Oak Bluffs departures with licensed captains, small-group adventures for families, couples, and friends.
Private charters, jet ski tours, parasailing, waterski/wakeboard charters, and boat rentals — options for up to six guests.
water-activities · Vineyard Haven
Discover the thrill of watersports with Martha’s Vineyard Oceansports. Whether you’re a beginner or a seasoned rider, enjoy wakeboarding, waterskiing, and tubing on stunning Vineyard waters with expert guidance.
Martha's Vineyard Oceansports operates from Oak Bluffs, Massachusetts, offering a broad selection of boat rentals, guided tours, and watersports experiences around Martha’s Vineyard. The company runs private charters, sunset cruises, jet ski tours and rentals, parasailing flights, waterski and wakeboard charters, banana boat rides, and fishing-ready center-console rentals. Trips accommodate up to six passengers and are led by licensed U.S. Coast Guard captains or trained crew.
Fleet options range from jet skis and 17’ Boston Whalers to 38’ Fountain charters and modern center-console boats equipped for fishing. Popular excursions include a guided 2-hour jet ski tour from Oak Bluffs to Edgartown and intimate 1.5-hour private sunset cruises across the Elizabeth Islands. Watersports charters provide wakeboarding, waterskiing, kneeboarding, and tubing suitable for beginners and experienced riders. Parasailing flights use Paracraft Warrior and Patriot boats with dry take-offs and landings, and offer optional water dips.
Reservations are available daily for many experiences, and safety equipment, coolers, and ice are provided for private charters and sunset cruises. Professional instruction accompanies jet ski rentals and watersports to ensure a safe, enjoyable outing. The operation emphasizes small-group experiences, local knowledge of Vineyard waterways, and certified operation to deliver reliable, memorable days on the water. For visitors seeking guided sightseeing, adrenaline sports, fishing outings, or relaxed sunset cruises, Martha's Vineyard Oceansports provides a range of licensed, family-friendly options launched from Oak Bluffs. Booking information and seasonal availability are posted online and through local Oak Bluffs kiosks during peak summer months for visitor planning and group inquiries.
“Every outing is organized with local river knowledge, basic safety instruction, and equipment checks before departure.”
Small, private outings
Launch point on Martha’s Vineyard
Experienced, certified operators
Water sports, charters, tours
Open the individual experience guide to confirm current availability, pricing, policies, conditions, and inclusions before booking.
The operator provides clear meeting points, departure times, and destination coordinates for all outings.
Personal flotation devices, emergency protocols, equipment checks, and paddling orientations are provided before departure.
Recommended layering, water shoes, sunscreen, and dry bags are detailed in each experience guide.
Guides share rich knowledge of regional flora, fauna, scenic landmarks, and river navigation.
A glimpse into the experiences, natural landscapes, and adventures waiting on your next trip.
Images supplied on the current Martha's Vineyard Oceansports listing.
Martha's Vineyard Oceansports offers a variety of guided outdoor excursions, scenic routes, rentals, and custom itineraries tailored for families, couples, and adventure enthusiasts.
Yes. Most trips feature comprehensive safety orientations, equipment fittings, and calm routes suited for first-time adventurers. Check the details on individual experience guides for specific age and skill requirements.
Standard safety equipment (such as certified life vests and essential gear) is supplied for each booking. Detailed checklists regarding weather-appropriate attire and personal items are provided prior to departure.
Secure private charters, jet ski tours, parasailing flights, or watersports charters with licensed captains — check schedules and book through verified listings.
water-activities · Oak Bluffs
Join a thrilling 2-hour jet ski tour around Martha’s Vineyard, starting from Oak Bluffs. Experience breathtaking views, spot local wildlife, and explore Cape Pogue—all with expert guidance.
boat-charters · Vineyard Haven
Join Martha's Vineyard Oceansports for an exclusive sunset boat cruise that offers stunning views, peaceful moments, and a chance to create unforgettable memories on the water. Perfect for small groups and special occasions.
water-activities · Edgartown
Discover the coast of Martha's Vineyard on a private boat tour designed for small groups. Experience personalized adventures with stunning views, wildlife sightings, and a relaxed vibe. Keep reading to find out more!
water-activities · Vineyard Haven
Discover the thrill of wakeboarding and waterskiing on Martha’s Vineyard with Oceansports, where fun meets safety in a stunning coastal setting. Perfect for all skill levels, this activity promises a memorable day on the water.
water-activities · Vineyard Haven
Looking for an adrenaline rush on the water? Martha's Vineyard Oceansports offers jet ski rentals that deliver speed, fun, and stunning coastal views. Perfect for thrill-seekers and water lovers alike!
water-activities · Vineyard Haven
Take to the skies over Martha's Vineyard with a thrilling parasailing adventure. Perfect for all ages, this activity offers stunning views and unforgettable moments above the Atlantic Ocean.
water-activities · Oak Bluffs
Set sail from Martha's Vineyard with a Boston Whaler rental—an exhilarating way to enjoy the island’s rugged coastline and lively marine life. Discover why this is a top water activity for visitors seeking fun on the water.
boat-charters · Edgartown
Set sail on a personalized adventure with Martha's Vineyard Oceansports. Whether you're after sunset serenity or a full-day cruise, their private charters offer unmatched views and intimate experiences on the water.
fishing · Oak Bluffs
Set sail from Oak Bluffs with Martha's Vineyard Oceansports aboard the Island Reef Sportsman #2, a powerful 19’ fishing boat perfect for groups up to six. Enjoy advanced electronics, comfortable fishing amenities, and easy access to some of New England’s best coastal waters.
water-activities · Oak Bluffs
Ride the waves along State Beach with Martha’s Vineyard Oceansports’ family-friendly banana boat tours. Choose your pace and group size for a memorable coastal adventure everyone can enjoy.
Click into any experience card above to view current dates, live availability, transparent pricing, cancellation policies, and booking details.