Rating Level: EasyNew England’s most beloved vacation playgrounds were made for bicycling!
From your base in charming Chatham, you’ll follow a car-free, paved trail with well-marked crossings, enjoying stunning Atlantic views as you roll along Cape Cod’s protected shoreline. Then, ferry to Martha’s Vineyard, where dedicated bike paths reveal natural wonders like local wildlife, colorful cliffs, white-sand beaches and spectacular ocean views. You’ll also experience New England’s long seafaring tradition, explore Oak Bluffs’ Victorian cottages around the town green, visit historic lighthouses and enjoy time at leisure in lively Edgartown. Don’t miss this opportunity to experience classic New England at its best!
ENJOY riding on routes specifically for cycling
ADMIRE the gingerbread-style Victorian cottages of Oak Bluffs
TAKE in splendid harbor views as you visit historic lighthouses
MARVEL at the colorful cliffs of Aquinnah
RETREAT to comfortable accommodations in the heart of Chatham and Edgartown
WALK to world class galleries and restaurants from our centrally located inns.
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 on Cape Cod and the islands, roughly July 4 to August 21, roads and paths can be very busy and this may create a more challenging experience.
Rating Level: Easy
Daily Mileage: 18 - 45 miles
Daily Cycling Time: 2 - 4 1/2 hours
Make your own arrangements for travel to Boston and the Fairmont Battery Wharf.
When you arrive at the Fairmont Battery Wharf, ask at the reception desk for your VBT Information Packet, which is full of useful ideas to make the most of your time in “Beantown.”
Your hotel is conveniently located for easy access to the city's highlights. Boston is a great walking city, with many highlights concentrated in the old, established downtown area. Maybe you'll decide to take one of the amphibious landing vehicle “duck” tours that originated here in Boston.
Make your own arrangements for travel to Chatham Wayside Inn. If you're flying to Massachusetts, you may utilize VBT Active Vacations' 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 inn at 12:30 p.m. Shuttle reservations are not required or available. Meet the driver outside Terminal C, ground level (Arrivals/Baggage Claim), in the Shared Vans area. The driver will be holding a VBT Active Vacations sign. The shuttle will be coming from the pre-extension hotel with VBT guests. Please allow for traffic delays.
If you are scheduled to arrive at the airport after 12:30 p.m. or are delayed, you must take a taxi or bus at your own expense. If you are driving to the tour, we recommend that you leave your vehicle in Chatham while on tour. You can park at the Chatham Wayside Inn while a guest at the inn. When you leave Chatham, the leaders will help you with the transfer of your vehicle to another location while on Martha's Vineyard. You may return to this location at the end of the tour by way of the VBT van. If you are delayed or your travel plans change, please contact the first inn; they will pass your message to your VBT Trip Leaders.
VBT Pre-Trip Extension guests: You have another morning to enjoy Boston. At 12:00 noon, a shuttle will meet and transfer you to the Chatham Wayside Inn by way of Logan International Airport.
We meet at The Chatham Wayside Inn, located in Chatham, 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 Chatham. Check in at Chatham Wayside is at 4:00 pm. Your room may be ready earlier, please check with the front desk upon arrival. Later, join your fellow travelers at a wine and cheese reception, followed by dinner at the inn's Wild Goose Tavern.
Our morning cycle takes us from the inn to join the Old Colony Rail Trail and the Cape Cod Rail Trail. The Cape Cod Rail Trail follows a former railroad right-of-way for 22 miles through the towns of Dennis, Harwich, Brewster, Orleans, Eastham and Wellfleet. Its paved surface, few hills and well-marked automobile crossings make it ideal for cyclists.
Much of today's riding is through the protected Cape Cod National Seashore. 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, a comprehensive museum, and restroom facilities. Offering breathtaking views of Nauset Marsh, this Visitor Center is also convenient to the popular 1.5 mile Nauset Marsh Trail and the Buttonbush Trail.
After lunch, options include riding or shuttling back to Chatham, or continue on to visit Coast Guard Beach, Three Sisters Lighthouses and Nauset Light Beach, returning to Chatham along the bike path.
