Cruise Port Guide · 2 cruises visit Oak Bluffs →
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.
A bespoke, small-group narrated tour sweeping across all six of Martha's Vineyard's distinct towns — culminating at the breathtaking Aquinnah Gay Head Cliffs. The island's entire story unfolds in one unhurried, expertly guided arc.
An expert-led 90-minute walking tour tracing the remarkable, largely untold story of African American life on Martha's Vineyard — from the Inkwell Beach enclave to the grand Victorian homes of the Highlands. Profound, moving, and utterly exclusive to this island.
Step inside one of America's most enchanting — and least-known — National Historic Landmarks: the 19th-century Methodist Camp Meeting Grounds, a fairytale labyrinth of 300 hand-painted gingerbread cottages radiating from the open-air Trinity Park Tabernacle.
Climb to the Iron lighthouse perched on East Chop bluff — nicknamed 'Telegraph Hill' — for sweeping 360° views of Nantucket Sound, the Elizabeth Islands, and the Oak Bluffs shoreline below. An icon that rewards those willing to walk 15 minutes beyond the harbour.
Whirl on hand-carved horses that have spun since 1876 — America's oldest platform carousel, a National Historic Landmark on Circuit Avenue. Grabbing the brass ring is one of New England's most endearing and genuinely rare bucket-list moments.
Settle onto the crescent of dark-sand shore beloved since the 1890s by African American luminaries — writers, politicians, artists — who made this Oak Bluffs cove their summer sanctuary. Calm, warm-for-New-England waters and a story as rich as any museum.
⚓ 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.