• 23 Jun, 2026

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.

Discover Martha’s Vineyard from a local’s perspective with Cheap Therapy Charters, a family-run charter company offering personalized, private boat trips. Whether you're looking for a scenic cruise, fishing adventure, or a special event on the water, they’re dedicated to creating unforgettable island experiences.

Why Choose Cheap Therapy Charters?

  • Locally owned and operated by island natives Jen and Kyle.
  • Private trips for up to 6 guests – perfect for families, friends, or 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 iconic filming spot from Spielberg’s classic, with clear water sandbar anchoring and safe swimming.
  • Tarpaulin Cove on Naushon Island: A scenic Vineyard Sound cruise with a beach landing perfect for walking, swimming, or relaxing on deck.
  • Sunset Cruise: Private evening sail with the perfect view of the sun setting 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: Design your perfect day – lighthouse tours, memorial services, diving excursions, and more.

Meet the Family Behind Cheap Therapy Charters

Jen and Kyle, both second-generation islanders, run Cheap Therapy Charters with a commitment to safety, hospitality, and authentic Vineyard experiences. Kyle is not only your captain but also a longtime Oak Bluffs firefighter and paramedic, adding peace of mind to every journey.

The Boat

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

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.

Ready to plan your perfect day on the water? You can view all their charter options and request your trip directly below:

Request Now on CheapTherapyCharters.com

Supporting Local Business

MV Vacation is proud to showcase local, family-run businesses like Cheap Therapy Charters. We believe in building strong island connections, supporting each other, and sharing Martha’s Vineyard’s true character with all visitors. We encourage local businesses to get in touch if they're interested in collaborating, sharing links, or working together to promote the island authentically.

For more Martha's Vineyard charters and activities, explore our Activities Guide or subscribe to our newsletter for insider tips and hidden gems.


This feature was created as part of MV Vacation’s local partnership series, highlighting small businesses and family-run ventures across Martha’s Vineyard. No paid promotion — we simply love showcasing local experiences worth discovering.

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Continue Exploring Martha's Vineyard

⛴️ Island Tip of the Day — Ferry

The Island Queen from Falmouth to Oak Bluffs is just $20 one-way (35 min). Reservations are now required — book at islandqueen.com. Passengers only, no cars.

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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.
MV Vacation Blog

MV Vacation Blog

Your insider guide to Martha's Vineyard — beaches, dining, events, and island living. We share local knowledge to help you plan the perfect Vineyard getaway.

Please note: Content on MV Vacation is compiled from publicly available sources and personal experience. Prices, hours, access rules, and business details change frequently — we do our best to keep information current but cannot guarantee it is accurate or complete at any given time. This site provides general travel guidance only, not professional advice. Always verify details directly with the business, official website, or local authorities, and use your own judgment and due diligence before acting on any information. See our full disclaimer for details.

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