Cruise Port Guide · 4 cruises visit Marthas Vineyard →
The bucket-list things to do — and the private, expert-led way to do each.
Here’s the bucket list for your day ashore: the most extraordinary thing to do at each stop, and the private, small-group, or expert-led way to make it yours — your own pace, real access, none of the crowd.
Stand at the dramatic multicolored clay cliffs of Aquinnah — Martha's Vineyard's most breathtaking natural wonder — and climb the Gay Head Lighthouse for panoramic Atlantic views. A bucket-list moment that defines the island.
Trace 400 years of African American history across Martha's Vineyard with an expert guide — from the island's role in the abolition movement to its legendary status as a Black summer haven. One of New England's most profound cultural pilgrimages.
Board a private charter and glide past Edgartown's storied waterfront — lighthouse, harbour mansions, yacht-lined docks and the wild shores of Chappaquiddick — for the most elegant perspective Martha's Vineyard has to offer.
Spin on America's oldest platform carousel — a National Historic Landmark since 1876 — then stroll the fairy-tale streets of the Methodist Campground, lined with 300 hand-painted Victorian gingerbread cottages. Pure, irreplaceable Americana.
Ride a rugged over-sand vehicle across the wild, wind-sculpted barrier beach of Chappaquiddick to the remote Cape Poge Lighthouse — a wilderness adventure that most visitors never reach. Osprey, shorebirds, and pristine Atlantic coastline await.
Settle into Menemsha — Martha's Vineyard's legendary working fishing village — for a classic New England clambake of steamed lobster, clams, and corn, eaten literally on the beach as the sun drops into Vineyard Sound. The island's most iconic culinary ritual.
⚓ Your bucket-list concierge
Tell us your sailing and we'll send the bucket list for every port — the most extraordinary thing to do at each, and the private, expert-led way to make it yours.
No spam. The honest plan, even when it says skip the ship’s tour.