Martha's Vineyard, a Massachusetts island, sits in the Atlantic just south of Cape Cod. A longtime New England summer colony, Locals refer to being on The Vineyard as “on island.” It's accessible only by boat or air. Known for its miles of beautiful beaches, Martha’s Vineyard invites relaxation. To the north, Oak Bluffs displays the island’s remarkable charm in its gingerbread cottages and the Flying Horses Carousel, a National Historic Landmark. Bring your camera to snap photos of the pristine sandy beaches, the sailboats and the lighthouses.

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  • Full Island Tour

    See each of the six towns on Martha’s Vineyard during this all-encompassing drive through the rolling countryside and along the picturesque coast.

    After departing from the pier, you will begin a drive around the island, which a British fisherman named in 1602 to honor his daughter and the dominant vegetation. Only six towns dot the triangular-shaped island of Martha’s Vineyard, and you will see all of them.

    You will pass Oak Bluffs’ colorful gingerbread cottages and the complementary gazebo at Ocean Park. For a historical perspective of Martha’s Vineyard, there is Edgartown, the island’s first colonial settlement, which has long been known for its stately white Greek Revival houses that whaling captains built along the harbor. Edgartown was also one of the backdrops for the movie “Jaws,” as was its Chappaquiddick Island Ferry.

    In time, you will drive toward the center of Martha’s Vineyard, where you will pass through two wonderfully rural towns: West Tisbury and Chilmark. Both are spectacularly scenic because of the surrounding state forests, rich farmland and gorgeous beaches.

    You will also pause for photos in the small fishing village of Menemsha and stretch your legs in Aquinnah at the island’s far western tip. The red clay cliffs here are so magnificently scenic and geologically important that they have been named a National Historic Landmark.

    Ahead lies one last destination—Vineyard Haven, one of New England’s busiest ports when sailing vessels carried cargo. In fact, in 1835 nearly 14,000 ships (that’s 38 a day!) stopped here.

    Please note: This tour is conducted in vans. It is primarily panoramic in nature with limited optional walking at any stops. Guests must be able to make their own way in and out of the van with limited assistance. There is no storage space on the vans so guests needing to use a wheelchair cannot be accommodated. Those with mobility concerns are cautioned to carefully evaluate their personal level of stamina and ability. Weather appropriate casual clothing; sunglasses; and flat, comfortable shoes are recommended. The tour timing and tour sequence may vary.

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  • The Best of the Island

    Sit back and enjoy a driving tour around the island of Martha’s Vineyard, passing through its most characteristic towns and picturesque coastal areas.

    After departing from the pier, you will begin a drive around the island, which a British fisherman named in 1602 to honor his daughter and the dominant vegetation. Much of Martha’s Vineyard remains free from development, and only a few towns dot the triangular-shaped island. Paradise has never looked so inviting as you will soon discover.

    You will see Oak Bluffs’ colorful gingerbread cottages and the more than 100-year-old Flying Horses Carousel, which is a National Historic Landmark. For a different historical perspective, there is Edgartown, the island’s first colonial settlement.

    The town has been the county seat since 1642 and has long been known for its stately white Greek Revival houses that whaling captains built along the harbor. Edgartown was also one of the backdrops for the movie “Jaws,” as was its Chappaquiddick Island Ferry.

    In time, you will drive toward the center of Martha’s Vineyard, where you will pass through two wonderfully rural towns: West Tisbury and Chilmark. Both are spectacularly scenic because of the surrounding state forests, rich farmland and gorgeous beaches. You will also pause for photos in nearby Menemsha, a small fishing village.

    Ahead lies one last destination—Vineyard Haven, one of New England’s busiest ports when sailing vessels carried cargo. In fact, in 1835 nearly 14,000 ships (that’s 38 a day!) stopped here.

