Join us for a journey through Martha’s Vineyard where every town tells its own tale. From the cozy streets of Vineyard Haven to the historic vibes of Chilmark and West Tisbury, we’ve got the local scoop. Picture yourself at the iconic Gay Head Lighthouse, strolling through Edgartown’s whaling history or exploring Oak Bluffs’ quirky gingerbread houses. Let’s make memories, one charming spot at a time.

Tour Itinerary & Highlights

Note: This is a suggested itinerary – we can customize based on your preferences.

  • Vineyard Haven Delights: A cozy seaport bustling with local shops, eateries and a historic lighthouse guiding sailors home.
  • Majestic Aquinnah Cliffs: Feel the ocean breeze atop breathtaking cliffs, offering picturesque views. 
  • Gay Head Lighthouse Whispers: Stand close to history at the 1799 lighthouse, where every sunset tells a story.
  • Edgartown’s Past: Stroll through streets lined with elegant whaling captains’ homes, where history meets maritime charm.
  • Oak Bluffs Adventure: Wander among vibrant gingerbread cottages and discover unique shops and galleries in this lively town.

More Information:

  • The duration of the tour is four (4) hours.
  • This tour is offered all year round, seven (7) days a week.
  • You can customize the starting location of the tour to fit your schedule.
  • All stops, timing and inclusions of the tour are dependent on traffic and weather conditions.
  • Want to see something specific? We love to personalize our tours to suit your specific interests and passions!