Clear and practical sailing options abound in Martha’s Vineyard, with tours ranging from 2 to 6 hours departing from Black Dog Wharf.
The 2-hour harbor tour proves perfect for first-timers, while the 6-hour private sail (up to 12 people) offers the fullest experience of the island’s waters.
We especially love the 4-hour tour for its sweet-spot duration and the 3-hour lunch sail for its excellent value – combining great views with good food.
Every tour provides scenic coastal vistas and refreshment options.
Let’s explore our top sailing picks for Martha’s Vineyard.
Key Points
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The 2-hour sailing tour on a classic 60-foot ketch offers scenic views of the harbor, Nantucket Sound, and Vineyard Sound with a personalized experience for up to 6 passengers.
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The 6-hour private sailing tour on a 60-foot ketch can accommodate up to 12 people with a customizable itinerary and includes refreshments and the option to purchase lunch.
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The 4-hour private sailing tour on a 60-foot ketch provides a customizable experience exploring Martha’s Vineyard waterways, with refreshments included and the option to bring your own alcohol and meals.
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The 3-hour private sailing tour operated by Island Sailing Tours offers a scenic experience on the Tandemeer boat, with water, sodas, and snacks included, and the option to purchase lunch and alcoholic beverages.
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The sailing tours are available from May 23 to September 20, 2025, with departures from the Black Dog Wharf, and some tours may require a dock access fee.
2 Hour Sailing Tour of Vineyard Haven Harbor and Sound
For a captivating glimpse of Vineyard Haven’s storied waters, embark on a 2-hour sailing tour aboard a classic 60-foot ketch.
You’ll experience the charm of Vineyard Haven Harbor, Nantucket Sound, and Vineyard Sound, taking in views of the historic West and East Chop Lighthouses. This tour is ideal for first-time visitors and seasoned travelers alike.
Onboard, you’ll enjoy bottled water, snacks, soda, and even alcoholic beverages (bring your own if you’re 21+). You can also bring your own lunch or dinner, or arrange for catered meals at an additional cost.
With a maximum capacity of six passengers, you’ll enjoy a private and personalized experience.
The tour departs from the Black Dog Wharf in Vineyard Haven, with a $4 fee per person to access the Vineyard Haven Launch dock.
Be sure to confirm your start time with the local provider in advance, as the tour operates daily from May 23 to September 20, 2025, between 9 AM and 6 PM.
Read our full review: 2 Hour Sailing Tour of Vineyard Haven Harbor and Sound Review
Book now: Check availability
6 Hour Sailing Tour of Vineyard Haven Harbor and Sound
On a classic 60-foot (18-meter) ketch sailboat featured in “Trading Places,” you’ll embark on a 6-hour private sailing tour of Vineyard Haven Harbor, Nantucket Sound, and Vineyard Sound.
This tour accommodates up to 12 people, allowing you to explore the scenic waterways of Martha’s Vineyard with a customizable itinerary tailored to your group’s interests.
Throughout the journey, you’ll enjoy water, sodas, and snacks, with the option to purchase lunch and alcoholic beverages.
The tour departs and returns to the Black Dog Wharf in Vineyard Haven, MA, where you’ll access the boat via a launch.
Operating from May 23rd to September 20th, 2025, the tour runs daily from 9 AM to 3 PM, with the exact start time to be confirmed with the local provider.
While infants must sit on laps and children under 13 must wear life jackets, the tour isn’t recommended for those with serious medical conditions or back problems, as a moderate level of physical fitness is required.
Read our full review: 6 Hour Sailing Tour of Vineyard Haven Harbor and Sound Review
Book now: Check availability
4 Hour Sailing Tour of Vineyard Haven Harbor and Sound
Set out on a 4-hour private sailing tour of Vineyard Haven Harbor and Sound aboard a classic 60-foot (18-meter) ketch sailboat featured in “Trading Places.”
This personalized excursion allows you to explore the scenic waterways of Martha’s Vineyard with a customizable itinerary tailored to your group’s interests.
During your tour, enjoy refreshing soda, bottled water, and snacks. You’re welcome to bring your own alcoholic beverages and lunch or dinner if desired.
After disembarking at the Black Dog Wharf, you’ll need to pay $4 per person to ride the launch back to the meeting point.
Keep in mind that this activity isn’t recommended for travelers with back problems or serious medical conditions, and children under 5 aren’t permitted.
Life jackets are required for kids under 14. With a moderate fitness level, you can look forward to a memorable sailing experience on the waters of Vineyard Haven.
Read our full review: 4 Hour Sailing Tour of Vineyard Haven Harbor and Sound Review
Book now: Check availability
3 Hour Sailing Tour of Vineyard Haven Harbor and Sound
What can you expect from the 3-Hour Sailing Tour of Vineyard Haven Harbor and Sound? This private tour, operated by Island Sailing Tours, offers you the chance to explore the scenic waters around Martha’s Vineyard.
Starting from the Black Dog Wharf, you’ll launch to the Tandemeer boat, where you’ll enjoy water, sodas, and snacks throughout the 3-hour journey.
The tour is available daily from May 23rd to September 20th, 2025, with departures from 9:00 AM to 5:00 PM. While children under 5 aren’t recommended, kids under 13 must wear life jackets.
Lunch can be added for $15, and alcoholic beverages are available upon request.
With a total of 4 reviews and an average rating of 3.8, the tour has received positive feedback for the great service and beautiful boat. However, some travelers expressed concerns regarding the value for money.
Read our full review: 3 Hour Sailing Tour of Vineyard Haven Harbor and Sound Review
Book now: Check availability
Recap
Whether you’ve got a few hours or a full day, you’ll find a sailing tour in Martha’s Vineyard that suits your schedule. With options ranging from 2 to 6 hours, you can take in the stunning harbor and sound views at your own pace. So why not set sail and experience the beauty of this island paradise for yourself?