Itinerary

Day 1: Biking in Chatham

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. Distance: 8 miles, Optional Hiking – 1 mile

Day 2: Kayaking Pleasant Bay & Biking to Nickerson

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.
Breakfast, Lunch & Dinner. Distance: 19, 30, or 37 miles

Day 3: Ferry to Nantucket.

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, Optional Biking 20 miles

Day 4: Biking to Provincetown

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. Distance: 17, 39, or 58 miles & Hiking – 2 miles

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

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. Distance: 8 miles

* This is a general itinerary. Tour itineraries are subject to change based on the group, available accommodations and other unforeseen circumstances such as the weather, local conditions, government intervention, that may affect the quality of the trip and/or safety of the participants. Please view this itinerary as an outline as to what to expect on this tour.

Lodging

Charming Cape Cod & Nantucket

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.

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.

Included:

• Lodging in charming Inns
• Meals included: 4x breakfast, 2 x lunch and 4 x dinner.
• 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
• Whale watch tour, Kayak trip.
• Services of professional trip leader(s)
• Van support during the trip & porterage service
• Tour operators T-shirt, wool socks, water bottles & luggage tags.

Not included:

• Pre & post tour travel
• Alcoholic beverages
• Optional activities such as spa treatments
• Gratuities for your guides

Pricing / Tour dates

Tour price 2025 from: $ 3295.- pp.Single fee from $995
Tour dates 2025:
01 June – 31 Sep.
Between June and September you can choose any date you like, only available for a private tour for a MINIMUM OF FOUR PARTICIPANTS IN ONE BOOKING.
Price mentioned is a starting price, please ask for quote.

Conditions

Deposit $750.- pp
The deposit payment for a tour must be paid within two weeks after the booking is confirmed.
The remaining payment is due 90 days before the start of the tour.
For tours that are booked within 90 days before the start of the tour you will pay 100% of the tour price