Itinerary

Arrive in the beautiful city of Boston and take your private transfer to your hotel.

Spend the day exploring the fascinating history of the capital of Massachusetts. Known as America’s Walking City, Boston is very compact and a joy to explore on foot. The famous Freedom Trail begins at Boston Common, taking in over a dozen sites including Massachusetts State House, the site of the Boston Massacre and Paul Revere’s house. The trail ends at the USS Constitution, the world’s oldest commissioned warship. It can be done independently or you can book a guided tour to gain deeper insight into the history of the sites.

Explore some of Boston’s fascinating museums – the Kennedy Library and Museum, Museum of Fine Arts, Museum of African American History, and Boston Tea Party Ships and Museum.

Boston is one of the only eastern cities in the USA where it’s possible to take whale-watching tours to see humpbacks and other whales breaching out of the waters. We highly recommend taking a half-day tour from the city. One of the best destinations nearby is Stellwagen Bank Marine Sanctuary, a rich feeding ground for humpbacks, finbacks and minke whales, dolphins and sea birds.

Back in Boston, check out the city’s excellent, wide-ranging cuisine such as lobster rolls and clam chowder. The city’s North End is one of the best districts to eat seafood and Italian specialities. We recommend a walking food tour or a specialised seafood tour, taking in some of the city’s top eateries while learning about Boston’s culinary heritage.

You can spend another day exploring Boston’s historic and culinary highlights. Alternatively, take a day trip by ferry down the coast to Plymouth or Cape Cod and the islands.

“America’s hometown” Plymouth is the site where the Mayflower pilgrims landed in 1620, commemorated in Pilgrim Memorial State Park on the waterfront. Visit the full-size replica ship Mayflower II, the monument at Plymouth Rock and enchanting Plimouth Patuxet Museums, including recreations of a 17th century English village, a Wampanoag settlement and reconstructed Plimoth Grist Mill.

Alternatively, enjoy a day trip to Cape Cod. Cape Cod is a delightful summer playground with 40 miles of protected shoreline, peppered with historic towns. Provincetown has a thriving artistic community, overlooked by two lighthouses and the Pilgrim Monument. The island of Martha’s Vineyard is one of the region’s highlights with some of the best beaches on the east coast and half a dozen charming towns.

Another option is to take the ferry from Boston to the historic town of Salem (see day 4 for more details).

Pick up you hire car in Boston and drive north to Kennebunkport in Maine.

A great stop-off on the way is Salem, site of the 1692 witch trials. The Salem Witch Museum is the best of the town’s museums to learn about this troubling history with grisly re-enactments. Other highlights of Salem include the Satanic Temple and the Witch House. The town is particularly interesting to visit in October for the month-long celebration of Halloween, one of the biggest in the world.

Arrive in Kennebunkport, a beautiful harbour town with art galleries, historic homes, boutique stores and restaurants, well-known as a summer retreat of the Bush family.

Relax and explore town or head half an hour north for dinner in Portland. Known as “the restaurant city”, Portland frequently tops polls for the best food in the USA with a host of celebrity chefs, and hundreds of restaurants and breweries.

Drive further north today to Bar Harbor and Acadia National Park.

If you haven’t explored Portland, this is another chance to do so on the way. As well as the restaurants, city highlights include views from the observatory, the pre-civil war Victoria Mansion, Portland Museum of Art and Portland Head Light, one of New England’s most beautiful lighthouses.

About 3.5 hours’ drive from Kennebunkport is the vibrant seaside town of Bar Harbor with a wonderful coastal location on the edge of Acadia National Park.

Take a walk along the Bar Harbor Shore Path, and follow the Museum in the Streets, over 40 information panels around town charting the history of the area.

Bar Harbor is a great base for whale-watching tours from April to October, so if you didn’t go whale-watching in Boston, this is another chance to see humpback, finback, minke, as well as dolphins and seals.

Today it’s time to explore one of New England’s natural highlights – Acadia National Park. Diverse terrain of rocky headlands, mountains, lakes, forests, meadows and beaches covers half of Mount Desert Island, the second largest island on the Eastern Seaboard. The park is one of the USA’s top birdwatching destinations with over 300 species, including falcons, eagles, owls, loons, woodpeckers and warblers.

Included in your tour is a nature cruise along the southern shore. Watch seals basking on East Bunker Ledge, see bald eagles soaring overhead, view historic homes, visit the fishing village of Islesford on Little Cranberry Island, and take in the majestic peaks and shores of Somes Sound Fjord.

