
Massachusetts Fly Drive
From
£2,527pp
Massachusetts Fly Drive
Why Book?
✓Hays Travel Peace of Mind Guarantee
✓£49pp low deposit followed by 6 monthly Direct Debit payments of £413pp
✓Includes Compact - 2/4 Doors - Automatic - A/C CCAR FORD FOCUS OR SIMILAR
✓Add Travel Insurance from £82pp
- Guests: 2 Adults
- Duration: 14 Nights
- Board: Room Only | Bed & Breakfast
- Departing: Selected UK Airports
- Offer Date: 11th November 2025
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Get behind the wheel for to an exciting 14-night fly drive adventure around the USA state of Massachusetts. This road-trip begins and ends in the state capital of Boston and lets you experience the myriads of sights and attractions and eclectic towns and cities throughout Massachusetts, including Boston, Kennebunkport, Bar Harbor, Lincoln, Lenox, Worcester, and the finale of Cape Cod-Hyannis.
Days One to Three: Boston, Massachusetts
Fly into Boston in Maine where your 14-night Massachusetts fly-drive adventure gets underway when you pick up your car at the airport and drive to DoubleTree Suites by Hilton Hotel Boston Bayside for the next three nights. Perhaps ride one of the Swan Boats at Boston Public Garden; enjoy New England Aquarium’s Whale Watch experience; follow the HarborWalk to visit the Institute of Contemporary Art and the Boston Tea Party Ship; or stroll along the Freedom Trail taking in the State House, Old Granary and King's Chapel Burying Grounds, and Charlestown's USS Constitution frigate and Bunker Hill Monument.
Day Four: Kennebunkport
Drive to Kennebunkport in Maine for a night’s stay at Hampton Inn by Hilton Kennebunk-Kennebunkport. Head to Dock Square’s shops, galleries, and eateries; cross the bridge to Kennebunk, or follow Ocean Avenue around Cape Arundel to Walker’s Point – summer home of President Bush’s family. View the landmark Goat Island Lighthouse from Cape Porpoise or take a one-hour tour with Intown Trolley. Admire the trams, trolleys, and subway cars at the Seashore Trolley Museum and the 70,000+ artefacts at Brick Store Museum. Don’t miss the Wedding Cake House and Summer Street Mansions.
Days Five to Six: Bar Harbor
Your journey continues to Bar Harbor in Maine, where you’ll spend two nights at Hampton Inn Ellsworth/Bar Harbor. Go whale-watching on the Gulf of Maine or board a puffin cruise. Delve into the indigenous history and culture of the Wabanaki Nations at Abbe Museum. Step back to the Gilded Age at La Rochelle Mansion and History Museum. Stroll through 400+ plant species at the Wild Gardens of Acadia or take a scenic walk along the 4.4-mile Ocean Path. Embark on a road-trip on the 27-mile Park Loop Road around the east side of Mount Desert Island - connecting Acadia's lakes, mountains, and shoreline and with access to Sieur de Monts, Sand Beach, Otter Point, Jordan Pond, and Cadillac Mountain.
Day Seven to Eight: Lincoln
Your adventure continues with a drive to Lincoln for a two-night stay at the newly renovated Woodwards White Mountain Resort, BW Signature Collection. You’ll have chance to get up close to trained bears and ride the White Mountain Central Railroad at Clark’s Trading Bears. Visit the Flume Gorge at the base of Mount Liberty in Franconia Notch State Park and enjoy the ziplines and aerial course at Alpine Adventure. Indulge in splashing times at Whale’s Tale Waterpark and relish a wine tasting and ‘Meet the Winemaker’ at Seven Birches Winery. Perhaps take a spectacular drive along the 34.5-mile Kancamagus Highway and witness views of the White Mountains, the Swift River, Lower Falls, Sabbaday Falls, and the Rocky Gorge enroute.
Day Nine: Lenox
Drive to The Black Swan Lee - Lenox, Ascend Hotel Collection in an idyllic setting by Laurel Lake at the foothills of October Mountain State Park and check in for a one-night stay. Take a tour of Pulitzer Prize winning author Elizabeth Wharton’s home, The Mount, or the restored and listed Jacobean revival Ventfort Hall Gilded Age Mansion & Museum. Wander around downtown Lenox and seek out Lenox Library and admire the ecclesiastical architecture of The Church on the Hill, Trinity Church, and St Ann’s. Keep your eyes peeled for the resident beavers as you follow the trails through forests, meadows, wetlands, and along the slopes of Lenox Mountain at Mass Audubon Pleasant Valley Wildlife Sanctuary.
Day Ten: Worcester
Hit the open road for a drive to Worcester for a one-night stay at Hilton Garden Inn. Maybe pay a visit to the indoor/outdoor EcoTarium complex with its digital planetarium, wildlife exhibits, tree-top walkway, and narrow-gauge railway. Go to see Worcester Art Museum’s vast collection of Roman mosaics, medieval armour, and Impressionist paintings. Stop by the museum in the restored 18th-century, Georgian-style Salisbury Mansion or wander through Tower Hill Botanical Gardens. Leave the city behind to step back in time to the early 1800s at Old Sturbridge Village living history museum with its 40 historic homes, farm buildings, and shops demonstrating New England crafts and daily life.
Days Eleven to Thirteen: Cape Cod-Hyannis
Your road-trip continues with a drive to Hyannis on Cape Cod, where you’ll check into Holiday Inn Cape Cod-Hyannis for a three-night stay. You’ll have lots of opportunity to wander along vibrant Main Street and around Hyannis’ waterfront district. Fit in a spot of retail therapy at Cape Cod Mall or escape to Cape Cod National Seashore with its beaches, woodlands, and hiking trails. Pay a visit to Hyannis’ Cape Cod Maritime Museum and John F Kennedy Museum. Go on a thrilling whale-watching cruise from nearby Barnstable Harbor or take a short ferry ride to experience Martha’s Vineyard and the settlement of Nantucket.
Day Fourteen: Boston, Massachusetts
Today’s road trip takes you back to Boston, where you’ll check into Element Boston Seaport District Boston for your final night’s stay in Massachusetts. Perhaps you’ll have time to retrace portions of the Freedom Trail; taking in Boston Common, King's Chapel, the Boston Massacre site, and the many pubs and taverns where America's Founding Fathers toasted freedom. Maybe shop at Quincy Market for last-minute keepsakes and souvenirs to take home with you or even sample some tempting local fare including Lobster Rolls, Clam Chowder, Fried Clams, Boston Baked Beans, followed by a slice of Boston Cream Pie.
Day Fifteen: Boston to UK
Check out of your hotel and drive to Boston Airport in time for your flight back to the UK – hopefully with many happy memories to look back on of your Massachusetts fly drive adventure.
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