Back in Chatham, relax around the inn's swimming pool, stroll the village's beaches or explore the town with its myriad of shops. There are a number of great restaurant options for dinner tonight. Leaders will be happy to help with recommendations.
After a leisurely breakfast, shuttle from Chatham west towards Hyannis. It was in the former Hyannis Armory that President-elect John F. Kennedy gave his victory speech on November 9, 1960.
Late morning, we board a passenger ferry in Hyannis for the 55-minute trip to Oak Bluffs on Martha's Vineyard. We will have free time in Oak Bluffs to have lunch and explore while our bikes and the VBT support van travel via the vehicle ferry from Woods Hole. 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!
“The Vineyard,” as locals call 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. In the mid-afternoon, we rejoin our bikes and support van in Oak Bluffs for a gentle ride along the ocean-side bike path to Edgartown and our lodging for the next three nights, the Harbor View Hotel & Resort.
For a few more miles, board the “Chappy” ferry for a three-minute sail across the 300-yard-wide straight separating 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.
Return to the inn and settle into our rooms at the resort and perhaps take a swim in the heated pool before our included dinner at the inn this evening.
After breakfast, we will be ride out of Edgartown towards North Tisbury. Along the way, we'll cycle through Manuel F. Correllus State Forest. Located in the center of the island, this forest is a 5,000 acre pine and scrub-oak forest crisscrossed with hiking trails and circled by a paved bike path.
After exiting the bike path, we'll enter Lambert's Cove Road, known for it's towering trees and winding curves. Back on the main path, stop and visit Chilmark Pottery in West Tisbury. The gallery at Chilmark Pottery is filled with an array of colors and wares for sale.
Cycle back to Edgartown by way of West Tisbury, along one of the island's dedicated bike paths typically separated from car traffic by a planted median. You can enjoy lunch in West Tisbury as you visit the town, or back in Edgartown.
The rest of the day and dinner is at your leisure.
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 be all the way to 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. The beaches below are a delightful spot to picnic and swim.
Continue on to Menemsha. The fishing village of Menemsha was used as the setting for the film Jaws. Menemsha village area continues to serve as a working fishing port and as home to the U.S. Coast Guard. A convenient and fun bike ferry connects Menemsha with Aquinnah (seasonal).
Tonight, rejoin the group for a farewell dinner at one of Edgartown's celebrated restaurants.
There are two rides this morning, both to the same location. We'll offer an early morning ride to Katama Beach, and another one a bit later if you're not an early riser. Katama Beach is three miles of barrier beach on the South Shore at the end of Katama Road with a beautiful expanse of sand and surf. Energetic guests can complete both rides this morning.
After returning to the hotel for a shower and check out, we will transfer to Vineyard Haven for a final lunch. All aboard! Our Steamship Authority ferry leaves for a 45-minute crossing to Woods Hole. A shuttle from Woods Hole Ferry Terminal to Boston International Airport will be provided with a departure time from Woods Hole at 3:30 p.m. We recommend a flight out of Boston no earlier than 7 p.m.
If you parked your car at the start of the tour, the VBT van will transfer you back to Chatham to collect it.
VBT Post-Trip Extension guests: The shuttle from Woods Hole to Boston's Logan International Airport will stop also at the Fairmont Battery Wharf. Explore the city at your leisure.
Boston is a fascinating city to explore. Your hotel is conveniently located for easy access to the city's highlights.
Enjoy your final morning of Boston exploration. Your extension ends with checkout from the hotel today.
|
May 64° Jun 73° Jul 79° |
Aug 78° Sep 72° Oct 62° |
|
September 12, 2010 |
$2,195 |
|
September 19, 2010 |
$2,145 |
|
September 26, 2010 |
$2,145 |
|
October 3, 2010 |
$2,145 |
|
October 10, 2010 |
$2,045 |
When visiting Boston, you'll discover neighborhoods with distinct character, quaint brownstone-lined streets, the beloved Red Sox and big-city entertainment. Begin or end your Cape Cod & Martha’s Vineyard trip with a relaxing stay at the new, harbor-front Fairmont Battery Wharf. Located just steps away from the Freedom Trail, the North End, the Rose Kennedy Greenway, the Institute of Contemporary Art and the Fairmont Battery Wharf, is the ideal location to discover Boston by foot.
