Inspiration for your own tailor-made trip
New England
100% customisable for you
Your New England adventure kicks off today, so head to the airport, whizz through security and settle in for your seven-and-a-half-hour evening flight to Boston. On arrival, hop in a cab to the city centre, about half an hour’s drive away.
Check into your chic hotel in the heart of the city and put your feet up after all the travelling. Worked up an appetite? Check out our detailed Dossier for the best places to eat nearby. Whether you’re after a sophisticated restaurant, a local spot, or just craving a midnight treat before bed, we have you covered.
After a hearty breakfast at your hotel, discover Boston's popular landmarks and hidden corners on a private two-hour guided tour. Follow in the footsteps of Bostonians through the ages as you stroll from Back Bay to Downtown. Admire the combination of contemporary and historic buildings as you explore the foundations of the city and the United States, from the American Revolution to the abolition of slavery.
This afternoon, indulge in some retail therapy at Copley Square’s designer shops and Newbury Street's high-end boutiques. History buffs? Learn all about the American War of Independence at the nearby historic battlefields in Lexington and Concord instead.
Come evening, take your pick from a range of restaurants, be it an authentic Italian (well, Italo-American) trattoria in North End or a delicious dim sum dinner in Chinatown.
It’s your final full day in Boston, so pick up your hire car and cruise around the city to admire the sights (if you’re feeling energetic, why not explore on foot?). Head to the acclaimed Harvard University, just across the river in nearby Cambridge, to visit the Harvard Museum of Natural History and take in the iconic Charles River, where you might spot rowing eights training. Then, park up or stop mid-walk for a tasty burger at Mr Bartley's Burger Cottage – a Harvard Square staple.
Spend the afternoon at Fenway Park, the oldest stadium in Major League Baseball and home to the legendary Red Sox. If the Sox are playing at home, we can pre-purchase tickets, but even if they’re on the road, you can enjoy a guided tour of the stadium and watch the game on TV in one of the stadium bars.
Your road trip officially begins today, so hop in your hire car for a two-hour drive north via Interstate 95 to Maine. Wave goodbye to Boston as you journey along the coast through upstate Massachusetts, cutting across New Hampshire's small stretch of coastline and into Portland, Maine, where you’ll spend the next two nights. En route, there are plenty of places for a pitstop: Salem, known for the 1692 to 1693 witch trials; Ogunquit, renowned for its art galleries; and Kennebunkport, a famous seaside resort.
Once you’ve settled into your waterfront hotel, head to the area’s ‘Maine’ attraction (pun definitely intended) – Portland Head Light. Just seven miles from Portland, this iconic lighthouse was commissioned by George Washington in 1791. Whether you’re keen to explore the coastal trails or fancy a relaxed stroll along the shoreline, it’s a great way to stretch your legs after a morning spent in the car.
Rise and shine for a full day of exploring in Maine. For a relaxing morning, choose from our detailed list of local beaches, then set off on a two-hour road trip past six of the region’s historic lighthouses, including the Portland Breakwater Light (dubbed Bug Light) and the Spring Point Ledge Light.
Culture lovers can explore the Arts District on a guided tour before diving into Portland’s local beer scene with a tour of its thriving microbreweries. Fancy a different activity? We can arrange everything from sailing to cycling, as well as recommend the best shopping and must-visit food spots in Portland’s charming converted wharves. Come evening, tuck into some of the East Coast's freshest lobster and enjoy a sunset stroll along the beach.
This morning, head inland on a four-hour drive to the heart of Vermont, the so-called ‘Green Mountain State’. Take the scenic route through New Hampshire, passing unspoilt woodlands such as the White Mountain National Forest, and beautiful bodies of water, including Lake Winnipesaukee.
With English country house architecture and Scottish-style landscapes aplenty, British visitors will feel very at home in Vermont. On arrival at your charming hotel, stretch your legs on a lovely woodland walk and enjoy a delicious dinner made with the region's fabled farm produce.
