Spend several days in this charming town in the heart of Cape Cod

Cape Cod Bicycle Tour, Massachusetts

Duration
6 days
Site savings
$43
From
$4,252 USD

One of the largest barrier “islands” in the world, the easternmost arm of Massachusetts is part of a thin line of archipelagic islands formed by retreating glaciers. Artists have long been drawn to the Cape’s landscapes and soft light. Unspoiled sand dunes line beaches for nearly 30 miles along the Cape Cod National Seashore. Charming villages feature historic homes and picturesque harbors that still host working fishing fleets. Country roads and the Cape Cod Rail Trail invite exploration by bicycle. Experience one of New England’s most beloved seacoast vacation destinations on this 6 day Cape Cod bike trip.

  • Category
    Road Cycling
  • Type
    Fully Guided
  • Duration
    6 days
  • Culture Level
    Familiar
  • Skill Level
    2 - Novice
  • Activity Level
    2 - Moderate
  • Elevation
    2 - Moderate
  • Terrain
    Coastal
  • Distance
    110 miles
  • Avg. Daily Distance
    21.7 miles
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Quick Stats

  • Duration
    6 days
  • Main Destination
    United States
  • Distance
    110 miles
  • Avg. Daily Distance
    21.7 miles
  • Elevation
    2 - Moderate
  • Terrain
    Coastal

Route Map (click to view larger image)

Itinerary Details

  1. Day 1Yarmouth to Chatham

    This morning, a private coach will transfer you from Boston’s Marriott Long Wharf to the start of your first ride in the town of Yarmouth. The route winds along quiet streets lined with the classic grey-shingled homes so characteristic of Cape Cod’s seaside towns. Your tour leaders will provide a delicious picnic lunch in Harwich before continuing on to connect with the lower Cape section of the Cape Cod Rail Trail. Follow this paved bike path all the way to Chatham and your lodging for the next two evenings at New England’s finest oceanfront resort, the acclaimed Chatham Bars Inn. This elegant property seamlessly blends 100 years of history with the finest of contemporary amenities. Chatham Bars Inn is a distinguished member of The Leading Hotels of the World and the Conde Nast Gold List. The Inn, overlooking Chatham Harbor, features its own dining room, tavern, private beach, swimming pools, and luxurious spa. It is just steps from the venerable Chatham Fish Pier where you can watch the daily catch being unloaded and packed to be delivered to restaurants in Boston. Dinner this evening will be in the private dining room overlooking the harbor.

    • 19.9 miles
    • Chatham Bars Inn, Chatham
    • Lunch and Dinner
  2. Day 2Chatham Village and Pleasant Bay

    Begin your morning with a sumptuous breakfast as the sun casts its rays upon the harbor. Today’s ride explores the nooks and crannies of the town of Chatham, whose abundant coastline at the Cape’s secluded elbow, makes it one of New England’s coveted locations. Ride along quiet lanes and past lovely homes and visit Monomoy National Wildlife Refuge Visitor Center before continuing to Chatham Lighthouse. Browse shops and galleries in the village center or return to the Inn to relax on the private beach. This afternoon, gain a different perspective of the area during a private cruise across Chatham Harbor and into Pleasant Bay. In the winter of1987, a powerful nor’easter unexpectedly broke through the lower end of Nauset Beach allowing the Atlantic Ocean to surge into Chatham Harbor. The “Chatham Break” is now a growing channel and constantly changing the once protected waters of Pleasant Bay. Due to the safety of large sandbars formed by the channel, upwards of 1500-2000 grey and harbor seals frequent the waters of Chatham and can often be viewed basking on the sandbars at low tide. It’s quite likely that you will get an up-close glimpse of seals during your cruise this afternoon. Enjoy dinner on your own in town this evening or at one of the inn's acclaimed restaurants.

