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Cape Cod & Martha’s Vineyard

National ParksShaped like an arm in a welcoming embrace, Cape Cod retains much of the maritime charm of its long-gone whaling days. We’ll bike along the Cape Cod National Seashore on a converted rail trail now made for cycling before hopping a ferry to explore an island fit for a Presidential retreat—Martha’s Vineyard.

  • Activity Level: Easy
  • Daily Mileage: 18 - 62 mi
  • Daily Biking: 2 - 4 1/2 hr
  • Small Groups: 20
  • Biking Activity
  • Perfect for those trying a bike vacation for the first time.

Why You'll Love This Tour


Cape Cod & Martha's Vineyard​

Dramatic cliffs crowned with historic lighthouses … quaint gingerbread cottages and thriving artists’ colonies … a picturesque rail trail with sweeping views of sea and shore … the taste of salt air and salt water as you swim in the sea … these are just a few of the pleasures that await you in an idyllic escape that has drawn everyone from sun worshippers to Presidents. This well-crafted itinerary also features handpicked accommodations that put you at the heart of the region you’ve come to see.

Cultural Highlights

  • Cycle the lovely Cape Cod Rail Trail, among the finest on the East Coast
  • Delight in views of Nauset Marsh at the Salt Pond Visitors Center
  • Enjoy 5 nights at renowned resort inns, with plenty of time for recreation
  • Cycle through the Cape Cod National Seashore, gathering for a picnic lunch
  • Discover historic East Chop Lighthouse, on Martha’s Vineyard
  • Share a picnic lunch in West Tisbury, historically the agricultural heartland of the island
  • Pedal along the Vineyard’s State Beach bike path
  • Admire the work of Vineyard Haven’s wonderful artisans
  • Cycle through beautiful Cornelius State Forest
  • Ride by breathtaking Aquinnah cliffs and through Menemsha village

What to Expect

This tour offers mostly easy terrain with the occasional rolling hill and the opportunity for some longer moderate rides. Our VBT van support shuttle is always available throughout the trip. During peak season, roughly July 1 to August 25, there is more traffic on the Cape and Islands, but you will get to experience the best weather and have the opportunity to explore lively bike paths, beaches, shops, and restaurants.

Average Daily Mileage: 18 – 62 miles
Average Cycling Time: 2 – 4 1/2 hours

Climate Information

Average High/Low Temperature (°F) – Edgartown
May 64°/46°  Jun 73°/56°  Jul 79°/62°  Aug 78°/61°  Sep 72°/55°  Oct 63°/45°

Average Precipitation (in.) – Edgartown
May 3.8  Jun 3.2  Jul 2.8  Aug 4.1 Sep 3.6  Oct 3.8

What’s Included:

  • 2 nights in villas and 3 nights in quintessential island inn
  • 10 meals – 5 breakfasts, 3 lunches, 2 dinners
  • FREE use of our custom VBT bicycle and helmet
  • Service of two VBT Trip Leaders
  • Daily route directions and maps
  • Welcome reception
  • Sightseeing and cultural activities
  • Transfers
  • 5% Frequent Traveler Credit to use on your next VBT vacation. See details.

Dates & Prices
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Tour Begins: Sunday, June 24
Tour Ends: Friday, June 29

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Tour Ends: Friday, August 3

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Tour Ends: Friday, October 12

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Land Only Single Supplement: $745

Please note: Web Special savings cannot be combined with any other offer. Standard Terms & Conditions apply when purchasing this trip. Ask our Tour Consultants for details. Every effort has been made to produce this information accurately. We reserve the right to correct errors. Prices are based on preferences selected above, including meals and sightseeing as specified in What’s Included. All prices are subject to change. Departure dates and prices shown may be updated several times daily, and apply to new bookings only.

Itinerary & Map
Or, Expand All Days
Day 1: Arrive in Brewster / VBT Bicycling Vacation begins / Cape Cod

Travel to Cape Cod and the Ocean Edge Resort & Golf Club. If you’re flying to Massachusetts, VBT offers a shuttle from Boston’s Logan International Airport. The shuttle works on a “show and go” basis and will make its only departure from the airport to the resort at 12:30 p.m. Shuttle reservations are not required or available. Meet the driver outside Terminal C, on the upper (second) level, at the second island out. Your shuttle bus will carry “Access Express” titles, and the driver will be holding a VBT sign. Please allow for traffic delays.

