We’re all part of this community. Adventure Cycling’s Guided Tours response to COVID-19 here.

Cape Cod & The Islands

Historic Shores to Island Destinations
Price :
Surface :
Duration :
8 days
Support :
Self Contained
Difficulty :
Level 1

Spend a week cycling along the beautiful Atlantic Ocean shoreline. On this tour, we’ll view the seaports, glacially formed kettle ponds, and lighthouses of southeastern Massachusetts, visit historic sites from the days of colonial America, and explore quaint shops on Cape Cod and Martha’s Vineyard. Attractions of special interest include Cape Cod National Seashore; a full-scale reproduction of the Mayflower; the preserved village of New Bedford, once the whaling capital of the world; and the Chatham Marconi Maritime Center. Every day on this tour is spent within 15 miles of the Atlantic, and each night close to a large body of freshwater or saltwater.

This tour is suitable for all riders and is a great choice for anyone looking to learn the basics of self-contained touring, or for an experienced bicycle traveler looking for a week of relaxed cycling. The riding is relaxed, services are plentiful, and the campgrounds are outstanding. 

Photos by Selina Kok | Lijuan Guo | Shawme Crowell
Sep 11 - Sep 18, 2021
Space still available

"Loved seeing seals frolic in the ocean at Race Point, chatting with fishermen, riding the Chappy ferry and seeing "the bridge" and Provincetown action on Saturday afternoon."


Day 1. Plymouth, Massachusetts, 0 miles

We'll meet just outside Plymouth, Massachusetts, home to the first sustainable settlement for the Pilgrims after they wintered near Provincetown. Those arriving early can explore the Plymouth Plantation, the Mayflower II (a full-scale reproduction of the original), and the famous Plymouth Rock, traditionally regarded as the spot where William Bradford and the Mayflower Pilgrims disembarked on the mainland.

Day 2. Plymouth to Sandwich, 26 miles

We'll enjoy the gently rolling hills, cranberry bogs, and lovely lowlands of southeastern Massachusetts as we ride westward, then northward, toward our destination for the evening. We'll head into the cranberry bogs, traveling along quiet farm roads on the approach to "old Cape Cod." We'll finish the day with a 15-mile ride along the Cape Cod Canal and cross the Sagamore Bridge onto the Cape to our home for the night.

Day 3. Sandwich to Martha's Vineyard, 28 miles

Turning south again, we'll ride along the Cape Cod Canal proceeding southward to Falmouth and Woods Hole. More bike trails are in store for us today, along with a few short but very steep hills known as "sand rollers." You should have plenty of time to explore the famous Woods Hole Oceanographic Institute, where guided walking tours are a great way to learn about its history and research. Later we'll hop aboard the ferry to Martha's Vineyard and take a short ride to our lodging for the next two nights: a wooded island campground.

Day 4. Layover day in Martha's Vineyard, 0–40 miles

You can ride gear-free today on a 40-mile trip around Martha's Vineyard, or leave your bicycle behind and just hang out on the white sandy beaches of the Vineyard. Other options include riding to one or more of the Vineyard's four lighthouses and sampling the amazing seafood in the island ports of Vineyard Haven, Oak Bluffs, and Edgartown.

Day 5. Martha's Vineyard to Nantucket Island, 40 miles (shorter option available)

After an early morning ferry ride, we'll explore Nantucket Island on a loop ride that will showcase the best of the island as well as take us to our evening destination. We won't be here long enough for you to read Moby-Dick, but you'll be able to take in the area's rich history before settling into a cozy hostel for the night.

Day 6. Nantucket Island to Brewster, 40 miles

We will reboard the ferry but head to Hyannis Harbor on our way to our evening destination of Nickerson State Park via the Cape Cod Rail Trail. The upper campsites at Nickerson are in a setting that feels more like the piney woods of the Carolinas than Cape Cod, where sand dunes and salt marshes are more often the norm. These woods slope down to a series of freshwater kettle ponds, which have no inlet streams -- they're entirely dependent on groundwater and precipitation, so their water levels fluctuate seasonally. We will throw in a side trip to Chatham, home of the Chatham Lighthouse.

Day 7. Brewster to Provincetown, 40 miles

Continuing along the Cape Cod Rail Trail, we can visit the Cape Cod National Seashore's information center and a trio of lighthouses, or the Chatham Marconi Maritime Center, celebrating the history and science of 20th century radio communication. Our last night of camping will be along the inner Cape, a mere stone's throw from the mighty Atlantic.

Day 8. Provincetown to Plymouth, 12 miles

We'll wind down our Cape Cod trek with a quick jaunt up the bike path to Race Point Beach from Provincetown, the first landing site of the Pilgrims before they continued on to Plymouth. We can spend the morning exploring the shops, restaurants, museums, eclectic architecture, and picturesque docks of Provincetown before taking a shuttle back to Plymouth in the afternoon.


Additional Details
Start Location:
Plymouth, MA
End Location:
Plymouth, MA
Logan Intl. (BOS)
Total Days:
Riding Days:
Layover Days:
Tour Leader:
Average Daily Mileage:
Shared cooking
Level 1
Rolling Hills
Restricted Bike Type:
eBike, eTrike