4 Hour Sailing Tour of Vineyard Haven Harbor and Sound

Exploring the enchanting waters of Martha’s Vineyard has never been easier thanks to this captivating 4-hour sailing tour. Setting sail from the historic Black Dog Wharf, passengers embark on a unique maritime adventure aboard a classic 60-foot ketch sailboat. Whether you’re seeking breathtaking vistas, opportunities to spot marine life, or simply a relaxing day on the waves, this private cruise offers an unparalleled experience. With complimentary snacks and beverages, and the option to bring your own fare, this tour caters to all tastes. But the real magic lies in the journey itself, as you learn about the captivating Vineyard Haven Harbor and the stunning Nantucket and Vineyard Sounds.

Key Points

• Enjoy a 4-hour private sailing cruise aboard a classic 60-foot ketch sailboat featured in "Trading Places" exploring Vineyard Haven Harbor, Nantucket Sound, and Vineyard Sound.
• Cruise accommodates up to 6 passengers and provides water, soft drinks, and snacks, with the option to bring your own alcoholic beverages and food.
• Depart and return to Black Dog Wharf in Vineyard Haven, with access via the Vineyard Haven Launch dock and a $4 fee per person.
• Tour operates daily from 10:00 AM to 5:00 PM from May 23 to September 20, 2025, with confirmation of start time required.
• Not recommended for those with back problems or serious medical conditions, as moderate physical fitness is required, and infants must sit on laps.

Tour Overview

The tour offers a 4-hour private sailing cruise in the picturesque waters of Martha’s Vineyard.

Guests will board a classic 60-foot (18-meter) ketch sailboat, featured in the film "Trading Places." This vessel can accommodate up to six passengers.

The tour explores Vineyard Haven Harbor, Nantucket Sound, and Vineyard Sound, providing ample opportunities to take in the stunning coastal scenery.

Passengers 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 departs and returns to the Black Dog Wharf in Vineyard Haven, with access via the Vineyard Haven Launch dock.

Included Amenities

Water, soft drinks, and snacks are all provided on the sailing tour.

Guests are welcome to bring their own alcoholic beverages if they’re 21 or older.

There’s also the option to have a catered lunch or dinner delivered for an additional cost.

Those who prefer to bring their own food can do so as well.

The sailing cruise accommodates up to six passengers, making it a perfect private outing.

With a variety of refreshment choices and flexible dining options, you can customize your sailing experience to suit your preferences.

Meeting and Pickup Details

Black Dog Wharf, located at 20 Beach St in Vineyard Haven, MA 02568, serves as the meeting point for this sailing tour.

Guests can access the Vineyard Haven Launch dock to reach the wharf, with a $4 per person fee payable to the launch driver.

The activity concludes at the same meeting point. Guests should confirm the start time with the local provider in advance, as the tour operates daily from 10:00 AM to 5:00 PM between May 23 and September 20, 2025.

This private tour is only for your group, so you’ll have the boat all to yourselves during the 4-hour sailing experience.

Sailing Schedule and Availability

This sailing tour operates daily from 10:00 AM to 5:00 PM between May 23 and September 20, 2025.

Guests should confirm the start time with the local provider in advance, as departure times may vary.

The classic 60-foot ketch sailboat, featured in the film "Trading Places," is available for private tours, suitable for up to six passengers.

Guests can explore Vineyard Haven Harbor, Nantucket Sound, and Vineyard Sound during the 4-hour cruise.

Confirmation is provided at the time of booking, and the tour concludes at the same meeting point at Black Dog Wharf in Vineyard Haven, Massachusetts.

Participant Requirements

The sailing tour isn’t recommended for travelers with back problems or serious medical conditions, as moderate physical fitness is required.

Infants must sit on laps, and children under 5 aren’t permitted. Kids under 14 must wear life jackets.

The tour isn’t wheelchair accessible, and participants should have a reasonable level of mobility. Pregnant women or those with other special needs should consult with the tour provider before booking.

The private sailing experience is open to groups of up to six passengers, ensuring an intimate and personalized adventure on the waters of Martha’s Vineyard.

Sailing Vessel Highlights

A classic 60-foot (18-meter) ketch sailboat, featured in the film "Trading Places," serves as the vessel for this captivating sailing tour of Vineyard Haven Harbor. This historic sailboat offers an authentic and immersive experience, transporting guests back in time as they explore the picturesque harbor and surrounding waters.

Vessel Specifications	Details
Length	60 feet (18 meters)
Type	Ketch
Appearance	Classic design, featured in "Trading Places"
Capacity	Suitable for up to six passengers

The spacious and well-appointed sailboat provides a comfortable and scenic platform from which to enjoy the serene and stunning vistas of Vineyard Haven Harbor, Nantucket Sound, and Vineyard Sound.

Explore Vineyard Haven and Sounds

On this captivating sailing tour, guests can explore the picturesque Vineyard Haven Harbor, as well as the adjacent Nantucket Sound and Vineyard Sound.

The classic 60-foot ketch sailboat, featured in the movie "Trading Places," provides an authentic maritime experience.

Sailing across the tranquil waters, guests will be treated to stunning views of the Vineyard’s coastline and landmarks.

The tour offers the chance to observe local marine life and birdwatching opportunities.

Whether seeking a relaxing afternoon or a thrilling adventure, this sailing excursion provides a unique way to experience the natural beauty and charm of Martha’s Vineyard.

Additional Considerations

What additional factors should prospective guests consider when booking this sailing tour?

First and foremost, the tour may not be suitable for those with back problems or serious medical conditions.

Plus, the tour isn’t wheelchair accessible, requiring a moderate level of physical fitness.

Lastly, while infants are welcome, they must sit on laps, and children under 14 are required to wear life jackets.

These considerations ensure the safety and comfort of all guests throughout the 4-hour private sailing cruise.

Frequently Asked Questions

Can I Disembark and Explore the Island During the Tour?

No, guests cannot disembark and explore the island during the 4-hour private sailing cruise. The tour is limited to the boat, and passengers must remain onboard throughout the duration of the activity.

Is There an Option to Extend the Duration of the Tour?

Yes, there is an option to extend the duration of the tour. Guests can coordinate with the local provider to arrange for a longer sailing excursion to explore more of Martha’s Vineyard and the surrounding waters.

Can I Bring My Own Food and Drinks on Board?

Yes, guests can bring their own alcoholic beverages (for those 21 and over) and they have the option to bring their own lunch or dinner, or request catered options for an additional cost.

How Stable Is the Sailboat in Rough Weather Conditions?

The sailboat is designed to be stable in rough weather conditions, with a sturdy 60-foot ketch frame that can handle choppy waters. However, guests should exercise caution and listen to the captain’s guidance during inclement weather for a safe and enjoyable experience.

Are There Any Age Restrictions for Children Participating in the Tour?

The tour has an age restriction – no children under 5 are allowed, and kids under 14 must wear life jackets. The tour is not recommended for travelers with back problems or serious medical conditions.

Recap

A private sailing tour of Martha’s Vineyard aboard a classic 60-foot ketch sailboat offers a unique and enchanting way to experience the island’s stunning natural beauty. Passengers can enjoy complimentary snacks and beverages as they explore the picturesque Vineyard Haven Harbor, Nantucket Sound, and Vineyard Sound, with opportunities to spot marine life along the way. This memorable maritime adventure provides breathtaking views and a truly one-of-a-kind experience in a serene and picturesque setting.