10 Superb ‘Datecation’ Itineraries for You and Your Better Half

From helicopter tours in Kauai to rope-swinging in Charleston

By Tanner Garrity

10 Superb ‘Datecation’ Itineraries for You and Your Better Half
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28 November 2018

“You go to Montreal with your friends. You go to Quebec City with someone special.”

Some advice from a helpful Quebecker we talked Canadian cities with a few months back.  

Got us thinking: Which cities, towns and islands would top the list for a weekend away with your better half?

Our criteria: spots rich in activities, relaxation or both, where couples can make a quick, easy escape without doing a ton of legwork. Why now? Because once the holidays are over — or hell, during them — you two should set aside some time to appreciate one another.

So below, 10 destinations ideal for some old-school canoodling, all just a quick flight away.

For Less Clothing and More Views
Kauai, Hawaii
The Digs: Ko’a Kea Hotel & Resort sways over Poipu Beach on Hawaii’s oldest and wildest island. It’s a boutique as Hawaiian hotels go, but that’s the point. Perfect for launching daily adventures and tucking in to some seared Hokkaido scallops each night.
The Eats: Eating House 1849 touts local fare by Roy Yamaguchi. Try the honey mustard grilled beef short ribs.
The Play: If you’ve never surfed, book a lesson with Kauai Surf Experience. Luan’s been surfing since he was five and’ll have you guys up on a board in two hours. Also — book the Waterfall Tour with Safari Helicopters for a ridiculous view of IRL screensaver Na Pali State Park.

For an Old West Mountain Town and Hot Tubs
Crested Butte, Colorado
The Digs: Vail shmail. Crested Butte is one mountain town that hasn’t yet traded in its swinging saloon doors. Make Scarp Ridge Lodge your base camp for a weekend of skiing and soaking. There’s a heated hot tub on the roof and a saltwater pool inside.
The Eats: It’s important, nay, it’s imperative, that you and your partner can eat casual on vacation. A) To save some coin for other points of interest, and B) because local “fast” food is often where the flavor is. Head to Teocalli Tamale for immaculate burritos from a roadside burrow.
The Play: Cat skiing in Irwin, which gets three times the amount of snows as Crested Butte. Coming out of season? Hop on a horse with Fantasy Ranch Outfitters.

For a New York Getaway, Minus the Crowds
Catskills, New York
The Digs: Pancakes in the morning, tartare at night? Sure. Massive pool open in the summer, roaring chiminea come winter? Check, and check. Scribner’s Catskill Lodge gets it. This is the all-season couples mid-week go-to. Set your status to WFH and set up shop in the library.
The Eats: Brushland Eating House. Eat the pork chops. Please eat the pork chops.
The Play: Skiing, of course, if Hunter Mountain (seen from Scribner’s) suits your fancy. We recommend a bit of a drinking tour, though, assuming you’ve got phones and can call an Uber. Try Wayside Cider, Tuthilltown (for Baby Bourbon Whisky) and Union Grove Distillery for apple-wheat distilled vodka.

For a Stroll or Seven
Charleston, South Carolina
The Digs: Charleston is about moving slooow. As in, “Wow, it’s 2:00 in the afternoon and we still haven’t left the hotel” sort of slow. Not unlikely to happen at The Restoration Hotel, renovated last year to the tune of $27M. It shows, with the rooftop Indigo Pool, on-site coffee bar, spa and mercantile. The place’ll even let you two take a ‘66 Ford Mustang out for a spin.
The Eats: If you’ve seen Bourdain’s Charleston episode, you’re familiar with Husk Restaurant and creator Sean Brock. Get ready for fried catfish, oysters and duck.
The Play: Doesn’t get more pleasantly random than this. Take a break from ambling and try a high ropes course with Wild Blue Ropes.

