Nothing beats sailing around Martha’s Vineyard‘s pristine waters – it’s simply one of New England’s finest maritime experiences.
The island offers well-organized tours ranging from quick 2-hour harbor hops to full 6-hour coastal explorations. I especially love the 3-hour private sails, which provide just the right amount of time to soak in the scenery while avoiding tourist crowds.
The 4-hour option works perfectly for families wanting extra time to spot wildlife and visit hidden coves.
What makes these tours special is their mix of entertainment and education – skippers share fascinating local maritime history while guests enjoy complimentary drinks and unmatched island views.
Our tested and approved sailing tours showcase the best of Martha’s Vineyard’s seafaring charm.
Key Points
For a 2-hour scenic sunset sail, the Black Dog Wharf offers a popular and highly-rated tour with complimentary water, snacks, and soda.
A 6-hour all-inclusive sailing experience is available, offering a private group tour with lunch and alcoholic beverages on the Tandemeer launch dock.
The 3-hour private sailing tour from Black Dog Wharf provides an exclusive group experience with complimentary refreshments and optional lunch.
A classic 60-foot ketch offers a 4-hour private sailing adventure for up to six passengers, with complimentary drinks and catering options.
Sailing tours in Martha’s Vineyard cater to various fitness levels, with some restrictions for young children and those with medical conditions.
2 Hour Sailing Tour of Vineyard Haven Harbor and Sound
The 2-hour sailing tour of Vineyard Haven Harbor and Sound, operated by Island Sailing Tours, offers visitors a chance to soak up the picturesque views of Martha’s Vineyard’s scenic coastal landscapes.
With a 4.5 overall rating from 7 reviews, the tour provides a relaxing experience on the water, highlighted by the beautiful sunsets and friendly service from the captain and crew.
The tour departs from the Black Dog Wharf in Vineyard Haven, where guests take a $4 per person Vineyard Haven Launch dock to board the Tandemeer.
Once aboard, passengers can enjoy bottled water, snacks, soda, and even bring their own alcoholic beverages if they’re over 21.
While lunch and dinner aren’t included, guests have the option to bring their own or arrange for catered meals at an additional cost.
The tour operates daily from May 23 to September 20, with confirmed start times coordinated in advance with the local provider.
Infants can join the tour, sitting on laps, though it’s not recommended for travelers with back or heart problems due to the moderate physical fitness level required.
Read our full review: 2 Hour Sailing Tour of Vineyard Haven Harbor and Sound Review
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6 Hour Sailing Tour of Vineyard Haven Harbor and Sound
Spanning an impressive 6 hours, the sailing tour of Vineyard Haven Harbor and Sound offers a comprehensive exploration of Martha’s Vineyard’s stunning coastal landscapes.
With a 5.0 rating based on 2 reviews, this tour is a must-try for visitors seeking to enjoy the island’s nautical charm.
The tour departs from the Black Dog Wharf, where you will be transported to the Tandemeer launch dock. Throughout the journey, guests can enjoy complimentary water, sodas, and snacks, while a la carte lunch and alcoholic beverages are also available.
Catering to a range of fitness levels, the tour is suitable for most travelers, though it’s not recommended for those with back problems or serious medical conditions.
Infants must sit on laps, and children under 13 are required to wear life jackets. The tour is a private experience, ensuring your group will be the only participants.
With operating hours from 9 AM to 3 PM, seven days a week, from May 23rd to September 20th, 2025, this sailing adventure is a must-do for anyone visiting Martha’s Vineyard.
Read our full review: 6 Hour Sailing Tour of Vineyard Haven Harbor and Sound Review
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3 Hour Sailing Tour of Vineyard Haven Harbor and Sound
For visitors seeking a more intimate sailing experience, the 3-Hour Sailing Tour of Vineyard Haven Harbor and Sound offers a captivating exploration of Martha’s Vineyard’s picturesque coastline. Operated by Island Sailing Tours, this private tour allows only your group to participate, ensuring a personalized and exclusive excursion.
During the 3-hour journey, you’ll navigate the tranquil waters of Vineyard Haven Harbor and Sound, taking in the stunning views and serene atmosphere. The tour includes water, sodas, and snacks, with a lunch option available for $15. Alcoholic beverages can also be ordered, providing the perfect accompaniment to your sailing adventure.
The tour departs from the Black Dog Wharf in Vineyard Haven, with a launch cost of $4 per adult and $2 per child. While not recommended for those with back problems or serious medical conditions, the tour requires a moderate level of physical fitness.
Children under 5 aren’t allowed, and those under 13 must wear life jackets. This sailing tour offers a delightful way to experience the natural beauty of Martha’s Vineyard.
Read our full review: 3 Hour Sailing Tour of Vineyard Haven Harbor and Sound Review
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4 Hour Sailing Tour of Vineyard Haven Harbor and Sound
Embarking on a captivating 4-hour private sailing tour, guests aboard the classic 60-foot (18-meter) ketch sailboat featured in “Trading Places” can explore the picturesque waters of Vineyard Haven Harbor, Nantucket Sound, and Vineyard Sound.
With a capacity for up to six passengers, this sailing experience offers an intimate and personalized adventure. Guests can enjoy complimentary water, soft drinks, and snacks, and have the option to bring their own alcoholic beverages (21+) or arrange for a catered lunch or dinner at an additional cost.
The tour begins and ends at the Black Dog Wharf in Vineyard Haven, accessible via the Vineyard Haven Launch dock for a $4 per person fee.
Operating daily from 10 AM to 5 PM between May 23 and September 20, 2025, this sailing tour requires moderate physical fitness and isn’t recommended for those with back problems or serious medical conditions.
Infants must sit on laps, and children under 14 must wear life jackets.
Read our full review: 4 Hour Sailing Tour of Vineyard Haven Harbor and Sound Review
Book now: Check availability
The Sum Up
Martha’s Vineyard offers a variety of sailing experiences to suit every interest. Whether you prefer a quick 2-hour tour or a more leisurely 6-hour excursion, you’ll be able to explore the island’s stunning harbors and sounds in comfort and style. With knowledgeable captains and well-equipped vessels, these sailing tours provide an unforgettable way to experience the natural beauty of this picturesque island destination.