Martha's Vineyard & Nantucket Bike Tour
Martha's Vineyard & Nantucket Bike Tour
Martha's Vineyard & Nantucket Bike Tour
Martha's Vineyard & Nantucket Bike Tour
Martha's Vineyard & Nantucket Bike Tour
Martha's Vineyard & Nantucket Bike Tour
Martha's Vineyard & Nantucket Bike Tour
Martha's Vineyard & Nantucket Bike Tour
Martha's Vineyard & Nantucket Bike Tour
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Martha's Vineyard & Nantucket Bike Tour

Massachusetts’s Colonial Islands

Couples, Friends & Solos

5 days 4 nights

Activity Levels 1-3

Premiere Hotels

From: $3,999 - $4,099 pp dbl occ

($1,100 for sgl occ)

It'll be early on. You'll round a corner on a beach road, maybe in 'Sconset or Aquinnah. And it will hit you. The quiet. The open Atlantic pulsing on the shore. Seabirds above and a breeze fanning the dunes. You'll imagine selling your possessions and buying a lobster boat. It's OK, the urge passes eventually. But you'll have five days to enjoy it. 

Martha's Vineyard & Nantucket Biking Tour map
Martha's Vineyard & Nantucket Biking Tour map


Start Nantucket Town / End Vineyard Haven

Start/End locations may vary. Do not book flights until your trip details are confirmed.


  • Circle Martha's Vineyard on two wheels, pedaling past scenic beaches, historic homes, woodland and cranberry bogs
  • Pedal over rolling hills to the red-clay cliffs of Aquinnah, with a 200-year-old lighthouse and panoramic views over the Elizabeth Islands
  • Explore Edgartown’s colonial roots, art galleries and spectacular architecture, not to mention plenty of ice cream shops
  • Bike around the island of Nantucket followed by a journey through maritime history at the Nantucket Shipwreck & Lifesaving Museum
The Backroads Experience
The Backroads Experience
Biking Tours
Biking Tours
Backroads Trip Leader
Meet Our Leaders


Accommodations may vary based on departure date.
5 Days Premiere Hotels
Accommodations may vary based on departure.
Days 1-2

Downshift into island life on Nantucket | A gentle ride to Cisco Beach leads past 18th- and 19th-century sea captains' homes and lighthouses | Explore the island by bike with gardens, cranberry bogs, harbors and dunes enlivening your route | Refresh yourself at a favorite local watering spot offering much-loved microbrews and wines | Take a fascinating look at the island’s maritime history at the Nantucket Shipwreck & Lifesaving Museum, which exhibits original boats, relics of the island’s legendary shipwrecks and photographs of thrilling sea rescues | Up for a stroll along the Atlantic? Siasconset and Surfside Beaches beckon with pristine stretches of sand.

White Elephant Hotel
White Elephant
Nantucket Town
| Premiere Hotel

A "stylishly refurbished in-town hotel on a quiet waterfront, a brief walk from the historic district," noted Andrew Harper. (spa)

Days 3-5

Soak up the rich history of Nantucket Town on a walking tour | A private boat transports us to Martha’s Vineyard | Explore the unique town of Oak Bluffs, home to colorful gingerbread cottages | Pedal to the port town of Vineyard Haven, cruising by stately homes on the West Chop peninsula | Arrive in Edgartown, known for amazing Greek Revival, Federal and Victorian architecture | Cycle inland through forests and open meadows | Fond of art? Galleries tempt you off your bike with watercolors, photography and sculptures by local and world-renowned artists | Explore Chappaquiddick and Cape Poge Light—the lighthouse's first keeper in 1801 was appointed by Thomas Jefferson | Take in the exhilarating sea air and more spectacular ocean views on your ride to Katama Beach | Pass through the Great Plains of Martha's Vineyard before a farewell lunch.

Hob Knob Inn
Hob Knob
| Premiere Hotel

This 19th-century Gothic Revival home is now a country-style boutique hotel with lovely gardens. (spa)

Activity Level: 1-3

Every Backroads trip is designed to appeal to a wide variety of interests and fitness levels. Several routes and a range of levels are offered each day so you can choose how much or how little activity you want to do. Learn more about how we determine activity levels.

