Cape Cod Tour

Charming Cape Cod and Nantucket

Price:  $3,295+

Duration:  6 Days / 5 Nights

Level:  Easy / Intermediate

Terrain:  Flat / Rolling

Rich with coastal New England charm, the Cape and Islands are at their most beautiful during our summer and autumn visits. You’ll cycle the car-free Cape Cod Rail Trail through coastal villages alongside cranberry bogs, lush marshlands and rolling sand dunes. With visits to Chatham, Nantucket, Provincetown and points in between, you’ll discover why so many people are drawn to the region. All this and you’ll still have free time to relax and explore on our Cap Cod Tour.


Day 1: Biking in Chatham‍ (8 miles, Optional Hiking – 1 mile) You’ll start your trip shuttling from Boston to your first night’s lodging in Chatham on Cape Cod. After a brief orientation, you’ll go for a short spin passing Chatham Lighthouse along the way and have the chance to hike on Morris Island. Tonight you’ll enjoy your first dinner together with the group at a local favorite restaurant, just a short walk from our lodging. Meals included: Dinner

Day 2: Kayaking Pleasant Bay & Biking to Nickerson‍‍‍ (19, 30, or 37 miles) Today you head into Orleans to enjoy a relaxing two-hour kayak on Nauset Marsh before lunch. After your paddle, you’ll head on to Brewster and Nickerson State Park on the blissfully car-free Cape Cod Rail Trail. If you’re looking for more mileage, you can pedal on to the town of Dennis before making your way back to Chatham. Tonight you’ll dine at the Impudent Oyster in downtown Chatham. Meals included: Breakfast, Lunch & Dinner

Day 3: Ferry to Nantucket (Optional Biking 20 miles) After breakfast you’ll make the 80-minute ferry crossing to the former whaling port of Nantucket. You can learn about the island’s history at the whaling museum as a docent explains the whaling past and Quaker roots of Nantucket. If you’d rather, take a bike ride to Siasconset at the easternmost part of the island, or you can stay in town and visit more historical sights along the cobblestoned streets of the town center. At the end of the day you’ll ferry back to the Cape then shuttle to Chatham, where you’ll enjoy a delicious clambake. Meals included: Breakfast & Dinner

Day 4: Biking to Provincetown (17, 39, or 58 miles & Hiking – 2 miles) This morning you bid farewell to Chatham and head down the Cape to Provincetown. You’ll return to the Cape Cod Rail Trail and take it to the end in Wellfleet before spinning along the country roads to the tip of the Cape. Along the way, you’ll be able to stop and tour a lighthouse and hike the surreal White Cedar Swamp Trail. As you travel through Wellfleet and Provincetown, the number of art galleries and unique shops you’ll pass are testimony to the thriving artist community on the Lower Cape. Meals included: Breakfast & Lunch

Day 5: Whale watching cruise After yesterday, you’ve earned the right to relax a bit. You’ll enjoy a pleasant four-hour cruise on our whale watching vessel out to the plankton-rich feeding grounds where you may see minke, finback or maybe even the majestic white-fluked humpback whales. After your cruise, you’re free to enjoy lunch at the restaurant of your choice and explore, at your own pace, the many shops and sights of Commercial Street in Provincetown. You’ll enjoy a farewell dinner by the water as you recall the week’s events and stories. Meals included: Breakfast & Dinner

Day 6: Biking the Province Lands (8 miles) After yet another delicious breakfast, you’ll hop on your bike and head toward the very tip of the Cape. You’ll be able to stop at the Cape Cod National Seashore Visitor Center and learn more of the natural history of this coastal region. After our ride, you’ll have the chance to shower & pack up before we shuttle you back to Boston. Meals included: Breakfast


Chatham Wayside Inn– 3 nights Set in the heart of the quaint seaside village of Chatham, Cape Cod, the Chatham Wayside Inn offers stylish accommodations, comfortable dining and outstanding service creating the perfect Cape Cod experience year-round. Chatham’s strolling Main Street, an exclusive mile of boutique shops, art galleries, restaurants, and other seaside activities is just steps from your door.

B‍rass Key Guesthouse– 2 nights The Brass Key Hotel’s extraordinary lodgings, gracious staff and stunning grounds will satisfy tastes from hip and chic, to elegant and antique. A unique haven of nine historically restored buildings enclosing a terraced courtyard, infinity edge pool and oversized in-ground spa, the beautifully landscaped private enclave is unlike any other hotel in Provincetown.


  • Lodging as outlined in lodging section above based on double occupancy
  • Meals as noted in itinerary above
  • Non-optional activities as outlined in itinerary above
  • Ride-friendly snacks and beverages throughout each day
  • Hybrid or alloy road bike rental – carbon road bike or E-bike available for an upgrade fee
  • Services of professional trip leader(s)
  • Van support during the trip & porterage service
  • Black Sheep Adventures reusable water bottle, wool (baaaah) socks & luggage tags
  • Pre & post tour travel
  • Alcoholic beverages
  • Optional activities such as spa treatments
  • Gratuities for your BSA guides





Single Supplement


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