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Quaint New England Towns

12 Days
Prices From:
US$ 3,156

MODERATE | SELF DRIVE: A delightful itinerary around New England that starts and ends in Boston, but reveals the beauty of Massachusetts, Maine, New Hampshire, and Vermont through its enchanting small towns. The scenery is breathtaking throughout, with stunning coastal areas, including Cape Cod, and the magnificent White and Green Mountains. There’s the witches of Salem, Norman Rockwell’s home, the famous ‘Covered Bridges’, a replica of the Mayflower, lighthouses and the Mystic Pizza restaurant.

You’ll fall in love immediately with the warm character of New England’s most picturesque towns on this 12-day self-driven tour. Step back in time as you stroll down historic walkways and explore cultural centres surrounded by leafy foliage and seaside views as you loop around the east coast, from city to ocean to mountain.

Don’t let Boston’s modern skyline fool you: this is a city steeped in American revolutionary history, which you can discover on the famous Freedom Trail, a 2.5 mile stretch that passes through 16 monuments crucial for the beginnings of democracy in America. The capital of Massachusetts is also flowing with art, which you’ll see from a stroll through the art galleries and boutiques housed in the brick townhouses of Boston’s elegant Back Bay. Allow your eyes to follow the snaking ivy to the Harvard campus, cozying up afterwards in one the area’s many independent coffee shops.

Massachusetts’ beauty extends beyond city life, which you’ll find in Salem, whose town contains an incredibly rich history. While it may be known for its infamous Witch Trials in the 17th century, you’ll also find yourself bewitched at its Victorian architecture and beautiful harbour. The east coast has been an inspiration for artists over the years, concentrated in colourful towns like Manchester-by-the-Sea and Rockport.

You’ll be in lighthouse country as you continue northwards into Maine, following their circular beams. Roll down your window to feel the salty air in your hair as you pass by seaside cottages and long stretches of sandy beach in Kennebunkport, Camden, Bar Harbour, Portland, and Bristol. Two of the United States’ most beautiful lighthouses can be found in these parts, including Portland’s Head Light and Bristol’s Pemaquid Point. You’ll marvel at the crystal blue water juxtaposed against the rugged coastline at Acadia National Park, which seem like scenes from a postcard. Don’t forget to try some world-famous Maine lobster or any fresh catches of the day at the various seafood stalls that line the coast!

Moving inland, you’ll explore the quaint towns nestled into the White Mountains of New Hampshire, whose peaks traverse state boundaries. Those who want to add a little thrill to their day can drive to the top of Mount Washington, home of the “world’s worst weather” where you can check out a fascinating weather station. Whether you’re a thrill seeker or not, you’ll want to stop at Pinkham Notch, a mountain pass with plentiful hiking trails that can take you deep into the verdant heart of the landscape. The towns of North Conway and Hanover will charm you with their handmade crafts, delicious bakeries, and warm pubs ready to welcome you after a day of climbing.

In Vermont, you’ll explore the Green Mountains, whose pastoral beauty will capture your eye year round. You’ll find beautiful covered bridges lining your route, making for great photo ops against the range of colours spread out around you. Stockbridge invites you to explore the Norman Rockwell Museum, home to the American illustrator’s most striking everyday works.

Carry on to Connecticut’s Gold Coast, one of the most beautiful areas in the state and home to rich culture. Marvel at the home of Katharine Hepburn in Old Saybrook and explore the harbour village of Mystic, whose scenery and history is every bit as magical as its name suggests. Its Main Street includes tons of mom ‘n pop restaurants, ranging from fresh seafood to Mystic Pizza, made famous by the movie of the same name.

Stop in Newport, Rhode Island, whose harbour is bustling full of boat activity from fishermen to sporty yachts. The rich and famous have loved Newport for centuries, similarly to Cape Cod, where seafood shacks, white cottages, and calm waves await you. The Massachusetts coast is anything but impatient, renowned for its laid-back lifestyle that allows you to indulge as you lounge along the ocean.

Return your car back to the airport in Boston for your flight home, or continue frolicking in the tides of the New England coast.

At Goway we are experts at designing personalized itineraries to suit your special interests, tastes and budget. Let us arrange your ultimate travel experience today.
12 Days
Prices From:
US$ 3,156

Itinerary View Trip Map

Day 1


Arrive at Logan International Airport and transfer independently to your hotel. Depending on your time of arrival you might be able to explore a little of the city known as the cradle of American liberty. Maybe a stroll along the Freedom Trail walking route, including Beacon Hill, a delightful area with steep cobbled streets and lined with a mix of buildings, including Victorian brick houses, lit by antique lanterns. The Massachusetts State House, resplendent with a gold dome, yet also site of the Boston Massacre, is near Charles Street with its chic boutiques and antique shops. Also consider the city’s historic North End, fashionable Newbury Street, a visit to Fenway Park which is home to the Boston Red Socks and the Esplanade.

Overnight Boston.

