Famed for its shingle-clad houses, lobster rolls, lighthouse-dotted coastlines, and the legendary Red Sox, New England offers iconic cities, rugged mountains, wild, secluded shores, and rolling countryside.
Despite being composed of six states – Massachusetts, Rhode Island, Vermont, Connecticut, New Hampshire, and Maine – the region is relatively compact, making it the ideal road trip territory: varied, scenic, and manageable without blowing your entire annual leave allowance. Alice Howarth finds out how.
Day 1-2: Boston, Massachusetts
One of America’s oldest cities, Boston is often seen as the unofficial capital of New England. Steeped in history but today a bustling modern hub, it’s renowned for its world-class universities (Harvard and MIT sit just across the river), seafood and, of course, sport.
Stay
Raffles’ first North American outpost, this city-centre spot is the perfect (and most luxurious) springboard for exploring Boston. Rooms are exactly what you’d expect: marble bathrooms, marshmallow-soft feather-topped beds and jackpot views of the skyline. As any proper five-star should, it also boasts a serious spa and a handful of excellent restaurants and bars that attract hotel guests and in-the-know locals nightly.
Rates start from £610 per night. Book it here
Eat & Drink
Things are done properly at Grill23. Martini glasses are fully frozen before served, waiters don white dinner coats and seafood towers are stacked high atop piles of chipped ice. It feels like stepping into a late 20th-century dining room – all low lighting, dark mahogany and brass finishes. Go for a steak with a side of the seriously moreish crispy tots.
For Italian, the North End divides opinion - it’s Boston’s official Little Italy - but many argue the best spots lie elsewhere. That is, except for Carmelina’s (carmelinasboston.com). A firm favourite with locals, it’s a no-fuss sort of place with a waiting list that stretches for months. If you snag a table, don’t miss the iconic ‘Sunday Macaroni’ (served daily): homemade penne served with meatballs, sausage and beef rib slow-cooked in tomato sauce and topped with a dollop of whipped ricotta.
Do
If the Red Sox are playing, Fenway Park is a must, complete with a foam finger and super-sized Bud in hand. For those in the mood for art, Isabella Stewart Gardner Museum is a tranquil gallery built in the style of a 15th-century Venetian palace and the site of a legendary art heist (a $10m reward still stands for information). If you head to Harvard for a campus visit, drop by the Harvard Natural History Museum to see the exquisite collection of over 4000 glass-blown flowers.
Drive to Hyannis Port, Massachusetts: 1 hour 50 minutes
Ferry to Nantucket, Massachusetts: 1 hour
Day 3, 4 & 5 : Nantucket, Massachusetts
Thirty miles off Cape Cod, Nantucket has long been the summer retreat of the New England elite. Cobbled and impossibly pretty, it’s all white picket fences, cedar-clad cottages and bursts of vivid hydrangeas.
Stay
The White Elephant is like being on the set of the latest ‘rich people behaving badly’ Netflix series (think The Perfect Couple, Sirens etc.) and it’s all the more fabulous for it. Right on the ocean, immaculately manicured and full of white-jeaned East Coasters jetting in for a weekend of R&R. Everything is taken care of, supremely comfortable, and its location is just a short walk from the picture-perfect centre of the island.
Rooms start at £370 per night (off-season). Book it here
Eat & Drink
A sceney spot, CRU (crunantucket.com) sits right on the wharf overlooking the harbour and is popular with the younger crowd (often in town for weddings) who rock up at the bar post dinner. You can’t go wrong with any order – the food is excellent – but make sure to start with a glass of champagne and a platter of the perfectly-shucked local oysters. Toppers (wauwinet.com)is part of historic The Wauwinet hotel and the place for fine dining. Expect jus, foams, microgreens and artful smears of reductions – it’s a performance but a delicious one at that.
For a hearty breakfast, head to the island favourite Black Eyed Susan’s (blackeyedsusansnantucket.com). This intimate, upscale diner-style spot features an open kitchen and counter — the kind of place where huevos rancheros, fluffy buttermilk pancakes, and towering breakfast sandwiches are morning staples.
