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

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.