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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.
A family-run boat charter out of Oak Bluffs: Cheap Therapy Charters runs private trips, 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 is 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.
Their 28-foot Bertram yacht combines 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.
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