Top Martha's Vineyard Cruises & Sailing

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.

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.

Explore Martha’s Vineyard with this private, half-day tour. Get picked up at the location of your choice and set out on a tour that includes Oak Bluffs, Edgartown, and the Aquinnah Cliffs. See popular landmarks including the Flying Horses Carousel and check out local architecture from Victorian cottages to Greek Revival houses. Maximize time in Martha’s Vineyard with this private, customizable tour.

Visit Martha's Vineyard highlights on a 3 hour, small group tour from the Statute across Oak Bluffs Ferry Terminal. You’ll make the most of your time on the island as you check out Oak Bluffs, Edgartown, and the Aquinnah Cliffs, learning stories about island history and cultures along the way. This Martha’s Vineyard tour is limited to 14 people for personal service from the local guide, and it includes two 15 minute breaks to explore Menemsha and the Aquinnah Cliffs.

Discover a local’s eye view of Martha’s Vineyard—and see many of the island’s top landmarks in the space of a few hours—on this flexible, convenient bus tour. Meet your guide (a third-generation Martha’s Vineyard resident) in the afternoon, hop aboard, and set off. See local highlights ranging from the Aquinnah Cliffs and East Chop Lighthouse to the Menemsham fishing village, and learn about the history as you go.

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.

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.

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.

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)