If you are scheduled to arrive at the airport after 12:30 p.m. or are delayed, you will take a taxi or bus at your own expense. VBT does recommend that guests try to arrange their arrival at Logan International Airport prior to 12:30 p.m. as Brewster is approximately an hour and 45 minutes from Boston. If you are delayed or your travel plans change, please contact the resort; they will pass your message on to your VBT Trip Leaders. If you are driving to the Cape, we recommend that you leave your vehicle in Brewster in a remote lot at the Ocean Edge Resort while there. You will need to move your car to Woods Hole at the remote parking lot near the ferry terminal while on the island on Day 3 of the tour. The cost will be approximately $15 per day.

The tour begins at our Cape Cod accommodations, Ocean Edge Resort & Golf Club, located in Brewster, Massachusetts. After settling in, meet your Trip Leaders at 3:30 p.m. for a safety and bike-fitting session, followed by a short warm-up ride and introduction to the area. Check in is at 4:00 p.m. Your room may be ready earlier; please confirm with the front desk upon arrival. Later, join your fellow travelers over a wine and cheese reception, followed by dinner at the inn.

Hotel: Ocean Edge Resort & Golf Club
Meals: D
Daily Options: 3 miles

Day 2: Cape Cod Rail Trail / Cape Cod National Seashore

Your cycling this morning takes you from the resort to the Cape Cod Rail Trail. The rail trail follows a former railroad passage through the towns of Brewster, Orleans, Eastham, and Wellfleet. Its paved surface, few hills, and well-marked automobile crossings make it ideal for biking. You’ll stop along the way for an included picnic lunch.

Much of today’s riding is through the protected Cape Cod National Seashore. You’ll stop en route at the Salt Pond Visitor Center in Eastham. This is Cape Cod National Seashore’s primary visitor center, with frequent orientation movies, a well-stocked bookstore, and a comprehensive museum. Offering breathtaking views of Nauset Marsh, the center also offers convenient access to the popular 1.5-mile Nauset Marsh Trail and the Buttonbush Trail.

Back at the resort, enjoy some free time to relax around the swimming pool, play some tennis or golf, or take the complimentary resort shuttle service to Crosby Landing public beach from the Villages side of the property. There are great restaurant options for dinner on your own tonight. Your Trip Leaders will be happy to help with recommendations.

Hotel: Ocean Edge Resort & Golf Club
Meals: B, L
Daily Options: 22.5 and/or 8 miles or 45 miles

Day 3: Ferry to Martha's Vineyard / Oak Bluffs / Edgartown / Chappaquiddick Island

AAfter a leisurely breakfast, you’ll shuttle (approximately 1.5 hours) to Woods Hole and board a ferry to Martha’s Vineyard. “The Vineyard,” as locals know it, is New England’s largest island (23 miles long by 9 miles wide). Under the protective arm of Cape Cod, the cold Labrador Current is warded off while waters warmed by the Gulf Stream flow up from the south. Enjoy a packed lunch as the ferry cruises to Martha’s Vineyard.

Your leaders will unload your bicycle at the park upon exiting the ferry. Oak Bluffs has been a summer resort since the early 1800s, and its history is reflected in the colorful gingerbread cottages surrounding the village green. The town’s Flying Horses Carousel has been in operation since 1884! You’ll ride along the State Beach bike path to Edgartown and your Martha’s Vineyard hotel for the next three nights.

If you’d like a few more miles of riding, board the “Chappy” ferry for a three-minute sail across the 300-yard-wide strait that separates Martha’s Vineyard from Chappaquiddick Island. Having short trips and no timetable, the Chappaquiddick Ferry is always on time. The island’s main attractions are, of course, the infamous Dike Bridge, along with the Mytoi Japanese Garden.

Later, return to the inn, settle into your room, and perhaps take a swim in the heated pool. There are many options to enjoy one of Edgartown’s celebrated restaurants. Your Trip Leaders will have suggestions for you.

