5 Cool Date Ideas For Cool, Cozy Winter Nights

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5 Cool Date Ideas For Cool, Cozy Winter Nights
Editor At Large

Winter nights don't have to be frigid and uninspiring. In fact, they can actually be more romantic than — OHHHHH, THOSE SUMMER NIGHTS — (to quote Grease). Something about the chill in the air makes a perfect excuse to grab your honey, get close, and create your own warmth: whether it's by cozying up fireside, digging into a piping-hot dinner of comfort food (fact: calories don't count in the winter; I don't make the rules), or warming up your hands with a hot toddy. To get the winter wheels rolling and avoid the seasonal blues, we've gathered five cool date night ideas for cool nights (clever, we know) so that you can keep the heat up all winter long.

1. Go babyless for a weekend at a boutique hotel

What is it? After receiving an unprecedented six bookings in one month for new parents taking their first getaway after welcoming a baby, the Deer Path Inn (a boutique hotel modeled after traditional English innkeeping in Lake Forest, IL, a charming suburb located outside of Chicago) decided to further encourage the trend by creating a first-time parents getaway package, which includes in-room massages and mani-pedis, a luxe gourmet dinner for two, and a “create-your-own-cocktail” mixology class.

What to try? Um, everything? But if you can't accomplish that, certainly don't miss the chance to elevate your breakfast experience with an opulent brunch spread in the elegant English Room or the mixology class with Jorge at the White Hart Pub: he's truly a world-class cocktail master (and has awards to prove it). He'll expertly (and patiently) show you how to whip up your partner's favorite cocktail of choice, all while supplying you with a bevy of insider bartender tips and tricks. (Plus, you'll get to frequent the pub while it's a bit less busy.) You'll leave the class feeling like an accomplished mixologist plus if you're friendly, Jorge might even concoct his famous Frosted Flakes apertif. (Trust us, it's as festive and fun as it sounds.) 



A post shared by Deer Path Inn (@deerpathinn) on Nov 30, 2019 at 6:56am PST

Why it's a great date spot: If you're in need of comfort, a reboot on romance, and a truly unmatched standard of sophistication — and what new parent isn't? — both in the accommodations (suites, which have all recently been renovated) and in the service itself, a weekend of pure bliss awaits you at Deer Path Inn. Pair a soaking bath with an in-room massage and check your worries at the (hotel) door: this is the type of stress-free, comfortable getaway where they've already taken care of everything — including the small details you haven't even thought about. For those who are big on creating a dreamy mood, fear not: the romantic architecture of the hotel has maintained its history — the original inn was built in the 1860s on the site of an old hunter's log cabin — and evokes pure English coziness and charm, down to the daily afternoon tea. A weekend you and your partner won't soon forget.



A post shared by Deer Path Inn (@deerpathinn) on Nov 23, 2019 at 3:41am PST

2. Glamp till your heart's content

What is it? Luxury camping AKA glamping overlooking Wrigley Field at Hotel Zachary? Sign us up! Within signature canvas tents, you and boo can relax on comfy couches and enjoy cozy festive décor, complete with hot toddies and fire cauldrons to stay warm. Don't forget to pack your plaid — the luxuriously snug tents are an Instagrammer's winter paradise.

What to try? A selection of barreled, large-format cocktails including the 'Oaxacan Old Fashioned' with reposado tequila, mezcal and notes of chocolate and mole bitters as a riff on the classic, and the 'El Diablo Gone Camping', an iconic tequila cocktail with crème de cassis, lime and ginger beer. Another winter-y option for the chocolate lover is the 'Chocolate De Olla', a hot chocolate spiked with agave and served with toasted marshmallow. Creamy and cozy!

Why it's a great date spot: The whole glamp-y vibe is cozy-chic and uber-romantic. Cuddle close in the tent and toast your outsides by the fire, while warming up your insides with a toasty drink.



