Martha’s Vineyard Bike Tour

Experience a Jewel of Massachusetts on our Marth’as Vineyard Bike Tour

There’s never been a better time for a Martha’s Vineyard bike tour! Five miles off the coast of Massachusetts sits a jewel of an island: Martha’s Vineyard, better known locally as the “Vineyard”, is a place of exceptional beauty that simply begs to be explored by bike. Bike paths and country roads wind past cool forests, tranquil harbors, island farms and pristine beaches, offering the perfect opportunity to fully appreciate island life. Great Freedom Adventures’ three-day tour of Martha’s Vineyard draws from decades of Vineyard biking to bring you the best of this most beautiful of MA islands.

  • 3 Day Adventure
  • May 12th – 14th – $1,895 (SOLD OUT)
  • September 29th – October 1st – $1,895
A woman holding her bike in front of the Nantucket Ferry on a Great Freedom Adventures bike tour.

Great Freedom Adventures is your premire provider for Martha’s Vineyard bike tours!

Great Freedom Adventures has been solely operating Cape Cod, Martha’s Vineyard, and New England for several years. Our Martha’s Vineyard bike tour is designed to bring you to the best parts of Cape Cod, Nantucket, and Martha’s Vineyard itself. Your guides will make sure your trips run seamlessly as you enjoy the cuisines and iconic hotels that make this part of Massachusetts so special. This bike tour is a great way to get introduced to our trips, or is even perfect for the most seasoned traveler. As our trips tend to fill up, you’ll have the chance to meet and connect with cyclist from all over the country, accentuating your trip and making memories and freindships that last! If you would like more information about our Martha’s Vineyard bike tour, do not hestitate to call and speak with our knowledgable travel consultants to help you plan your next trip. We hope to see you soon!


  • 2 nights lodging
  • 2 dinners
  • 2 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


Inclusions and Amenities

All Inclusions and amenities are subject to change, should we change our stay or dinner options, comparable options will be provided. 

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

Rider Level


Lodging Options

Standard Room at Various Hotels and Inns

Max Occupancy: 2 Guests

Single supliment available

Throughout the tour, guests will stay in a selection of upscale Inns and Hotels along the way. As many are Historic Inns, rooms may vary in design, aesthetics, and layout. We’ve provided some sample images to give you a sense of what your accommodations may look like. Please note in the room selection process; we ask that you choose between a shared or double occupancy room and a private room for individual guests.



Meals Included

Private Rooms

Martha’s Vineyard Bike Tour Itinerary

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.


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

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

Booking Information


7 days prior to the adventure departure.


A deposit is due upon booking – $750 per person for five to eight day tours and $500 per person for three to four day tours. Payments may be made by check or credit card. Our receipt of the deposit, registration form, and signed Release form will secure your reservation.

An invoice for the balance will be emailed and final payment is due no later than 30 days (exceptions made for last minute booking) before the tour departure date. Payment may be made by check or online with a credit card. If final payment is not received by the due date, Great Freedom Adventures reserves the right to cancel the reservation.


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.)


Travel insurance is available from a number of insurers or their representatives, such as CSA Travel Protection or Travel Guard. You may compare prices and policies at Insure My Trip. We do not sell insurance or recommend any particular insurer or policy, but we highly recommend that you obtain travel insurance.