Martha’s Vineyard Vacation Bike Tour – Great Freedom Adventures
tour-item-template-default,single,single-tour-item,postid-3578,mkd-core-1.1.1,mkdf-social-login-1.1,mkdf-tours-1.3,voyage child theme-child-ver-1.0,voyage-ver-1.3,mkdf-smooth-scroll,mkdf-smooth-page-transitions,mkdf-ajax,mkdf-grid-1300,mkdf-blog-installed,mkdf-header-standard,mkdf-no-behavior,mkdf-default-mobile-header,mkdf-sticky-up-mobile-header,mkdf-dropdown-default,mkdf-light-header,mkdf-medium-title-text,wpb-js-composer js-comp-ver-6.6.0,vc_responsive

Martha’s Vineyard Vacation Bike Tour

Martha’s Vineyard Vacation Bike Tour

per person


Island Idyll Martha’s Vineyard Vacation Bike Tour

Bike a MA Island of Extraordinary Beauty with MA-Based Experts

Seven 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.

The Martha’s Vineyard Vacation Bike Tour
Bike an oceanside ridge of pitch pine, scrub oak and rose hips, where the wind through the trees evokes the spirits of Wampanoag ancestors who for 10,000 years farmed these lands and fished these waters – and who remain sovereign today in this poignant place. Spin effortlessly alongside fields of wildflowers where hundreds of butterflies flit from flower to flower. Cycle past dunes catching glimpses of white beaches and blue waters at the end of sand paths. Pedal and walk fishing villages of weathered cottages draped in roses and towns of narrow brick byways leading to stately mansions built by sea captains. Explore harbors where hard working fishing boats rest alongside sleek yachts. Bike past some of the most iconic lighthouses on the Eastern Seaboard that still protect boaters from dangerous shoals.

marthas-vineyard-vacation-bike-tour-2Stay in Elegant Edgartown, the Sparkling Gem of Martha’s Vineyard
Stroll the historic, lantern-lit streets of Edgartown, our home base, and view fine examples of Federal, Greek Revival and Victorian architecture. Visit boutique shops with unique treasures and dine at restaurants offering expertly prepared local foods. Great Freedom Adventures’ guests stay at a lovely inn designated a Historic Hotel of America and perfectly located in the center of town across from the waterfront. With all tour details taken care of for you, the only challenge will be tearing yourself away at the end of this captivating island idyll.

Tour Highlights:

  • Stay in the heart of Edgartown’s historic district, in view of the harbor and steps to shops and restaurants
  • Bicycle past iconic lighthouses, gorgeous beaches, heather-covered dunes and pitch pine barrens
  • See the famous red cliffs at Aquinnah
  • View the gingerbread cottages in Oak Bluffs
  • Learn fascinating colonial history, whaling heritage and local lore on a private walking tour of Edgartown
  • In season, ride the iconic bike ferry
  • Visit the Black Dog Tavern and unique island shops in Vineyard Haven
  • Ferry to Chappaquiddick and pedal along quiet lanes
  • Visit a quintessential New England fishing village
  • Bike past salt-water farms and estates fit for presidents
  • Pedal lesser-known island landscapes of tranquil beauty
  • See meticulously preserved mansions built by whaling captains
  • Step back in time in a region first inhabited by the Wampanoags
  • Cycle bike paths along wildlife-filled salt ponds
  • Taste foods fresh from the ocean and local farms
  • Enjoy exceptional service throughout your carefree tour of Martha’s Vineyard

Tour Reviews & Testimonials


    Day 1

    marthas-vineyard-vacation-bike-tour-10Meet on Martha’s Vineyard mid-day where your guides will provide you with welcome refreshments and your bike if needed. 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 predate 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. Cycling mileage: 10 (with options for more)

    Day 2

    marthas-vineyard-vacation-bike-tour-13Pedal 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 - and a place where scenes from Jaws were filmed. Take the bike ferry across the cut, then pedal quiet roads through a 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 and relax or shop, then enjoy a private walking tour of town with a resident expert who peppers the tour with local color while sharing colonial history, whaling heritage and Jaws lore. Enjoy dinner at another of the town’s fine restaurants. Cycling mileage: 25, 30 or up to 52 depending on desire.

    Day 3

    marthas-vineyard-vacation-bike-tour-gfaAfter 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. Cycling mileage: 18   Please Contact Us for detailed itinerary and arrival and departure information.

    harbor-view-hotel-2Harbor View Hotel, Edgartown, MA - 2 Nights The historic Harbor View Hotel overlooks Edgartown Harbor and the Edgartown Lighthouse. Rockers on the wide veranda beckon guests to sit and enjoy the splendid view. The inn features a refined island decor and amenities include a tavern, restaurant and a heated pool with a poolside bar.  

    2022 Dates

    May 20-22  |  June 10-12  |  June 15-17  |  July 10-12  |  Aug 23-25  |  Sept 14-16  |  Sept 23-25

    2022 Prices (Good till 11/15/21)

    May & June Departures: $1,650, per person based on double occupancy. July, Aug & Sept Departures: $1,750. Single Supplement: $695

    Trip length

    3 days, 2 nights


    Martha's Vineyard

    Cycling level

    Easy (Moderate on Day 2 with full distance)

    Daily Mileage

    10-30 (up to 52 with longer options)


    Relatively flat with hills in some parts. Roads and bike paths.

    Bikes: You may bring your own bike or use one of ours. GFA bikes are high quality, lightweight, available with either drop or straight handlebars and are equipped with computer, mirror, waterbottle, handlebar bag, map case and seat pack with essentials. What's Included:
    • Two nights lodging
    • Two dinners
    • Two breakfasts
    • Welcome refreshments
    • Three days of guided cycling
    • Bicycle and helmet rental
    • Two dedicated guides
    • Van support
    • Luggage Transport
    • Private, guided walking tour of Edgartown
    • Daily snacks and cold drinks
    • Cycling maps and cue sheets
    • Chappaquiddick and bike ferry tickets
    • Tax and gratuities for meals and side excursions
    • Waterbottle
    • Lightweight, reflective mesh vest
    • Dedicated, friendly service throughout your care-free tour
    Frequent Adventurers, GFA alumni, may deduct 5% from the tour price. Please contact us for youth and group rates. Custom dates and duration are available for groups of six or more. Please Contact Us for detailed itinerary and arrival and departure information.

    Be The First To Know About New Tours

    Be the first to get latest updates and information about new tours straight to your email inbox.