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Biking the Back Roads
BIKERS - Sick of 66? Rumble down our Ramblin\' Roads!

This Fly-Drive makes for a great motorcycle ride.  Enjoy beautiful scenery, great sights and delightful food on this exciting tour which has been specifically designed to be enjoyed on a motorcycle.
DAY 1: Boston
Arrive Boston. This evening, enjoy one of Boston’s many restaurants, take in a show in Boston’s theater district or stroll through lively Quincy Marketplace.

DAY 2: Boston – Portland, ME (95mi/152km)
This morning, a private car will transfer you to the motorcycle facility to pick up your bike. Travel north to Portsmouth, New Hampshire, a working port since colonial days and a treasure trove of shops, taverns and historical sites. Then follow along Coastal Route 1A into Maine. Ride through York and into Ogunquit. Take a walk along the Marginal Way, a magnificent mile-long footpath which follows the edge of the Atlantic atop rugged cliffs and have a lobster at Perkins Cove. Continue up the coast through Kennebunkport and cut over to South Portland for the night.

DAY 3: Portland – North Conway, NH (65mi/104km)
The smell of the sea air, the sound of a foghorn, and the chatter of seagulls add to an atmosphere that is undeniably Portland. Stroll down cobblestone streets and experience the funky yet quaint charm of this city before traveling through Maine’s picturesque lakes region. Follow Route 302 flanking Sebago Lake, across Moose Pond and into North Conway for the overnight.

DAY 4: North Conway – Killington/Rutland, VT (146mi/234km)
Venture along the Kancamagus Scenic Byway, Route 112 passing through the heart of the White Mountains while traversing the side of Mt. Kancamagus, filled with scenic areas and overlooks. Continue through Franconia Notch and see natural wonders such as Indian Head, the Flume Gorge, or take a tram to the summit of Cannon Mountain for breathtaking views of the surrounding area. Scenic routes and covered bridges will take you into Vermont, the Green Mountain State. Visit Woodstock, a quintessential New England village replete with the charms of Vermont. Stay near Killington in Rutland for the overnight.

DAY 5: Killington – Williamstown – Stockbridge – Lenox, MA (130mi/208km)
Head south along Route 7, a winding two lane highway through rural towns into Massachusetts’ Berkshire Hills. Take time in Williamstown to explore this famous college community. See Tanglewood, the Boston Symphony’s summer home in Lenox and visit the Norman Rockwell Museum in Stockbridge, which houses his paintings of America past. Highlights include paintings from Rockwell’s Saturday Evening Post covers. Overnight in Lenox.

DAY 6: Lenox – Sturbridge – Hyannis (150mi/240km)
Head east towards Cape Cod. En route, visit Plymouth, “America’s hometown” to see Plymouth Rock and the Mayflower II, an exact replica of the ship that carried the Pilgrims to the New World. Then cross the Cape Cod Canal and follow Route 6A though the village of Sandwich to Hyannis. Overnight for the next 2 nights in Hyannis, where one can find plenty of taverns, restaurants and white sand beaches.

DAY 7: Hyannis – Provincetown – Hyannis (140mi/224km)
Today, ramble along the Cape Cod National Seashore all the way to Provincetown at the tip of Cape Cod. Explore lighthouses, quaint coastal communities, and natural scenic beauty. \"P-town” is known for its beaches, harbor, artists, unique shops, and its reputation as a gay village. Take a whale watch, enjoy another lobster or just relax at one of the many local hangouts.

DAY 8: Hyannis – Boston (70mi/112km)
Morning to relax on the Cape. Drop your bike off just outside of Boston. A private car will offer transfer to airport.





Courtyard Tremont


BW Merry Manor

Harraseeket Inn ( Freeport)

N Conway

Green Granite

Christmas Farm Inn Jackson

Rutland / Stowe

Holiday Inn (Rutland)

Golden Eagle Resort (Stowe)


Yankee Inn (Lenox)

Williams Inn (Williamstown)


Heritage House

Hyannis Harbor Hotel

Package Includes:
  • Accommodation
  • Taxes
  • Motorcycle
  • Helmets for driver and passenger
  • Transportation from Boston Hotel to motorcycle rental facility and return to Boston Airport
  • Fly - Drive directions and information packet at hotel upon arrival
Package may also be purchased without motorcycle.