A Road Trip Itinerary: America’s East Coast

Nantucket may be home to the US’s 1% but the island never once felt pretentious or showy; on the contrary, the most magical thing was the groups of children and teenagers who waved goodbye to their parents each morning and spent the days surfing and snacking without supervision, so safe and comfortable is the environment. The shopping is great too – pop-ups are taken each summer by cult brands like Staud, Hill House Home, Jenny Bird and DÔEN, plus, we became incredibly familiar with the endless tourist shops selling everything from very chic table linen to branded merch and fridge magnets.

If Faraway Nantucket is like a gap year student, Faraway Martha’s Vineyard is its polished, high-achieving older sister. Perched at the very edge of Edgartown, the largest and most stylish of the island’s five towns, it has slick interiors, a sizeable pool and a buzzy sushi restaurant. It’s also sandwiched between some of the most beautiful homes I’ve ever seen, with white picket fences, piles of hydrangeas and bright blue sea views and private docks – you can spend a morning wandering around the neighbourhood drinking in the beautiful houses. If you’re looking for a more classic stay, we ended up at Harbor View Hotel after a stroll and fell for its Ralph Lauren-inspired charm and wraparound deck. The beauty of both hotels is they’re mere steps from everything worth visiting in the town – that includes the lighthouse peering off the edge of the idyllic sandy dunes and The Seafood Shanty, an unassuming spot that makes outrageous shrimp-adorned bloody marys and, naturally, banging lobster rolls.

Edgartown was the filming spot for Steven Spielberg’s Jaws, and one of its key tourist attractions is the infamous bridge. I wish I could say that I hadn’t bottled the jump but I’m just not as brave as the swarms of teenage boys throwing themselves into the icy waters. However, packing a picnic and hopping on bikes down to the pretty beaches that surround the bridge was a good consolation prize. There’s not a great deal more to report from the island – we had a show-stopping dinner at 19 Raw Oyster Bar  (order the octopus with cheesy grits), sipped morning iced coffees from Behind the Bookstore, which is as quaint as it sounds, and snacked on fudge from Murdick's Fudge, a Martha’s Vineyard institution. Ultimately, it’s a place to come and soak up the sun, sip on cocktails and admire real estate, which we did on repeat for 48 hours.

Forgive the detour. The Berkshires are not a natural extension of this east coast trip – just two hours north of Manhattan, it would have made more sense to continue straight up to Maine. But after a dreamy stay in the Catskills two years ago, we’ve been hankering after another dose of upstate magic, so took the opportunity to divert inland. We booked Berkshires Untold via Mr & Mrs Smith – a classic roadside motel that’s had a serious upgrade. Its strip building remains intact but otherwise features none of the tropes of a typical US pitstop, kitted out instead with large comfy beds, Crittall bathrooms, huge fire pits and a double-height mid-century style bar and restaurant. This isn’t a holiday destination in its own right but from afternoons languishing on the banks of the little local lakes to pretty hiking routes and lunch and rosé at Balderdash Cellars (a huge outdoor spot with live country music) it’s a lush, verdant escape from city life. The food scene is less refined but local breakfast spot Haven Café & Bakery had Luke’s Diner vibes and made some stunning chocolate chip pancakes. Elsewhere, breaking up rounds of table tennis with portions of fried chicken at trendy Prairie Whale in Great Barrington made for a memorable evening.

A highlight of the whole trip was sitting on the grass in the sunshine with hundreds of others at 10.30am on a Saturday whilst the Boston Symphony Orchestra rehearsed for their recital the next day – it just so happened that Lang Lang was their guest performer that weekend. Tanglewood is the orchestra’s home outside of the city, and locals rock up every weekend with picnic chairs or take part in yoga on the lawn to hear them practice – a seriously cool way to experience live classical music. Drinks at Prospect  were also memorable – a Soho Farmhouse-style opening this year, the bar and restaurant are surrounded by a glass-like lake, and as the crickets chirped in the surrounding forest, it felt as far away from reality as you could hope to be.

I don’t play hotel favourites, but White Barn Inn, another Auberge Collection property, was this trip’s standout. We pulled into Kennebunkport in southern Maine on a cool, drizzly afternoon – the firepits roared, the chintzy interiors excelled and the hotel’s fleet of Maybachs and G-Wagons stood on guard to deliver us to The Clam Shack, a local institution famed for – you guessed it – lobster rolls. Wrapped up in the Auberge x Barbour collab jackets, we guzzled hot clam chowder before returning to the wooden cloisters of the hotel bar, sipping wine to the tune of the tinkering piano, before braving the rain for dinner at Rosella KPT, a Hamptons export for the freshest sushi.

The next day, with the sun blazing, was an opportunity to see this special coastal town in all its glory. I mentioned already that tourist trinket shops were a common denominator for every spot, and none were better than in Kennebunkport, which has the perfect mix of novelty and stylish interiors destinations, perfectly curated boutiques and trendy vintage stores. Lupine Books and its stylish next-door-neighbour were our favourites. A morning stroll to Coffee Roasters is essential – featuring a 100-year-old press, its DIY coffee bar and selection of local jams and preserves made for a special start to the day. One morning, as we drank in the sunshine, a man set up a keyboard and played piano, which echoed down the street as we wandered up to KPort Bagel, a reliable New York-style bagel site.

The pool at White Barn Inn was the perfect pitstop in between excursions. A little like the Massachusetts islands, this Maine destination isn’t full of things to do but boiled lobster at Mabel’s Lobster Claw, blueberry pie ice cream at Big Daddy’s, steak cooked on the roaring outside firepit at The Lost Fire and s’mores in the hotel’s garden all accounted for not only the extra pounds we carried home but also the delight we found in our first Maine trip.

The next few days were made up of challenging hikes, bracing sea swims, perfect lakes and breathtaking views. You can’t move for tourists in some national parks and after battling the crowds in Yellowstone last year, the almost complete isolation we felt in Acadia – as well as the coastal setting – was not taken for granted. We refuelled each morning with blueberry pancakes at Jordan’s Restaurant, a no-frills diner, and ate dinner both nights at Sweet Pea’s Café in Bar Harbor, a festoon-draped winery that makes homemade pizzas and where children run through the vineyards as the sun sets. We had a slightly disastrous attempt at dinner at a local lobster restaurant but returned a few hours later for ice cold beer from giant buckets and blueberry pie and ice cream served from a docked boat and marvelled in the absolute idyllic feeling that this leg had brought us.

So, to our penultimate stop, The Claremont Hotel – just 30 minutes south of Acadia and a strong contender for our most picturesque hotel. I can’t pretend our experience was sunshine and roses – we were pretty unimpressed with the service. However, the space was beautiful – it’s where the The Beverly Hills Hotel meets coastal grandma – and the little fish shack on the hotel’s shore had great food and a fun atmosphere, even on a rainy day. On our final night, as we stood outside a quintessential lobster joint that was so perfect it felt like AI must have made it, with huge tanks, rickety wooden terraces, bulging rolls and the happiest 80s music blaring, we looked out to the grey Maine seas and felt incredibly grateful for the food, scenery and removal from reality the road trip had given us.

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