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Massachusetts: Cape Cod & Provincetown

For the most serene and charming cycling experience, look no further than our Cape Cod bike tour. You’ll cycle breathtaking coastal routes with sweeping Atlantic vistas, passing coffee-colored sandbars and pristine beaches protected as part of the Cape Cod National Seashore. Witness a colony of resident harbor seals during a relaxing cruise of Chatham Harbor. And follow the famed Cape Cod Rail Trail and the Province Lands bike path among coastal forest, lagoons rich in birdlife, and undulating dunes that rise from unspoiled shores. Along the way, explore the quintessential Cape communities of Chatham and Provincetown, and sample renowned Wellfleet oysters and just-caught seafood at its freshest and delicious wines from the sea-kissed vines of Truro Vineyards. Join this richly rewarding cycling sojourn of Old Cape Cod!

Tour Highlights

  • Pedal the lovely vistas along the Cape Cod Rail Trail, traversing scenic woodlands past kettle ponds, marshes, and cranberry bogs.
  • Explore lively Chatham—one of New England’s hidden gems, brimming with captivating history, seaside ambiance, and old-fashioned charm.
  • Embark a guided boat-tour of Chatham Harbor to witness fragile sand bars dotted with colonies of harbor seals.
  • Ride the breathtaking Province Lands bike path, winding through the dunes at the very tip of the Cape Cod National Seashore.
  • Experience the arts culture and rich sense of community in Provincetown, poking in the galleries and shops along the town’s beloved Commercial Street.

What to Expect

This tour offers mostly easy terrain with the occasional rolling hill and the opportunity for some longer moderate rides. Our VBT support vehicle is always available throughout the trip. While early summer and late summer months are quieter than July and August, there is still some traffic on the roads from May through October. Despite off-peak season dates, guests will get to experience the best weather and have the opportunity to explore lively bike paths, beaches, shops, and restaurants while avoiding the largest of crowds.

  • Daily Mileage: 12 - 34 miles|
  • Biking: 2 - 5 hours|
  • Group Size: 20
Activity Easy/Moderate Easy / Moderate
Bar Graph Beginner - Experienced
Vehicle Support Vehicle

Average High /
Low Temperature (°F):






May3.7 in

Jun3.6 in

Sep3.9 in

Oct4.0 in

Tour Only

3 nights at a renowned resort Check
6 meals: 3 breakfasts, 1 lunch, 2 dinners Check
Transportation from Boston to Chatham Bars Inn Check
Transportation from Provincetown to Boston Check
Step-Over (Diamond) Comfort Bicycle 8

Step-Over (Diamond) Comfort Bicycle

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Road Bicycle (Carbon frame) 39

Road Bicycle (Carbon frame)

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Electric-Assisted Bicycle (E-bike) 8

Electric-Assisted Bicycle (E-bike)

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Biking Packages Include:

Custom VBT Bike and Helmet

Two Local, Bilingual Trip Leaders

Support Vehicle

Luggage Transportation

Ride with GPS and Daily Route Notes

Welcome Reception

Facilitated Cultural Experiences

Your Choice of VBT Branded Gear for Your Adventure


Sun, Oct 1 to Wed, Oct 4 - 2023

Show Itinerary:

Travel to Cape Cod and the Chatham Bars Inn. If you’re traveling from Boston, VBT offers a shuttle from the Seaport Hotel Boston at the World Trade Center Pier in South Boston. The shuttle works on a “show and go” basis with no reservations accepted and will leave the hotel at 9:00 a.m.  Meet the driver outside the Seaport Hotel Boston front lobby. Your shuttle bus will be a black executive mini-coach, and the driver will be holding a VBT sign. Should you have trouble finding the shuttle driver, please call the transportation company, DPV Transportation Worldwide, at 877.378.4445.

