iExplore Cape Cod Active(Trip #65841)

Tour Overview

Welcome to Cape Cod! Fond of sand dunes, salty air and quaint little villages? Then you’ll fall in love with Old Cape Cod. Nostalgic song lyrics aside, “the Cape” and Nantucket Island overflow with coastal charm and a rich history linked to the sea. You’ll cycle the car-free Cape Cod Rail Trail past cranberry bogs, lush marshlands, historic lighthouses, and rolling sand dunes. Off the bike, stroll fine-sand beaches, browse villages brimming with artist galleries, explore the coast by kayak, and search offshore for the humpback whale. You will find the Cape at its most beautiful during our summer and autumn visits. And you’ll find the accommodations at the Wequassett Resort breathtaking- one of Conde Nast Traveler’s Top 100 mainland U.S. hotels. Join us for an unforgettable multisport vacation and seaside adventure you’ll fondly remember for years!

Day by Day Itinerary

Day 1: Arrive Boston- 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.

Meet in Boston at 10:00am at the Four Seasons Hotel.

Set prominently atop a rise facing Pleasant Bay and the Atlantic Ocean, the striking Wequassett Resort and Golf Club is an idyllic Cape Cod luxury resort nestled within 22 acres of shoreline, salt marshes and woodlands. Providing a truly secluded paradise, this unrivaled four-diamond resort offers a vast array of activities and resort amenities in a striking ocean-side setting.

After getting oriented, you’ll go for a short spin passing Chatham Lighthouse along the way and have a chance to hike on Morris Island.

Tonight you will enjoy your first dinner together with the group at Wequassett’s premier restaurant, Twenty-Eight Atlantic.

Distance cycled: 8 miles, optional hiking: 1 mile

Meals: Dinner
Wequassett Resort and Golf Club

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 are 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.

Distance cycled: 19, 30 or 37 miles.

Meals: Breakfast, Lunch, Dinner
Wequassett Resort and Golf Club

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 islands 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.

Distance cycled: optional biking 20 or 39 miles.

Meals: Breakfast & Dinner
Wequassett Resort and Golf Club

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 Cape Cod. 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.

Distance cycled: 39 or 58 miles. Hiking: 2 miles

Meals: Breakfast & Lunch
Wequassett Resort and Golf Club

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 the cruise, you are 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.

Distance cycled: Optional biking province Lands- 8 miles

Meals: Breakfast & Dinner
Wequassett Resort and Golf Club

Day 6: Biking to Dennis- Boston- Depart
After yet another delicious breakfast, you will 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. We will finish in Boston at the airport.

Distance cycled: 12 miles

Meals: Breakfast

Trip Total: 78 miles minimum, 154 miles maximum, plus kayaking and hiking.