Practical boat excursions around Martha’s Vineyard offer visitors efficient ways to see the island’s historic harbors and scenic shores. The most worthwhile options include 2-hour sailing trips from Vineyard Haven (perfect for budget travelers), and half-day private cruises (ideal for families wanting flexibility). Our favorite mid-range choice is the 3-hour tour – it provides the right balance of sightseeing and comfort, with included refreshments and the ability to customize your route. For maximum value, the 4-hour excursions deliver excellent views of both the coastline and Nantucket Sound while including meal options. Let’s explore the top-rated boat tours worth your time and money.
Good To Know
- Sailing tours on a classic 60-foot ketch vessel, featured in “Trading Places,” offer 2-hour, 3-hour, 4-hour, and 6-hour experiences around Vineyard Haven Harbor.
- The 2-hour sailing tour accommodates up to 6 passengers and includes bottled water, snacks, and soda, with alcohol allowed for those 21 and older.
- The 3-hour sailing tour offers a customizable itinerary, water, sodas, snacks, and an optional $15 lunch add-on, but is not recommended for those with back or heart issues.
- The 4-hour sailing tour can accommodate groups of up to 6 and includes water, soft drinks, and snacks, with catered meals available for an additional cost.
- The 6-hour private sailing cruise can accommodate up to 12 participants, with a customizable itinerary, water, sodas, snacks, and options to purchase lunch and alcohol.
2 Hour Sailing Tour of Vineyard Haven Harbor and Sound
The 2-hour sailing tour of Vineyard Haven Harbor, Nantucket Sound, and Vineyard Sound aboard a classic 60-foot (18-meter) ketch offers visitors a chance to experience the beauty and history of Martha’s Vineyard from the water.
This vessel, featured in the movie “Trading Places,” can accommodate up to six passengers, providing an intimate and personalized sailing experience. Along the way, guests will enjoy scenic views of the historic West and East Chop Lighthouses.
The tour includes bottled water, snacks, and soda/pop, and guests are welcome to bring their own alcoholic beverages if they’re 21 or older. Visitors can also arrange for catered meals for an additional cost or bring their own lunch/dinner.
The tour departs from Black Dog Wharf in Vineyard Haven, with guests taking a short launch ride to the sailing vessel, Tandemeer.
Operating from May 23 to September 20, the tour runs daily from 9 AM to 6 PM, with the exact start time confirmed with the local provider in advance.
While the experience is suitable for most, it’s not recommended for those with back problems, heart issues, or serious medical conditions. Children under 5 aren’t permitted, and those under 14 must wear life jackets.
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
With the classic 60-foot (18-meter) ketch sailboat featured in the movie “Trading Places” as the vessel, visitors can embark on a 6-hour private sailing cruise around Vineyard Haven Harbor, Nantucket Sound, and Vineyard Sound.
The tour accommodates up to 12 people and provides water, sodas, and snacks. Lunch and alcoholic beverages can be purchased additionally. The itinerary is customizable based on the group’s interests.
The meeting point is the Black Dog Wharf in Vineyard Haven, where participants can access the launch dock and request transport to the sailboat, Tandemeer.
The tour operates from May 23 to September 20, with daily availability from 9 AM to 3 PM. Guests are advised to confirm the start time with the local provider in advance.
While the tour isn’t wheelchair accessible, it’s located near public transportation. Infants must sit on laps, and children under 13 must wear life jackets.
This moderately physically demanding activity isn’t recommended for those with serious medical conditions or back problems.
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
An exhilarating 3-hour sailing adventure awaits visitors to Martha’s Vineyard as they embark on a tour of Vineyard Haven Harbor and the surrounding Nantucket Sound.
Aboard a classic 60-foot ketch sailboat from 1980, guests can soak up the stunning coastal views and experience the thrill of sailing in this picturesque setting. The tour, which has a 3.8-star rating based on 4 reviews, allows for a customized itinerary based on the group’s interests.
Included in the tour are water, sodas, and snacks, with an optional $15 lunch add-on. Alcoholic beverages are also available for purchase.
Participants will meet at the Black Dog Wharf in Vineyard Haven and take a short launch ride to the tour boat. The experience isn’t recommended for travelers with back or heart problems, and children under 5 aren’t permitted.
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
For an exhilarating 4-hour private sailing experience, visitors can embark on a comprehensive tour of Vineyard Haven Harbor, Nantucket Sound, and Vineyard Sound aboard a classic 60-foot (18-meter) ketch sailboat featured in the film “Trading Places.”
Designed for groups of up to six people, this tour offers a unique opportunity to explore the picturesque waterways of Martha’s Vineyard. Guests can enjoy water, soft drinks, and snacks provided, and they’re welcome to bring their own alcoholic beverages if they’re 21 or older.
The tour also provides the option to arrange a catered lunch or dinner for an additional cost. To participate, visitors must meet at the Black Dog Wharf in Vineyard Haven, where they’ll board the Vineyard Haven Launch dock, paying $4 per person.
The tour concludes back at the meeting point. Operating from May 23 to September 20, this sailing adventure is available daily from 10 AM to 5 PM, with guests advised to confirm the start time with the local provider in advance.
Read our full review: 4 Hour Sailing Tour of Vineyard Haven Harbor and Sound Review
Book now: Check availability
Frequently Asked Questions
What Are the Age Restrictions for the Boat Tours?
Most boat tours and cruises don’t have strict age restrictions, but they may require children to be accompanied by an adult. Some tours may have minimum age requirements for safety reasons. It’s best to check with the tour operator beforehand.
Do the Tours Accommodate Passengers With Disabilities?
Most boat tour companies strive to accommodate passengers with disabilities. They’ll typically offer special assistance to help those with mobility, hearing, or vision impairments board and enjoy the tour safely and comfortably.
Can We Bring Our Own Food and Drinks on the Tours?
Passengers are generally allowed to bring their own food and drinks on boat tours, though some operators may have restrictions or additional fees. It’s best to check with the tour company beforehand to understand their specific policies.
Are There Any Additional Fees or Charges for the Tours?
Most boat tour and cruise providers allow passengers to bring their own food and drinks, but there may be additional fees or charges for things like alcoholic beverages, special events, or private/group bookings. It’s best to check with the specific company for their policies.
How Can We Ensure Availability for the Tours During Peak Seasons?
To ensure availability for tours during peak seasons, it’s best to book well in advance. Many companies offer online reservations to secure spots, and some may have flexible cancellation policies to accommodate last-minute changes.
The Sum Up
Martha’s Vineyard offers an array of boat tours and cruises to suit every traveler’s preferences. Whether you’re seeking a quick 2-hour sail or a more comprehensive 6-hour voyage, the island’s waters provide a scenic backdrop for discovering its charm. These tours deliver an immersive experience, allowing visitors to fully appreciate the island’s coastal beauty and rich maritime heritage.