Your Cape Cod bike tour begins at our accommodations, the Chatham Bars Inn, located in Chatham. After settling in, meet your trip leaders at 11:30 a.m. for welcome meeting and safety and bike-fitting session, followed by your first ride and introduction to the area. Your 17-mile jaunt will give you views of the Atlantic Ocean at the Chatham Lighthouse & Coast Guard Station. You trace the surf-lashed contours of Chatham Harbor, pass the Tern Island Sanctuary that lies just offshore, and make your way to scenic Pleasant Bay, pedaling past the inlets and saltwater ponds that lend the Cape its seaside charms. Enjoy a leader-prepared picnic lunch in downtown Chatham before returning to the Inn.

Check in is at 4:00 p.m., but your room may be ready earlier. This evening, join your fellow travelers for a welcome reception of wine and cheese, followed by dinner at the inn.

Today’s Ride Choices

Afternoon: Chatham Loop — 11 miles

What to Expect:

Your first ride gives you the opportunity to get acquainted with your bicycle. You will follow gentle terrain on paved roads around Chatham and out to the beautiful cliffs overlooking Pleasant Bay.

Cumulative Distance Range: 11 miles

Included Meals: Lunch, Dinner

This morning, your route takes you from the resort to the Cape Cod Rail Trail. The rail trail follows a former railroad passage all the way to Orleans. The paved surface, few hills, and well-marked automobile crossings—as well as a unique bicycle “roundabout” where three segments of the rail trail converge—make for an ideal and fun outing.

Following lunch in Orleans, you cycle into the protected Cape Cod National Seashore, stretching some 40 miles along the cape’s eastern coast. This was the American site of the first transatlantic radio telegraph transmission—sent from President Theodore Roosevelt to England’s King Edward VII in 1903 and commemorated at the Marconi Station. Pause during your beachside idyll to admire Coast Guard Beach, Nauset Light Beach, Nauset Light, and the Three Sisters Lighthouses, a trio of lighthouses built in the 19th century to provide guidance to sailors. Today’s longer option leads you along a bayside loop featuring quiet roads and breathtaking coastal scenery.

Shortly after returning to the Inn, you embark a cruiser boat for a guided excursion on Chatham Harbor to the outer beaches of Pleasant Bay. Enjoy another perspective of the Chatham seashore, watching for harbor seals lounging on the sandbars and outer beaches. After, enjoy dinner on your own in Chatham. There are great restaurant options and your trip leaders will be happy to help with recommendations.

Today’s Ride Choices

Morning: Chatham to Orleans — 18 miles

Afternoon: Orleans to Campground Beach — 12 miles

What to Expect:

After a start on local roads, our morning ride follows the Cape Cod Rail Trail 18 miles to Orleans on a mostly flat, paved path with clearly marked automobile crossings. After lunch, continue on the rail trail, then head east to the Cape Cod National Seashore and Nauset Lighthouse. Then cycle west across the width of the Cape to the “bayside,” the Cape Cod Bay basin formed by the arc of the Cape. Here, quiet roads pass breathtaking beaches lined by dramatic dunes. Your ride ends at Campground Beach. Avid cyclists may bike back to Chatham but you may need to forego the boat excursion in the afternoon.

Cumulative Distance Range: 12 — 30 miles

Included Meals: Breakfast

After breakfast, travel to the Salt Pond Visitor Center in Eastham, where today’s ride begins. This is Cape Cod National Seashore’s primary visitor center, with frequent orientation movies, a well-stocked bookstore, and a comprehensive museum. Offering breathtaking views of Nauset Marsh, the center also offers convenient access to two popular walking trails — the 1.5-mile Nauset Marsh Trail and the Buttonbush Trail.

Hop back on the Cape Cod Rail trail from Eastham to the path’s terminus in South Wellfleet, where a delightful French patisserie rewards you at PB Boulangeri Bistro. Savor a croissant or other pastry here before following quiet back roads high along the towering cliffs of the coast. Atlantic beaches of Lecount Hollow, White Crest, and Cahoon Hollow provide perfect photo opps. Then cycle over to the bayside once again, where a winding descent past kettle ponds brings you to the charming town of Wellfleet, known for its rural seaside character and magnificent natural features. Enjoy lunch on your own in town and perhaps sample some famous Wellfleet Oysters at Mac’s on the Town Pier.