    Please note: This tour is conducted in vans. It is primarily panoramic in nature with limited optional walking at any stops. Guests must be able to make their own way in and out of the van with limited assistance. There is no storage space on the vans so guests needing to use a wheelchair cannot be accommodated. Those with mobility concerns are cautioned to carefully evaluate their personal level of stamina and ability. Weather appropriate casual clothing; sunglasses; and flat, comfortable shoes are recommended. The tour timing and tour sequence may vary.

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  • The Perfect Vineyard Introduction

    Enjoy a leisurely drive through Oak Bluffs and Edgartown, two classic settings on the immensely scenic eastern coast of Martha’s Vineyard.

    After departing from the pier, you will soon begin driving through beautiful Oak Bluffs, which was known as Cottage City when settled in the 17th century. The name changed about 100 years ago to reflect the prominent view from the sea of oaks perched on the bluff.

    Today, Oak Bluffs is known more for its 300-plus gingerbread cottages from the 19th century that encircle an open-air tabernacle once used for revival meetings. The Flying Horses Carousel, a beloved National Historic Landmark, is another highlight, as is the Victorian-style gazebo in Ocean Park. Artists and writers have always found Oak Bluffs to be inspiring, and creative arts and crafts abound in the galleries and shops.

    Edgartown, the island’s first colonial settlement, offers a different perspective of Martha’s Vineyard. The town has been the county seat since 1642 and has long been known for its stately white Greek Revival houses that whaling captains built along the harbor. Other buildings predate the whaling era, such as the Vincent House, which was built in 1672.

    The lighthouse is also an Edgartown icon, and you will see it up close while pausing for photos. The town’s coastal setting looks so picture perfect that is was used as one of the backdrops for the movie “Jaws,” as was its Chappaquiddick Island Ferry. Following the drive through Edgartown, you will return to the pier.

    Please note: This tour is conducted in vans. It is primarily panoramic in nature with limited optional walking at any stops. Guests must be able to make their own way in and out of the van with limited assistance. There is no storage space on the vans so guests needing to use a wheelchair cannot be accommodated. Those with mobility concerns are cautioned to carefully evaluate their personal level of stamina and ability. Weather appropriate casual clothing; sunglasses; and flat, comfortable shoes are recommended. The tour timing and tour sequence may vary.

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  • Historic Walking Tour of Oak Bluffs

    Stroll the enchanting streets of Oak Bluffs, stopping to admire the historical landmarks and learn about the town’s founding.

    Departing from the pier on foot, you will soon find yourself walking through beautiful Oak Bluffs, which was known as Cottage City when settled in the 17th century. The name changed about 100 years ago to reflect the prominent view from the sea of oaks perched on the bluff. While it is the second smallest of the six island towns geographically, it is the largest in population on a year round average, only second during the summer season.

    Today, Oak Bluffs is known more for its 300-plus gingerbread cottages from the 19th century that encircle an open-air tabernacle once used for revival meetings. The architectural style of the cottages is Carpenter Gothic, which is characterized by a liberal use of turrets, spires and pointed arches, often without a logical relationship to the remainder of the cottage.

    The oceanfront Overton House is another significant historical building, but more for its past guests than for its architecture. The original owner, Joseph Overton, was a Harlem labor leader and opened his house to the likes of Martin Luther King, Jr., Jesse Jackson and Harry Belafonte. It’s no wonder that the Overton House was known as the Summer White House of the Civil Rights Movement.

    The Flying Horses Carousel, a beloved National Historic Landmark, is another highlight on the walking tour. Constructed in 1876, it’s America’s oldest carousel and has been lovingly restored with such attention to detail that the horses’ manes and tails are real horsehair.

    After approximately two hours, you will find yourself back at the pier, having gained a greater understanding of Oak Bluffs’ history and architecture.

    Please note: This tour is a walking tour that includes approximately 2 hours of easy to moderate walking. There will be some uneven surfaces and a few steps to negotiate. The tour is not available to wheelchair guests or those with walking difficulties. Weather appropriate casual clothing; sun cap; sunglasses; a bottle of water from the ship; and flat, comfortable walking shoes are recommended. The tour timing and tour sequence may vary.

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