The 9 Best Private Tours in Martha's Vineyard, Massachusetts (MA)

November 20, 2021 Stefan Strunk

Yes, getting there is a bit of a project. But vacationers have been braving the ferry for years, and this tiny island off Cape Cod remains one of the most popular and picturesque destinations in New England. Among the island's towns, you're sure to find the Vineyard that's right for you. With stately Greek revival houses dating back to the whaling era of the early 19th century, Edgartown is a seaside village of boutique shopping and pristine harbor views. For more of a "beach town" feel, Oak Bluffs has the Flying Horses carousel, an arcade and an easy walk to the beach, plus the history and charm of the "gingerbread" houses in the Methodist campgrounds. Vineyard Haven offers visitors a blend of both. For a real retreat, Chilmark/Aquinnah is the place to get away from it all. In the off-season, the island is quieter and far less crowded, but the shore is always beautiful. Whenever you visit, leave your car behind! Cabs are plentiful and greet the incoming ferries to help you reach your destination. Most visitors prefer to explore the island on a bicycle, scooter or tourist-friendly public buses.
Restaurants in Martha's Vineyard

1. AFAM History Tour

1 Seaview Ave, Oak Bluffs, MA 02557, USA HomeGrown Tours
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5.0 based on 1 reviews

The af/am history tour is one of the most treasured tours here. We will visit most or all of the sites that have to do with af/am history and heritage. There are 27 sites to visit. We will see the Rebecca Amos farm, The Shearer Cottage, the Denniston House of worship, The Highlands, and many many others. We will also visit places that are not listed on the trail.... This tour can take 2 hours or up to 5 hours depending on what you would like to see...

Inclusions: Bottled water, Snacks, Air-conditioned vehicle, Private transportation, Screen to see what certain sites looked like in the 1800s

Exclusions:

Reviewed By Ebony3052404

Very informative but wish we could have time for more questions and answers. But she was thorough and enjoyed it. Can someone contact me so I can tip her? Unfortunately we didn't have cash and I couldn't find her in Venmo. Her tip is well deserved and I whirls really like to give it to her

2. 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! ????

3. Martha's Vineyard Leisure Sightseeing Cruise

Owen Park Way, Tisbury, MA 02568, USA Island Time Charters
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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! ????

4. Boston to Woods Hole & Martha's Vineyard Ferry Private Chauffeur Service

Elite Limo Boston

Door-to-door Boston to Woods Hole Martha's Vineyard Ferry "flat rate" service is easy and affordable. Forget about dealing with traffic and paying for parking, when you can book our Point to Point service for close to the same cost. Time is money, start traveling in style and get some work done on the way or just enjoy the scenery.

Inclusions: Base fare, Gratuities - a 20% driver gratuity is included in the base rate., 3.00 STC fee, Bottled water, We always try to arrive 15 minutes early in case we run into traffic at no additional charge., Some vehicles are equipped with:, Free WiFi, Tablets for your entertainment. go to TripAdvisor's Travel Guide to find things to do or watch HBO, Netflix or Listen to Spotify or Pandora, Phone Chargers, Leather Seating, Tinted Windows, Divider or blinds for Privacy, Flat Panel TVs with AM/FM/CD/DVD/MP3 stereo w/ available 3.5mm input or Bluetooth Audio, Dual Zone Heating and Air Conditioning.

Exclusions: For service between the hours of 12:00am and 5:00am please add an additional $25.00, Child safety seats are available upon request for an additional $30 each., All applicable additional charges will be itemized on your receipt. Stop time, Wait time, Holiday surcharges, Tolls, Taxes, Parking, and a 7% fuel surcharge. The Voucher amount will be deducted from your total bill, Ferry tickets to Martha's Vineyard

Reviewed By dmsibert08

My goodnes it was all good! Dave was amazing and knew his stuff. The views were awesome! I enjoyed it!

5. Private tour of Martha's Vineyard with lunch included

Discover Africa

Originally inhabited by the Wampanoag people, Martha's Vineyard was known in the Massachusett language as Noepe, or "land amid the streams". In 1642, the Wampanoag numbered somewhere around 3,000 on the island. By 1764, that number had dropped to 313.[10] A smaller island to the south was named "Martha's Vineyard" by the English explorer Bartholomew Gosnold, who sailed to the island in 1602. The name was later transferred to the main island. It is the eighth-oldest surviving English place-name in the United States. English settlement began with the purchase of Martha's Vineyard, Nantucket, and the Elizabeth Islands by Thomas Mayhew of Watertown, Massachusetts from two English "owners". He had friendly relations with the Wampanoags on the island, in part because he was careful to honor their land rights. His son, also named Thomas Mayhew, began the first English settlement in 1642 at Great Harbor (later Edgartown, Massachusetts)

Inclusions: Lunch, Bottled water

Exclusions: Tips

6. Oak Bluffs, Martha's Vineyard Audio Tour

Ocean Park, 2 Seaview Ave, Oak Bluffs, MA 02557, USA Knockabout Travel

Knockabout Travel takes you to Martha's Vineyard, with this self-paced audio tour of the most popular town on the island. Discover the origin story of how Oak Bluffs developed from its humble beginnings as a religious camp into a summer destination for business moguls, celebrities, and US Presidents. On the tour, we discuss the development of the Martha's Vineyard Camp Meeting Association, home to the "campground" and the famed gingerbread cottages. Learn how the area around Ocean Park and Circuit Avenue was developed with tourism in mind, and how that conflicted with the original Methodist campers. Along the route, you will be introduced to some of the finer points and lesser-known history of the town, as well as places to grab lunch or a drink. The tour includes 45 minutes of narration and can be completed at a leisurely pace in about 90 minutes including brief stops at various points of interest. Audio easily streams from an embedded web player - no need to download files!

Inclusions: Audio Files (streaming or download available), GPS Guided Interactive Maps, Self-Guided Audio Tour, Begin Tour at Your Leisure

Exclusions: Audio Device (Smartphone), Headphones, Food/Drink

7. 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.

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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.

8. 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.

9. 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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