Cape Cod + The Islands Bike Tour

  • Region: North America
  • Destination: United States
  • Duration: 4 Days / 3 Nights
  • Level: Two
  • Price From: $3295
  • Single Supplement: $650


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Join us on a Cape Cod + the Islands Bike Tour and cycle the blissfully car-free Cape Cod Rail Trail past cranberry bogs, lush marshlands, historic lighthouses, and rolling sand dunes. Meander through the quaint village of Wellfleet filled with art galleries and unique shops. Explore the islands of Nantucket and Martha’s Vineyard on this scenic cycling getaway. Visit historic lighthouses and learn about the famous local whaling industry. You’ll delight in sampling some of the freshest seafood including lobster, oysters, and the famous Cape Cod clam chowder.


Tour by Day

Day One: Welcome to Cape Cod!
After a high-speed ferry ride from Boston, your guides will meet you at the dock in Provincetown, and the adventure begins! Begin with the essentials: bike fitting, safety talk, and map review, then we’re off to explore. Pedal along rolling country roads to Wellfleet—a thriving artist community full of art galleries and unique shops. Here, hop on the Cape Cod Rail Trail, a car-free bike trail, and continue all the way to Chatham. Delight in dinner at the Impudent Oyster in downtown Chatham.

Meals: Lunch / Dinner
Destinations: Provincetown, Cape Cod Rail Trail, Cape Cod National Seashore, Chatham
Accomplished: 17 miles / 27.5 km

Day Two: Exploring Nantucket
This morning we’ll take the 80-minute ferry crossing to the former whaling port of Nantucket. Here, opt to learn about the island’s history at the whaling museum on a docent-led tour, take a bike ride to Siasconset along the easternmost part of the island or stay in town and visit more historical sites along the cobblestoned streets of the town center. This afternoon, we’ll ferry back to the Cape. Tonight head into the seaside town of Chatham to explore and dine there, or opt to dine at the hotel.

Meals: Breakfast / Lunch
Destinations: Nantucket Town, Whaling Museum, Siasconset
Accomplished: 20 miles / 32.5 km

Day Three: Cycling on Martha’s Vineyard
Begin with a ride up the arm of the Cape to board another ferry to Martha’s Vineyard. Explore the Vineyard’s small port town on foot before we hop back on our bikes to pedal “up island” to the painted cliffs and the over 200-year-old lighthouse at Aquinnah. Marvel at the breathtaking coastline at this westernmost point of the island before heading off to Edgartown. Choose to cycle the final leg of the journey or transfer back in the van. Tonight we’ll celebrate our last night together with a delicious meal at one of Edgartown’s finest restaurants.

Meals: Breakfast / Gourmet Picnic / Dinner
Destinations: Martha’s Vineyard, Aquinnah Cliffs, Gay Head Light, Edgartown
Accomplished: 21 miles / 34 km

Day Four: Katama Beach and Return to Boston
Start with a ride on some of Martha’s Vineyard’s dedicated bike paths to visit the island’s best beach—South “Katama” Beach. Then cycle along State Beach, crossing “Jaws” bridge, aptly named for its appearance in all three Jaws movies. Enjoy a leisurely breakfast and relax before hopping back on the ferry to the mainland. From there we’ll shuttle you back to Boston where we’ll say our goodbyes.

Meals: Breakfast
Destinations: South “Katama” Beach, State Beach
Accomplished: 15 miles / 24.5 km