Cape Cod Bicycle Tour Itinerary

Day 1: Biking in Chatham
You’ll start your trip shuttling from Boston to your new home for the week, the breathtaking Wequassett Resort in Chatham on Cape Cod. After getting oriented 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 the Wequassett’s premier restaurant, Twenty-eight Atlantic.

Meals: Dinner
Distance cycled: 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 Pleasant Bay 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 an elegant restaurant in downtown Chatham.

Meals: Breakfast, Lunch & Dinner
Distance cycled: 19, 30, or 37 miles cycling

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 to Chatham, where you’ll enjoy another fine dining experience.

Meals: Breakfast & Dinner
Distance cycled: Optional biking 20 or 39 miles

Day 4: Biking to Provincetown
This morning you’ll 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 toward 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: Breakfast & Lunch
Distance cycled: 39, or 58 miles cycling & 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 again at Twenty-eight Atlantic as you recall the week’s events and stories.

Meals: Breakfast & Dinner
Distance cycled: Optional Biking Province Lands – 8 miles

Day 6: Biking to Dennis
After yet another delicious breakfast, you’ll have the chance to take a quick spin around Chatham or relax and have a leisurely morning at the hotel.  Your leaders will then shuttle you back to Boston.

Meals: Breakfast
Distance cycled: 12 miles

TRIP TOTAL: 78 miles minimum, 154 miles maximum, plus kayaking and hiking