You continue north through the protected rural inland beech forests of the Cape Cod National Seashore. Known by some as the “wild Cape,” this remote stretch of road harkens back to a time when the land was rugged and unspoiled. The terrain is undulating, but the peaceful environment and quiet back roads encourage you to take your time.

Your destination is Truro, built on fishing, whaling, and shipbuilding in the 18th century. Visit the active Highland Lighthouse. Originally erected in 1797, it is the oldest and tallest on the Cape. Your day’s ride concludes at the lovely Truro Vineyards and South Hollow Distillery, where you may sample local wine and spirits before traveling back to Chatham.

Back at the resort, enjoy some free time to relax around the swimming pool and hot tubs, play some tennis, relax on the beach, or take a stroll into the quaint New England village of Chatham. Gather for a farewell dinner tonight with your trip leaders and travel companions.

Today’s Ride Choices

Morning: Eastham to Wellfleet — 12 miles

Afternoon: Wellfleet to Truro Vineyards — 13 miles

What to Expect:

Cycle the last stretch of the Cape Cod Rail Trail before taking quiet back roads to Wellfleet and Truro. The rural landscape is more undulating than previous days but the views are well worth the effort as you progress north to the Outer Cape.

Cumulative Distance Range: 12 — 25 miles

Included Meals: Breakfast, Dinner

After breakfast and check-out, a one-hour journey brings you to the heart of Provincetown – MacMillan Pier. “P-town,” as it’s known to locals, is where Pilgrims first settled before they relocated to Plymouth. The Mayflower Compact was written and signed here. Today, it is one of New England’s major arts and culture centers.

You cycle through Provincetown’s quiet West End before reaching the very tip of the Cape—the dunes and small ponds of Province Lands. Pass Herring Cove Beach and Race Point Beach, stopping along the way at the Province Lands Visitor Center where you may learn about the historic maritime station that rescued shipwrecks at a time when this spit of land was notoriously difficult to navigate. Rejoin the bike path for a thrilling ride through beech forest, past kettle ponds, and along picturesque dunes with stunning ocean views before returning to town.

Enjoy free time for lunch and exploration in Provincetown. Browse some of its many photo and art galleries or perhaps climb the Pilgrim Monument Tower for stupendous vistas of the tip of Cape Cod – an ideal way to wrap up your adventure. Say goodbye to your trip leaders before the included return journey to Boston.

Today’s Ride Choices

Morning: Province Lands Ride — 14 miles

What to Expect:

Begin your ride in the center of Provincetown at MacMillan Pier. Cycle down lively Commercial Street into the quieter West End before reaching the very tip of the Cape Cod National Seashore. Ride along the road to Race Point Beach and Province Lands Visitor Center before joining the bike path through beech forest, kettle ponds, and the picturesque dunes along the coast.

Cumulative Distance Range: 14 miles

Included Meals: Breakfast

Massachusetts: Cape Cod & Martha's Vineyard 1

Download PDF Itinerary:

Tour Only (PDF)

Accommodations (May vary depending on departure date. )

81 out of 85 (95%)
4.7 out of 5 stars.
Read More Reviews

Fun itinerary, lovely bike paths and great scenery esp on Martha’s Vineyard. A few hills but mostly easy riding.


Cape Cod & Martha’s Vineyard

Loved this trip. The rides were beautiful, the lodging spectacular and the food was amazing. Loved that the ride was split between Cape Cod and Marthas Vineyard. The bike routes were a nice way to avoid traffic.

Mary Beth, Rochester NY

Cape Cod & Martha’s Vineyard

Dates & Prices

Select Year :

Tour Only

4 Days. Includes bike vacation only.

Single Supplement: From $695

Sun, Oct 1 - Wed, Oct 4, 2023


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For more information, call: 800-245-3868

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