Tender Port: Ships anchor offshore and tender to Vineyard Haven or Oak Bluffs. Weather can affect tendering operations.
From the Logbook
The gingerbread cottages of Oak Bluffs look like a Victorian fever dream—pastel colors, elaborate trim, tiny porches where families have gathered for summer evenings since the 1860s. The Camp Meeting Association was once a Methodist revival site; now it's simply one of America's most distinctive architectural collections, preserved by residents who understand that history is worth maintaining.
I biked to the Gay Head Cliffs as the afternoon light turned the clay striations into a painter's palette—red, orange, white, gray, millions of years of geology exposed to the Atlantic wind. The Wampanoag people have lived here for 10,000 years. The Kennedy compound is a few miles away. Martha's Vineyard exists at the intersection of Indigenous history, American aristocracy, and tourists like me on rented bicycles.
The Cruise Port
Martha's Vineyard has no deep-water cruise terminal. Ships anchor offshore and tender passengers to either Vineyard Haven or Oak Bluffs—both walkable town centers with immediate access to shops, restaurants, and attractions.
Vineyard Haven: More year-round working town. Shops, galleries, ferry terminal.
Oak Bluffs: Tourist-oriented with gingerbread cottages, Flying Horses Carousel, and lively waterfront.
What to See
Oak Bluffs Gingerbread Cottages
The Camp Meeting Association's 300+ cottages form a unique neighborhood of ornate Victorian "gingerbread" architecture. Originally built for Methodist camp meetings in the 1860s-70s. Walk the narrow streets and admire the detail.
Edgartown
The island's most upscale town—white captain's houses, pristine streets, high-end shopping. The Edgartown Lighthouse and harbor views reward the 15-minute taxi ride or scenic walk.
Gay Head Cliffs (Aquinnah)
Dramatic multi-colored clay cliffs on the island's western tip. Wampanoag tribal land with cultural significance. Lighthouse and overlook accessible. About 30 minutes from Oak Bluffs by taxi.
Flying Horses Carousel
America's oldest platform carousel (1876) in Oak Bluffs. National Historic Landmark. Grab the brass ring for a free ride.
Lighthouses
The island has five historic lighthouses. Edgartown Harbor Light and Gay Head Light are most accessible for cruise visitors.
Getting Around
On Foot
Oak Bluffs and Vineyard Haven are walkable. The gingerbread cottages, shops, and beaches are accessible without transport.
Bicycle
Bike rentals available near tender landings. Paved bike paths connect towns. Pleasant way to see more of the island.
Taxi/Shuttle
Taxis serve the island. Edgartown and Gay Head require transport from tender landing. Ship excursions handle logistics.
Bus
Vineyard Transit Authority runs buses between towns. Inexpensive but timing may not suit short port calls.
Practical Information
Best Season
Summer (June-August) is peak season—crowded and expensive. Fall foliage cruises (September-October) offer stunning colors, fewer crowds, and comfortable temperatures.
Money
US Dollar. Credit cards accepted widely. ATMs in both towns. Prices are high—this is an affluent destination.
Weather
Maritime climate. Summers 20-27°C (68-80°F). Fall brings cooler temperatures and changeable weather. Layers recommended.
Port Map
FAQs
Which tender port is better?
Oak Bluffs offers the gingerbread cottages and carousel within walking distance. Vineyard Haven is more commercial. Both work well; check which your ship uses.
Can I visit the Kennedy compound?
The Kennedy Compound is in Hyannis on Cape Cod, not Martha's Vineyard. The Vineyard has Kennedy associations but no compound.
Is Martha's Vineyard worth a cruise stop?
For New England charm, historic architecture, and quintessential American summer culture—yes. Those seeking beaches or adventure may prefer other ports.
Author's Note: Martha's Vineyard rewards wandering. Skip the organized tour and explore the cottages and harbors at your own pace.