Book A Room
Masks Required Indoors See Details

All tours begin and end at the historic Harbor View Hotel. With 130 years of history behind it, the historic Harbor View Hotel has been faithfully restored. Dubbed the Crown Jewel of Martha’s Vineyard, Harbor View Hotel was at the heart of the tourist trade that saved Edgartown after the dawn of the whaling industry. This grand hotel continues to attract a diverse guest list from the famous and far flung to families and couples looking for the perfect summertime escape. A local tour guide will meet you at the hotel, give you a brief history of the historic hotel and then take you on a private Island tour.

Private Tours Are Available Daily

Starting at 10am & 4pm

(Time is flexible based on availability)

Tour vehicle will be a 6-passenger van with a capacity of 6 people, plus the driver.

For groups of more than 6 people, we will utilize a larger transit van, and the price will be the base price + $100 for each additional person over 6 people. Capacity for the transit van is 13 passengers.

Cancellation Policy: Payment must be made in full at time of booking to secure the reservation. If you need to cancel, you will be required to notify Harbor View Hotel 10 days prior to the event in order to receive a full refund, less 10% transaction fee.

Towns You Will Explore:

Edgartown – Surreal, with a harbor and waterfront edged by stately white Greek Revival houses built by whaling captains. The Old Whaling Church stands tall thanks to six massive columns, and along with the Edgartown Harbor Lighthouse and the historic Harborview Hotel, Edgartown really belongs in a museum!

Oak Bluffs – We’ll walk among the story-book gingerbread cottages and see the oldest carousel in America. Here, if you grab the brass ring, you get a free ride! We’ll stroll along the lively little harbor or meander through Ocean Park.

Aquinnah – Travel to the end of the island to witness the red, clay cliffs of Aquinnah. Look down on the spectacular beaches and scour the horizon for the Elizabeth Islands off in the distance. If you’re feeling energetic climb to the top of the Gayhead lighthouse, which we moved a couple of years ago so it wouldn’t fall into the sea!

Menemsha – Onwards to the fishing village of Menemsha. We drive past rolling hills that run to the sea, dotted with sheep and horses and framed by the miles of British-style stone walls. We will have a picnic on the docks in Menemsha, where we will eat the freshest of fresh seafood while enjoying a complimentary bottle of wine.

West Tisbury – Home to the oldest store on-island; Alley’s General Store, which first opened in 1858. We’ll pick up some fresh fruit in the farm stand out back to snack on as we peruse the art at the Field Gallery across the road.

The African American Heritage Trail (Part of the Cultural Tour) – The African American Heritage Trail of Martha’s Vineyard is a physical entity comprised of 30 sites dedicated to the formerly unrecognized contributions made by people of African descent to the history of the island. At each of these sites, a descriptive plaque has been placed. Several of these plaques can be found in Oak Bluffs and a few in Menemsha and Edgartown along the tour.

Get Social

Share Your View with #HarborViewHotel

Plan an unforgettable trip to the beautiful island of Martha's Vineyard!