Things to do in Vineyard Haven, Massachusetts (MA): The Best Private Tours

September 22, 2021 Mikaela Didonna

Vineyard Haven is a community within the town of Tisbury, Massachusetts on Martha's Vineyard. It is listed as a census-designated place (CDP) by the U.S. Census Bureau with a population of 2,114 as of the 2010 census.
Restaurants in Vineyard Haven

1. Martha's Vineyard Private Sunset Sightseeing Cruises by Island Time Charters

Owen Park Way, Tisbury, MA 02568, USA Island Time Charters
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5.0 based on 13 reviews

Island Time Charters offers Martha's Vineyard sunset/cocktail cruises which are ideal for those who want to celebrate a special occasion such as bachelorette parties, proposals, first time island visitors or just want to celebrate life. We will pick you up by boat and take you on a private sightseeing harbor cruise while you comfortably enjoy the sunset sipping on your favorite cocktail. There are 3 different routes to choose from giving our guest the opportunity to experience different areas of Martha's Vineyard.

Inclusions: A fully fueled 26' Bennington Pontoon Boat, Soft drinks, towels, blankets ​

Exclusions: Can be arranged for an additional charge., Guest are encourage to their own snacks and BYO, Gratuities

Reviewed By Nina24k

This was the most memorable experience on the island. The boat was spectacular and our captain was incredible! I definitely would recommend this cruise. It was amazing! ????

2. Martha's Vineyard Leisure Sightseeing Cruise

Owen Park Way, Tisbury, MA 02568, USA Island Time Charters
Excellent
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5.0 based on 5 reviews

Island Time Charters offers Martha's Vineyard Sightseeing cruises which are ideal for those who want to celebrate a special occasion such as bachelorette parties, proposals, first time island visitors or just want to celebrate life. We will pick you up by boat and take you on a sightseeing cruise while you comfortably enjoy breathtaking views sipping on your favorite beverage. There are 3 different routes to choose from giving our guest the opportunity to experience different areas of Martha's Vineyard.

Inclusions: A fully fueled 26' Bennington Pontoon Boat, towels, blankets ​

Exclusions: Guest are encourage to their own snacks and BYO, Can be arranged for an additional charge., Gratuities

Reviewed By Nina24k

This was the most memorable experience on the island. The boat was spectacular and our captain was incredible! I definitely would recommend this cruise. It was amazing! ????

3. 4 Hour Sailing Tour of Vineyard Haven Harbor and Sound

Black Dog Wharf, 20 Beach St, Vineyard Haven, MA 02568, USA Island Sailing Tours

Sailing is the best way to see and experience Vineyard Haven Harbor, Nantucket Sound and Vineyard Sound. Tandemeer is a big beautiful 1980 classic 60' ketch made famous in the 1982 hit movie "Trading Places" with Eddie Murphy, Dan Akroyd and Jamie Lee Curtis. Fun in the Sun in Style.

Inclusions: Water, sodas & snacks included. Lunch & Alcoholic beverages available a la cart.

Exclusions:

Reviewed By 465gw

Four girlfriends and I took this charter during our recent annual MV vacation. I was a little concerned being in a close space because of COVID, but the the captain, Sequoia and his first mate (can’t remember her name) took precautions— masks and hand sanitizers so we felt comfortable. We brought all our own food, drinks and utensils for an added layer of comfort. It was a beautiful day and Captain Sequoia shared with us points of interest as we sailed. We were really just looking for a relaxing day on the water so we weren’t very interested but he was knowledgeable should that be something a group is interested in. The trip was three hours but it felt shorter and I could have used a few more hours on the water. Boat was a little bit on the old/not modern side but clean and spacious enough for our group and the boat staff. Would recommend for kids and adults looking for a few hours of fun on the ocean.

4. Private Half-Day Trip to Lake Tashmoo

Beach Road, Beach Rd, Tisbury, MA 02568, USA Marthas' Vineyard Leisure Charters

MV Leisure Charters is Marthas Vineyards Original power boat day sail. Helping create memories for 20 years, we can help you experience the island like a local. Captain Ed has spent over 40 years on the water, the last 30 off the shores of Martha’s Vineyard. Our boat is named Island Time. We love the name and the idea of "island time", which is to be unhurried, away from the pace and madness of mainland life. Our trips are chill, casual and relaxing. We appreciate and enjoy each group that I meet and take out. Island Time has played host to celebrities, weddings, engagements and engagement reunions, – but mostly it is a sanctuary for friends, families, couples and individuals to relax and enjoy the unique beauty of Martha’s Vineyard in a way that can only be done from the water.

Inclusions: Captain

Exclusions: Bottled water, Snacks, Alcoholic Beverages

Reviewed By Br5517

Knows where and when to go. Great experience in Menemsha: Lobster on the boat. Best ever. A great day exploring the island from the water.

5. 6 Hour Sailing Tour of Vineyard Haven Harbor and Sound

Black Dog Wharf, 20 Beach St, Vineyard Haven, MA 02568, USA Island Sailing Tours

Sailing is the best way to see and experience Vineyard Haven Harbor, Nantucket Sound and Vineyard Sound. Tandemeer is a big beautiful 1980 classic 60' ketch made famous in the 1982 hit movie "Trading Places" with Eddie Murphy, Dan Akroyd and Jamie Lee Curtis. Fun in the Sun in Style.

Inclusions: Soda/Pop, Bottled water, Snacks

Exclusions: Guests are welcome to BYO alcohol beverages for those over 21., Guests are welcome to BYO Lunch or we can arrange a catered lunch for an extra cost., Guests are welcome to bring their own dinner or we can arrange a catered dinner for an extra cost.

Reviewed By 465gw

Four girlfriends and I took this charter during our recent annual MV vacation. I was a little concerned being in a close space because of COVID, but the the captain, Sequoia and his first mate (can’t remember her name) took precautions— masks and hand sanitizers so we felt comfortable. We brought all our own food, drinks and utensils for an added layer of comfort. It was a beautiful day and Captain Sequoia shared with us points of interest as we sailed. We were really just looking for a relaxing day on the water so we weren’t very interested but he was knowledgeable should that be something a group is interested in. The trip was three hours but it felt shorter and I could have used a few more hours on the water. Boat was a little bit on the old/not modern side but clean and spacious enough for our group and the boat staff. Would recommend for kids and adults looking for a few hours of fun on the ocean.

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