Daily Route Options

* Includes shuttle.
Day 1
Level 1 | 10 miles | 200 ft. gain
Day 2
Level 1 | 21 miles* | 500 ft. gain
Level 2 | 26 miles | 700 ft. gain
Level 3 | 40 miles | 1100 ft. gain
Day 3
Level 1 | 6 miles | 100 ft. gain
Level 1 | 11 miles | 300 ft. gain
Level 2 | 22 miles | 800 ft. gain
Nantucket Town Guided Walk (1.25 hours)
Boat Ride (1.5 hours)
Day 4
Level 1 | 10 miles | 300 ft. gain
Level 2 | 23 miles* | 800 ft. gain
Level 3 | 36 miles* | 1200 ft. gain
Level 4 | 51 miles | 1900 ft. gain
Day 5
Level 1 | 10 miles | 100 ft. gain

What's Included

Available Bike Options

The key to a stellar day's ride is a bike that's perfectly in tune with your cycling style… Backroads has you covered with the best bike fleet in the world! Read on for bike options specific to this trip (click the arrow to see more). Please note that bike requests, including e-bikes and Carbon bikes, are subject to availability and prioritized based on the date they're submitted.

Backroads Performance Road Bike
Backroads Performance Road Bike
Performance Road Bike

Included in your trip price

This custom-designed titanium bike is lightweight and responsive, featuring Shimano Ultegra Di2 electronic shifting, 11-speed compact gearing, a premium Mavic Ksyrium Pro wheelset and a full carbon fork. 

Backroads Touring Bike
Backroads Touring Bike
Touring Bike

Included in your trip price

A proven classic, our most popular custom-designed titanium bike is suited for a wide range of cyclists. It features a comfortable ergonomic seat and a long wheel base that add to the bike’s control and stability.

Backroads Electric-Assist Bike
Backroads Electric-Assist Bike
Electric-Assist Bike

Included in your trip price

Keep pace or zip ahead, pedaling with an electric boost. This bike provides plenty of power to flatten the hills and more than enough battery range to cover the distance.
Min. age to ride e-bike: 16+

Cannondale Synapse Pro Carbon Bike
Cannondale Synapse Pro Carbon Bike
Carbon Bike

Ride like a pro with the top-of-the-line carbon Cannondale Synapse Hi-Mod Red ETAP AXS. Delivering phenomenal acceleration and handling in a light and powerful package.
$400 rental fee; subject to availability

Co-Motion Torpedo Tandem Bike
Co-Motion Torpedo Tandem Bike
Tandem Bike

This hand-built frame features Co-Motion's custom-designed cro-moly steel tubeset, powerful Avid disc brakes, Shimano Ultegra drive train, and a custom, upgraded wheelset. For experienced tandem riders.
$400 rental fee

Also Included

  • All breakfasts, 4 lunches, 3 dinners
  • Expertise and services of our experienced Trip Leaders
  • Snacks and beverages between meals
  • Additional guides and experts from the region on many trips
  • Van shuttles to support a variety of route options
  • Comprehensive Travel Planner with detailed pre-trip information
  • Private guided tours at museums, historic sites, wineries and other select attractions as noted in the Travel Planner
  • All gratuities at hotels and restaurants
  • Special events, including wine tastings and other select attractions as mentioned in the Travel Planner
  • On biking and multi-adventure trips, use of fully equipped Backroads titanium bike plus helmet and accessories
  • Trailercycles, carriers, and kid-sized helmets for Family Trips
  • Equipment and experienced guides for kayaking, rafting, snorkeling, sailing and canoeing as described
  • Park and other entry fees
  • Fares for trains, ferries and other modes of travel as listed in the Travel Planner
  • Select coach transfers
  • Baggage transfers and porterage

Ask a trip expert

Have a question and need expert advice? Our team of Trip Consultants is here to help! You can also visit our FAQ's.

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