“Love is when two people whose weirdness is compatible join forces.” – Dr. Seuss.
This one is for the couples who are crazy in love and, well, also share a crazy kinda love for the craziest things.
It’s time to get weird on date night with this to-do list of weird, wacky and whimsical Florida roadside attractions near Orlando and beyond.
RELATED: Only in Florida Adventures to Experience Together
Florida Roadside Attractions in Greater Orlando
Monument of States
- Location: 300 E. Monument Ave., Kissimmee, FL
Couples who appreciate public art displays should venture out to see this peculiar piece, situated on the shore of Lake Tohopekaliga. Towering 50 feet high, the Monument of States features at least one rock from every U.S. state. Find your home state (and the home state of your date), then find a nearby shady tree to picnic under at Kissimmee Lakeside Park.
Citrus Tower
- Location: 141 N. Hwy 27, Clermont, FL
Long before giant theme park skylines dominated Central Florida, the Citrus Tower was literally the top landmark to visit. Standing 226 feet tall, this retro Florida roadside attraction offers awesome views from the Observation deck of rolling hills, lakes and sprawling citrus groves. Couples looking for a low-key scenic stop will love the Citrus Tower, especially around sunset. Oh, and grab a hot beverage in the on-site coffee shop.
Presidents Hall of Fame
- Location: 123 N. Highway 27, Clermont, FL
If a couple’s getaway to Washington, D.C. is beyond your travel budget right now, hop in the car for a quick trip to this Clermont locale. The Presidents Hall of Fame is a unique Florida roadside attraction that displays wax figures of our nation’s leaders and first ladies, a 60-by-20-foot replica of the White House and authentic artifacts, including gowns worn by first ladies, historical documents and seats from the Oval Office and Ford Theater where Lincoln was assassinated. Presidents Hall of Fame is charmingly old-school and surprisingly entertaining for couples who appreciate quirky Americana.
Showcase of Citrus
- Location: 15051 Frank Jarrell Rd., Clermont, FL
Thanks to refreshing scents from more than 50 varieties of citrus, let your nose guide you to Showcase of Citrus, a 2,500-acre adventure ranch. Farm-to-table foodies can pick Florida oranges and feed chickens, goats, pigs, a miniature horse, a kangaroo and a donkey.
Adrenaline junkies can climb aboard a modified monster truck, dominating at 14-feet wide, 16-feet tall and 40-feet long! During the one-hour Monster Truck Safari Tour, you’ll trek through woodlands, swamps and pastureland to see zebras, watusi, water buffalo, alligators, snakes and native birds.
Back at the general store, stock up on honey, jelly, other condiments and more. Lastly, settle into the on-site bar to sip distinctive beverages, such as wine smoothies or Showcase of Citrus’ signature drink, “The Eclipse,” made with dark champagne and fresh-squeezed orange juice.
Reptile World Serpentarium
- Location: 5705 East Irlo Bronson Mem. Hwy., St. Cloud, FL
There are so many fun animal encounters in Orlando. But for couples who want to avoid crowded attractions, know that Reptile World Serpentarium is a local Florida roadside attraction worth visiting. It’s home to hundreds of reptiles and famous venom extraction demonstrations. So, slither to St. Cloud for this educational, slightly nerve-wracking and memorable date night.
Try These Other Florida Attractions:
- Gatorland (Orlando)
- Orange World (Kissimmee)
- Paint the Trail (Longwood)
- Statue Parade (Gotha)
- World’s Largest Nativity Scene (Altamonte Springs)
Florida Roadside Attractions Just Beyond Orlando
Dixieland Dragon
- Location: 118 W. Park St., Lakeland, FL
If you’re missing the days of snuggling on the couch to watch Game of Thrones together, you may want to check out the Dixieland Dragon, one of Florida’s most random treasures. This giant dragon sculpture, built from recycled industrial materials, looks like something a medieval knight would discover behind an auto repair shop. It’s bizarre, creative and perhaps worth the stop for couples embarking on a Lakeland day-trip.
Spook Hill
- Location: 321 Dr. JA Wiltshire Ave., Lake Wales, FL
This famous gravity hill is basically a couple’s challenge disguised as a Florida roadside attraction. Put your car in neutral at the marked spot. And brace yourself as it appears to roll uphill all by itself! Is it an optical illusion? You decide.
