Whether you’re vacationing as a couple or with family, the perfect vacation isn’t complete without the perfect date night. Here are our ideas from Bar Harbor to Key West that give you that quality time together and go deep into the destination to make it a night to remember.
Shuffle Your Heart Out [St. Petersburg, FL]
On Friday nights, travelers and locals alike have the unique opportunity to try their hand at game that’s nearly gone extinct: shuffleboard. But before you get any ideas about this being a date night activity fit for the geriatric set, rest assured – the St. Petersburg Shuffleboard Club is not your grandpa’s shuffleboard club. The club has been around since the mid-1920s, but it has been making shuffleboard cool again since the institution of the weekly St. Pete’s Shuffle in 2005. On Fridays, they open their doors to non-members. You’ll find families with young kids next to groups of hip millennials, with a few veteran shuffleboard players mixed in. Bring your own food and drink (just no glass bottles) – we’d recommend a quick stop at the St. Pete’s Taco Bus for some tasty date night dinner on the run.
Modern American Theater [Sarasota, FL]
Sarasota might be an unexpected location for one of the premier professional theaters in the southeastern US in Sarasota, but rather than scratch your head, just go ahead and book your tickets for a show at Asolo Repertory Theater. A powerhouse in Sarasota’s vibrant arts scene, the Asolo stage plays host to shows that range from Broadway hits to Shakespeare’s beloved plays. After the show, head over to Social Eatery & Bar for a handcrafted cocktail and a post-show conversation. We’d recommend the Social Sazerac, a blend of white whiskey, barrel-aged brandy, absinthe, and a touch of orange bitters and zest.
Comedy in Old School Square [Delray Beach, FL]
Laughing so hard you cry should be a required part of every vacation. Our recipe in Delray: a comedy show in Old School Square at the Crest Theatre or the Fieldhouse from the lineup of veterans and rising stars. Before the show, wander through this amazing school campus turned arts and entertainment center, a central piece in Delray Beach’s thriving nightlife. After the show, it’s time for a night cap on Delray’s famous Atlantic Avenue that has everything from cozy, intimate spots to pulsing nightclubs. We suggest 50 Ocean and one of the signature cocktails at the backlit quartz bar.
A Breakfast Date with Gourmet Donuts and Cuban Coffee [Key West, FL]
In Key West, anything goes, so why not switch out the tired date night activities for a breakfast date instead? Head over to Glazed Donuts for what might be the best donuts you’ll ever have (lauded by none other than Food & Wine, USA Today, and more) for a mixed dozen of this feisty little shop’s finger-licking donuts. Tuck your donuts safely in the backseat (we’d advise a seatbelt for the box – these donuts are that good), and make your way to Cuban Coffee Queen’s downtown location, where you should order the largest Café Con Leche they have. Take your coffee and donuts for a drive over to Fort Zachary Taylor Historic State Park, a pristine little postage stamp of quiet beach super close but oh so far from Duval Street’s hustle and bustle. It’s also our pick for the best swimming spot on the island ripe for a morning dip.
Where to Stay Sunset Key Cottages
More than Just a Date Night [Naples, FL]
For couples looking for more than just a night out, Edgewater Beach Hotel’s special Anniversary Celebration Package extends the romance throughout the day. Your one-night accommodations come with a welcome bottle of Veuve Clicquot champagne and strawberries, a picnic-style brunch on the beach, and use of a luxury beach bed. But the cherry on top is the signature Dinner by the Sea, a private dinner with a table set on the beach (which you can still book separate from this package). Your four-course meal, which you devise personally with the chef, includes a champagne toast and butler-style dining service.
Where to Stay Edgewater Beach Hotel
Lobster and Blueberry Beer [Bar Harbor, ME]
If you can believe it, there’s only one place that can deliver the quintessential coastal Maine dinner out experience in Bar Harbor. On esteemed West Street, formerly the home to the rich and famous of the Gilded Age, Stewman’s Lobster Pound is a working lobstering pier that juts out over Frenchman Bay. Take in the view of the harbor, Bar Island, and countless bobbing boats while diving in to a Maine lobster, steamers, and corn on the cob with a slice of blueberry pie to finish it off. But the date night activities don’t end there – head over to Atlantic Brewing Company’s downtown tasting room to grab a pint or two of their famous Blueberry Ale. No really – in an age of cloyingly sweet fruit beers, this is a classic worth tasting.
Olympic Date Night Activities [Lake Placid, NY]
Lake Placid’s Olympic Center makes for a novel date night out that you’re bound to remember for years. In the winter, get out on the ice to experience Olympic skeleton, the 30-mph grown-up version of the sledding you remember from your childhood. In summer, grab a couple of tickets to the Saturday Night Ice Show, where you’re likely to see a future Olympian on the ice, showcasing gravity-defying leaps from their training.
Where to Stay Lake Placid Lodge