Couples’ Long Weekend Itinerary

Planning a long weekend getaway in Kissimmee for just the two of you? Leave the daily grind (and the kids) behind and check out our vacation ideas for couples that make planning a romantic retreat effortless.

A couple on a date at the F&B Cafe in the Ette Hotel, sitting at a table drinking martinis

F&B Cafe

Stay in style on this adventure for two full of romance and relaxation. Wine and dine your way through Kissimmee's hot date-night spots as you explore all that the heart of central Florida has to offer. 

Day 1: Stay in Style

Feeling a cozy vacation home for your Kissimmee stay? Or maybe an inclusive resort experience? We’ve got accommodations for every style and budget that you’ll both love.

Bohemian Hotel Celebration

A Condé Nast “Top 200 Hotel,” settle in for some time together at this iconic hotel that combines classic elegance and turn-of-the-century charm on the edge of tranquil Lake Rianhard in Celebration Town Center. Stroll through the Grand Bohemian Art Gallery or enjoy an evening swim at the hotel’s pool.

Omni Orlando Resort at ChampionsGate

For when you want to indulge, soak in all this tropical-inspired paradise has to offer with a championship golf course, separate adult pools and spaces, and seven on-site restaurants. Grab a cocktail and float away the day in a 850-foot lazy river.

Jeeves Florida Rentals

From one-bedroom suites to mega mansions that'll have you living your movie star fantasy, Jeeves Florida Rentals offers all kinds of options for a romantic escape. Think crackling fire pits, in-house movie theaters, and cool infinity pools.

Magic Village Yards

Want all the amenities of a resort with the privacy of a vacation home? Then Magic Village Yards is the place for you two! Spend a relaxing night in and make dinner together at your home’s outdoor summer kitchen, then watch the sunset from a bubbling Jacuzzi.

Day 2: Adventure for Two

After some downtime, add some thrill to your couples’ long weekend with adventurous activities to add a spark to your Kissimmee vacation.

Bob’s Balloon Rides

These views are worth waking up for. Nothing says romance more than raising a glass of champagne from 1,000 feet up on a breathtaking flight in a hot air balloon over Central Florida. Soak in views of lush natural landscapes and spot a few theme parks along the way.

Zip Line at Gatorland

Ready for a real leap of faith? Head to Gatorland and soar 65 feet in the air above Cuban and Nile Crocodiles before flying over the alligator breeding marsh where 130 gators are hanging out below.

SeaWorld Parks & Resorts Orlando

From happy penguins and sea turtles to pink flamingos and bottlenose dolphins, this is the perfect place for animal lovers. Get up close with playful porpoises at Dolphin Cove, then — for a little extra adventure — challenge your partner to ride MAKO, Orlando’s tallest, fastest, and longest coaster.

House of Blues

Dance to the sounds of sultry blues music at the House of Blues at Disney Springs. Enjoy free live tunes in the courtyard every night of the week, plus big ticket shows to make for a memorable night out.

Day 3: Romance & Relaxation

To perfectly balance a day full of thrills, plan time to chill with relaxing moments that let you enjoy some quality time together. 

The Paddling Center at Shingle Creek

Paddle at your own pace along the calming waters of Shingle Creek, spotting all sorts of birds, alligators, and turtles along the way. It’s a great way to get back to nature and reset during your long weekend getaway.

Lazy H Ranch

Saddle up for a spur-of-the-moment date! Enjoy serene scenes while riding beautiful horses through winding trails along the Kissimmee Valley – passing by hundred-year-old oak hammocks and the shore of Lake Tohopekaliga.

Le Macaron French Pastries

Stop by Le Macaron French Pastries and treat your sweetie to some sweets! Choose from macarons and gelato in both classic and inventive flavors including bubble gum, rose, and lemon cream. Order to go, have a picnic along the edge of Lake Rainhard, and watch the world go by.

Vivian’s Day Spa

Kissimmee locals know Vivian’s is a hidden gem for spa goers looking to indulge in total relaxation. If you’re short on time, they offer amazing 30-minute express services, but to really treat yourselves, we suggest the luxurious Spa Serenity Package.

Day 4: Dine and Wine 

For whatever you’re craving, you’ll find wow-worthy Kissimmee dining experiences that are sure to set the mood.

Sleuths Mystery Dinner Shows

For an evening served with a side of intrigue, visit Sleuths Mystery Dinner Shows. Investigate and interrogate this cast of outrageous characters, then see if you can solve this whodunnit mystery before dessert is served.

Formosa Winery Tasting House

Whether you need something to go with dinner at your vacation home, or you’re simply in search of a new favorite, the fruit wines at Formosa Winery Tasting House pair with just about everything. Stop by for Saturday or Sunday brunch and sip sangria and mimosas as you stroll through the vines.

Thai Thani

This family-owned local favorite is sure to add just the right amount of spice to date night. With authentic Thai decor and fresh, bold flavors, start with the Thai Sampler to share and sip creamy Thai iced tea.

Estefan Kitchen

Modern style meets the electric energy of a 1950s Havana nightclub at this celebrated restaurant owned by Gloria and Emilio Estefan. Try a sizzling steak and fresh, fruity mojitos, and enjoy the bustle of the Promenade at Sunset Walk.