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Cape Cod & The Islands

Day 1:  Arrival Day

  • Transport to Hotel
  • Build Bikes
  • Short Ride
  • Hotel: Long Wharf Marriott
  • Dinner: Opening Reception

Day 2: Boston to Plymouth

Take the Commuter Boat from Long Wharf, Boston to Hull, MA.   After departing the boat, you will meander along the South Shore coast through the towns of Cohasset, Scituate, Duxbury, Marshfield and finishing in Plymouth.   Each community has a distinctive personality but all sit on the beautiful seashore of the Atlantic Ocean.   The day ends in Plymouth, where the Pilgrims landed.   You will have an opportunity to view Plymouth Rock and wander this historic town.

  • Level: Moderate
  • Mileage: 50 miles
  • Hotel: Hotel 1620
  • Dinner: On Own

Day 3: Plymouth to Woods Hall/Martha’s Vineyard

The route will cross over the manmade Cape Cod Canal on the Sagamore Bridge and travel towards Wood Hole along the water.  In Woods Hole, we will board a ferry to Martha’s Vineyard to spend a day exploring the island.

  • Level: Moderate
  • Mileage: 45 Miles
  • Hotel: Kelley House
  • Dinner: On your Own

Day 4: Martha’s Vineyard

We will head out after breakfast and ride around the entire Island seeing all the highlights including Oak Bluffs, Vineyard Haven, West Tisbury, Menemsha, Chilmark, Aquinnah (formerly known as Gay Head), Katama – South Beach and back to Edgartown.  After returning from the ride there will be plenty of time to explore areas of interest such as the Methodist Cottages in Oak Bluffs or Chappaquiddick Island.  Martha’s Vineyard has been home to many artists and authors, and a vacation spot for the likes of President Obama, the late John Belushi, as well as Hollywood stars such as Reese Witherspoon and Jake Gyllenhaal.    There will be a group dinner and then early to bed for an early morning ferry back to the mainland.

Day 5:  Woods Hole to Brewster

After the ferry boat ride, you will ride across the Cape to Old King’s Highway.  You will ride through the quintessential Cape Cod towns of Sandwich, Yarmouth and Dennis, finishing at the luxury Ocean Edge Resort in Brewster.  This is old Cape Cod with kettle ponds and weather worn shingled cottages.

Day 6:  Brewster to Provincetown

The last day of riding takes you through the Outer Cape. The five outermost towns (Provincetown, Truro, Wellfleet, Eastham and Orleans) are more commonly and collectively known as the “Outer Cape”. This area is home to the Cape Cod National Seashore, a national park that encompasses much of the Outer Cape, including the entire east-facing coast from Orleans to Provincetown. The Outer Cape is home to some of the most popular beaches in the United States, such as Nauset Light Beach and Coast Guard Beach in Eastham, Race Point Beach in Provincetown, Ballston Beach in Truro, and Skaket Beach in Orleans. At the very tip of Cape Cod is Provincetown.   Referred to as “P-town” or “P’town”, the town is known for its beaches, harbor, artists, tourist industry.

  • Level:  Easy
  • Mileage: 38 Miles
  • Hotel:
  • Dinner:  On Own

Day 7:  Provincetown to Boston

Everyone will board a boat to Boston, while the bikes and luggage are driven back.  If you are lucky you will get to see a whale or two!

Tour Date:
September 9 – September 16, 2017

Fee: $3,250 (Single Supplement $850)


  • 7 days/6 nights
  • Full van support
  • Professional Ride Leaders
  • Primal Wear CST Jersey
  • 5 Breakfasts, all lunches & 3 dinners
  • Hydration & nutrition along the route
  • Ferry Ride from Boston to Hingham
  • Ferry Ride from Provincetown to Boston
  • All airport transfers in Boston
  • Option & additional:
    • Bike rental

Does not include:

  • Transportation to and from the tour including airfare, or train travel
  • Meals not listed in the itinerary
  • Alcohol during meals
  • Ride Leader gratuity

Let us know if you would like to receive a full itinerary by filling out the form below.

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Address : 1515 E 9th Ave #311
Denver, CO 80218 United States
Phone: +1 303-931-6455
Email: deirdre@cyclingsightstours.com
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