Bike Tour of Cape Cod / Martha’s Vineyard

6-DAY/5-NIGHT BIKE TOUR – $2,495
June 23-28, Sept. 29-Oct. 4, Oct. 6-11, 2019

We stay three nights at the prestigious and newly renovated Harbor View Hotel in Edgartown where our premier rooms are all in the historic main building.

This tour has everything! On the Cape we follow beach roads and a beautiful bike path as we weave our way past salt marshes, cranberry bogs, wooded bird sanctuaries, barrier beaches and tidal flats filled with egrets, geese and ducks.

A scenic ferry ride takes us to Martha’s Vineyard and elegant Edgartown, a colonial seaport whose rows of handsome 18th-century houses are reminders of the great wealth of the early whaler captains. Our gorgeous cycling takes us to Katama with its beautiful three mile barrier beach, and to historic West Tisbury. We visit Vineyard Haven, ride past historic West Chop Light and ride “up island” to the spectacular lookout at Aquinnah Cliffs (formerly Gay Head). We enjoy a picnic in the picturesque fishing village of Menemsha where we bike down to the harbor and stroll along beautiful Menemsha Beach. Our last day we can opt for an early morning ferry ride to Chappaquiddick before cycling along a beautiful bike path to Oak Bluffs. Here we explore famous labyrinthine streets lined with fanciful rainbow-colored gingerbread cottages and visit the town’s antique Flying Horses Carousel before returning to the inn.

Our two inns are the best! On the Cape we stay at the charming Palmer House Inn perfectly situated in the tree-lined historic district of Falmouth. And in Edgartown, we enjoy the wonderful rooms at the Harbor View Hotel where you can look out past the Edgartown Lighthouse and Chappaquiddick Island. From here, you can enjoy walking the narrow streets of this former whaling seaport with its handsome 18th- century houses, manicured lawns and white picket fences, as well as its renowned high-end boutiques and art galleries.

Cape Cod/Martha’s Vineyard Bike Tour Itinerary

Sunday  |  Arrival day | Palmer House Inn
Sunday we are welcomed to Cape Cod by the innkeepers at the Palmer House Inn in Falmouth. The inn is a delightful Victorian property perfectly situated in the tree lined historic district … and only a 4-minute walk from all the wonderful shops, galleries and restaurants of Falmouth. In the evening we gather for the short stroll to one of the area’s finest restaurants followed by a friendly get together in the common areas of the inn.

Monday  |  Distance: 24 or 34 miles  |  Terrain: Easier | Palmer House Inn
Monday’s ride is spectacular. Part of the day we follow the famous Shining Sea Bikeway as we weave our way past salt marshes, cranberry bogs, bird sanctuaries, beaches and harbors. We follow some quiet roads to the shores of Vineyard Sound in Falmouth, and then follow Surf Drive and Beach Road past Little Pond and Inner Harbor where hundreds of yachts and sailboats sway at anchor. We skirt past Oyster Pond and can pause here to breathe in the sea air or watch osprey and heron or take a brief side trip to Spohr Gardens where we are treated to an array of over 100,000 daffodils, lilies, magnolias and azaleas.

Rejoining the bike path we cruise along the Sound before cycling into the historic seaside village of Woods Hole. Here you will want to wander around the village. This was once a wealthy whaling town as evidenced by the many handsome 19th-century estates and the still-bustling commercial harbor. There are several nice shops to visit before we continue to bike northerly to our excellent lunch under the umbrellas at Dana’s Café.

Our return ride takes us north along Buzzards Bay where we are treated to more awe-inspiring views as we ride through Great Sippewissett Marsh on an elevated causeway and pass through tidal flats loaded with egrets, geese and ducks.

Tuesday  |  Distance: 30 or 40 miles  |  Terrain: Easier | Harbor View Hotel
After a superb breakfast, we ride back into Woods Hole to start our ferry ride to Martha’s Vineyard. This is a delightful transition from mainland to island and includes gorgeous views of the harbor and Vineyard Sound.  We arrive 45 minutes later in Vineyard Haven and ride from there along a lovely route (that includes a sea side bike path) to the easterly end of the island. Streets lined with handsome Eighteenth 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. Our home is here for the next three nights where we are guests at the prestigious Harbor View Hotel located near the Chappaquiddick Ferry landing and just a few minute’s walk from all the boutique shops and waterfront galleries for which Edgartown is so rightfully famous.