Duration1 night
Day 2

Boston - Kennebunkport

Head north along the scenic New England coast through Massachusetts. Infamous for the Salem Witch Trials of 1692, Salem is a colourful city with a rich maritime heritage, Victorian architecture and fascinating stories that span nearly 400 years. Continue through Manchester-By-The-Sea, made famous by the award-winning 2016 movie of the same name and historic Rockport, an inspiration to painters since legendary American painter Winslow Homer spent two summers in this area. After exploring charming Rockport, head to Portsmouth, New Hampshire, settled in 1623, boasting a strong cultural and historic past. It's also a gateway to New Castle, one of New Hampshire's smallest towns and home of the Fort Constitution Historic Site. After exploring the fort, depart for Maine, where your first stop is Ogunquit, named by the Abenaki tribe, meaning 'beautiful place by the sea'. Enjoy the vintage feel of this lovely place, stroll among quaint buildings, or explore the Marginal Way Ocean path. The final stop today is Kennebunkport, Maine located by the Atlantic Ocean and Kennebunk River. Settled in the 1600s and a long-time ship building centre, the city's resident sea captains built fine mansions here, some of which have been transformed into lovely inns.

Overnight Kennebunkport

Duration1 night
Day 3

Kennebunkport - Camden

Today's first stop is Old Orchard Beach. Here, you can enjoy seven miles (11 kilometres) of sandy beach and Old Orchard Beach Pier, stretching more than 500 feet (150 metres) over the Atlantic Ocean. Continue north to the historic seacoast city of Portland with its funky galleries, one-of-a-kind shops, diverse restaurants, and many lighthouses (six within 30 minutes' drive of the city, among them, Portland Head Light, one of the most photographed in the USA). Take your time to explore the Arts District and Old Port historic district. As you continue through the mid-coast region of Maine, past quaint New England cottages and quiet coves, be sure to stop at Pemaquid Point Lighthouse in Bristol. The lighthouse itself is beautiful and the unusual rock formations bordering the structure make this a fabulous photo spot as well. Rockland, known as the 'Gateway to Penobscot Bay', is a classic working harbour town and home to galleries, craft shops, fine dining, and the Maine Lighthouse Museum with its fine collection. The final stop today is in Camden, where locals say, 'the mountains meet the sea'. A culinary mecca, Camden features charming little streets, huge schooners, and locally owned art galleries, making it the perfect destination to overnight.

Overnight Camden area

Duration1 night
Day 4

Camden - Bar Harbor

Follow the scenic shoreline of Penobscot Bay to Lincolnville in the heart of the Maine coast. This off-the-beaten-path place is a perfect spot to enjoy breathtaking views of the bay. Next, visit the picturesque town of Blue Hill to enjoy a laid-back and charming getaway. In addition to its historical architecture and shipbuilding roots, Blue Hill is also a gateway to Acadia National Park. Today's final stop is Bar Harbor on Mount Desert Island, featuring elegant Victorian architecture, and situated between the blue waters of Frenchman Bay and the woodlands of Acadia National Park.

Overnight Bar Harbor area

Duration1 night
Day 5

Bar Harbor - Bethel

Before travelling inland, take the morning to explore Acadia National Park, known for its rugged beauty. Expect to see glorious mountains and abundant wildlife and hear the thunder of crashing waves. Steep slopes rise above the rocky shore, including Cadillac Mountain, which at 1,529 feet (465 metres) is the highest peak on the U.S. Atlantic Coast. Travel east to Bethel, one of Maine's popular mountain villages, and a hub of outdoor activities from skiing in winter to hiking and biking in summer. The walkable city centre has everything visitors need.

Overnight Bethel area

Duration1 night
Day 6

Bethel - North Conway

Take a full day to explore the White Mountains of New Hampshire, joining Highway 15, also known as Three Rivers Scenic Drive which takes you past Mount Washington and the mountain pass known as Pinkham Notch. Adventurous visitors might want to stop to take the cog railway or drive to the summit of Mount Washington, home of the ‘World's worst weather' to visit the weather station and Extreme Mount Washington museum. Outdoor lovers won't want to miss Pinkham Notch, a stunning natural landmark created by glaciers, erosion, and rivers, and separating three mountain ranges. Take the opportunity to hike trails that accommodate all skill levels or relax on a Gondola ride and enjoy the views in Wildcat Mountain Ski Area. The journey ends in North Conway in the heart of Mt. Washington Valley, home to nearly 100 stores, fine art galleries, locally made crafts, restaurants, pubs, and live entertainment.

Overnight North Conway

Duration1 night
Day 7

North Conway – Londonderry - Rutland

From North Conway, explore more of the White Mountains, taking the scenic Kancamagus Highway with a terrific photo opportunity at Albany Covered Bridge along the way. Next, stop at Flume Bridge, a covered bridge open to cars, on your way to spectacular Franconia Notch State Park with its many trails, aerial tramway, wildlife watching and other recreational activities. Journey through Hanover, New Hampshire, home to Dartmouth College, and on to Woodstock, Vermont, which is full of quintessential New England charm, with a village green, covered bridge and historic architecture. Continue to Londonderry at the gateway to the Green Mountains towards Rutland.

