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.
What to expect
Board a comfortable van steps from the Oak Bluffs pier and settle in as your knowledgeable local guide weaves history, folklore, and insider color through every town from Vineyard Haven to Edgartown. The highlight is a leisurely stop at the Aquinnah Cliffs — ochre and rust-red bluffs plunging toward the Atlantic, sacred to the Wampanoag people. With only 14 guests, questions are welcomed and the itinerary breathes. You're back in Oak Bluffs with time to spare.
Good to know
Tours depart from 1 Seaview Avenue, Oak Bluffs — a short walk from the ferry/cruise tender dock. Pre-book directly via the website; summer dates fill quickly. The 2.5–3 hr duration fits comfortably within a typical all-aboard window. Wear comfortable shoes for the Aquinnah stop.
Sail there
Luxury cruises that call at Oak Bluffs — book through us, the fare is identical and your concierge stays on your side.
More to do in Oak Bluffs
- Martha's Vineyard African American Heritage Trail: Oak Bluffs Walking Tour
- Martha's Vineyard Gingerbread Cottages & Camp Meeting Grounds Self-Guided Immersion
- East Chop Lighthouse & Blufftop Panorama: Oak Bluffs' Hidden Crown
- Flying Horses Carousel: A Ride on America's Oldest Platform Carousel
- Inkwell Beach Morning: Oak Bluffs' Most Iconic, History-Laden Shore