
Photoworthy, Seasonal, Sports & Active Life
Event website:
https://joyraft.com/event/the-12-best-boston-boat-experiences-to-enjoy-in-summer-2024-boston-458906
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) Kayak or Paddleboard on the Charles River
When: April 1 - October 31
Where: The Charles River & 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 Paddle Boston.
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.
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.
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) The Tall Ship Oyster Bar & Waterfront Experience
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) Rent a Boat on Boston Harbor with Boston Electric Boats
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) Sunset Sail of Boston Harbor on a Tall Ship
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.
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) Explore the Boston Harbor Islands
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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