Overnight Rutland area

Duration1 night
Day 8

Londonderry - Stockbridge

Today, explore Vermont's Green Mountains National Forest, beautiful in all seasons. Autumn is the most colourful time of year here, due to the brilliance of the changing foliage, but this area has something for outdoor enthusiasts year-round. Enjoy pastoral views as you travel along Route 7a through Manchester and Bennington, Vermont, where you should stop to photograph the beautiful, covered bridges before arriving in North Adams, Massachusetts for lunch. Continue to Stockbridge, home to the Norman Rockwell Museum, well worth a visit for its extensive collection of the beloved American illustrator's original works.

Overnight Stockbridge area

Duration1 night
Day 9

Stockbridge - Mystic

From Stockbridge, travel south to the Connecticut coast and Westport. The waterfront has a row of attractive red brick buildings, and the area enjoys some of the prettiest scenery in the state, making this a good stop for a picnic or a stroll through town. Further along the coast, stop at Old Saybrook, famous for being the home of Katharine Hepburn (now home to The Katharine Hepburn Cultural Arts Center). Filled with impressive architecture and many remarkable buildings, including historic manor houses and the Saybrook Breakwater Lighthouse, this is a perfect stop for lunch. Continue to Mystic, an attractive seaside village with a rich heritage. Originally one of the area's most important seaports, its history has been preserved at the Mystic Seaport, one of the country's largest maritime museums. Visit Main Street, with its many delicious seafood restaurants, quaint shops, and the famous Mystic Pizza restaurant, made famous in the 1988 movie ‘Mystic Pizza’.

Overnight Mystic

Duration1 night
Day 10

Mystic - Cape Cod

Take Highway 1 to Narragansett, Rhode Island, known for its sandy beaches, and continue on Highway 1a along the coast and across the Jamestown Bridge to Newport, one of the USA's original playgrounds for the rich and famous. Newport retains a luxurious charm and many of its Gilded Age mansions are open to the public for tours. If you are tennis fan, also check out the International Tennis Hall of Fame in Newport. Next, drive to charming Cape Cod, where your day's journey ends.

Overnight Cape Cod area

Duration1 night
Day 11

Cape Cod - Boston

You might want to do a little research ahead of time to select which of Cape Cod’s beach towns you wish to see. Your choices include the bustle and fun of Falmouth on the Lower Cape, the flower-adorned cottages of Orleans, or the dune-swept beaches of Eastham and Truro on the Outer Cape. Busy Provincetown, an LGBT-friendly city at the tip of the Outer Cape, offers eclectic shops, galleries, and restaurants, as well as natural beaches and stellar whale watching. The Cape's scenic out islands - Martha’s Vineyard and Nantucket - can be reached via ferry or small plane. Summer is high season on Cape Cod, and the shoulder seasons of spring and autumn offer quieter experiences. After your visit to Cape Cod, drive to Plymouth, 'America's hometown', where the Pilgrims landed in 1620 in search of a home and religious freedom. Plimoth Plantation is a must-visit, a fascinating, interactive view of the life of the early American colonists in a harsh land. Depart Plymouth and continue your drive to Boston.

Overnight Boston

Duration1 night
Day 12


Make your way to Boston’s Logan International Airport for your flight home unless you plan to extend your stay in New England

Other Information


Daily departures: April 1 - October 31, 2024


  • 12 days Intermediate Car Rental with unlimited mileage (Mazda 3 or similar)
  • Detailed day by day itinerary
  • 1 night moderate accommodations in Boston
  • 1 night moderate accommodations in Kennebunkport
  • 1 night moderate accommodations in Belfast
  • 1 night moderate accommodations in Ellsworth
  • 1 night moderate accommodations in Gorham
  • 1 night moderate accommodations in North Conway
  • 1 night moderate accommodations in Rutland
  • 1 night moderate accommodations in Lenox
  • 1 night moderate accommodations in Mystic
  • 1 night moderate accommodations in Hyannis
  • 1 night moderate accommodations in Boston


  • Car rental insurance
  • Travel insurance
  • International and domestic airfare & airfare taxes
  • Entrances fees to sites not explicitly listed as included
  • Meals and beverages not mentioned
  • Road tolls
  • Gratuities
  • Items of a personal nature
  • Visa fees if applicable


  • Spend an afternoon enjoying the Museum of Fine Arts’ extensive collection or the eye-opening exhibits at the Museum of Science (optional)
  • Visit the picturesque town of Blue Hill to enjoy a laid-back and charming getaway
  • Travel east to Bethel, one of Maine’s popular mountain villages, and a hub of outdoor activities from skiing in winter to hiking and biking in summer
  • Take the opportunity to hike trails that accommodate all skill levels or relax on a Gondola ride and enjoy the views in Wildcat Mountain Ski Area
  • Visit the Cape’s scenic out islands - Martha’s Vineyard and Nantucket can be reached via ferry or small plane. Summer is high season on Cape Cod, and the shoulder seasons of spring and autumn offer quieter experiences



Prices are "from" per person based on twin/double share accommodation and for travel in low season. Seasonal surcharges and blackout dates may apply. Limited seat/spaces and all pricing is subject to change and availability. Rates for single or triple travellers are available on request. Additional terms and conditions apply for car rental - please inquire.

1 Oct 2024
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