Nantucket and Martha's Vineyard Bike Vacation

September 7-12, 2025

September 14-19, 2025

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 almost 90 miles of paved 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.

Highlights

  • Enjoy 44 miles of paved bike trails on Martha’s Vineyard
  • Explore classic New England harbor towns + visit eight different lighthouses
  • Cycle to galleries & studios that feature (and celebrate) the many island artists
  • Visit the original Black Dog shop, try a scoop of lobster ice cream, and sample fantastic seafood
  • Take a trip on the bicycle ferry operated by Hugh (brother of James) Taylor
  • Discover the quiet solitude of Chappaquiddick Island
  • Marvel at the 300 tiny cottages of Oak Bluffs, each adorned with whimsical gingerbread trim
  • Savor the sunset aboard a 60-foot catamaran sailboat

2025 Tour Dates

Sept. 7-12 Book Now
Sept. 14-19 Book Now

Rave Reviews

From start to finish, the trip was fabulous: spectacular scenery, first rate accommodations, delicious food, fun happy hours. Daria C.

2025 Tour Cost

$3,995 per person
(based on double occupancy)
Single supplement +$1,350

Level of Difficulty

Easy to Moderate – 25-40 miles/day, with total mileage of 80-170. Lots of paved bike paths, and one day with hills. Cycle at your own pace. Get a lift in the van whenever you like. E-bikes available (limited supply).

Highlights (continued)
  • Enjoy another 35 miles of paved bike paths on Nantucket, an island without any traffic lights, neon signs, or fast-food restaurants
  • Visit charming seaside villages, where iconic cottages and whaling-era mansions are adorned with climbing pink roses on gray cedar shingles
  • Easy bike rides to local beaches, passing famous cranberry bogs and iconic lighthouses, and stopping at Cisco Brewery for live music & beer tasting
  • Celebrate sunset during our beachside happy hours
  • Explore the many shops & galleries on Nantucket’s cobblestoned streets

What’s included?

  • 5 nights of lodging on the islands (3 nights in Martha’s Vineyard, 2 nights in Nantucket)
  • 9 meals (5 breakfast, 2 lunches, 2 dinners), catering to all dietary needs
  • Free use of our bikes, plus helmet, rear rack bag for your personal items, rear safety light + triangle, water bottle, and T-shirt. E-bikes available
  • Superior level of support throughout your stay (each trip comes with one 15-passenger van and three professional bike tour guides)
  • Ride with GPS navigation (using your own phone) or paper route notes
  • Exclusive GBT activities, including private walking tour of the Gingerbread Cottages of Oak Bluffs, sunset sail aboard a 60-foot catamaran, and a fun trip on a 6-person bike ferry
  • Admission to Nantucket Whaling Museum, Nantucket Shipwreck & Lifesaving Museum, and the Cisco Brewery (beer tasting + live music)
  • Full access to our online photo gallery with photos/videos from your trip
  • Small group size of 15-20 people (or organize your own private trip)
  • Ferry from Martha’s Vineyard to Nantucket, and from Nantucket to Hyannis

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 two exclusive trips 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

As Featured In

Trip Advisor Awards Great Bike Tours

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 two exclusive trips 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

As Featured In