Cycling the Best of Cape Cod (TourzPlus!)

  • Itinerary Summary

    One of the largest barrier "islands" in the world, the eastern-most arm of Massachusetts is known for its pristine beaches, captivating history, and old fashioned charm. Pedal through charming villages, past gray-shingled cottages, and along much of the Cape Cod Rail Trail, whose paved surface and gentle terrain are ideal for cyclists. This new tour encompasses the best of Cape Cod's unique landscapes and seaside character. Diverse scenery, cycling routes and distinctive accommodations allow you to experience the "Cape" in comfort and style. Explore the lovely town of Chatham-one of New England's hidden gems-and enjoy a two-night stay at the renowned Wequassett Resort on Pleasant Bay. Venture off the beaten path to visit lighthouses and cranberry bogs, explore seaside villages, and bask in the expanse of the undeveloped beaches of the Cape Cod National Seashore. Follow a bike path through the dunes of Provincetown, at the outermost point of the Cape, and visit the Old Harbor Lifesaving Museum. Enjoy a spectacular cruise to nearby Stellwagon Bank Natural Marine Sanctuary for up-close encounters with several types of whales. Return to Boston from Provincetown on a cruise across Massachusetts Bay.
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    1. Day 1: Chatham Village and Pleasant Bay

      Highlights: Wequassett Resort

      This morning, a private coach will transfer you from Boston's Marriott Long Wharf to the start of your first ride. The ride winds along quiet streets lined with classic gray-shingled homes so characteristic of Cape Cod's seaside towns. Your tour leaders will prepare and serve a delicious picnic lunch along the route. Follow the paved Old Colony Trail toward Pleasant Bay and your lodging for the next two evenings at Cape Cod's only member of Preferred Hotels & Resorts Worldwide - the acclaimed Wequassett Resort. Named by the native Wampanoag for the land upon which it is situated, "Wequassett" means crescent on the water. Nestled in a quiet cove with two expansive private beaches, this elegant property seamlessly blends 100 years of history with the finest of contemporary amenities. Enjoy east facing views across Pleasant Bay to the Atlantic Ocean. The Resort features swimming pools, tennis, boating, and several dining venues. Dinner this evening will be in a private dining room overlooking the bay.

      No Cycling Today.

      Lodging: Wequassett Resort

    2. Day 2: Chatham Village and Pleasant Bay

      Highlights: Monomoy Wildlife Refuge, Chatham Lighthouse

      Begin your morning with a sumptuous breakfast overlooking the bay. Today's ride takes to the town of Chatham whose seclusion at the Cape's elbow, abundant coastline, and exclusivity make it one of New England's hidden gems. Ride past lovely homes and visit Monomoy National Wildlife Refuge Visitor Center before continuing past Chatham Lighthouse and into town. Browse the shops and galleries in the village center or return to the Resort for a dip in the pool. This afternoon, gain a different perspective of the area during a private cruise from Pleasant Bay into Chatham Harbor. In January 1987, a powerful nor'easter unexpectedly broke through the lower end of Nauset Beach, allowing the Atlantic Ocean to surge into Chatham Harbor. The "Chatham Break" is now a growing channel and constantly changing the once protected waters of Pleasant Bay. Due to the safety of large sandbars being created by the channel, upwards of 1500-2000 gray and harbor seals frequent them in the waters of Chatham. Enjoy dinner on your own in town this evening or at one of the Resort's own restaurants.

      Distance: 22-31 miles.

      Lodging: Wequassett Resort

    3. Day 3: Cape Cod Rail Trail

      Highlights: Monomoy Island Cruise, Cape Cod Baseball League

      Wind your way out of town to connect with the Cape Cod Rail Trail. This wonderful paved bike path passes through pine forest, past cranberry bogs, and the Cape's unique kettle ponds. Stop for a snack at the coffee shop or to visit the bike shop in Orleans as you make your way to Eastham, often referred to as the Gateway to the Cape Cod National Seashore. At the Salt Pond Visitor Center you will learn about the unusual geologic features of Cape Cod as well as the history of the National Seashore. The Cape Cod National Seashore was established by the late President John F. Kennedy in 1961 to protect the unspoiled beauty of the eastern shore of Cape Cod along a nearly 40 mile expanse of seashore. After settling into your room at the inn, enjoy a walk along Salt Pond that offers several stunning vistas. Built in 1870, this handsome Queen Anne Victorian is a former sea captain's mansion and has retained its prominence as one of the centerpieces of the area. This evening, join your fellow travelers for dinner at a popular restaurant featuring fresh local products.

