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Cape Cod & Martha’s Vineyard

Shaped 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 retreats—Martha’s Vineyard.

  • Activity Level: Easy
  • Daily Mileage: 18 - 58 mi
  • Daily Biking: 2 - 4 1/2 hr
  • Small Groups: 20
  • Biking
  • Easy

2016 departure dates now available below!

Why You'll Love This Tour


Cape Cod & Martha's Vineyard​

Explore the wonders of Massachusetts’ southeastern coast and biggest island on a cycling vacation through the Bay State’s most scenic destinations. We set out from our bayside resort and follow the famous Cape Cod Rail Trail to many seaside vistas along a National Seashore where we’ll learn about this fragile ecosystem while dipping our toes in the refreshing Atlantic waters. Our sojourn continues on the island of Martha’s Vineyard as we ride by its sleepy fishing villages, past sandy beaches and through 5,000-acre forest of pine and scrub oaks. Join VBT and experience the essence of coastal New England like we can reveal.

Cultural Highlights

  • Cruise along a scenic rail trail to the Cape Cod National Seashore’s Salt Pond Visitor Center and explore its comprehensive museum.
  • Browse the shops of Oak Bluffs and admire the colorful 19th-century gingerbread cottages that surround the village green.
  • Browse the hand-made wares of local artisans in stores like Chilmark Pottery, Martha's Vineyard Glassworks, and the Granary Gallery.
  • Explore the Vineyard’s best-known natural feature, the vibrant clay Aquinnah Cliffs and the beach they tower over.
  • Explore the Vineyard’s best-known natural feature, the vibrant clay Aquinnah Cliffs and the beach they tower over.
  • Take a unique bike ferry to the fishing port of Menemsha, famously known as the filming locale for Jaws’.

What to Expect

This tour offers mostly easy terrain with the occasional rolling hill and the opportunity for some longer rides. Our VBT van support shuttle is always available throughout the trip. During peak season, roughly July 4 to August 21, 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 Daily Temperature (°F) – Edgartown
Apr 54°  May 63°  Jun 72°  Jul 78°  Aug 77°  Sep 71°  Oct 62°

Average Rainfall (in.) – Edgartown
Apr 4.1  May 3.5  Jun 3.5  Jul 3.1  Aug 3.9  Sep 3.5  Oct 3.9

What’s Included:

  • 5 nights in historic New England inns
  • 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
  • Ride to and visit the Cape Cod National Seashore's main visitor facility - Salt Pond Visitor Center
  • 5% Frequent Traveler Credit to use on your next VBT vacation
  • Special Good Buy Discount
  • The option to add our Low-Cost Trip Extension: Pre-trip: Boston – 2 nights for only $495*

*Please note: For those traveling in 2015, the Pre-Trip is $395, single supplement $245.


Dates & Prices
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Departure &
Return Dates

Now Showing:

Land Only

Air Not Included,
Departs after Air Package Plus.
Sun, Oct 11
to Fri, Oct 16
Departure: Sunday, October 11
Return: Friday, October 16
From $2,145
  • From $2,145
  • (800) 245-3868

2015 Land Only Single Supplement: $645 | 2016 Land Only Single Supplement: $695

Please note: Web Special savings cannot be combined with any other offer. Standard Terms & Conditions apply when purchasing this trip. 2015/2016 Prices include all airline surcharges and Government taxes and fees. 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, Cape Cod

Travel to Cape Cod and the Ocean Edge Resort & Golf Club. If you’re flying to Massachusetts, VBT will offer 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 pm. Shuttle reservations are not required or available. Meet the driver outside Terminal C, on the 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 pm or are delayed, please 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 pm 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 resort, while on tour. You may return to this location at the end of the tour by way of the VBT van. We will shuttle to Woods Hole on Tuesday to ferry onto Martha’s Vineyard. If you’d like to park your car in Woods Hole at the ferry terminal and avoid the shuttle back to Brewster at the end of the tour, the cost will be approximately $12 per day. Shuttle time is approximately one hour and 30 minutes.

