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Cape Cod Bike Tour Slideshow
Cape Cod & Martha’s Vineyard Bike Tour

6 Day Inn Tour


Meet: Hyannis, MA

Time: 3:30pm

Terrain: Moderate Mostly flat terrain with some short, gently rolling sections. Moderate cycling level.

Trip Price:

Includes: 5 nights lodging, 5 breakfasts, 3 picnic and sack lunches, 4 dinners, snacks, ferry to/from Martha’s Vineyard, van support, maps, cue sheets and trained guides.

Travel Arrangements: Fly or take the train in and out of the Boston airport. Then take the Plymouth-Brockton shuttle to our starting hotel. Or drive and leave your car at our starting hotel for the week. We will provide a complimentary shuttle at the finish of the tour back to our starting hotel by 2:00pm. Or take the ferry or fly back to the Boston.

Single Upgrade:

Rental Bike: $175

Tour Lodging (subject to change):

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Cape Cod & Martha’s Vineyard Bike Tour

We can’t wait to show you some of the diversity of Cape Cod and Martha’s Vineyard. Their quiet roads and gorgeous bike paths will take you by salt marshes and cranberry bogs, windmills and lighthouses, sand dunes and fishing villages.

It’s fascinating to see the weathered, rickety lobster boats docked beside the slick, white fast ferries. Or the family-run Portuguese bakery beside the store selling logo’d hoodies. It’s a summer retreat for fast-paced financiers of Boston, and a year-round home for writers and painters seeking a quieter pace. We hope, like us, you’ll want to go back every year.

DAY 1: We begin our tour in Hyannis on Cape Cod. We meet at 3:30pm for a rental bike fitting, 5:30pm for an orientation and 7:00pm for dinner. If you arrive early, visit the JFK Museum or explore some of the shops along Main Street of Hyannis. 0 miles.

DAY 2: Our day begins with breakfast and then a ferry ride to Martha’s Vineyard. The island is named after the daughter of the 17th-century explorer Bartholomew Gosnold who discovered the island full of grapes growing wild. Now full of unspoiled beaches, gingerbread-adorned houses and sophisticated shops, the island is rich in diversity.

You’ll have your choice of two loops to explore the towns and see the island’s natural beauty. Ride the shorter loop on all bike paths or choose to take a side trip to Chappaquiddick. Lunch is on your own today. You can stop while you’re on your bike in the swanky town of Edgartown or the honky-tonk village of Oak Bluffs. Or walk to a cafe from our inn at Vineyard Haven. 24 or 36 miles.

DAY 3: We take another day to continue to explore Martha’s Vineyard. We’ll ride to the auburn cliffs of Gay Head at the farthest tip of the island. Along the way, you’ll see expansive views of moors, dunes, and old stone-walls of sheep farms. Enjoy your sack lunch at the end of the island overlooking the cliffs and the endless beaches below. 47 miles.

DAY 4: We’ll begin the day with a short ride to our ferry back to the Cape. Then it’s a flat ride to Eastham

Tour Map

and our inn for the night. Much of the day’s ride is on the beautifully paved Cape Cod Rail Trail.

We’ll pass by salt marshes, cranberry bogs and the Nickerson State Park.

The Pilgrims settled Eastham in 1644 and it is home to the Cape’s oldest windmill, built 300 years ago, and the Nauset Lighthouse, dating back to 1877. Stop in at the Salt Pond Visitor Center for more geological and historical information of this area. 36 miles.

DAY 5: After breakfast, we hop back on the flat Cape Cod Rail Trail until it ends in the art gallery-filled town of Wellfleet. The hilly part of the week begins as we bike the dunes of a narrow stretch of the Cape. At the top of the short, but tallest hill, we’ll be able to see Pilgrim Monument in Provincetown off in the distance. Then our ride flattens out again as we bike past tiny roadside cottages lining the vast, slim beach in Truro.

We should reach our destination of Provincetown in time for lunch on your own in one of the plentiful cafes that line the bay. You’ll have plenty of time to window shop along Commercial Street or relax by the water. After dinner, you may choose to sample some of the colorful nightlife – stand-up comedians, song and dance shows and female impersonators are everywhere to entertain you. 27 miles.

DAY 6: Our last day of cycling takes us to pristine Herring Cove Beach and the dunes of Province Lands on another paved bike trail. After a picnic lunch, we’ll say our good-byes.

If you have driven your car to the tour, then the WomanTours van will shuttle you back to Hyannis by 2:00pm. If you need to return to Boston, take the bus, ferry or fly from Provincetown at your leisure. 17 miles.

"This was a beautiful area to ride in and explore. I enjoyed riding on the Cape Cod Rail Trail. Even though the weather the first two days wasn’t the best, it was still fun and the rest of the days were gorgeous. "
Lynn M., Cupertino, CA