The park has more than 50 miles of hiking and biking trails along traffic-free Carriage Roads, and a great option is to hire an e-bike to cover more ground. The 27-mile Park Loop Road is the best drive, taking in popular areas Boulder Beach, Sand Beach, Otter Point, Jordan Pond, and Cadillac Mountain, the highest point in the region and famously the best place to view the first sunrise in the USA.

This morning, you head inland into New Hampshire and the White Mountains, a gorgeous haven for hiking and climbing.

This vast mountain range is part of the Appalachians, and its waterfalls are a particular highlight – New Hampshire has more than 100 falls.

We recommend a trip on the Cog Railway, the second steepest rack railway in the world to the summit of Mount Washington, commanding stunning views on clear days.

Other great train rides include the Hobo Railway along the Pemigewasset River, and the Conway Scenic Railroad across the Crawford Notch.

Spend another day enjoying the wonderful scenery of White Mountains.

Enjoy one of the most beautiful drives in New England along the Kancamagus Highway through the White Mountains National Forest between Conway and Lincoln.

Other charming towns worth visiting include Sugar Hill, famous for its maple syrup with panoramic views from Sunset Hill Ridge, and North Woodstock near the Lost River Gorge, where a trail leads through a canyon past waterfalls to a dozen boulder caves. Hikers can tackle parts of the Appalachian Trail that stretches from Maine to Georgia.

This morning you drive into Vermont, possibly New England’s most beautiful state, famous for its incredible autumn colours.

Arrive in Stowe, a stunning mountain town at the foot of Vermont’s highest peak Mount Mansfield. In winter, Stowe Mountain Resort is a winter sports haven, while in summer hiking, ziplining and the Gondola Skyride are popular.

Continue exploring beautiful Vermont. There are more than 45 hiking and cycling trails in the Stowe area including the Stowe Recreation Path and the historic Long Trail.

Explore other Vermont towns, including state capital Montpelier, famous for its gold-domed State House and Burlington, famous for its shopping and scenic location on the eastern shore of Lake Champlain.

Head south today to Woodstock, in many ways the quintessential New England village, surrounded by stunning scenery in Vermont’s Green Mountains.

Not to be confused with the New York State town that hosted the famous 1969 festival, Woodstock Vermont is renowned for its historic architecture and covered bridges.

Highlights of the town include the mansion and gardens of Marsh-Billings-Rockefeller National Historic Park, the 200-acre working dairy farm Billings Farm & Museum, and the Quechee Gorge, the deepest canyon in Vermont.

Head south back into Massachusetts this morning and gorgeous scenery of The Berkshires. This is a region of hills, forests, lakes and towns bursting with creativity – art galleries, historic mansions and open-air summer performances.

Cultural highlights of the Berkshires include the Clark Art Institute in Williamstown, the enormous Mass MoCa (Massachusetts Museum of Contemporary Art), the Norman Rockwell Museum and Gilded Age mansion Naumkeag.

The countryside of the Berkshires is ideal for hiking, including the Ashuwillticook Rail Trail and Mount Greylock, the highest peak in Massachusetts.

Head south this morning to the coast of Connecticut.
On the way it’s worth stopping in state capital Hartford, where one of America’s greatest authors Mark Twain wrote many of his famous novels including Huckleberry Finn. The Mark Twain House and Museum in Hartford houses a fascinating exhibition on the author.

Arrive in the historic town of Mystic. Explore Olde Mistick Village, a recreated 18th century New England village then delve into the town’s shipbuilding history. Mystic Seaport Museum encompasses 19 acres of American maritime history with a preserved shipyard, a 19th-century seafaring village, and exhibitions.

Today you visit Rhode Island, known as the Ocean State for its hundreds of miles of shoreline. Rhode Island is famous for its beaches, Gilded Age mansions, sailing community and seafood.

Along Bellevue Avenue and Ocean Drive, several mansions are open to the public. We recommend a guided tour, including the interior of the 70-room Breakers built by the Vanderbilts.

Other highlights of Newport include the Newport Cliff Walk with panoramic ocean views past many of the most opulent properties, the 10-mile Ocean Drive is equally spectacular by car or bike, and Fort Adams, the largest coastal fortification in the USA.

Drive north for about 1.5 hours back to Boston, drop your hire car at the airport and take your flight home.