Legacy Trail

Cupid's Corner: Valentine's Day Ideas in Sarasota County

Do you have a sweetie or sweet friend in mind as February 14th draws near? Celebrate being love-struck in sun-filled Sarasota.

Lovers and friends on the lookout for 2024 Valentine's Day happenings in Sarasota County have come to the right place. Our "Cupid's Corner" roundup features this year's options for an amorous outing on the town. From special menus and artistic experiences to unique date ideas and even a vow renewal ceremony, those in the mood for all kinds of romance will find it on Cupid's favorite holiday in Sarasota.

Romantic Dinner & Dessert for Two

sharkys on the water

Valentine's Day comes with a breathtaking Sarasota Bay vista at Marina Jack. In addition to Marina Jack Valentine's Day dining specials and music in the dining room and Deep Six Lounge and Piano Bar, the restaurant-marina are offering a romantic sightseeing lunchtime cruise, as well as two evening cruises featuring live music and a special Valentine's menu buffet. 

Often regarded as Sarasota's "Most Romantic Restaurant," Euphemia Haye in Longboat Key is a foolproof choice for an evening of date-wooing fine dining. Valentine's Day at Euphemia Haye will be serving a full a la carte menu and nightly specials, along with an extra surprise from Chef Ray. Follow your evening by making a trip upstairs to The Haye Loft for luscious homemade desserts to satisfy both of your sweet tooths. 

Top off the night at Cupid's Cocktail Lounge at The Lounge at element. The decorated, intimate lounge right on the corner of downtown's Main Street will host a cheeky Valentine's Day pop-up bar on the evening of February 14th, complete with an Ex Picture Shredding Station, a Love Note Wall and, of course, craft cocktails and bar bites. 

Treat your significant other with a specially curated three-course, prix-fixe dinner at Jack Dusty Coastal Cuisine & Crafted Cocktails, located at The Ritz-Carlton, Sarasota. The gorgeous restaurant and bar plays host to a wonderful evening of bay views, top-tier service and luxurious suites to extend the holiday further. 

Performing Arts Date Night on the Sarasota Stage


Who doesn't love a good laugh? Better yet, some belly laughs with your loved one? Florida Studio Theatre Improv will be hosting Treble in Paradise: An Improvised Romantic Musical on February 10th. For one night only, FST Improv brings the audience a rom-com-themed show. Inspired by one location and three random notes on the keyboard, the cast weaves a fully improvised musical love story. Be sure to order a bottle of bubbles for your table to let loose and enjoy the candid banter. 

Capturing all your favorite love songs from Broadway, opera and beyond, snag tickets for you and your significant other to witness the hypnotic sounds of The Pops Orchestra. Guest artists Anne Tormela and Nick Palance team with The Pops for this extra-special Valentine's show, I Love You to the Moon & Back. Fall in love with your favorites again during this uniquely crafted production centered around amore! The show will take place on Sunday, February 11th at 3pm at Riverview Performing Arts Center in Sarasota. 

Enjoy Breakfast in Bed at a Luxury Resort

longboat key club resort

Nothing says romance quite like waking up to your love and elevated breakfast treats brought right to your door. Opt for the honeymoon suite and room service the morning of Valentine's Day at one of Sarasota's exquisite hotels and resorts. Whether overlooking the Gulf of Mexico, Downtown Sarasota or the beautiful Bayfront, you'll never forget a morning of mimosas and pancakes in the comfort of your hotel room with your beau or bestie while taking in the "winter" views of sunny Sarasota.

Catch the Sunset by the Bay or Beach


If you love long walks on the beach, Sarasota has you covered. Grab your galentine or crush for a sunset stroll along any of Sarasota's six barrier islands and beaches. Sunsets on the Florida Gulf Coast boast a cascade of colorful clouds and reflections on the water. Whether you grab a bench seat at The Bay Park, meander through the marina of Bayfront Park, find a parking spot with an unobstructed view at Venice Jetties or throw towels down on the #2 Beach in America, there's a coastal locale to take in golden hour and send off another Hallmark holiday. 

Renew Your Wedding Vows in Sarasota

Celebrate love everlasting by saying "I Do – Again" on Siesta Key Beach and Venice Beach. The local, annual Valentine's Day tradition dates back more than 30 years. Every year since 1989, on February 14th, married couples of all ages and duration of matrimony have gathered at Siesta Key Beach for a non-denominational renewal service. The event grew so popular over the years that a second location was added at Venice Beach.

The event is open to all at both locations, but couples should pre-register in advance or register the day of. In the past, the registration fee included your renewal certificate, commemorative gift, flowers, music on the beach and light refreshments. For more information, call Sarasota County Parks & Recreation at 941-861-7275.

Admire the Arts & Listen to Love Poems

sarasota art museum

Whether a first date, your longtime lover or galentine, art aficionados alike will gather for an immersive Valentine's Day event at Sarasota Art Museum, the region’s first museum dedicated to contemporary art. Featuring cocktails, dinner, artists and performers flowing throughout each of the museum’s spaces, guests will be able to interact, activate and “be the art" at Unconventional Evening 2024, starting at 6pm on Wednesday, February 14th. 

Bibliophiles and poets unite – Bookstore1 is hosting an event in its upstairs loft on Pineapple Ave. Ode to Love: A Special Valentine's Evening will include decadent desserts paired with wine, beverages, the soft sounds of live music and readings of Pablo Neruda's love poems (in both English and Spanish), performed by professional actors. The event runs from 8pm – 10pm and is a great time to shop the selection of books while enjoying a unique nightcap after your dinner downtown. 

Stop & Smell The Roses in the Gardens

selby botanical gardens

You'll be hard-pressed to turn down flowers on Valentine’s Day. While roses symbolize love and passion, Marie Selby Botanical Gardens celebrates February 14th with a vast assortment of flower and tropical plant varieties. In the morning, grab your yoga mat and a group of girlfriends to participate in Yoga in the Gardens for a Galentine's Day stretch on the green. And those who'd like to get a little sappy with their special someone in a scenic landscape can explore the exhibitions throughout the beautiful botanical gardens and bayfront grounds.