Studies show that, even before it’s over, you begin grieving for the end of your holiday, a more intense version of the Sunday scaries. We’re starting to feel that way about the tail end of summer, staring in the mirror at our faded tans, longing for the still waters and cold beers of that long-weekend sailing trip. Sigh. We’re still about a month away from the annual debate about the seasonality of white clothing, so there’s time to shake off the blues and plenty of adventures to be had in the next month. You’ve been hoarding that annual leave for a reason. With the notable exception of one island getaway, we’ve found six destinations within a few hours drive of a city.

All this talk of the next Bond outing being filmed in Jamaica is as good a reason as any to visit the island paradise. At this time of year, you can catch its glistening beaches at lower decibels and for about half the price. Everyone has their resort of choice. Some prefer the chic vibes of Jakes, others the charm of Rockhouse. If you want to go full Bond and save a little, too, you can even book a stay at GoldenEye, where author Mr Ian Fleming wrote the books. The legendary resort is offering special renovation deals. It would be perfectly agreeable to spend your days sipping rum libations on white-sand beaches, but you’d be missing out on Jamaica’s more offbeat adventures, such as raft rides along the jungle-lined Blue Lagoon, authentic roadside jerk stands such as Scotchies that cook on pimento-wood grills and hikes through the lush forests of the Blue Mountains.

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The idea of escaping to the Hamptons simply to relax is not entirely new, but going there to find something closer to Zen, as you’re invited to do at the recently opened retreat Shou Sugi Ban House, seems entirely fresh. Shou Sugi’s network of structures, including 13 studios, a tea lounge and a wellness barn, are made from soothing pale timber that borrows from the Japanese ryokan tradition while nodding to the local surroundings. Three-, four- or six-night stays are available, all with itineraries that include yoga classes. Spend the days sharpening your meditation practice, unwinding with hydrotherapy treatments or wandering around the property’s three acres. What’s more, the food is soothingly simple and incorporates local foraged finds, thanks to Noma co-founder Mr Mads Refslund, who conceived the menu.

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Tofino in Canada is not your typical sun-drenched beach destination, but its panoramas are certainly postcard-worthy. A couple of hours from Vancouver where fog still roams, this improbable surf town offers great waves with views of wild evergreen forest. Besides having surf that’s suitable for pros and beginners alike, Tofino doesn’t boast overwhelming crowds. Stay in one of Wickaninnish Inn’s cliff-hugging rooms that feel like well-appointed cabins. When not catching the waves at Cox Bay, the main break in town, hike through the coastal rainforest and rest your muscles with a soak in the local hot springs.

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The lakeside Suttle Lodge in Deschutes National Forest in Oregon was dreamt up by the same people who opened the Ace Hotel in Portland, 150 miles northwest. So you can count on two key things: the design of the 11 rustic rooms is handsomely stylish and the food and drinks are unparalleled. Spend your days floating along in a canoe, fly-fishing in the trout-rich local waters or playing croquet and cornhole. Nights are for enjoying the fruits of chef Mr Joshua McFadden’s labours. Acclaimed for his hyper-seasonal Ava Gene’s in Portland, Mr McFadden serves knockout dishes, such as chowder loaded with veggies, and mac and cheese, that are comforting and dead simple.

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A favourite rustic luxury escape for discerning chefs, restaurateurs and food critics, Blackberry Farm in rural Tennessee recently expanded its empire in a quite ambitious way. It took over a mountain. The sister compound, Blackberry Mountain, spans 5,200 acres where you can forage mushrooms, ride horses, shoot clay pigeons… The list of activities goes on and on. It’s basically the adult sleepover camp of your dreams, minus the cafeteria-style buffet. The real reason you’re making the trek to the Great Smoky Mountains is the seasonal-driven menu of chef Mr Josh Feathers. On any given night, his Three Sisters restaurant could be delivering grilled grouper with tangy yoghurt, beets that have been charred on an open fire or ribeye burgers served with plenty of southern hospitality. The plush, traditional rooms start at £1,000 a night, but the splurge is well worth it.

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Some would argue that Chicago has the best bars, restaurants and design in the US. No one would argue it has the best weather. But now, in late summer, is the ideal time to explore the Midwestern city’s spoils. Anchor yourself at either Soho House for sexier, high-end comfort or the Chicago Athletic Association for an architectural gem that is easier on the wallet. Both are easy jumping-off points for the experimental art at the Museum of Contemporary Art, where you can catch the genre-defying Virgil Abloh: “Figures of Speech” exhibition until 22 September. Hit Cellar Door Provisions for any meal of the day. Grab crisp cannele and coffee for breakfast, custard-like quiche for lunch or seasonal dishes such as burnt spaetzle with clouds of ricotta for dinner. Go to Kitsune for a welcome fusion concept: Japanese dishes improved by forage-fresh ingredients, such as ramen with ramps (wild spring onions). For a truly one-off dining experience, grab a seat at The Aviary, the dream child of mad-scientist chef Mr Grant Achatz, where otherworldly cocktails take centre stage.

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