VermontMassachusettsConnecticutRhode Island

Explore vibrant small cities and bucolic towns in Vermont, Massachusetts, Connecticut and Rhode Island on this intriguing New England road trip loop.
With Boston as its gateway, this route will explore the unique cultural, historical and culinary offerings of New England’s urban centres and picturesque villages. Leaving Boston, drive north to Vermont, then south through western Massachusetts into Connecticut before looping along the coast to Rhode Island and Cape Cod, finishing back in Boston. Along the way, pause to enjoy cultural attractions, vibrant neighbourhoods, mountain vistas, iconic islands and vast beaches.

Itinerary Highlights

  • Take a steamboat cruise in Mystic, Connecticut
  • Take a short flight to Martha’s Vinyard
  • Learn about America’s modern history
  • Explore historical homes
  • Discover seaside villages steeped in history

What’s included

  • Rental car included
  • Meet & greet airport service
  • Luxury or boutique accommodation at your chosen level
  • Expert guides in each destination


This is an example itinerary. It is fully flexible; you can add or detract days and include hotels at your chosen budget. It departs daily.



Price Guide

$TBC pp

Our quotes are bespoke for your customised trip. The prices displayed are indicative only, read more

Day 1

Fly to Boston

plan line
Day 2-3

Manchester, Vermont

This morning, pick up your rental car, leave the city behind and drive northwest through the picturesque Green Mountains of Vermont to Manchester. The town has become a shopper’s paradise with numerous designer outlet stores mixing well with locally owned boutiques and antique shops.

Manchester is home to truly unique institutions, including the American Museum of Fly Fishing, housing the world’s largest collection of angling-related items, and the Pastime Pinball Museum Arcade, where more than 60 classic pinball machines are all set to free play for endless family fun. Hildene is a must for any visitor to the area; the former summer home of Robert Todd Lincoln, the eldest son of President Abraham Lincoln, is a 167-hectare estate with the original mansion, 14 other historic buildings, a formal garden, greenhouse and a 1903 Pullman car all available to explore.

On its many hiking trails, wander meadows, an apple orchard, vegetable gardens, wetlands and Sunbeam, a solar-powered goat dairy and cheese-making facility. Just out of town, the North Meadow Farm offers more agricultural insights and flavors; buy fresh cheese, eggs and other produce grown on-site at the farm store. Guided tours and sleigh and wagon rides take you around the charming complex, where you can interact with over 50 animals.

North of town, the Southern Vermont Arts Center is a 28-room mansion featuring art galleries and exhibition spaces, as well as the largest sculpture park in Vermont and The Arkell Pavilion auditorium, where the back walls open to allow for concerts in the fresh air.

Day 4-5

Stockbridge, Massachusetts

Drive directly south through the rolling hills of the Berkshire Mountains of western Massachusetts, stopping in historic Stockbridge. Begin your explorations on Main Street, the charming heart of this picturesque town. The Red Lion Inn, founded in 1773 and visited by presidents and famous authors, and the Stockbridge Library offer clues about the town’s history. Learn about Stockbridge’s most famous former resident at the Norman Rockwell Museum, home to the largest collection of the famed illustrator’s work and his original studio, all in a gorgeous setting overlooking the Housatonic River Valley.

History buffs will want to tour Naumkeag and Chesterwood, two splendid country estates that date to the late 1800s. Built by a prominent New York City lawyer, Naumkeag is noted for its large, terraced gardens, landscaped grounds and 44-room country house filled with the family’s artwork. At Chesterwood, tour the Georgian Revival former summer home and studio of famed sculptor Daniel Chester French (among many other works, he designed the huge statue of Abraham Lincoln in the Lincoln Memorial).

In the Berkshire Botanical Gardens, visitors will find one of the oldest public display gardens in the Northeast, with sections dedicated to herbs, daylilies, native plants and more. For many in the know, the name “Stockbridge” is synonymous with “Tanglewood” – a famous outdoor music centre that draws aficionados from across the region to a full calendar of events, including the Boston Symphony Orchestra’s summer festival. Choose the direct route to the next stop – New Haven, Connecticut – or opt for a scenic route, stopping in tiny Great Barrington and other hamlets tucked away in valleys.

Day 6-7

New Haven, Connecticut

In New Haven, Yale University isn’t just an Ivy League institution of higher education – it’s also a visitor destination home to museums and art collections well worth seeing. Stroll around campus to discover historic buildings juxtaposed with modern architecture. Marvel at the Gutenberg Bible and John James Audubon’s “Birds of America,” on permanent display at the Beinecke Rare Book & Manuscript Library, and check out the American decorative arts collection in the Yale University Art Gallery.

Then get some fresh air – head to East Rock Park, a popular recreation destination where you can see the 1887 Soldiers’ and Sailors’ Monument and take in clifftop views of New Haven and Long Island Sound. In addition to great water views, Lighthouse Point Park offers nature trails and a historic carousel – take a spin for 50 cents. The park is on a migratory bird flyway, so watch for cedar waxwings, tree swallows and Cooper’s hawks. Now that you’ve worked up an appetite, sample New Haven’s celebrated take on pizza at Frank Pepe Pizzeria Napoletana or Sally’s Apizza. Take a pizza tour to delve into heaven’s finer points on a plate. In the morning, head east along the Connecticut coast to reach Mystic.