A post shared by PartySlate (@partyslate) on Dec 26, 2019 at 8:09am PST

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3. Soak in an ancient thermal bath

What is it? Inspired by the tradition of baths from ancient Roman, Greek and Ottoman civilizations, AIRE ancient bath experiences all take place in restored historical buildings in the center of cities: currently New York, Chicago, Barcelona, Sevella, Almería, and Vallromanes. They've taken the thermal bath as the main element and created an atmosphere of pure magic and sophistication around it — and of course, couples can complement their experience with massage and other romantic add-ons.

What to try? The 'Escape Together' package, which in addition to the thermal bath circuit includes a 45-minute relaxing couples massage and features hot compresses designed to release muscle tension and relax the mind.

Why it's a great date spot: Dim lighting. Warm baths. Candles. Custom couple's experiences built around romance and enchantment. Quite honestly: Winter's never looked so hot. 



A post shared by AIRE Ancient Baths US (@aireancientbaths_us) on Jan 13, 2020 at 7:07am PST

4. Pair steak night with a show

What is it? For the steak and theatre-lovers in the group, pair a hearty dinner and a show. Located n the center of the Fox River in Aurora, IL, Stolp Island Social is a brand new seasonal kitchen and steakhouse offering a warm, relaxed atmosphere, with a vibe reminiscent of 1920s Aurora meets Coco Chanel. Adjacent to the restaurant is award-winning Paramount Theater, which has been open since 1931 and is iconic for it's impeccably-preserved art-deco architecture and Broadway quality productions.



A post shared by Paramount Theatre (@paramountaurora) on Oct 9, 2019 at 8:01am PDT

What to try? Obviously, the steak. But beyond that, it's hard to go wrong anywhere on this Amy Morton-approved menu (yes, that Amy Morton of famed Morton's Steakhouses) but we recommend the kale salad, the whole roasted branzino, and the deviled eggs —​ all paired with a glass of vino, of course. For dessert: we died over the carrot cake.

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Why it's a great date spot: It's a classic crowd-pleaser two-fer that appeals to everyone, plus it's the traditional dinner + a play —​ only elevated and extremely elegant.



A post shared by Stolp Island Social (@stolpislandsocial) on Dec 31, 2019 at 3:31pm PST

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5. Nom on gnocchi straight from the southern region of Italy

What is it? Osteria Trulli, an authentic Pugliese kitchen located in Arlington Heights, IL. Focusing on “La Cucina Povera” (cooking of the poor), executive chef, long-time restauranteur, and Puglia native Giovanni DeNigris celebrates his passion for the humble coastal cuisine that defines one of Southern Italy’s most brilliant regions. A tribute to the deep-rooted traditions of Puglia’s culinary identity, the menu offers unrivaled presentations of fresh seafood, house-made pasta, wood-fire brick oven pizza, creamy risotto, succulent roasted meats, and more.

What to try? You absolutely can't go wrong with anything, but if we have to choose: As a self-proclaimed gnocchi aficionado, I hereby boldy make the claim that the homemade gnocci with black truffle cream is the best gnocchi outside of Italy I've ever had the pleasure of eating. The panzerottini (calzones filled with cheese and mozarella sauce) are like little pockets of piping-hot love in your mouth. And don't dare to even consider walking out the door without devouring the mini cannollis — share one if you're too full of pasta (we wouldn't blame you.)

Why it's a great date spot: Not only is it comfy and intimate — two adjectives ideal for the making of any great date night — the restaurant truly feels like home. It focuses on impressing you with its food and kitchen-like coziness, rather than with over-the-top decor and unnecessary ornamentation — which really is a signal that the focus is where it should be: filling customer's bellies with homemade Italian scrumptiousness. 



A post shared by 303eatschi  (@alyssa.capalbo) on Jun 6, 2016 at 7:28pm PDT

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Andrea Zimmerman is the editor-at-large at Yourtango. She enjoys reading, traveling, and reading while traveling. Follow her on Instagram @angiecat86 or email her at andreaz@yourtango.com.