MA Martha’s Vineyard Tour

3 Day Adventure




  • Street Biking
  • Wellness


  • Intermediate
  • Expert









  • Two nights lodging
  • Two dinners
  • Two breakfasts
  • Welcome refreshments
  • Three days of guided cycling
  • Free bike and helmet rental
  • Two dedicated guides
  • Van support
  • Edgartown walking tour
  • Luggage transport to and from ferry docks
  • Daily snacks and cold drinks
  • Tax and gratuities for meals and side excursions
  • Cycling maps and cue sheets
  • Chappaquiddick ferry tickets
  • Bike ferry tickets (in season)
  • Waterbottle

Packing List

  • 2 pairs of bike shorts so you can alternate every day
  • 1 pair of quick dry pants for cycling
  • 2-3 pairs of biking socks + 1 pair of waterproof socks
  • Bike shoes
  • 2 quick dry cycling jerseys + one long-sleeved jersey if the weather is colder
  • Arm warmers, leg warmers
  • Rain gear, including a helmet cover, shoe covers, pants, and jacket
  • Cycling gloves
  • Sunglasses
  • Bandana

Lodging Options




Meals Included

Private Rooms


Meet at Ocean Park, Oak Bluffs at 1:45 pm on Day 1. This park is visible from the ferry dock – look for the large gazebo. The GFA van will travel over on the 12:00 ferry from Woods Hole. You may take that ferry or an earlier one if you wish for more time in Oak Bluffs.

Day 1:

Meet on Martha’s Vineyard mid-day, where your guides will provide you with welcome refreshments and fit bikes for those renting. Explore Oak Bluffs, viewing the colorful Victorian gingerbread cottages, the most perfectly preserved collection of Carpenter Gothic style architecture in the world. Visit the Flying Horses Carousel, the nation’s oldest operating carousel. Next, cycle bike paths following the coast to Edgartown and our inn in the heart of town. This 19th-century seaport village is remarkably well preserved, and the stately Greek Revival houses built by whaling captains have been meticulously maintained. Many fine colonial homes pre-date the whaling era, and walking these lantern-lit streets is like taking a trip back in time. Climb to the top of Edgartown Light for spectacular views, then enjoy a delicious dinner together.

Available Mileage: 7 Miles

Day 2:

Pedal bike paths to a favorite Vineyard beach, then travel “up-island” past tranquil forests, quiet harbors, and fields of wildflowers. View the dramatic, multi-colored clay cliffs at Aquinnah and the Gay Head Lighthouse, a stunning setting that attracts visitors and photographers from around the world. Visit a picturesque hamlet that epitomizes a classic New England fishing village. Hop on the iconic bike ferry (seasonal) piloted by Paul Simon’s brother to travel across the cut. Then, pedal quiet roads through a less-visited region of salt-water farms, ancient stonewalls, distant ocean vistas, and island villages with grey shingled cottages framed by white picket fences and cascading flowers. Return to Edgartown, relax for a bit, then enjoy a private walking tour of the town, hearing about colonial history, whaling heritage, and Jaws lore. Enjoy dinner at another of the town’s fine restaurants – and for a well-earned evening treat, perhaps an ice cream at Mad Martha’s.

Available Milage: 33 or 41 Miles

Day 3:

After breakfast, hop on the Chappy ferry to explore a bit of tranquil Chappaquiddick Island. Next, bike past a stately lighthouse, wide beaches, and wildlife-filled ponds to Vineyard Haven. Enjoy the unique shops and cafes in town and if you like, refuel at the Black Dog Tavern. By the end of your bike tour, you’ll have seen the most beautiful sites and scenes Martha’s Vineyard has to offer. After only three days, this jewel in the Atlantic will surely have captured your heart as it did ours many years ago.

Available Milage: 10 or 18 Miles

Departure Instructions

On Day 3, the biking finishes either at the Vineyard Haven or Oak Bluffs ferry dock, depending upon tour dates. Van departure times are 2:30 pm from Vineyard Haven or 1:15 pm from Oak Bluffs. You may return on the same ferry as the van, or you may opt to go earlier or later as you prefer.

Booking Information

7 days prior to the adventure


Full payment is due at time of booking.


A booking may be cancelled within 30 days of the reservation with no penalty. See more details below.
A change to a different tour in the same calendar year will be allowed up to 60 days before the original tour departure date if space permits. There is no charge for this. Changes within 60 days of the original tour departure date are subject to cancellation fees as outlined below. Changes/transfers do not apply to custom tours.
All cancellations must be submitted in writing; refunds will be based on the day we receive written notice. Please purchase trip cancellation/travel insurance because exceptions to our cancellation policy cannot be made for any reason, including personal emergencies, illness or injury, canceled or delayed flights or ground travel to the tour departure point, or weather. Refunds will not be made for a participant arriving late or departing early from a tour, or for a participant not using accommodations, meals, or other services offered as part of a tour.
Cancellation Fees Are as Follows (Per Person):
Cancel 30 days or less from booking date – No charge (Does not apply to custom or private tours or to US tours booked within 60 days of departure or overseas tours booked within 90 days of departure.)

91 or more days before trip – $150
61-90 days before trip – $750 or $500 (loss of deposit)
31-60 days before trip – 50% of trip price
30 or less days before trip – 100% of trip price (20% of your payment may be applied to another of our tours departing within one year of original tour start date.)
If a tour is postponed by GFA due to COVID-19, all payments made will be applied as a credit for travel by 12/31/23 less any applicable third-party fees and a $150 per person administrative fee.


Travel and medical insurance are not included in this package. We strongly recommend that you purchase insurance to cover personal injury, cancellation, or interruption for your experience. You will need to separately purchase any trip interruption insurance through an outside provider. This must be done shortly after making your reservation (some require insurance to be purchased within 15-20 days of initial trip deposit).
We also recommend that you carry insurance to cover the risk of injury while you are at your destination. If you are injured, you will be charged the ambulance expenses associated with your evacuation as well as any expenses related to your medical care. Medical and evacuation insurance will help to cover these costs.

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