Day 8-9

Mystic, Connecticut

Founded in 1654, modern Mystic has a population of less than 5,000, but in the 18th and 19th centuries, it was a significant seaport, with more than 600 clipper ships built there. These days, Mystic is where you’ll find one of Connecticut’s most-visited attractions – the Mystic Seaport Museum, which provides insight into the town’s rich maritime history.

Climb aboard the last wooden whaling ship in the world, take a short cruise on the Mystic River on a steamboat or explore on a rented sailboat, rowboat or pedal-powered boat. Back on land, watch blacksmiths, coopers and printers hard at work in the 19th-century village. Then head to Main Street, where you can browse in shops, dine on fresh seafood or eat at the original Mystic Pizza restaurant, made famous in the 1988 romantic comedy film of the same name.

Work off the pizza by hiking through woodland, wetland and meadow habitats at the Denison Pequotsepos Nature Center, where you can observe rescued hawks and owls. Looking for a little retail therapy? Olde Mistick Village is a shopping and dining destination built in the style of an 18th-century village. When you’re ready to hit the road again and head toward Providence, Rhode Island, take a side trip to Narragansett or Newport for lunch and coastal sightseeing.

Day 10-11

Providence, Rhode Island

With a thriving arts community and vibrant, diverse neighbourhoods, Rhode Island’s capital city, Providence, is a lively place to visit. Two world-class educational institutions set the tone for this city on the Providence River – the Ivy League Brown University and the Rhode Island School of Design, one of the nation’s most prestigious art schools.

The RISD Museum is filled with high-quality items made by students and faculty, so the exhibits are engaging and ever-changing. Art in this city isn’t just inside buildings; take all or part of a 1.5-hour self-guided walking tour to discover public art – sculptures and murals – across downtown, then explore other neighbourhoods. Wander along Benefit Street, admiring its grand architecture from the Colonial and Victorian eras, reflecting the lives of its thriving merchant class dating to the early 1800s. Also, explore Federal Hill, Fox Point and other historic and hip neighbourhoods.

Right downtown, Waterplace Park is famous for the seasonal WaterFire installation, an award-winning series of fire sculptures on Providence’s three rivers. The installation is best viewed while strolling along Riverwalk’s 1.2 kilometres of cobblestone walkways. Venice-styled pedestrian bridges span the river, and gondola rides are available. It’s a classic way to wrap up your stay in Providence before driving 90 minutes east to the beaches and towns of Cape Cod.

Day 12-13

Cape Cod, Massachusetts

As you head east into Massachusetts, continue driving until you reach Cape Cod, a popular vacation destination where you’ll find a series of quaint beach towns that range from rustic to regal. Take your pick from Falmouth (home to the Woods Hole Science Aquarium), Orleans (with both ocean and bayside beaches), Eastham (featuring the Three Sisters Lighthouses), Truro (a quiet town on the Outer Cape) and Provincetown (a lively town at the tip of the Cape with inns, restaurants and nightlife).

Take a whale-watching cruise from P-town, as the locals call it, and dine on fresh seafood. Driving back down the Cape, be sure to stop at Cape Cod National Seashore – it’s a can’t-miss stretch of pristine beaches and woodlands ideal for outdoor recreation. Continue on to Hyannis, where you can visit the John F. Kennedy Museum and jump on a ferry or small plane to visit the coastal islands of Martha’s Vineyard and Nantucket, known for their dramatic beaches, folksy charm and traditional New England architecture.

On the mainland, drive north to Plymouth, where the Pilgrims landed in 1620. Check out Plymouth Rock and views of Plymouth Harbor at Pilgrim Memorial State Park. Tour Plimoth Patuxet, an interactive living museum that re-creates the Pilgrims’ 17th-century settlement, complete with costumed role players. To wrap up your road trip, drive to Boston.

Day 14

Fly home

A note on price

The prices outlined above are a rough guide to give you an idea of costs and enable you to budget for your trip.

Guide prices are generally for private arrangements based on twin share, in well located, good quality accommodation (excluding international flights).

Please note costs are indicative and may vary due to a number of factors such as; travel date, hotel choice, room category, number of people travelling and prevailing exchange rates.

Price Guide $TBC per person

When to travel

jan feb mar apr may jun jul aug sep oct nov dec

The weather across the United States varies greatly depending on the region you plan to visit. In general, the summer months tend to be hot and humid in the south, while the west experiences dry heat. The northeast can be milder with occasional rain showers. However, it’s important to always check the weather forecast before traveling to ensure you are prepared for any unexpected changes. Regardless of the weather, there are plenty of exciting destinations to explore in the USA, from the beaches of Florida to the mountains of Colorado.

Add on’s

This New England itinerary has many add-on holiday options; for example, you could head to New York City and explore Times Square and the Statue of Liberty or head further south to Washington D.C. to visit the Smithsonian museums and the White House.

Want a quote on a trip like this?

Speak to one of our travel specialists and we’ll create your personalised itinerary just for you