    Cycling Options: 37km (23mi) or 51km (32mi)

    • 23 miles
    • Chatham Bars Inn, Chatham
    • Breakfast
  3. Day 3The Cape Cod Rail Trail

    Wind your way out of town to connect with the Cape Cod Rail Trail. This wonderful, paved bike path passes through pine forest, past cranberry bogs and a number of the Cape’s unique kettle ponds. Stop for a snack at a popular coffee shop in Orleans or visit the bike shop as you make your way to Eastham, often referred to as the gateway to the Cape Cod National Seashore. At the Salt Pond Visitor Center, you will learn about the unusual geologic features of Cape Cod as well as the history of the National Seashore. In 1961, Cape Cod National Seashore was established by the late President John F. Kennedy to protect the unspoiled beauty of the eastern shore of Cape Cod along a nearly 64km (40mi) expanse of seashore. You might enjoy following the network of walking trails that commence from the visitor center and offer expansive views over salt marshes. After exploring the trails and seashore, your leaders will shuttle you back to the Chatham Bars Inn. This evening, join your fellow travelers for dinner at a popular restaurant featuring fresh local products.

    Cycling Options: 35km (22mi) or 51km (32mi)

    • 21.7 miles
    • Chatham Bars Inn, Chatham
    • Breakfast and Dinner
  4. Day 4Wellfleet and Truro Vineyards

    Following a short morning shuttle, enjoy the Cape Cod Rail Trail through pine barrens to its terminus where you can stop to sample the wealth of baked goods at renowned PB Boulangerie Bistro. Relax over a delicious French pastry or rich espresso before continuing your ride past lighthouses, through small fishing villages, and along lightly traveled roads that overlook expansive beaches to the charming village of Wellfleet. Continue to family-owned Truro Vineyards where you will relax on the lawn while sampling local wines over a delicious picnic lunch served by your leaders. Continue along Cape Cod Bay toward Provincetown and the charming and upscale West End. The West End is just a short walk from the heart of the commercial district’s shops, galleries, and restaurants, yet feels worlds removed and Land’s End Inn sits in the heart of it, atop one of the highest points in Provincetown. The Inn’s elegant rooms are surpassed only by its stunning views over the bay. The evening is yours to explore the vibrant downtown area and dine at one of many wonderful restaurants.


    • 32.9 miles
    • Land’s End Inn, Provincetown
    • Breakfast and Lunch
  5. Day 5Provincetown & the Outer Cape

    This morning, enjoy a ride along the National Seashore’s bike paths and roadways that wind among the dunes. Visit the Province Lands Visitor Center where you can learn more about the region's native people and the constantly changing landscape of the dunes of the Outer Cape. Visit the historic Old Harbor Life Saving Station or walk the beach to Race Point Lighthouse which marks the northern most point of Cape Cod. This afternoon you might climb the Pilgrim’s Tower, browse shops and galleries in town, or join a whale watch to nearby Stellwagen Bank—one of the world’s richest marine habitats and a favored feeding ground for large numbers of whales. The 252’ tall Pilgrim’s Monument offers sweeping views over the entire Outer Cape and across Cape Cod Bay to Boston. In 1620 when the Pilgrims first landed in the New World, they stopped in Provincetown for five weeks before continuing on to Plymouth where they ultimately settled. If you prefer to put a few more miles on your bike, venture to the bayside highlands of North Truro. This evening, stroll along Provincetown’s narrow streets lined with period architecture and take advantage of the late daylight for photos. Join your fellow travelers for a final dinner together at a favorite restaurant in town.

    Cycling Option: 19km (12mi) or 32km (20mi)

    • 11.8 miles
    • Land’s End Inn, Provincetown
    • Breakfast and Dinner
  6. Day 6Cruise Across Cape Cod Bay

    Following a leisurely breakfast this morning, do some last-minute shopping in town before making your way to MacMillan Wharf for the ferry crossing to Boston. It is a 90-minute trip to Boston where, upon arrival, those departing from Logan International Airport can take a water taxi (ten-minute trip) directly from the ferry dock to the airport. For those planning to remain in Boston, water taxis are available to a variety of locations throughout the city.

    • Breakfast