Martha's Vineyard & Nantucket Biking
The Quaint Island Retreat & Nearby Nantucket
Off the coast of Cape Cod, the relaxed pace and simple pleasures of island life reign supreme, and the small-town hospitality of Nantucket and Martha's Vineyard will make you feel right at home. Join Backroads for a carefree spin in this idyllic playground. Pedal leisurely through pine forests and beachside, passing solitary lighthouses, grassy dunes and cranberry bogs. Browse the charming shops and classy galleries of weathered fishing villages and indulge in seafood fresh from the Atlantic. Come evening, succumb to the luxurious comforts of peaceful inns in this laid-back paradise.
Trip Planning Links
- 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
- Pick up maritime history at the Nantucket Life-Saving Museum
The Day-to-Day Itinerary
Days 1-2 nantucket town
Meet in Nantucket Town 
Take advantage of the island's extensive network of bike paths, riding past lighthouses, white-sand beaches bordered by tall grasses and beautiful 19th-century mansions Break from your bike to stroll along the ocean at Siasconset and Surfside beaches, or walk out by a cranberry bog Visit the Nantucket Life-Saving Museum, where daring sea rescues are chronicled Spin along picturesque cobblestone streets lined with shops and galleries Feast on fresh scallops, clams and lobster at one of the island's hip restaurants.
Days 3-5 edgartown
Enjoy a relaxing ride past old barns, osprey nests, wildflowers and verdant island grasses Board a private chartered boat for Martha's Vineyard, simply called "The Vineyard" by locals Stroll through historic Oak Bluffs, now a chic stop for shoppers Pedal on a seaside path toward Edgartown, a 19th-century whaling port known for its spectacular Greek Revival, Federal and Victorian architecture Explore roadside galleries filled with local and world-renowned artists' watercolors, photography and sculptures Follow both bike paths and roads on gentle grades and up a few steeper climbs to the great sand barrens and colorful Gay Head Cliffs Take in exhilarating sea air and spectacular ocean views as you spin to Vineyard Haven Ride past one of the island's many bird sanctuaries Ferry back to the mainland at Woods Hole.
- Premiere Inns: These lodgings possess both elegance and authentic regional flair.
- Casual Inns: These lodgings are comfortable and appropriate to the area with such characteristics as authenticity, scenic settings and proximity to our activities.
- Deluxe Family Camping: We set up the tents (and take them down), handle every camp chore and perform culinary magic.
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Look at what other guests are saying 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!- Napa, CA All Guest Reviews
For 30 years, Backroads has been perfecting the art of active travel. We are the Massachusetts tour experts. For biking tours in USA, trust our in-depth connections. To see all our USA biking tours click here. For our selection of award-winning USA walking and hiking tours click here. For our selection of award-winning USA multisport tours click here.
Martha's Vineyard & Nantucket Biking
ELEGANT HAVENS: Premiere Inns
White Elephant
Nantucket Town (2 nights) This landmark harborside inn is known for its elegantly furnished guest rooms, ocean views, spa and gracious hospitality.
Hob Knob Inn
Edgartown (2 nights) Located in the heart of historic Edgartown, this country-style boutique hotel features charming gardens, individually decorated guest rooms and a cozy library.
Martha's Vineyard & Nantucket Biking
Daily Mileage Options & Cumulative Elevation Gain
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.
| Activity Level | Average Time | Biking Average | Walking Average |
|---|---|---|---|
| Insider Trips | Explore at a leisurely pace—on village walks, market strolls, art history excursions, hands-on cooking classes and more. | ||
| 1 | 2-3 hours | 10-20 miles | 2-5 miles |
| 2 | 2-4 hours | 21-30 miles | 5-7 miles |
| 3 | 3-5 hours | 31-40 miles | 7-9 miles |
| 4 | 4-6 hours | 41-55 miles | 9-11 miles |
| 5 | 5-7+ hours | 56-75+ miles | 11-13+ miles |
Day 1
- Level 1 1 Route Option Available
- 9 miles
- 0 - 500 feet elevation gain
Day 2
- Levels 1 to 2 2 Route Options Available
- 19, 24 miles
- 0 - 500 feet elevation gain
Day 3
- Level 1 4 Route Options Available
- 6, 7, 14, 16 miles
- 0 - 500 feet elevation gain
Day 4
- Levels 2 to 4 3 Route Options Available
- 23, 28, 45 miles
- 0 - 500 feet elevation gain
Day 5
- Level 1 2 Route Options Available
- 7, 12 miles
- 0 - 500 feet elevation gain