Cheap Therapy Charters – Family-Owned Private Boat Tours on Martha’s Vineyard

Cheap Therapy Charters – Family-Owned Private Boat Tours on Martha’s Vineyard

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.

The short version

  • Locally owned and operated by born-and-raised islanders Jen and Kyle.
  • Private trips for up to 6 guests: families, friends, celebrations.
  • Restored 28-foot Bertram yacht with modern safety and comfort features.
  • Customizable itineraries including fishing, sightseeing, swimming, and sandbar lounging.

Popular Charters Offered

  • Washburn Island / Waquoit Bay: Calm, shallow waters ideal for family swimming, lounging, and relaxing with a surprise visit from the local ice cream boat.
  • Jaws Bridge Adventure: Visit the filming spot from Spielberg’s classic, with clear water sandbar anchoring and safe swimming.
  • Tarpaulin Cove on Naushon Island: A Vineyard Sound cruise with a beach landing: walk, swim, or stay on deck.
  • Sunset Cruise: Private evening trip, with the sun going down over Vineyard Sound.
  • Fishing Trips: Target local species including seabass, fluke, striped bass, and bluefish. Gear provided for all skill levels.
  • Choose Your Own Adventure: Lighthouse tours, memorial services, diving trips, and whatever else you have in mind.

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Meet the Family Behind Cheap Therapy Charters

Jen and Kyle, both second-generation islanders, 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

The Cheap Therapy charter boat at night on Martha’s Vineyard
Aboard · the boatPhoto by MV Vacation

The boat is rigged for light-tackle and family trips, with room for a small group and gear provided for everyone aboard.

Their 28-foot Bertram yacht combines classic design with modern upgrades:

  • Spacious seating and dining area
  • Private restroom onboard
  • Wi-Fi, radar, sonar, GPS, and VHF communications
  • Fresh water, shaded lounging space, and modern electronics
Trip Wizard (in-article)

Booking Details

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

Supporting Local Business

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.

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Island tip of the dayInsiderNo. 84 of 86New tip at midnight, island time

A 502-foot breach opened at Norton Point on January 1, 2026, cutting the sand link between Katama and Chappaquiddick: the Chappy Ferry is once again the only way across, likely for years. OSV drivers should check current beach access with the town of Edgartown.

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Disclaimer: The information in this article is provided for general guidance only and was accurate at the time of writing. Beach conditions, hours, prices, lifeguard schedules, ferry fares, and business operations change frequently and without notice. Ocean swimming carries inherent risks including rip currents, undertow, and cold water shock. Always verify current conditions with official local sources before your visit. MV Vacation assumes no responsibility for any loss, injury, or inconvenience resulting from the use of this information. Swim only where lifeguards are on duty, supervise children at all times near water, and follow all posted safety signs.
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