Top Martha's Vineyard Private Sightseeing Tours

An excellent choice for first-time visitors to Martha’s Vineyard, this tour is led by a third-generation local and offers a good overview of the island. Listen as your host shares stories and history and even passes around items such as shells and wool for you to see and feel. There’s time for photos, shopping, and snacks along the way.

We love to give our customers a real experience of Martha's Vineyard we cover it all. We take time with you leaving you enough time to shop, explore and walk around the Island. Plus we’ll stop and have a harbor side picnic! You’ll snack on the freshest seafood and sip on your complimentary wine!

Explore Martha’s Vineyard on your own terms and see the sites that interests you with this self-guided audio driving tour. Enjoy the flexibility to travel at your own pace and schedule, hands-free functionality, and offline access. Includes map, full itineraries, travel tips, professionally narrated audio, videos, text, and hidden gems.

Go at your own pace, anytime! It's your tour. On our historic walking tour of the Edgartown, you will see the iconic sights and secret gems including the whaling church, the oldest buildings, underground railroad locations, the Carnegie library, filming sights of Jaws, the lighthouse and much more. And I’ll tell you this town’s stories of the settlers, natives, whaling, ghosts, myths and legends, the Kennedy’s, it’s history and much more. Pro narration and production! Best deal in town :)

If you have limited time but still want to see all that Martha’s Vineyard has to offer, then book this private sightseeing tour. You’ll pass through the six island towns with a local guide, who will tell you all about the area, and allow time for plenty of photo stops. You’ll also be driven from place to place in a comfortable, luxury minivan.

Experience Vineyard Haven Harbor, Nantucket Sound, and Vineyard Sound on this sailing tour of Martha's Vineyard. Hop aboard a classic 60-foot (18-meter) ketch (a two-masted sailboat), which was made famous in the hit movie "Trading Places.” Along the way, take in views of the historic West and East Chop Lighthouses and soak up the sun while on the water.

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 is GPS guided with turn-by-turn directions and audio tracks that play automatically at the right time and place so you're free to simply enjoy the tour.

Offering private tours of beautiful Marthas' Vineyard Island specifically for small groups of people (4 max) looking for a truly unique experience. Relax and enjoy this narrated tour as we drive along the scenic coast, stop for photos, talk about famous people, learn about local history, all while passing through the 3 down-island towns. For those travelers coming over for the day with limited time, who would like to see the down Island towns, this is the perfect tour.

Go sailing in Martha’s Vineyard with this half-day private tour. Explore Nantucket Sound by water during this outdoor adventure aboard a 1980 classic 60-foot ketch sailboat. Experience the Martha’s Vineyard tradition of sailing and see local landmarks from a fresh perspective. Customize the itinerary according to your interests and maximize time in Martha’s Vineyard.

Explore some of the best spots for fall foliage on the East Coast, including Acadia, Shenandoah, and Great Smoky Mountains national parks, Kancamagus Highway, Blue Ridge Parkway, Bar Harbor, Newport, Salem, and the Freedom Trail, with this self-guided driving tour. Enjoy the flexibility to travel at your own pace, with hands-free functionality, turn-by-turn directions, and offline access. Includes full itineraries, travel tips, audio guide, and text.

Go sailing in Martha’s Vineyard with this 6-hour private cruise for you and your group of up to 12 people. Climb aboard the classic 60-foot (18-meter) ketch sailboat made famous by the movie “Trading Places” and soak up the sun, sea, and views as you sail around Vineyard Haven Harbor, Nantucket Sound, and Vineyard Sound.

Go sailing in Martha’s Vineyard with this 4-hour private cruise for you and your group of up to six people. Climb aboard the classic 60-foot (18-meter) ketch sailboat made famous by the movie “Trading Places” and soak up the views as you sail around Vineyard Haven Harbor, Nantucket Sound, and Vineyard Sound.

Tour apx time is 5-6 hr. Max 4 ppl. Price is per person 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)