MA Cape & The Islands Tour

3 Day Adventure




  • Street Biking
  • Wellness


  • Intermediate
  • Expert









  • 6 days of guided biking
  • 5 nights lodging**
  • 5 breakfasts
  • 3 dinners
  • 1 lunch
  • Welcome refreshments
  • Daily hearty snacks and cold drinks
  • Bicycle and helmet rental
  • Three ferry passages for passenger and bike
  • Historic lighthouse visits
  • 2 dedicated guides
  • Van support
  • Luggage transfer
  • Cycling maps and cue sheets
  • Tax and gratuities for meals and side excursions
  • Featherweight, high visibility, reflective vest
  • Water bottle
  • Dedicated, friendly service throughout your tour
  • **Rates are based on double occupancy. Single occupancy is subject to availability.

Packing List

  • 2 pairs of bike shorts so you can alternate every day
  • 1 pair of quick dry pants for cycling
  • 2-3 pairs of biking socks + 1 pair of waterproof socks
  • Bike shoes
  • 2 quick dry cycling jerseys + one long-sleeved jersey if the weather is colder
  • Arm warmers, leg warmers
  • Rain gear, including a helmet cover, shoe covers, pants, and jacket
  • Cycling gloves
  • Sunglasses
  • Bandana
  • Bike: You may bring your bike or use one of ours. GFA bikes are high quality, lightweight, available with a drop or straight handlebars, and equipped with a computer, mirror, water bottle, handlebar bag, map case, and seat pack with essentials.

Lodging Options



Meals Included
Private Rooms


This tour will start in Provincetown however our recommendation is for guests to meet up in Plymouth as transportation back to Provincetown at the end of the tour will not be provided.

To get to Province town from Plymouth guests have two options.
Our van service or the Provincetown fast ferry. Ferry options are not included in the price of the tour.
Free overnight parking is available in Plymouth and guests will be sent instructions on where to park.

Day 1:

Start at the tip of Cape Cod in fascinating Province Town. Bike spectacular trails in the 4,000 acres Province Lands. Pedal through maritime forests and emerge onto an open, vast dune system with far reaching views of the ocean. These parabolic dunes, some reaching 100′ in height, are unique to the Cape in this part of the world. Stop at the visitor’s center offering stunning 360° views of this extraordinary landscape. See Race Point Beach and Light and pedal alongside Herring Cove Beach on returning to Provincetown.

Day 2:

Bike along the coast through classic Cape towns, including the seaside artist community in Wellfleet. Explore another part of the Cape Cod National Seashore while pedaling past Nauset Light, Nauset Beach, and Coast Guard Beach. Visit the Salt Pond Visitor Center to learn about the seashore’s unique ecosystems and enjoy panoramic views of marsh, ocean, bogs, pond, and woodlands. Finish in Chatham, among the most picturesque towns on the Cape.

Day 3:

Cycle a short loop viewing the Chatham Fish Pier, Chatham Lighthouse, the US Coast Guard Station, and beautiful Chatham Light Beach. Walk an oceanside trail in the Monomoy National Wildlife Refuge to see sensational views and beaches where gray and harbor seals haul out. Watch for seals frolicking in the shallow waters. Pedal past quaint shingled cottages and magnificent seaside estates. Relax at the beach or inn pool, explore the many unique boutiques and art galleries, take a seal-watching cruise or explore more of the area by bike. The afternoon in Chatham is free to enjoy as you wish.

Day 4 and 5:

Travel to Nantucket, once the whaling capital of the world. Discover the beautifully preserved village architecture that looks almost as it did 200 years ago and explore cobble-stoned streets lined with gas lamps. Pedal bike paths to pristine beaches and stately lighthouses while enjoying breathtaking views along the way. Next, ferry to Martha’s Vineyard and discover quintessential fishing villages, island farms, and miles of beaches. See the gingerbread cottages in Oak Bluffs, the sites in Vineyard Haven, and the meticulously preserved mansions of Edgartown, a lovely colonial-era town. 

Day 6:

This morning, take one last ride on Martha’s Vineyard, pedaling flat bike paths to the island’s most famous beach. Bike a quiet road to view fields of wildflowers embraced by soft dunes and framed by the sparkling Atlantic. Pedal back to the inn, then depart for the mainland, where you may wish to spend a bit of time exploring Woods Hole, a charming fishing village that is home to numerous shops, cafes, and the Woods Hole Oceanographic Institution. Return to your car or your transportation to Boston. By the tour’s end, you will have experienced much of the finest of Cape Cod and the Islands – and this extraordinary place will undoubtedly have captivated your heart.

Departure Instructions

Van service will be available back to our original departure spot in Plymouth on the last day.

Booking Information

7 days prior to the adventure


Full payment is due at time of booking.


A booking may be cancelled within 30 days of the reservation with no penalty. See more details below.
A change to a different tour in the same calendar year will be allowed up to 60 days before the original tour departure date if space permits. There is no charge for this. Changes within 60 days of the original tour departure date are subject to cancellation fees as outlined below. Changes/transfers do not apply to custom tours.
All cancellations must be submitted in writing; refunds will be based on the day we receive written notice. Please purchase trip cancellation/travel insurance because exceptions to our cancellation policy cannot be made for any reason, including personal emergencies, illness or injury, canceled or delayed flights or ground travel to the tour departure point, or weather. Refunds will not be made for a participant arriving late or departing early from a tour, or for a participant not using accommodations, meals, or other services offered as part of a tour.
Cancellation Fees Are as Follows (Per Person):
Cancel 30 days or less from booking date – No charge (Does not apply to custom or private tours or to US tours booked within 60 days of departure or overseas tours booked within 90 days of departure.)

91 or more days before trip – $150
61-90 days before trip – $750 or $500 (loss of deposit)
31-60 days before trip – 50% of trip price
30 or less days before trip – 100% of trip price (20% of your payment may be applied to another of our tours departing within one year of original tour start date.)
If a tour is postponed by GFA due to COVID-19, all payments made will be applied as a credit for travel by 12/31/23 less any applicable third-party fees and a $150 per person administrative fee.


Travel and medical insurance are not included in this package. We strongly recommend that you purchase insurance to cover personal injury, cancellation, or interruption for your experience. You will need to separately purchase any trip interruption insurance through an outside provider. This must be done shortly after making your reservation (some require insurance to be purchased within 15-20 days of initial trip deposit).
We also recommend that you carry insurance to cover the risk of injury while you are at your destination. If you are injured, you will be charged the ambulance expenses associated with your evacuation as well as any expenses related to your medical care. Medical and evacuation insurance will help to cover these costs.

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