Do
Whatever the season, spend time on the beaches. The wave-swept swathes of unspoilt sands are perfect for sunbathing or bracing walks in the colder months. With Nantucket being the former whaling capital of the world, the Whaling Museum is well worth visiting. Stroll around the island’s centre and pop into the antique shops — you won’t score any bargains, but you will view beautiful collections. Where a serious deal can be found is the Hospital Thrift Shop (hospitalthriftshop.org). Since it’s a faff to take things on and off the island, locals tend to donate their homeware and clothing when they redecorate or leave. With homes averaging $5m on the island — you can expect to find some <seriously> nice cast-offs.
Ferry to Hyannis Port, Massachusetts: 1 hour
Drive to Watch Hill, Rhode Island: 2 hours 20 minutes
Day 6 & 7: Watch Hill, Rhode Island
Tucked in the state’s sleepy southwestern corner, Watch Hill is home to Rhode Island’s grand dame hotel and counts Taylor Swift among its residents. Fringed by the Atlantic Ocean, it’s drawn holidaymakers since the mid-19th century.
Stay
Reminiscent of some sort of magnificent Victorian lemon jelly, Ocean House makes quite the impression, sitting high on the bluffs of Watch Hill. One of the quintessential New England summer resorts – it’s an old school luxury destination where impeccable service reigns supreme. Rooms lean into coastal chic – natural woods, blue accents, splashes of summery florals and stripes. For the complete experience, be sure to secure an ocean-facing room.
Rates start at £520 per night (off-season). Book it here
Eat & Drink
As a Relais & Châteaux property, food is central at Ocean House. COAST (oceanhouseri.com) is the award-winning fine-dining restaurant, while The Bistro serves classics like risottos, burgers and steaks throughout the day. The Verandah, open only in summer, boasts a full raw bar; Dalia, also a summer-only venue, specialises in Spanish tapas; and Théa is the relaxed, oceanfront beach restaurant offering casual options like kebabs, sandwiches and pizzas.
Do
If you drive via Newport (45 minutes away), stop by the Newport Mansions – a collection of opulent summer ‘cottages’ built by America’s wealthiest families during the Gilded Age. Expect rooms made entirely of European Marble, custom frescoes and gold-leafed ceilings. For a refresher, head to the White Horse Tavern (whitehorsenewport.com), America’s oldest inn and a favourite of Jackie Kennedy Onassis.
At Ocean House, lounge on the private beach, take in the sweeping Atlantic views or join in activities from croquet to Pilates and wine tastings. Don’t miss the hotel’s Ludwig Bemelmans collection — the largest private collection in North America — featuring works from his “Farewell to the Ritz” series alongside full-colour illustrations and sketches from the Madeline book series.
Drive to Barnard, Vermont: 4 hours
Day 8 & 9: Barnard, Vermont
Vermont is New England at its most pastoral – rolling hills, red barns and winding country roads. A state with true seasons – it offers a wholly different experience, whether blanketed in snow, bursting with its world-famous foliage or blooming in summer.
Stay
Surrounded by meadows, mountains and woodlands, Twin Farms is like something out of a storybook. Centred around an 18th-century farmhouse that once belonged to Nobel laureate Sinclair Lewis, today the adults-only, all-inclusive is made up of standalone log cabins, cottages and luxury tree houses that spread over the property’s idyllic 300 acres. The interiors are eclectic and luxe with each space distinct, balancing whimsical accents and antiques with contemporary art and sculptural furniture. Simply put, this hotel is a complete oasis from everyday life.
Rates start from £2410 per night. Book it here
Eat & Drink
With everything included in your stay, the sky’s the limit when it comes to being fed and watered. After a glass of Champagne? No problem. A burger at 1am? It’ll be right with you. A bespoke 5-course tasting menu complete with wine pairings? On the house! If you are there in spring or summer, do go on a hike and take them up on the offer of a picnic delivered to the mountain – you’ll be thrilled with a chilled bottle of wine and a delectable lobster roll at the top of it.
Do
Paddle board on the private lake, bicycle in the surrounding area, thrash the opposition on the Pickleball court or try your hand at axe throwing. For those less inclined to exertion, book the private Japanese onsen, take a watercolour class or wile away the day trying your hand at an (impossible but addictive) hand-crafted Stave puzzle.
