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Martha's Vineyard Getaway Bike Tour

  • Bay view Martha's Vineyard
  • Picture of Martha's Vineyard Getaway Bike Tour
  • Lobster dinner
  • Seashore on Martha's Vineyard
  • Harbor quiet
  • Oak Bluffs house
  • Aerial view Martha's Vineyard
  • Picture of Martha's Vineyard Getaway Bike Tour
DURATION
4 Day(s)
DAILY BIKING
28 miles
TRIP DIFFICULTY
2-Easier to Intermediate
STARTING FROM
$1595
SINGLES ADD FROM
$500

Trip Overview

This bike tour is an easy getaway! Arrive by car ... or take the bus from Boston's Logan Airport right to the Woods Hole ferry. You unpack once and stay three nights at the lovely Harbor View Hotel in Edgartown, Massachusetts, where your premier room is in the historic main building. You can look out past the Edgartown Lighthouse and Chappaquiddick Island and enjoy walking the narrow streets of this former whaling seaport with its handsome 18th-century houses and white picket fences, as well as high-end boutiques and art galleries.

A scenic ferry ride on the first morning takes you to Martha’s Vineyard. Cycle to Katama with its beautiful barrier beach, and to historic West Tisbury. Plus, visit Vineyard Haven, ride past historic West Chop Light and ride “up island” to the spectacular lookout at Aquinnah Cliffs. Enjoy visiting a sculpture garden and the picturesque village of Menemsha, where you bike down to the harbor and stroll along the beach. From near the hotel, there is a 2-minute ferry ride to Chappaquiddick. And don't miss cycling along a beautiful bike path to Oak Bluffs. Here you explore famous labyrinthine streets lined with fanciful rainbow-colored gingerbread cottages and visit the town’s antique Flying Horses Carousel.

Take a four-day getaway with us for some salt air, cycling and seafood on gorgeous Martha's Vineyard!

Itinerary

From start to finish, check out the route.

DAY 1 - Welcome to Martha’s Vineyard
Arrival day | Distance: 30 or 40 miles | Terrain: Easier | Harbor View Hotel
We will meet at 10 a.m. for our ferry ride together to Martha’s Vineyard. This is a delightful transition from mainland to island and includes gorgeous views of the harbor and Vineyard Sound. You arrive 45 minutes later in Vineyard Haven. Ride from there along a lovely route (that includes a seaside bike path) to the easterly end of the island. Streets lined with handsome 18th-Century houses surrounded by white picket fences and topped with widow walks announce that you have arrived in Edgartown, a world- renowned seaport that still reflects the wealth and good taste of the phenomenally successful whaler captains of the early 1800’s.

Now’s a great time for a short stroll and lunch. If the rooms are not ready yet, then cycle to a 2-minute ferry crossing to Chappaquiddick for a spin. You return via the short ferry to Edgartown to check in at the elegant Harbor View Hotel — your home for the next three nights — just a few minutes’ walk from all the boutique shops and waterfront galleries for which Edgartown is so rightfully famous. Dinner is together tonight.
DAY 2 -
Distance: 23 or 38 miles | Terrain: Easier to Intermediate | Harbor View Hotel
Today’s ride first takes you to Menemsha, a supremely picturesque fishing village situated on Menemsha Pond and Vineyard Sound. This historic harbor serves as the point of departure for most of the local fishermen and is usually bustling with activity. Then head through quaint and quiet villages that evoke the island’s maritime past.

Indulge your artistic side with a visit to the Field Gallery and Sculpture Garden. Then ride out to Aquinnah Cliffs (formerly Gay Head), one of the most spectacular spots on the island. After enjoying the multi-mile views from the lookout, you take the boardwalk to the beach so as to better see the mosaic of colors for which the cliffs are rightfully famous. You might also stop at the top of the cliffs to visit the several interesting shops owned by the indigenous Wampanoag Indians. Dinner is on your own tonight.
DAY 3 - Artists, galleries & cottages
Distance: 26 or 40 miles | Terrain: Easier to Intermediate | Harbor View Hotel
Follow bike paths to West Tisbury, home to a number of Vineyard artists, and galleries, and to Alley’s, a quintessential New England general store. You then weave your way past Lambert’s Cove and take back roads into Vineyard Haven where you visit the handsome West Chop Lighthouse with its great view over Vineyard Sound. Here you might also enjoy the numerous small shops in the village and maybe stop for refreshments at the iconic Black Dog Tavern. Then cycle along a beautiful bike path to Oak Bluffs. Here you explore famous labyrinthine streets lined with fanciful rainbow-colored gingerbread cottages and visit the town’s antique Flying Horses Carousel. You may also want to splurge at one of the local ice cream emporiums before finishing the day’s ride along the Beach Road bike path as it cuts its way between the ocean on one side and beautiful salt marshes on the other. You end your ride in Edgartown to get ready for our celebratory last evening together.
DAY 4 - Departure Day
Distance: 17 miles | Terrain: Easier
On Friday you ride to Katama, where you can relish the morning light along the beautiful three-mile barrier beach, then return to the hotel for a quick shower. You end your tour with a ride on the ferry back to Woods Hole, scheduled to arrive at 1:10 p.m., where we shuttle you to your car. Or catch the 2:15 p.m. bus from the Woods Hole ferry bus stop back to Boston’s Logan Airport.

Map

Dates & Pricing

Prices are per person based on double occupancy (2 people in one room). Single supplement for private room is listed at the top of this page. A deposit of $500 holds your reservation for most tours. For weekend tours, the deposit is $300.

Start End Cost Availability

What’s Included

3 nights' lodging, 3 breakfasts, 2 dinners (on your own for 1 dinner in Edgartown). Ferry to and from Martha's Vineyard and to Chappaquiddick. We also include detailed maps and itineraries, experienced guides, full van support — plus use of a bike and helmet. Airfare and parking at ferry is not included.

Dates & Pricing

Prices are per person based on double occupancy (2 people in one room). Single supplement for private room is listed at the top of this page. A deposit of $500 holds your reservation for most tours. For weekend tours, the deposit is $300.

What’s Included

3 nights' lodging, 3 breakfasts, 2 dinners (on your own for 1 dinner in Edgartown). Ferry to and from Martha's Vineyard and to Chappaquiddick. We also include detailed maps and itineraries, experienced guides, full van support — plus use of a bike and helmet. Airfare and parking at ferry is not included.

Inns

Where you stay along the way.

Harbor View Hotel
Built in 1891, overlooking Martha’s Vineyard’s Edgartown Lighthouse, Edgartown Harbor and Chappaquiddick Island, the Harbor View Hotel is flanked by historic homes from 19th Century whaling captains. With stately elm trees lining the streets, you can walk from the Harbor View to everything in Edgartown. They have been rated one of the “World’s Best Hotels” by Travel + Leisure and the “Best Overall Place to Stay” by Martha’s Vineyard Magazine.

Gallery

Images from this tour. Click each to see it larger.

Bay view Martha's Vineyard Picture of Martha's Vineyard Getaway Bike Tour Lobster dinner Seashore on Martha's Vineyard Harbor quiet Oak Bluffs house Aerial view Martha's Vineyard Picture of Martha's Vineyard Getaway Bike Tour