VBT Pre-Trip Extension guests: You have another morning to enjoy Boston. At 12:50 pm, a shuttle will meet you at your Boston hotel and transfer you to the Ocean Edge Resort & Golf Club. Please wait for the shuttle just outside the School Street entrance to the lobby. Your shuttle bus will carry “Access Express” titles, and the driver will be holding a VBT sign. The shuttle will be coming from Logan International Airport with other VBT guests. Please allow for traffic delays.

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 pm 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 pm. 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

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

Much of today’s riding is through the protected Cape Cod National Seashore. We’ll stop en route at the Salt Pond Visitor Center in Eastham. This is Cape Cod National Seashore’s main visitor facility, with frequent orientation movies, a well-stocked bookstore, and a comprehensive museum. Offering breathtaking views of Nauset Marsh, the visitor 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 or private beach, or play some tennis or golf. There are some 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: 20 or 42 miles

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

After breakfast, we shuttle 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. We will be able to stretch our legs on the way to Oak Bluffs during a quick stop at the historic East Chop Lighthouse, which was built in 1878. Once there, we will join together for a picnic lunch, then have free time in Oak Bluffs to explore the small town. 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! Afterwards, we’ll ride along the State Beach bike path to Edgartown and our Martha’s Vineyard hotel for the next three nights, the Harbor View Hotel & Resort.

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, we return to the inn, settle into our rooms, and perhaps take a swim in the heated pool. There are many options to enjoy one of Edgartown’s celebrated restaurants. Your leaders will have suggestions for you.

Hotel: Harbor View Hotel & Resort
Meals: B, L
Daily Options: 11, 17 or 20 miles

DAY 4: Vineyard Haven / Art galleries & crafters

After breakfast, we will ride out of Edgartown toward Vineyard Haven along the bike path. During the ride we’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 we cycle along the Island’s interior, your Trip Leaders will point out lunch options in between 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 artisans.

After lunch, we’ll 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, this 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
Meals: B
Daily Options: 31 or 33 miles

DAY 5: Menemsha / Aquinnah Cliffs

Today, we 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 us 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 are sprinkled with tropical fossils. The Aquinnah lighthouse stands atop the cliffs, creating a very dramatic view, andthe beaches below are a delightful spot to picnic and swim.

Along the way, we’ll ride through the fishing village of Menemsha. Used as the setting for the film Jaws, the area continues to serve as a working fishing port and as home to the U.S. Coast Guard. A convenient and fun seasonal bike ferry connects Menemsha with Aquinnah.

Hotel: Harbor View Hotel & Resort
Meals: B, D
Daily Options: 20, 32 or 40 miles

DAY 6: Ride to Katama Beach / Depart

After breakfast, we’ll offer an early-morning ride to Katama Beach, also known as South Beach, where we 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, we will transfer to Vineyard Haven for an included lunch. 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 3:30 pm. We recommend a flight out of Boston no earlier than 7:00 pm.

If you parked your car at the start of the tour, the VBT van will transfer you back to Brewster to collect it.

Meals: B, L
Daily Options: 8 miles

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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 recently renovated rooms in the AAA Four Diamond Rated Mansion side of the resort.
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.
Free WiFi Included

Omni Parker House

This grand luxury hotel has been symbolic to Boston’s rich history and culture since 1855. Old-World charm and elegance are accompanied by all of the modern conveniences of a world-class establishment. Nestled in the heart of downtown Boston, Omni Parker House is located along the Freedom Trail and at the foot of Beacon Hill, Boston Common, Quincy Market and Faneuil Hall marketplace.

Cape Cod & Martha's Vineyard Bike Tour Photo Gallery
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Enjoy Your Vacation Longer With LOw-Cost Trip Extensions

Pre-Trip Extension - Boston

2 nights for only $495*

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Talk to a VBT Tour Consultant: (800) 245-3868