For California at Its Most Underrated
Carmel-by-the-Sea, California
The Digs: Two hours south of SF and four hours north of Santa Barbara sits little Carmel-by-the-Sea, a Monterey beach town that’s teeming with state parks and basilicas and has never known a swear word. You’re staying in one of Hotel Carmel’s cottage-style suites. Rejoice, the beach is a five-minute walk through the village.
The Eats: Restored farmhouse serving up racks of roasted New Zealand lamb do it for you? Head to Mission Ranch.
The Play: Save the Pebble Beach tee-off for another time. Put aside a day for hiking Point Lobos down to China Cave and at least one night for a sunset sail around Monterey Bay. If that one doesn’t work for him/her, we don’t know what to tell ya.

For R&R with an Extra Side of R
Canyon Point, Utah
The Digs: Sometimes, you just shouldn’t bother leaving the resort. Amangiri in southwestern Utah is your one-stop ready, set, relax: a raw encampment surrounded by … well, absolutely nothing. This is where you and the honey go full-restoration and spend as much time talking about your “centers” as you damn well please.
The Eats: There’s a wood-fired oven serving up everything from “Navajo Fry Bread Tacos” to foraged mushroom pizzas. Safe to say your taste buds are in good hands.
The Play: Save your energy for the Mesa Pool Suite. During the day, you’re headed to the pool or the spa, and engaging in smudging — a Native American ritual that involves burning white sage and fanning it over the body.

For All Those Dancing Lessons to Actually Pay Off
Miami, Florida
The Digs: Red-and-white striped umbrellas, silly views of the Atlantic and … a golden-plated woolly mammoth skeleton? That’s the Faena Hotel, and that’s more or less Miami Beach. There’s no time like the present to visit the now hyper-art-conscious Little Cuba.
The Eats: How to choose just one? Tear into short rib tacos at Amara at Paraiso, fresh-as-it-gets sushi at Makoto and roast chicken at Pinch Kitchen.
The Play: Don’t overthink this one. Salsa dancing is the official foreplay of Miami, and you’re headed to Ball & Chain for live grooves and a mojito or four.

For a Slice of Europe This Side of the Pond
Quebec City, Canada
The Digs: Auberge Place d’Armes is the sort of hotel with room names like “George Richard Renfrew” “Pierre-Joseph-Olivier Chauveau” and “Lord Buffington Stratenhoust III.” Ok, we made the last one up. Point is, the Auberge rightfully channels Quebec City’s over-the-top old world charm, while offering well-appointed coziness that’ll get the job done and then some at the end of the day.
The Eats: This is one case we endorse all-out elegance. Wear a suit and a peacoat, and head to L’Initiale. Expect respected food done the old way.
The Play: That little island just off the coast? In the Saint Lawrence River? It’s called Orleans, and you can totally go exploring on it. Join host Philippe on the Orleans Island Experience, and he’ll show you Montmorency Waterfall, live music, fruit farms (only in the warmer months, duh) and an array of chocolate shops.  

For an “Indiana Jones Hits the Beach” Vibe
Tulum, Mexico
The Digs: Honestly, what’s the point of spending a lot of money and going away if you don’t mouth a stupefied “Holy sh*t” upon reaching your destination? Azulik will have you cussing like a drunken sailor. Expect a row of eco-villas sporting palm-frond roofs, blue-green water and zero electricity.
The Eats: Hartwood’s an off-grid eatery with locally-harvested ingredients. The menu changes everyday based on availability (how’s that for fresh?) and reservations, as you might expect, are tough to find. Make sure to snag a table — you both deserve it.
The Play: Relaxation and adventure share the roost at Tulum’s Freediving Discovery. Spend the morning in yoga class harnessing your breathing, and the afternoon free-diving 23 feet into a limestone sinkhole.

For Those Bikinis Sitting in Her Add to Cart
Anguilla
The Digs: Your honeymoon flubbed? Belmond Cap Juluca will wave its magic Caribbean wand and sort it all out. This place evokes serious Santorini x Calypso vibes, flaunting an irresponsible number of infinity pools, and headache-curing views of Maundays Bay.
The Eats: Take a boat out to Sandy Island (it leaves once a day, at 10AM) for the best dang lobstah you’ve ever had.
The Play: If you can will yourselves out of your chairs in the surf, suit up for some shipwreck diving. The island’s iconic El Buen Consejo dates all the way back to 1772. Watch out for those cannons!

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