Arrive in Boston make your way to your hotel. The remainder of the day is yours to do as you please. A recommendation is to visit the Boston harbour where you can enjoy The Boston Harbour Walk. This walk is designed to connect the public to a clean and restored Boston Harbour.

Alternatively, you could visit Faneuil Hall Marketplace comprised of a collection of boutiques, eateries and pushcart vendors housed in converted 18th-century warehouses.

Hilton Boston Park Plaza or similar

Spend your day exploring this historic city.

Be sure to follow “The Freedom Trail”, a 2.5 mile pathway through Boston that passes by 16 locations significant to the history of the United States. It winds from Boston Common to the Old North Church and the Bunker Hill Monument in Charlestown. It is the perfect introduction to the colonial and revolutionary history of Boston.

You can also explore Quincy Market’s array of shops and eateries, catch street performances, and admire the local architecture. Alternatively, you could make your way to the Cambridge area, home to Harvard University and MIT (Massachusetts Institute of Technology). You can walk through Harvard Square and along the scenic Charles River Esplanade that offers beautiful views of the river and the Boston skyline.

Optional Experience – Boston Old Town Trolley Tour
Hop aboard one of these trolleys and you’ll experience ‘Transportainment’, a delightful combination of transportation and entertainment. Turn back the pages of history and relive colonial Boston. Coming from various backgrounds, each conductor narrates the sightseeing tour with his or her own blend of trivia, colourful anecdotes, and humorous stories to ensure that your experience is both enjoyable and informative.

Hilton Boston Park Plaza or similar

Collect your car this morning for your scenic road trip and make your way north, out of Boston.

As you depart Boston, you’ll pass by the picturesque New England coastline, between quaint towns and rolling hills adorned with vibrant foliage (during the fall months).

Along the route, you might choose to make a stop in the historic town of Salem, known for its witch trials and maritime industry, where you can explore museums, visit the Salem Witch Trials Memorial, or stroll along the scenic waterfront.

Continuing northward and you’ll encounter the coastal beauty of Portsmouth in New Hampshire, with its charming downtown area, historic homes, and bustling waterfront. Indulge in fresh seafood at one of the many waterfront restaurants or explore the city’s rich maritime heritage at the Portsmouth Harbour Lighthouse.

Finally, as you approach Kennebunkport, be sure to take in the breathtaking views of the Maine coastline, dotted with rugged cliffs, sandy beaches, and iconic lighthouses. Upon arrival in Kennebunkport, you’ll find a quaint seaside village brimming with boutique shops, art galleries, and delicious seafood restaurants, all set against the backdrop of serene coastal scenery.

Boston > Kennebunkport | 90 miles

Nonantum Resort or similar

The drive from Kennebunkport to North Conway is a delightful journey through the picturesque landscapes of coastal Maine and then the rugged beauty of the White Mountains.

Departing from Kennebunkport, you can explore the charming coastal towns of Wells and Ogunquit, known for their pristine beaches, scenic coastal trails, and vibrant arts scene. Don’t miss the chance to walk along the Marginal Way, a stunning oceanside path offering breathtaking views of the Atlantic coastline.

Continuing inland, the drive takes you through the scenic countryside of southern Maine, passing through quaint villages and rolling farmland. Along the way, consider stopping at the historic town of Fryeburg, home to the Fryeburg Fairgrounds and the Fryeburg Academy, founded in 1792.

As you approach North Conway, the landscape transforms into the rugged beauty of the White Mountains, From hiking and biking in the summer to skiing and snowboarding in the winter, North Conway serves as a gateway to the stunning natural wonders of this region. Explore the shops and restaurants of North Conway Village, or take a scenic drive along the Kancamagus Highway for panoramic views of the surrounding mountains and forests.

Kennebunkport > North Conway | 71 miles

North Conway Grand Hotel or similar

Departing from North Conway, you can immerse yourself in the majestic scenery of the White Mountains, passing through picturesque valleys, dense forests, and alongside rushing rivers.

As you make your way towards Stowe, consider stopping at the quaint village of Littleton, New Hampshire, known for its historic Main Street lined with shops, galleries, and eateries. Don’t miss the iconic covered bridge that spans the Ammonoosuc River, offering a perfect photo opportunity.

Continuing northward, the drive takes you through the scenic countryside of Vermont, where you’ll encounter rolling hills, working farms, and quaint villages. Consider a detour to the charming town of Montpelier, Vermont’s capital, to explore its historic downtown area and visit the Vermont State House.

Finally, as you approach Stowe, you’ll be greeted by the majestic beauty of the Green Mountains. Explore the shops and restaurants of Stowe Village, take a scenic drive along the Mount Mansfield Auto Toll Road for breathtaking views, or embark on a hike in Smugglers’ Notch State Park for an unforgettable outdoor adventure.

North Conway > Stowe | 141 miles

The Lodge at Spruce Peak or similar

From Stowe, you can savour the stunning beauty of the Green Mountains as the roads wind through lush forests and quaint towns.

As you journey southward, consider a stop in the charming town of Bennington, Vermont, known for its historic sites, including the Bennington Battle Monument and the Robert Frost Stone House Museum. Explore the quaint downtown area lined with shops and art galleries, or take a scenic drive along the Molly Stark Byway for panoramic views of the surrounding mountains.

Continuing into Massachusetts, you can explore the vibrant city of Springfield, home to attractions such as the Basketball Hall of Fame and the Dr. Seuss National Memorial Sculpture Garden. History buffs may also enjoy visiting Old Sturbridge Village, a living history museum showcasing rural New England life in the 19th century.

Finally, as you approach Mystic River in Connecticut, you’ll be enchanted by the coastal beauty and maritime heritage of this historic region. Explore the Mystic Seaport Museum, stroll along the picturesque waterfront, or embark on a scenic cruise along the Mystic River for a truly unforgettable experience.

Stowe > Mystic River | 276 miles

The Inn at Mystic or similar

The drive from Mystic River to Cape Cod offers a delightful journey along the scenic coastline of Connecticut and Massachusetts, showcasing charming towns, historic sites, and picturesque landscapes.

Departing from Mystic River, continue along the Connecticut coast, consider a stop in the historic town of New London, Connecticut, home to attractions such as the U.S. Coast Guard Academy and Fort Trumbull State Park. Explore the town’s charming waterfront area, lined with shops, restaurants, and historic buildings.

As you cross into Massachusetts, consider a detour to Hyannis, a bustling town on Cape Cod known for its beautiful beaches, vibrant arts scene, and historic landmarks such as the John F. Kennedy Hyannis Museum.

Finally, as you arrive in Chatham, Cape Cod, you’ll be greeted by the quintessential charm of this seaside town. Explore Chatham Lighthouse Beach, stroll along Main Street to browse boutique shops and art galleries, or embark on a seal-watching cruise for a memorable maritime adventure.

Mystic River > Chatham | 139 miles

Chatham Bars Inn or similar

Leave the Cape behind and travel back to Boston. Along the way you have the choice to stop by Plymouth Plantation, a 1627 English Village built as a re-creation of the small farming town built by English colonists in the midst of the Wampanoag homeland, or the famous Plymouth Rock, a powerful tribute to the courage of the 102 Mayflower passengers who founded the land we know as New England. 

Chatham > Boston | 89 miles