      Distance: 21 or 36 miles.

      p>Lodging: Inn at the Oaks

      Lodging: Chatham Bars Inn

    4. Day 4: The Cape Cod Rail Trail to Provincetown

      Highlights: Cape Cod Rail Trail, cranberry bogs, pine forest

      Following another delicious breakfast you will make your way by bicycle or by van to the Cape Cod Rail Trail. Follow this delightful paved path for 17 miles through pine forest, past cranberry bogs, and the Cape's unique kettle ponds. This former railroad line follows gentle contours as it carries you to the Outer Cape. Emerge from the rail trail in Welfleet where we recommend a stop for lunch at PB Boulangerie Bistro - truly a touch of a quiet French village in the midst Cape Cod. Their freshly baked breads, delicious pastries, and hearty sandwiches may finish you off for the day. At the Boulangerie you can make the decision to hop the van for the rest of the trip into Provincetown or continue cycling. The ride continues on quiet roads and through the charming town of Welfleet before following the bay to artsy Provincetown. Once in Provincetown, you will ride through the heart of downtown's shops, galleries and restaurants to the quiet West End. The West End is just a short walk from the heart of the commercial district yet feels worlds removed from the lively downtown area. The town's most well-tended historic homes line the street overlooking the bay. Land's End Inn sits atop one of the highest points in Provincetown and its elegant rooms are surpassed only by the amazing views from almost every point on the property. This evening the group will dine together at a restaurant in town.

      Distance: 17, 39, 49 miles.

      Lodging: Land's End Inn

    5. Day 5: Provincetown

      Highlights: Whale-Watching, Provincetown, Herring Cove Beach

      Following breakfast this morning, you will head for the town pier for a once in a lifetime whale watch trip offshore. Provincetown is the closest port to Stellwagen Bank - one of the world's richest marine habitats and a favored feeding ground for large numbers of whales. Provincetown's location - nearly 40 miles out to sea - means that whales are often sighted as soon as the boat leaves the port. This translates into greatly reduced travel times to viewing points. The trip is guided by an experienced naturalist and is virtually guaranteed to provide whale sightings. Dolphins and sea birds are also frequently sighted during the three-hour trip. Upon return to port, visit one of the many restaurants in town for lunch or grab a sandwich and head for the beach. The afternoon is free to explore the sites in town or relax at gorgeous Herring Cove Beach. There are many interesting shops and a large number of galleries in Provincetown. Those interested in cycling can join their leaders for a ride to the lighthouse in Truro. This evening, stroll the streets admiring the classic architecture or snapping photos in the late day light before joining the group for dinner in town.

      Distance: 12 miles.

      Lodging: Land's End Inn

    6. Day 6: Cruise Across Cape Cod Bay

      Highlights: Cape Cod National Seashore's Province Lands Visitor Center

      Following a leisurely breakfast this morning, do some last-minute shopping in town or visit the Pilgrim Monument before making your way to MacMillan Wharf for the ferry crossing to Boston. In 1620 when they first landed in the New World, the Pilgrims stopped in Provincetown for five weeks before continuing on to Plymouth where they ultimately settled. The 252' tall monument - the tallest all granite structure in the US - offers sweeping views over the Outer Cape and across Cape Cod Bay to Boston. It is a 90-minute trip to Boston where, upon arrival, those departing from Logan International Airport can take a water taxi (ten-minute trip) directly from the ferry dock to the airport. For those planning to remain in Boston, water taxis are available to a variety of locations.

    • Highlights

      Boston, Cape Cod Baseball League game, Whale Watching Cruise, Cranberry bogs, Chatham, Cape Cod Rail Trail, Provincetown, Herring Cove Beach
    • Includes

      Use of a 27-30 speed bicycle; 6 days, 5 nights' accommodation; 4 breakfasts, 2 picnic lunches, 3 dinners; van support; group shuttle from Boston on Day 1 and return Day 6; snacks
    • Countries

    • Begin/End

      Boston, MA
    • Arrive/Depart

      Boston, MA (BOS)
    • Total Distance

      73 - 126 miles
    • Daily Distance

      Average daily mileage 15 to 25
    • Rating

      101 The terrain is level to gently rolling terrain with significant portions on the Cape Cod Rail Trail.
    • Terms

      Terms & Conditions
  • Dates Price Private Room Charge Notes
    Sep 10-15, 2017 USD$2795 USD$895 Book it

    * We are happy to match solo travelers who would like to share a room with someone of the same gender. If no match exists, due to hotel pricing, we will charge 50% of the private room charge. This charge will be collected at the time of the final payment. If a roommate assignment is available it will be refunded at the conclusion of the tour.

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