Wednesday  |  Distance: 23 or 38 miles  |  Terrain: Easier to Intermediate | Harbor View Hotel
Wednesday’s ride first takes us to Katama where we can warm our feet in the sand on the beautiful three-mile barrier beach, then follow bike paths to West Tisbury, home to a number of Vineyard artists, and galleries, and to Alley’s, a quintessential general store. We then weave our way past Lambert’s Cove and take back roads into Vineyard Haven where we visit the handsome West Chop Lighthouse with its great view over Vineyard Sound. Here we might also enjoy the numerous small shops in the village and maybe stop for refreshments at the iconic Black Dog Tavern.

In the evenings we have plenty of time to explore Edgartown. Edgartown is a great place to walk and, if you are in the mood, a great place to shop as well. Most stores are boutiques for high end apparel, jewelry, etc. but arts and antiques are also represented. Rounding out the selection are the requisite T-shirt and souvenir shops and you will want to indulge in the time-honored tradition of sampling the fudge and brittle at Murdick’s.

Thursday  |  Distance: 26 or 40 miles  |  Terrain: Easier to Intermediate | Harbor View Hotel
Thursday’s ride takes us “up island” through quaint and quiet villages that evoke the island’s maritime past. We 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 we will take the boardwalk to the beach so as to better see the mosaic of colors for which the cliffs are rightfully famous. We might also stop at the top of the cliffs to visit the several interesting shops owned by the indigenous Wampanoag Indians.

On your way back from Aquinnah we will stop in the fishing village of 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. We will also plan to picnic here, perhaps after a scenic walk along beautiful Menemsha Beach.

Friday  |  Distance: 17 miles  |  Terrain: Easier
On Friday you can opt for an early morning ferry ride to Chappaquiddick before cycling along a beautiful bike path to Oak Bluffs.  Here we 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 tour with a ride on the ferry back to Woods Hole and a shuttle to the Palmer House Inn.


Make your reservation with confidence. Your tour is completely 100% refundable up to 60 days of the tour date.

reserveJune 23-28, 2019: $2,495
Reserve with $300 deposit

reserveSept. 29-Oct. 4, 2019: $2,495
Reserve with $300 deposit

reserveOct. 6-11, 2019: $2,495
Reserve with $300 deposit

Final payment due 60 days prior to your tour (personal check, Visa, MasterCard, American Express or Discover)

Single Supplement Fee for Private Room: $500

Cancellations: If you cancel your tour reservation, your cancellation fee will be determined as follows:

  • If you cancel 60 or more days prior to the start of your tour, there is no cancellation fee.
  • If you cancel between 45 and 59 days prior to the start of your tour, you will forfeit 50% of all tour payments.
  • If you cancel between 0 and 44 days prior to the start of your tour, all tour payments will be forfeited.


A charming bed and breakfast located in Falmouth, Massachusetts. Falmouth is a delightful New England village on Upper Cape Cod. Our romantic bed and breakfast is located in the Historic District, a quiet residential area of tree-lined streets, picket fences, colorful gardens, and elegant homes all decorated for the holidays. Beautiful beaches, quaint shops, ferry shuttles and excellent restaurants, are only a short stroll from our Cape Cod Bed and Breakfast.

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.

What’s Included

Round trip ferry to Martha’s Vineyard and the ferry to Chappaquiddick, 5 nights lodging, 3 dinners (you are on your own for dinner two nights in Edgartown), 5 breakfasts, a picnic, bicycle and helmet. Free transfer provided from/to Falmouth bus station at the start and end of tour. Arrival: 5:30 PM pickup at Falmouth Bus Station. Departure: 2:35 PM from Falmouth Bus Station.


We are happy to provide you with a bike to use at no charge. Our bikes come equipped with a front handlebar bag, rear carrier, water bottle, mirror and flat pedals. Pedal cages and soft gel seat covers are available on request. We are also happy to put your own clipless pedals (pedals that attach to your biking shoes) and seat on your bike if you wish. Specific details and styles of bikes available in each location are indicated under each photograph below. The make of bikes provided varies by location.

Virtual Tour of Cape Cod / Martha’s Vineyard