Combine your coastal getaway with Vermont's vivid autumnal colours. Visit from mid-September to mid-October when fiery reds, burnt oranges and warm yellows paint the landscape. We can use the ‘Fall Foliage Forecaster’ to help you time your visit, but even if you miss the full fall colour palette, Vermont still has plenty to offer. From mountain biking along picturesque trails to strolling through the state's postcard-perfect towns, there’s something for everyone.
Keen foodies should note that Vermont is also at the forefront of the farm-to-fork movement, so you can enjoy some mighty fine local produce. Think cheese, chocolate, and, of course, maple syrup. Thirsty? Vermont also boasts a delicious range of craft ales from several award-winning microbreweries (we can arrange a guided tour of the finest).
After breakfast, hit the road again for the longest stint behind the wheel so far. Stock up on snacks and tune into our destination-specific playlist for the four-hour journey to Rhode Island (allowing more time for plenty of photo stops en route). Head south along the Connecticut River Valley, passing through New Hampshire and Massachusetts before reaching Rhode Island.
Confusingly, most of the state of Rhode Island isn't an island at all, but part of the mainland New England coast. However, your destination, Aquidneck Island, is a true island and was a popular summer retreat in the Gilded Age for the wealthy elite. On arrival, check into your hotel in the main town of Newport, where you can experience the decadent comfort once enjoyed here by the super-rich in the 19th and 20th centuries.
Today is all about exploring the island in more detail. First, set off on a tour of the millionaires’ mansions. We can tailor a driving or walking route that maps out the island’s showiest properties, from French chateaux to 'Jacobethan' English manor houses and Italian palazzos.
Back in Newport, pop into the town's charming galleries and chic boutiques before grabbing a bite to eat at a seafood restaurant overlooking the harbour.
Along with its Gilded Age mansions, did you know that Rhode Island is also renowned for its sailing? Considered the spiritual home of the America's Cup and hosting many respected regattas, Newport prides itself on its maritime roots. Whether you’re after a private charter aboard an elegant 80s schooner, traditional sloop or an actual 60s America's Cup winning yacht, we have you covered. There's no better way to navigate the island’s waters than under sail.
Wake up bright and early to swap one quintessential New England spot for another, on a two-hour drive to Cape Cod. On arrival, check into your historic coastal retreat, kick back and relax.
Spend the rest of the day as you please: unwind on the beach, enjoy a nature walk, cycle along the Cape Cod Rail Trail or Province Lands Trail, or visit striking Modernist houses dotted along the peninsula – a bold contrast to the wild natural surroundings and cutesy cottages. For some serious R&R, why not retreat to the hotel spa? Alternatively, hop in your car and head down the road to Hyannis, a charming village and JFK's favourite spot in the States.
Another day, another drive, this time bound for former President Obama's favoured haunt: Martha's Vineyard, where you’ll spend the next two nights. Drive an hour to Woods Hole, then hop on the ferry to Oak Bluffs, which takes about 45 minutes.
Once ashore, Jaws fans will instantly recognise their surroundings as the fictional Amity Island; you can even grab a pint of Amity Ales at the Offshore Ale Company by the ferry port. While we don't advocate drinking and biking, cycling is a lovely way to explore the island (we can recommend the best places to hire bikes). A leisurely cycle around the entire island takes about four hours, and there’s plenty to see, from the harbour towns and lighthouses to the sandy beaches and farmland.
Sadly, this is the last day of your epic New England road trip. Begin your journey home by catching the ferry back to Cape Cod, before driving two hours to the airport in Boston. Drop off your hire car, breeze through security and unwind in the airport lounge before boarding your six-and-a-half-hour flight back to the UK.
Each of our trips is entirely tailor-made with originality, quality and cultural immersion in mind. Our team of destination specialists will craft itineraries based on your tastes, using their first-hand knowledge and the help of our in-country team of Concierges and guides. All trips are accompanied by a wide range of additional services, including a 24-hour helpline, the Original Travel app, fast-track airport services and much more.
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Our team of destination experts will get to know you and your unique requirements for your holiday
We work with you to build an ultra-personalised holiday itinerary with your choice of accommodation, experiences and activities
All of our holidays include little extras designed to make a big difference to your trip, from fast-tracking you through airport check-in and security to our network of local Concierges