Hotel: Harbor View Hotel & Resort
Alternate Hotel: Kelley House
Meals: B, L
Daily Options: 6, and/or 14 miles

Day 4: Vineyard Haven / Art galleries & crafters

After breakfast and a short shuttle, you’ll ride from Vineyard Haven. During the ride, you’ll have a chance to explore Vineyard Haven, Martha’s Vineyard’s only year-round port of entry, before continuing on an epic cycling loop to West Chop Lighthouse and Lambert’s Cove Road. As you cycle along the Island’s interior, stop in for visits to Chilmark Pottery, Martha’s Vineyard Glassworks, Polly Hill Arboretum, the Field Gallery, and the Granary Gallery. The Granary Gallery boasts the most amazing paintings, sculptures, and photography from more than 300 of the island’s most celebrated artists.

After a picnic lunch prepared by your Trip Leaders, cycle back to Edgartown by way of the paved bike path through the Manuel F. Correllus State Forest. Located in the center of the island, the forest is a 5,000-acre pine and scrub oak area crisscrossed with hiking trails.

The rest of the day and dinner are at your leisure.

Hotel: Harbor View Hotel & Resort
Alternate Hotel: Kelley House
Meals: B, L
Daily Options: 28 and/or 13 and/or or 15 miles

Day 5: Menemsha / Aquinnah Cliffs

Today you will be heading “up island.” The term comes from sailing days, when a vessel was running “up” its longitude when it was sailing west away from the prime meridian. In a similar manner, a ferry always comes “up” from Nantucket.

Today’s ride will take you to the breathtaking Aquinnah cliffs and beach on the western part of the island. Perhaps the best-known natural feature of the Vineyard, the brilliantly colored cliffs at Aquinnah are a mile long and sprinkled with tropical fossils. The Aquinnah lighthouse stands atop the cliffs, creating a very dramatic view, and the beaches below are a delightful spot to picnic and swim.

Along the way, you’ll ride through the fishing village of Menemsha. Used as the setting for the film Jaws, the village continues to serve as a working fishing port and home to a U.S. Coast Guard station. A fun and convenient seasonal bike ferry connects Menemsha with Aquinnah. Enjoy some free time back at the resort or in town before your farewell celebration dinner.

Hotel: Harbor View Hotel & Resort
Alternate Hotel: Kelley House
Meals: B, D
Daily Options: 17 and/or 24.5, 29 or 30 miles

Day 6: Ride to Katama Beach / VBT Bicycle Vacation ends / Depart

After breakfast, you may join in an early-morning ride to Katama Beach, also known as South Beach, where you can enjoy three miles of barrier beach on the South Shore of the island.

After returning to the hotel for a shower and to check out, you will transfer to Oak Bluffs. Your Trip Leaders can assist in recommendations to locate a packed lunch, or purchase lunch on board the ferry. All aboard! Our Steamship Authority ferry leaves for a 45-minute crossing to Woods Hole. A shuttle from Woods Hole Ferry Terminal to Logan International Airport will be provided with a departure time from Woods Hole at 1:30 p.m. We recommend a flight out of Boston no earlier than 5:00 p.m. Guests who parked their cars at the remote parking lot will board a complimentary ferry shuttle service back to the lot.

Meals: B
Daily Options: 8 miles

Cape Cod & Martha’s Vineyard Map

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Ocean Edge Resort Golf Club

The cornerstone of the resort is the Nickerson Family Mansion and Carriage House, overlooking Cape Cod Bay. Originally built in 1890, the Nickerson family home is listed in the National Register of Historic Places. VBT guests are accommodated in the villas on The Villages side of the AAA Four-Diamond rated resort. A/C is available.
Free WiFi Included

Harbor View Hotel & Resort

The Harbor View Hotel & Resort, located in the very heart of Edgartown, is the perfect Vineyard lodging, with its stunning ocean views and refined Martha’s Vineyard décor. A/C is available.
Free WiFi Included

Kelley House

Kelley House is a classic gem located in the heart of Edgartown and provides a casual seaside lifestyle experience. It opened its doors in 1742 and is one of the oldest hotels in America. The Garden House building offers 42 well-appointed cozy rooms just steps from the waterfront, shops, restaurants and a wide variety of attractions. A/C is available.
Free WiFi Included

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