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The 21 Best Luxury Vacations from Maine to Milan

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For Americans, visiting the Pine Tree State is a little like taking a quick trip to a foreign country. There’s the distinctive geographical blend of craggy stone beaches, storm-blue lakes and fuzzy, fir-topped mountains. The local cuisine, of fresh seafood augmented by hardy farm-to-table veggies and berries, is likewise famous beyond its borders. And there’s the general quiet, which you’ll find in forests, on the water and, often, among the stoic people who live there. Sailing, ­hiking, skiing, canoeing, fishing, hunting and hammocking are among the myriad restorative activities beloved by natives and visitors alike.
 
In other words, it’s a dream escape from urban life, which is why it’s grown more popular than ever over the past decade. Restaurant-jammed Portland added a few more in 2022, including Twelve, a dining room from former Eleven Madison Park chef Colin Wyatt, and the Danforth, a cocktail lounge by Death & Co partner Alex Day. An expansive rooftop bar, Luna, has also elevated the city’s nightlife, offering gorgeous harbor views from the new Canopy by Hilton Portland Waterfront hotel. Further Down East (that’s up the coast, in Maine-speak) on the vast Deer Isle, chef Devin Finigan has created a romantic destination with Aragosta at Goose Cove, which opened in 2019. Guests can stay at one of 12 cottages and suites and partake in a tasting menu of locally sourced halibut, lobster, oysters, kelp and duck or dine in a greenhouse perched right over the water. (There are also walk-in-only happy hours Mondays through Wednesdays.)
 
If a preppy paradise is what you’re searching for, fashion designer Todd Snyder has continued his partnership with the
Hidden Pond resort in Kennebunkport and designed 20 one-bedroom bungalows in an appealing rustic style. While there, take a boat ride, get a CBD-infused massage at the spa or simply relax on the beach. Some even have sand!


When to go: July through mid-October sees the most consistently good weather, with brilliant fall foliage starting in September. For winter sports enthusiasts, mid-January through mid-March bring ideal snow and ice conditions.
When not to go: April through mid-May is often rainy, cold and gray. For those who like to hike, fish and otherwise spend time in the outdoors, the brace-yourself conditions of the mud and black fly season can continue well into June.
Whom to call: Your Maine Concierge

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