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Cape Cod + the Islands Bike Tour

Scenic Eastern Seaboard: Nantucket, Provincetown, and Martha's Vineyard

4 days / 3 nights Level: 2Price From: $3,295Collection: Classic

Tour Highlights

  • Pedal to the painted cliffs and 200-year-old lighthouse on Martha’s Vineyard
  • Visit Nantucket, a onetime whaling port now famous for its flower-covered cottages and unchanged New England town center
  • Stroll the quaint cobblestoned streets of Chatham
  • Relish the breathtaking coastline, salty air, rolling sand dunes, and charming beachside villages


Classic New England seafood: lobster, Wellfleet oysters, clam chowder, and steamers


Reds, whites, and rosés from local Cape vineyards and a wide range of Massachusetts craft beers

As featured in:
Print Itinerary
  • Day 1

    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: 29 miles / 47 km, elevation gain: 149 meters
    Accommodations: Chatham Bars Inn

  • Day 2

    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: 23 miles / 37 km, elevation gain: 141 meters
    Accommodations: Chatham Bars Inn

  • Day 3

    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 / Lunch / Dinner
    Destinations: Martha’s Vineyard, Aquinnah Cliffs, Gay Head Light, Edgartown
    Accomplished: 22 miles / 36 km, elevation gain: 199
    Accommodations: Hob Knob Luxury Boutique Hotel & Spa

  • Day 4

    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: 13 miles / 21 km, elevation gain: 34 meters

DuVine itineraries may be subject to slight route changes, hotel substitutions, and other modifications.

Arrival Details

Airport City: Boston or Martha’s Vineyard, Massachusetts Pick-Up Location: Provincetown Pick-Up Time: 10:00 am
Departure Details

Airport City: Boston or Martha’s Vineyard, Massachusetts Drop-Off Location: Boston Drop-Off Time: Midday


  • Thoughtfully selected accommodations that reveal the true character of the region
  • Luggage transfers


  • Daily breakfasts, all lunches, nutritious snacks, and après velo cocktails
  • 2 gourmet dinners at our favorite local restaurants and renowned culinary establishments
  • Carefully selected local wine, beer, or spirits with every meal


  • Wine tastings and activities as outlined in the tour itinerary
  • Entrance fees to historic sites, museums, parks, and all other exclusive events
  • Gratuities for baggage, porters, and hotel service


  • Top-of-the-line bicycle selection and bike helmet
  • Complimentary DuVine gear, including a custom cycling jersey, DuVine t-shirt, water bottle, and drawstring bag
  • GPS in most destinations


  • Expert bilingual guides with extensive local knowledge
  • Support vehicle that follows the day’s route, distributes refreshments, and offers lifts
  • Pick-up and drop-off before and after your tour from predetermined meeting points
  • Daily bike maintenance to ensure optimal performance

See our FAQs page for answers to common questions.

See FAQs


Type: E-Bike