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Valentine's Day Experiences in Kissimmee

Kissimmee, Florida

As Valentine's Day approaches, consider the enchanting city of Kissimmee, where love takes center stage against the backdrop of vibrant events and delectable dining experiences.


In the heart of Old Town Kissimmee, the Valentine’s Day Convertible Car Show promises a unique celebration. Taking place on February 14 from 5 to 9 pm, participating convertibles not only steal the spotlight but also earn two tickets to the Old Town Ferris Wheel—a perfect setting for a romantic rendezvous.

Experience a royal romance at Medieval Times with an exclusive Valentine's Day wine package. This includes a bottle of wine, commemorative glasses, and a keepsake photo—a majestic enhancement to your medieval adventure.

Escape to Discovery Cove, named the #1 "Most Romantic Thing to Do in Orlando" by USA Today. This tropical oasis offers all-inclusive romantic packages, providing the perfect backdrop for proposals, weddings, or vow renewals.

For a unique proposal venue, consider Escapology Kissimmee at Sunset Walk. Enjoy escape games surrounded by restaurants and entertainment for a delightful night out.

Celebrate the art of love with the Orlando Ballet's enchanting performance of The Sleeping Beauty. From February 15-18, 2024, witness the timeless tale unfold in Steinmetz Hall at the Dr. Phillips Center for the Performing Arts. Recognized as one of the most successful and enduring classical works, The Sleeping Beauty captivates with demanding choreography and a lush musical score composed by Pyotr Ilyich Tchaikovsky.

Race into romance at Andretti Indoor Karting and Games with their Racing Hearts Valentine's Package, which includes two attractions, two one-hour timecards, and two races, available all month (excluding weekends) for you and your significant other.

Explore artistic expressions this Valentine's Day with Painting with a Twist in Kissimmee. Pop In and Paint during designated hours or opt for convenient Twist at Home kits, complete with all materials.

Make a romantic day of it with a chocolate decadence manicure or pedicure at Omni Orlando Resort at ChampionsGate’s Mokara Spa. Top it off with a culinary experience with a featured Valentine’s Day menu at David’s Club.

Food Offerings

For a brunch experience to remember, head to Kavas Tacos + Tequila on February 10 from 10 am to 2:30 pm. Indulge in the Galentine’s Day - Eras Brunch, featuring a specially curated menu for two. With Taylor Swift-inspired cocktails, this brunch promises a lively celebration of friendship and love.

Taverna OPA beckons with an authentic Greek love affair. Enjoy daily belly dancing entertainment as you indulge in their Prix-Fixe Menu for Two, offering a culinary journey through Greek delights, culminating in the sweet finale of Baklava.

Embark on a Caribbean love affair at the Caribbean Moonshine Distillery. On February 17 from 5:00 to 8:00 pm, enjoy a moonshine mixology event featuring passionfruit-flavored moonshine cocktails, Caribbean food, treats, and live music.

Paddlefish invites you to share a seafood love affair with their Cupid’s Boil, paired with sparkling cava. Do not miss the Scarlet Kiss cocktail for that perfect touch of romance.

Indulge in a culinary love story at Terralina Crafted Italian with a bone-in red wine slow-roasted beef short rib over white truffle cavatappi carbonara.

Get your girls together for a Galentine’s Day celebration at The Hampton Social. From Feb. 1 – 13 with your reservation, enjoy bottomless frosé and an appetizer. Or plan the perfect pair with two glasses of sparkling rosé and a half dozen oysters.

At SeaWorld Orlando, indulge in a special Valentine’s Day dining experience at Sharks Underwater Grill. Enjoy a red-carpet entrance, a four-course meal, a complimentary photograph, and an exclusive Sea Lion and Otter presentation.

Special Stays

Cozy up with ACO Vacation Homes, offering 5% off on Valentine's Day stays and an additional 5% off on pool heat—an ideal retreat for a relaxing getaway with your loved one.

Receive a wine basket and rose bouquet to celebrate your love when you book at Plus Vacation Homes.

Meliá Orlando Celebration Hotel invites you to romantic poolside movies and couples' quizzes every Friday and Saturday in February. Also, join Valentine's week workshops for paper flower bouquets, while kids craft cards and hearts on Friday evenings and weekends.

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