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Explore Martha’s Vineyard with Cheap Therapy Charters. Private, family-friendly boat tours, fishing trips, and sunset cruises run by local islanders.
Cheap Therapy Charters is a family-run boat charter out of Oak Bluffs. Every trip is private and follows your itinerary: scenic cruises, fishing, and special events on the water.
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Jen and Kyle grew up together on the island, are raising their kids here, and run the boat themselves. Kyle is the captain and also a longtime Oak Bluffs firefighter and paramedic, which makes him a good person to have aboard.
The boat is rigged for light-tackle and family trips, with room for a small group and gear provided for everyone aboard.
The restored 28-foot Bertram at anchor on a calm day, bimini up. Six guests is the limit, which is what keeps it private.
The 28-foot Bertram is a classic design with modern upgrades:
All trips are BYOB, limited to 6 guests for privacy and comfort, with flexible hourly add-ons. Prices vary by trip length and destination. Gratuity is not included.
All their charter options and the booking form are on their site:
Request Now on CheapTherapyCharters.com
We like writing about family-run island businesses like this one. If you run one and want to work together, get in touch.
For more charters and things to do, see our Activities Guide or subscribe to the newsletter.
This feature is part of our local partnership series. No paid promotion.
Oak Bluffs harbor at sunset, where the charter boats tie up. An evening cruise leaves from here and is back before the restaurants close.
Where to learn to sail on Martha's Vineyard, checked October 2026: Sail Martha's Vineyard's summer classes on Lagoon Pond, private lessons for adults, Sunfish rentals in Vineyard Haven and Menemsha, schooner and catboat sails, summer races you can watch or crew, and what the wind and currents are like.
Shellfishing on Martha's Vineyard town by town: what each of the six towns charges a visitor for a permit and what it covers, where to buy it, weekly limits and sizes, the 2026 to 2027 bay scallop dates published so far, how to check storm and rain closures, and keeping the catch safe to eat.
Every rule a visiting angler needs on Martha's Vineyard, checked October 2, 2026: who needs the $10 Massachusetts saltwater permit, freshwater and tuna permits, 2026 size and bag limits by species, what you can keep this month, the Derby, beach-driving permits, pier rules and Aquinnah parking.
Martha's Vineyard shore fishing spot by spot: the Oak Bluffs pier, Memorial Wharf, State Beach, Menemsha, Lobsterville, Dogfish Bar, Squibnocket, Lambert's Cove, Tashmoo, Cape Poge, Wasque, Norton Point and South Beach, with legal parking, resident-only rules, hazards and a monthly calendar.
Radio Science runs silent DJ after-parties on Martha's Vineyard: headsets kept on the island, three channels, headset wrangling for rentals, tents and lights. The island's answer to the 10 PM outdoor music curfew at weddings.
Take a guided Jaws tour of Martha's Vineyard with local guide Mike Currid. Walk the real Amity Island in Edgartown and book the “Amity” Walking Tour.
Island tip of the day Timing No. 61 of 79 New tip at midnight, island time
Visit Edgartown on a Tuesday or Wednesday. Same beautiful town, maybe 30% of the weekend crowds. Most restaurants have availability without reservations.
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