Note: Single supplement for this extension is $245.
When visiting Boston, you'll discover neighborhoods with distinct character, quaint brownstone-lined streets, the beloved Red Sox and big-city entertainment. Begin or end your Cape Cod & Martha’s Vineyard trip with a relaxing stay at the new, harbor-front Fairmont Battery Wharf. Located just steps away from the Freedom Trail, the North End, the Rose Kennedy Greenway, the Institute of Contemporary Art and the Fairmont Battery Wharf, is the ideal location to discover Boston by foot.
Note: Single supplement for this extension is $245.
Set in the heart of the quaint seaside village of Chatham, Cape Cod, the Chatham Wayside Inn offers stylish accommodations, comfortable dining and outstanding service, creating the perfect experience.
The Harbor View Hotel & Resort, located in the very heart of Edgartown, is the perfect Vineyard with stunning ocean views and refined Martha’s Vineyard décor.
Adjacent to the historic North End, Fairmont Battery Wharf luxury hotel embraces the rich history of its neighborhood. New in 2009, the hotel is dedicated to providing its guests with a contemporary and sophisticated retreat in the city’s most vibrant location.
|
May 64° Jun 73° Jul 79° |
Aug 78° Sep 72° Oct 62° |
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 on Cape Cod and the islands, roughly July 4 to August 21, roads and paths can be very busy and this may create a more challenging experience.
|
May 64° Jun 73° Jul 79° |
Aug 78° Sep 72° Oct 62° |

Occasionally, unforeseen circumstances may arise which may cause you to either cancel or interrupt your vacation. We are committed to providing the best value for your travel dollar. That is why we include an insurance program on your invoice.
|
TRIP CANCELLATION & TRIP INTERRUPTION |
TRIP COST |
|
TRAVEL DELAY ($150 MAXIMUM PER DAY) |
$750 |
|
BAGGAGE & PERSONAL EFFECTS |
$1,500 |
|
BAGGAGE DELAY ($150 MAXIMUM PER DAY) |
$750 |
|
ACCIDENT AND SICKNESS MEDICAL EXPENSE |
$50,000 |
|
EMERGENCY MEDICAL EVACUATION |
$100,000 |
|
ACCIDENTAL DEATH & DISMEMBERMENT |
$25,000 |
|
ONE CALL 24HR ASSISTANCE SERVICES* |
INCLUDED |
|
ONE CALL TRAVEL SOLUTIONS* |
INCLUDED |
|
ONE CALL CONCIERGE SERVICES* |
INCLUDED |
*These are non-insurance services provided by One Call Worldwide Travel Services Network.
Insurance is underwritten by United States Fire Insurance Company, Eatontown, NJ. This is only a brief description of the plan. The Plan Certificate, which fully details the Benefits, Limitations, and Provisions of the plan is available at www.vbt.com. This plan is administered by Trip Mate, Inc. (in CA, Trip Mate Insurance Agency), 9225 Ward Parkway, Kansas City, MO 64114 800-888-7292.
|
Tour Cost Per Person |
Plan Cost Per Person |
|
$1,001-$1,500 |
$119 |
|
$1,501-$2,000 |
$159 |
|
$2,001-$2,500 |
$189 |
|
$2,501-$3,000 |
$229 |
|
$3,001-$3,500 |
$269 |
|
$3,501-$4,000 |
$299 |
|
$4,001-$4,500 |
$329 |
|
$4,501-$5,000 |
$349 |
|
$5,001-$6,000 |
$419 |
|
$6,000-$7,000 |
$449 |
Please Note: The rates shown are per-person and are subject to change, and include coverage for the air portion of your itinerary if VBT Active Vacations is arranging your air transportation. The Travel Protection Plan cannot be purchased after you have made your final payment or once you are inside the penalty period, whichever comes first. The cost of your Travel Protection Plan is non-refundable.
Pre-Existing Medical Condition Exclusion is waived if the plan is purchased within 14 days of initial trip payment.