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Martha's Vineyard & Nantucket Bike Tour

Route Rating
Make It Private
Trip Highlights
  • Gentle, tranquil rides past scenic beaches and cranberry bogs
  • Fresh seafood and gracious island hospitality
  • Tackle hills to the red-clay cliffs of Aquinnah, with a 200-year-old lighthouse
  • Edgartown's Colonial roots and art galleries
  • Learn maritime history at the Nantucket Shipwreck & Lifesaving Museum

Call 800-462-2848, Every day 6am-6pm,PST

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Atlantic Islands & Beachside Villages

It'll be early on. You'll round a corner on one of the beach roads, maybe in 'Sconset or Aquinnah. And it will hit you. The quiet. The open Atlantic pulsing on the shore. Sea birds above and a beach breeze rustling the dunes. It gives you that "I'm never going back" feeling where you imagine selling all your possessions and buying a lobster boat. It's okay, the feeling passes eventually. But you'll have five days to enjoy it.

Days 1-2 Downshift into easygoing island life on Nantucket  A gentle ride to Cisco Beach leads past beautiful 18th- and 19th-century sea captains' homes and lighthouses Sample local microbrews, wine and even vodka during lunch at Cisco Brewery Circle the island on two wheels, with gardens, cranberry bogs, harbors, dunes and houses - sporting every shade of gray - enlivening your route The Nantucket Shipwreck and Lifesaving Museum chronicles the area's maritime heritage Up for a stroll along the Atlantic? Siasconset and Surfside beaches beckon with pristine stretches of sand.

Day 3 Edgartown's Colonial roots and art galleries  Soak up the rich history of Nantucket Town on a walking tour A private boat transports us to Martha's Vineyard, simply called "The Vineyard" by locals  Ride out to Katama Beach past beautiful homes tucked among pines and scrub oak along a stretch of unspoiled beach popular with local kite-surfers  Pedal a bike path to Edgartown, known for spectacular Greek Revival, Federal and Victorian architecture  Explore the unique town of Oak Bluffs, home to gingerbread cottages that were once part of a historic Methodist camp.

Day 4 The red-clay cliffs of Aquinnah, with a 200-year-old lighthouse  Spin 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 the Cape Poge lighthouse - its first keeper in 1801 was appointed by Thomas Jefferson.

Day 5 Exhilarating ocean views and breezes abound on our ride out to Vineyard Haven and Tisbury, with its large estates overlooking Nantucket Sound and the islands only year-round port  Enjoy lunch at the ever-popular Black Dog Tavern.

Guests Reviews About This Trip

This was one of the most memorable vacations I've ever had! The inns where we stayed were awesome. The museums really helped me to get a better historical perspective, especially in Nantucket. It was very clear to me that our leaders really wanted us to have the trip we desired. And that van was always there!
Mike Teichman - Napa, CA
Wonderful trip! Really beyond my expectations.
Marcus Haney - Pittsburgh, PA
Many things have changed since my first Backroads trip 30 years ago - but not the service. That's why you're still the best and that's why I'll keep coming back. Sometimes friends ask why would you spend that much for a bike trip. I just tell them that if they take a Backroads trip, they'll be amazed as to how much they got for their money.
Don Walsh - Bend, OR

Premiere Inns

White Elephant
White Elephant

Nantucket Town, Nantucket  (2 nights) A "stylishly refurbished in-town hotel on a quiet waterfront, a brief walk from the historic district," noted Andrew Harper. (spa)

Hob Knob
Hob Knob

Edgartown, Martha's Vineyard  (2 nights) This 19th-century Gothic Revival home is now a country-style boutique hotel with lovely gardens. (spa)

Private Trips Options & Pricing

Gather your favorite people to share a Backroads adventure on a ready-to-book Private Trip - featuring all the legendary Backroads hallmarks from expert leaders to unforgettable activities.

You can pick from a large selection of dates for your group of 8 or more. Call us for date availability.

If your party has fewer than 8 guests, or if your preferred date is not available, we'll create a departure just for you.

Pricing for Private Trips (prices may vary based on departure date)

8 - 9 guests $3,398 pp dbl. occ. 12 or more guests $2,798 pp dbl. occ.
10 - 11 guests $3,098 pp dbl. occ.

For groups of 2 to 7 guests, please call for Custom Trip pricing.

This Trip Is Rated Level 1-3

Routes For All Abilities
Every Backroads trip is designed to appeal to a wide variety of interests and fitness levels. We know your pace may vary from one day to the next-and your traveling companion's may differ somewhat from yours. So we present a range of mileage options, and each day you decide exactly what and how much you want to do.

Daily Route Options
Level 1 Level 2 Level 3 Level 4 Level 5
miles feet gain miles feet gain miles feet gain miles feet gain miles feet gain
1 10 50
2 19* 100 24 100 37 200
30 150
3 6 50
15 50
Guided City Walk (1.5 Hours)
Boat Ride ( 1.5 Hours)
4 10* 50 24* 350 36* 350 51 400
5 10* 50
15 100

* Includes a shuttle

For 35 years, Backroads has been perfecting the art of active travel. We are the Massachusetts tour experts. See our award-winning USA biking tours, USA walking and hiking tours and USA multisport tours.


Premiere Inns

5 days, 4 nights
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Trip Price**
  • $2,798 to $3,198 pp dbl. occ.
  • (+$860 for sgl. occ.)

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arrow View Bike Options and Available Upgrades


Nantucket Town, Massachusetts/Vineyard Haven, Massachusetts

Detailed Itinerary

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Dates & Prices

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2014 Classic Dates
Trip Notes

All meals included except 1 lunch, 1 dinner

Recommended Reads

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Cancellation Policy

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** Prices may change. Once you book your trip, your price is guaranteed.