Nantucket and Martha's Vineyard

The Jewels of Cape Cod

Imagine New England at its most rose-covered, cobblestoned, and picture-postcard perfect… and you have found the islands of Nantucket and Martha’s Vineyard. Join our six-day bike tour as we explore these jewels of Cape Cod.

The small size and flat terrain of these islands make them ideal places for bicycling. With 73 miles of bike paths to choose from, you’ll have a care-free time exploring the world of old whaling captains’ mansions and seaside cottages, with their climbing pink roses on gray cedar shingles, and exquisite gardens. Cycle through historic harbors containing quaint inns, boutique stores, galleries, blinking lighthouses, chowder shacks, and upscale dining delights.

2019 Tour Dates

• Sept. 8-13 (2 spaces left)
• Suggest your own private dates (min. numbers required)

2020 Tour Dates

Coming Soon

Tour Cost

• $2,775 per person
• Single supplement +$475

Highlights of the Island of Martha’s Vineyard

  • Stay three nights in the coastal villages of Edgartown and Oak Bluffs
  • Enjoy the 44 miles of paved bike trails that crisscross the Island
  • Explore the classic New England harbor towns of Edgartown, Oak Bluffs, and Vineyard Haven, each with their own distinct flavor
  • Savor the “quiet simplicity” of the up-island communities of West Tisbury, Chilmark, Aquinnah, and Menemsha
  • Go shopping for some legendary Black Dog merchandise (bike jerseys, shorts, water bottles) or dare to try a scoop of lobster ice cream from Mad Martha’s
  • Take a trip on the six-bike ferry operated by Hugh (brother of James) Taylor, and the next day hop aboard a larger bike ferry to Chappaquiddick Island
  • Admire the Aquinnah lighthouse and the famous multicolored clay cliffs
  • Cycle to numerous galleries, studios, and workshops that feature (and celebrate) the many island artists
  • Take a nostalgic ride on the oldest merry-go-round in the nation
  • Marvel at the 300 tiny cottages of Oak Bluffs, each adorned with whimsical gingerbread trim
  • Toast another perfect day as you set sail aboard a 60-foot catamaran at sunset

Highlights of Nantucket Island

  • Two night stay on Nantucket, an island without any traffic lights, neon signs, or fast food restaurants
  • Visit the charming village of Siasconset, where every seaside cottages competes for the attention of the artist with their watercolor paints
  • Enjoy the evocative exhibits at Nantucket Whaling Museum, ranked #1 of the 49 attractions on Nantucket Island
  • Cycle to fantastic local beaches: Pocomo Beach for outstanding seashell collecting; Madaket Beach for unbeatable sunsets; Jetties Beach for a great happy hour; and Cisco Beach for surf, seals, and morning coffee
  • Bike by one of the oldest cranberry bogs in Massachusetts
  • Visit the colorful Sankaty Head Lighthouse, one of the most important beacons of its time
  • Take a stroll (locals call it laning) on the narrow cobblestoned streets of the town’s historic district, viewing the grand whaling-era mansions
  • Go shopping for your Nantucket Reds, Lightship Baskets, or any garments emblazoned with the word ACK or the slogan “There was once a man from…” Oh, never mind
  • Dine at the local clam chowder houses, perfect with a pint of Whale’s Tale Pale Ale

What’s included?

  • 6 day/5 night tour (3 nights on Martha’s Vineyard, 2 nights on Nantucket)
  • Rental bike & helmet (or bring your own)
  • Full van support throughout your stay
  • All breakfasts, 1 lunch, 3 dinners
  • The services of 2-3 professional bike tour guides
  • Sunset sail aboard 60-foot catamaran
  • Daily route notes & maps, Great Bike Tours T-shirt & water bottle
  • Easy cycling (our easy bike tours are mostly flat but with the occasional hill, 25-40 miles/day)


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BOOK YOUR TRIP (or request more information)

September is the perfect time to visit the islands of Nantucket & Martha’s Vineyard;  the summer crowds have gone and the weather is cooler. We only offer one exclusive trip per year, so sign up soon before we sell out.

Great Bike Tours

3282 Mt. Philo Rd,
Charlotte, VT 05445

Have any questions? Contact us!

(802) 777-2009