Further afield, the quintessential New England town of Woodstock is 20 minutes away and full of flannel-wearing residents, tasteful boutiques, antique shops and sweet cafes. Stop by the Woodstock Inn & Resort (woodstockinn.com) for lunch before popping into Billings Farm & Museum for a novel look at Vermont farm life.
Drive to Portland, Maine: 3 hours
Day 10 & 11: Portland, Maine
Portland is often said to have more restaurants per capita than any other city in the United States. In recent years, its culinary scene – along with a thriving network of microbreweries and a burgeoning arts community – has exploded, making it one of the most sought-after small cities on the East Coast.
Stay
Set in the city’s leafy West End, within easy walking distance of cafes, shops and breweries, Blind Tiger Portland - Carleton Street is a boutique townhouse hotel with no reception desk or staff mingling around. You’ll let yourself into the building, there’s a help-yourself snack cupboard and breakfast will appear as if by magic outside your door each morning. With only six bedrooms, the space is intimate, with a home-away-from-home feel.
Rates start from £220 per night. Book it here
Eat & Drink
Think of Maine and you’ll likely think of lobster rolls (or how the locals would pronounce it: ‘lahb sta’ rolls) and Eventide Oyster Co. (eventideoysterco.com) is the spot to sample the brown butter delight. A few doors down, The Honey Paw (thehoneypaw.com) fuses Asian classics with New England influences — think Tom Yum served in a crab broth with mussels and pickled lobster or rare beef salad with smoked oyster mayonnaise. For a killer cocktail, swing by Lucky Cheetah (luckycheetahmaine.com) — the menu is eclectic and the drinks are expertly mixed. If you make only one reservation though, let it be at Twelve (twelvemaine.com). Helmed by Colin Wyatt — formerly of New York’s Eleven Madison Park, crowned The World’s Best Restaurant in 2017 — Twelve delivers refined, intricately composed plates without pretension. In the morning, head to Tandem Bakery (tandemcoffee.com) for a to-die-for pastry and iced coffee.
Do
Hike the headlands of Fort Williams Park to see Portland Head Light – Maine’s oldest, and some argue most beautiful, lighthouse. For those wanting to snag a Boat and Tote bag from L.L.Bean, head straight to the brand’s headquarters, about 25 minutes from the city’s downtown. For an afternoon spent like a local, settle into one of the city’s many micro-breweries.
Drive to Salem, Massachusetts: 1 hour 45 minutes
Day 12: Salem, Massachusetts
Best known as the site of the 1692 witch trials, Salem blends its maritime history with the supernatural. It’s a walkable city set on the coast and only one hour from Boston.
Stay
Dating back to the 18th century, The Merchant was once the home of a prominent sea trader but today is one of the leading design-led hotels in the city. Rooms are generous and homely with splashes of rich colours, mismatched prints and mixed antiques. Its central location makes it ideal for a whirlwind visit, with most of Salem’s main sites within walking distance.
Rates start from £150 per night. Book it here
Eat & Drink
Turner’s Seafood (turners-seafood.com), housed in the Lyceum Hall (where Alexander Graham Bell famously made the first public telephone call from in February 1877), is a Salem institution. Classics like Oyster Rockafellas, half lobster and seafood linguine are all on offer, but whatever you choose, start with the clam chowder. It doesn’t get more quintessentially Massachusetts than that.
Do
Embrace novelty at The Salem Witch Museum, where you’ll experience a kitsch retelling of the trials. A short Uber ride from the centre is Pioneer Village, a living history museum that recreates Salem as it was in the 17th century and where the opening scenes of Hocus Pocus were filmed. Back in town, dip into the many witchy novelty shops to stock up on Halloween decorations or, if you’re brave enough, have your fortune told.
Drive to Boston to depart: 1 hour
Details
Getting There: Virgin Atlantic operates twice-daily direct flights between London Heathrow and Boston. Return Economy fares start from £376 per person. For bookings and further information, visit virginatlantic.com or telephone 0344 874 7747. Fares are based on select departures and correct as of 29 July 2025; subject to change.
Ferry: Hy-Line Cruises runs a fast one-hour ferry service between Hyannis Port and Nantucket. Return fares from £68. More details at hylinecruises.com/nantucket-ferry.
Getting Around: We used the TomTom GO Superior 7", preloaded with route data for areas without Wi-Fi coverage. £309.99 at tomtom.com.
