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RI & Martha's Vineyard Cycle Tours: Itinerary

Islands and Seacoast Biking Tour

Four Fabulous Islands, One Incredible Biking Tour

Great Freedom Adventures biking tour

For the full itinerary and logistical information on this Islands and Seacoast Biking Tour, please contact us and we will be pleased to email it to you.

Day 1  After transfers to Point Judith, RI, board the early afternoon ferry to Block Island. Get acquainted while relaxing on the ferry to an island the Nature Conservancy termed one of the “Last Great Places.” Enjoy refreshments and ocean views at our hilltop inn while your guides fit your bike. We’ll begin our biking with an afternoon ride to Southeast Light and dramatic Mohegan Bluffs. Tour the lighthouse and museum and descend to the secluded beach at the base of the bluffs. Return to our island retreat and enjoy tapas and cocktails on the wide veranda. Perhaps try a game of croquet while watching the sun sink toward the Atlantic, then head to dinner together.

Day 2    After breakfast, our biking tour continues as we spin along ocean-front roads, past crescent beaches, through the Block Island National Wildlife Refuge to North Light. Slow to the pace of island life and walk the gorgeous and tranquil beaches surrounding the lighthouse. Bike to town, visit a shop or two then enjoy lunch on the ferry back to the mainland. Our cycle tour continues as we follow the coast to the resort area of Narragansett. Bike past fishing piers, wide beaches and extravagant “summer cottages.” Arrive at our second island, Conanicut, a pastoral place charmed by the spirits of the Wampanoags and Narragansetts. The island is home to national historic and state parks with panoramic ocean vistas, the historic Jamestown windmill and Revolutionary War fortifications. Cycle to Beavertail Lighthouse, the country’s third oldest, and enjoy sweeping views of Narragansett Bay. Bike to charming Jamestown then travel across the bay to our third island of Aquidneck, location of Newport and our home for the night. After dinner, enjoy a GFA exclusive lantern-light tour of Newport with our local historian as we journey back through 300 years of history to explore the waterfront and historic streets. Meander back to our own historic inn right in the heart of the Old Quarter.

cycle tours cape cod

Day 3  Our exploration of Aquidneck Island continues as we walk a section of the famous Cliff Walk finishing with a tour of the world-renowned Breakers mansion. Next, bike a spectacular route past commanding yacht clubs and gentlemen farms to the incredible vistas on Ocean Avenue. On one side, view opulent Gilded Age estates and catch a glimpse of the summer lives of the rich and famous, then and now. On the other, delight in nature’s breathtaking seascapes. Our biking tour continues past salt ponds to a pristine National Wildlife Refuge with panoramic views of ocean, beach, dunes, marsh and wildlife-filled maritime vegetation, where a sharp eye may spot a peregrine falcon among the 200 species of birds. The September tour is timed to coincide with the peak of the Monarch butterfly migration. Stroll trails through refuge grasslands where numerous Monarchs can be seen feeding on wildflowers as they rest en route to Mexico, and watch for hawks as well as this is the start of the hawk migration. Continue biking through seacoast to beautiful Greenvale Vineyards, listed on the National Register of Historic Places. Taste the award-winning estate grown wines, then depart for the boat to our fourth island – Martha’s Vineyard. Once ashore on “The Vineyard”, bike along the coast to elegant Edgartown, our home for the next two nights. Enjoy dinner at one of Edgartown’s fine restaurants then stroll the beguiling, lantern-lit streets of town.



MA biking trip

Day 4  Today’s biking tour of the Vineyard will take us to the island of Chappaquiddick past the Mytoi Japanese gardens to the infamous Dike Bridge. After “Chappy” we’ll travel “up-island” to 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. We’ll visit the picturesque fishing village of Menemsha with its salt-weathered buildings and beautiful beaches. Along the way we’ll find friendly islanders, unique shops with handcrafted treasures, delicious cafes, pristine beaches, serene island farms – and the desire to stay here forever. Explore the fine shops and historic streets of Edgartown. 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 you will thoroughly enjoy walking these historic streets.

biking tour the Vineyard

Day 5  After breakfast, we’ll head to Oak Bluffs and see 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, then bike past the East Chop Light enroute to our ferry back to the mainland. During the afternoon, enjoy truly superb cycling on quiet roads through hidden corners of Massachusetts and Rhode Island. Cycle within the Heritage Coastal Farm region of fragrant vineyards, horse farms, fertile farmland and gorgeous seacoast. Miles of old stone walls trace verdant fields that disappear into the ocean at the horizon. We’ll pedal through colonial era villages and affluent townships before arriving at our destination in Little Compton, RI. Here, the entire town commons is listed on the National Register of Historic Places. Our seaside estate, The Stone House, awaits to reward our journey with luxurious accommodations, a private beach, an indulgent spa, a speakeasy tavern and a top-notch restaurant.

MA biking tour

Day 6  The last morning offers many options: one last ride through this idyllic peninsula or a morning spent relaxing on the beach, indulging at the inn’s spa or simply enjoying the amenities. After check-out, we’ll return to the tour start and say our goodbyes to new friends who now understand as we do the beauty and richness of this very special part of America.

cycle tours


Dates and Prices:

For biking tour details, dates and prices, please go to the Islands and Seacoast biking holiday details page.

Questions? Please contact us and we'll be happy to help.

If you have only four days, you may wish to take a look at the Rhode Island vacation bike tour.

For another biking tour in coastal New England, please see our Maritime New England bike tour in MA and our active Block Island vacation.

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