3 Hour Sailing Tour of Vineyard Haven Harbor and Sound

Sailing enthusiasts and families alike can embark on a captivating 3-hour tour of Vineyard Haven Harbor and Sound offered by Island Sailing Tours. Departing from the charming Black Dog Wharf, this scenic journey showcases the region’s stunning natural beauty and historic waterfront sights. Guests can relax while enjoying complimentary snacks and beverages, with an optional lunch available. What’s more, the knowledgeable crew provides educational insights, making this an adventure that’s both relaxing and enlightening. But the true highlight? The breathtaking views that’ll leave you wondering what other hidden gems this picturesque island has in store.

This experience made our list of the 9 Best Tours In Marthas Vineyard.

Good To Know

• Scenic 3-hour sailing tour around Vineyard Haven Harbor and Sound, operated by Island Sailing Tours.
• Tour includes complimentary water, sodas, and snacks; optional $15 lunch available for purchase.
• Departure from Black Dog Wharf, with return to the same location after the tour.
• Recommended to arrive a few minutes early and bring cash for the $4 adult and $2 child launch fee.
• Tour offers views of local landmarks, marine life, and the natural beauty of Martha’s Vineyard.

Overview of the Tour

The 3 Hour Sailing Tour of Vineyard Haven Harbor and Sound offers visitors a chance to explore the picturesque waters surrounding Martha’s Vineyard.

Operated by Island Sailing Tours, this tour provides a unique opportunity to experience the island’s scenic coastline from the comfort of a sailing vessel. Lasting approximately 3 hours, the tour takes guests through the tranquil Vineyard Haven Harbor and into the waters of the nearby sound, offering stunning views of the harbor, local landmarks, and the island’s natural beauty.

With water, sodas, and snacks included, and the option to add a $15 lunch, this tour is an ideal way to spend an afternoon on the water.

Inclusions and Pricing

Alongside the scenic sailing experience, Island Sailing Tours offers a variety of inclusions and pricing options.

The tour includes complimentary water, sodas, and snacks for all passengers. Guests can also opt for a $15 lunch, and alcoholic beverages are available for purchase at varying prices.

Plus, a $4 launch fee per adult and $2 per child (cash only) is required to access the docks and embark on the tour.

Meeting and Pickup Details

Passengers embark on the 3 Hour Sailing Tour of Vineyard Haven Harbor and Sound at the Black Dog Wharf, located at 20 Beach St in Vineyard Haven, MA 02568.

The tour returns to the same meeting point. Participants should walk to the Vineyard Haven Launch dock and ask the driver for the Tandemeer boat.

The launch cost is $4 per adult and $2 per child, payable in cash only. Passengers are advised to arrive at the meeting point a few minutes early to ensure a timely departure.

Schedule and Availability

From May 23rd to September 20th, 2025, the 3 Hour Sailing Tour of Vineyard Haven Harbor and Sound operates daily, with departures scheduled from 9:00 AM to 5:00 PM.

Guests are advised to confirm the exact start time with the local provider in advance, as tour times may vary.

The tour runs on the following schedule:

1. Monday – Sunday: 9:00 AM – 5:00 PM
2. No tours on major holidays
3. Tours may be canceled due to inclement weather or unforeseen circumstances

It’s recommended to book the tour in advance to secure your preferred date and time.

Health and Safety Guidelines

Guests receive confirmation of the health and safety guidelines at the time of booking.

The tour isn’t recommended for individuals with back problems, heart issues, or serious medical conditions. Children under 5 aren’t permitted, and kids under 13 must wear life jackets.

The tour isn’t wheelchair accessible, and a moderate level of physical fitness is required. Infants must sit on laps.

The tour is private, with only your group participating. Guests should confirm the start time with the local provider in advance.

Customer Experiences

According to customer reviews, the sailing tour has received generally positive feedback.

Three customers in particular have shared their experiences:

1. Victoria_H praised the "wonderful sunset cruise with great food and views" in her August 2023 review.

2. Jeano-H commended the crew for "catering to needs and providing excellent service" in September 2021.

3. However, Robin_Y felt the charter "did not provide value for the price paid" and wouldn’t recommend it, in an August 2021 review.

Exploring Vineyard Haven Harbor and Sound

As the sailing tour departs from Black Dog Wharf, passengers are treated to a tranquil journey through the picturesque Vineyard Haven Harbor.

The boat glides past historic waterfront homes, docks, and marinas, offering a unique perspective of the charming coastal town.

Heading out into the Vineyard Sound, the tour provides stunning views of the Elizabeth Islands and the open ocean beyond.

Along the way, the knowledgeable crew shares insights about the local marine life, history, and points of interest.

With the gentle breeze and the rhythm of the waves, the 3-hour sailing tour allows visitors to enjoy the serene beauty of Martha’s Vineyard’s harbor and sound.

Things To Known

Are Dogs Allowed on the Tour?

The tour provider does not specify whether dogs are allowed on the sailing tour. Customers are advised to contact the local provider directly to inquire about their pet policy before booking.

Is the Boat Equipped With Restrooms?

The boat has no onboard restrooms. Passengers will need to use the facilities at the meeting point before boarding. As this is a private tour, there are no public restrooms available during the sailing portion.

Can I Bring My Own Alcoholic Beverages?

No, passengers cannot bring their own alcoholic beverages on this tour. Alcoholic drinks are available for purchase, with pricing varying based on the selection. The provider only allows their own alcoholic offerings to be consumed on the tour.

How Many Passengers Can the Boat Accommodate?

The boat can accommodate up to 6 passengers. According to the tour overview, it’s a private tour, so only your group will participate.

Is the Tour Suitable for Those With Motion Sickness?

The tour may not be suitable for those prone to motion sickness. The provider notes it’s not recommended for individuals with back problems, heart issues, or serious medical conditions, which could include susceptibility to seasickness.

Sum Up

Sailing through Vineyard Haven Harbor and Sound offers a serene and picturesque experience. Guests can enjoy stunning views, educational insights, and complimentary refreshments. This 3-hour tour from Island Sailing Tours is an ideal way to explore the beauty of Martha’s Vineyard, and it’s suitable for families with children over 5. The tour’s convenient departure from Black Dog Wharf makes it easily accessible for visitors.