Florida Railroad Museum
- Location: 12210 83rd St. E, Parrish, FL
The Florida Railroad Museum lets couples climb aboard vintage railcars for scenic excursions through Old Florida landscapes. It has major nostalgic energy, like stepping into a classic rom-com movie.
Penny Lane Beatles Museum
- Location: 730 Broadway, Dunedin, FL
Music-loving couples will absolutely adore this hidden gem in Dunedin, packed with Beatles memorabilia. The Penny Lane Beatles Museum feels cool and comfortable. Maybe I’m just biased because my son is named Jude (“Hey Jude…”). Even casual fans of The Beatles will appreciate the rare collectibles and leisure stroll down the shop aisles.
Weeki Wachee Springs State Park
- Location: 6131 Commercial Way, Spring Hill, FL
Weeki Wachee is one of the most iconic attractions, blending crystal-clear springs with live underwater mermaid performances. This Florida roadside attraction came to life in 1946 when Newton Perry invented a free-flowing air hose allowing humans (well, mermaids) to thrive underwater without a tank!
Related: 5 Central Florida Kayaking Experiences Every Orlandoan Needs to Have
Whimzeyland
- Location: 1206 3rd St. N, Safety Harbor, FL
Also known as the Bowling Ball House, Whimzeyland looks like a yard sale put on by the boldest artist in town. It’s colorful, chaotic and impossible not to be amazed. Couples looking for artsy, offbeat road trip stops will love wandering through this whimsical wonderland.
Wizard of Oz Museum
- Location: 333 West Cocoa Beach Causeway, Cocoa Beach, FL
- REOPENING MID-JUNE, 2026
Somewhere over the rainbow (and near the Space Coast) sits this wonderfully niche museum dedicated to all things Oz. Expect memorabilia, immersive exhibits and enough witchy wonders to keep you enthralled for hours. Sure, our Sunshine State may be famous for its beaches and theme parks, but this Florida roadside attraction is a hidden gem shining brighter than Emerald City.
Also Try These Florida Attractions:
- Don Garlits Museum of Drag Racing (Ocala)
- Fantasy of Flight (Polk City)
- Reptile Discovery Center (DeLand)
- Spongeorama Sponge Factory (Tarpon Springs)
- Swampy World's Largest Alligator (Ocala)
- Tampa Electric Company Manatee Viewing Center (Apollo)
Florida Roadside Attractions Worth the Drive
Mini Bridges
- Location: 101 State St. W., Jacksonville, FL
Jacksonville’s Mini Bridges attraction celebrates the city’s famous bridges with tiny replicas that are oddly fun to walk on. This Florida roadside attraction is small (no pun intended) but makes for a fun stop while exploring Northeast Florida.
Solomon’s Castle
- Location: 4533 Solomon Rd., Ona, FL
Built from recycled materials and covered in aluminum printing plates, Solomon’s Castle looks like something weird out of a fantasy novel. To craft your very own chapter of unique finds, head to this bizarre art-filled castle. Couples willing to venture off the beaten path, just over two hours south of Downtown Orlando, will be rewarded with one of the best Florida roadside attractions.
St. Augustine Pirate & Treasure Museum
- Location: 12 South Castillo Drive, St. Augustine, FL
In the heart of Florida’s most historic town, couples can make historic memories by channeling their inner pirates by exploring shipwreck artifacts, treasure displays and interactive exhibits. It’s touristy but playful. The Pirate & Treasure Museum is an unexpected stop amid the many attractions of St. Augustine.
UF Bat Houses
- Location: Museum Rd., Gainesville, FL
Watching thousands of bats emerge at sunset sounds either magical or mildly terrifying, depending on your personality. Fortunately, we at Orlando Date Night Guide think it's mostly enchanting. The University of Florida Bat Houses create one of the coolest natural spectacles in the state and make for an unexpectedly date-night stop, especially when seeking spooky experiences during fall and/or Halloween season.
Also Try These Attractions:
- Potter’s Wax Museum (St. Augustine)
- Fountain of Youth Archaeological Park (St. Augustine)
