7 Romantic Road Trips for a Uniquely Florida Getaway

Invariably when we think of romance or a romantic getaway in Florida, we think of Valentine’s Day, beach weddings, and happy anniversaries. And these are great reasons to embark on one of these romantic road trips in Florida.

Sometimes, though, we just need to get away and relax, perhaps at one of the romantic beaches in Florida or an adorable quaint small town where you can dip into cute boutiques for a little shopping. And that’s where a romantic road trip (or any road trip, tbh) comes in.

I know what you’re thinking. How is a road trip romantic? First, a romantic road trip in Florida has to be on one of Florida’s iconic small highways. Of course, it has to pass through or end at a small romantic town. And ideally, there are good places to watch a romantic sunset or do a little star gazing with your honey.

Knowing Florida as well as I do, these seven trips are the ones I know are the most romantic road trips in Florida. I chose them all over the state, so no matter where you live or visit, you can enjoy one of these romantic Florida road trips.

Romantic Road Trips in Florida

What makes a Florida road trip romantic? These are all on iconic (read: historic) Florida roads. These highways were some of the first roads in Florida and take us back to a time when every family took an old-fashioned road trip every year.

Along these highways we find some of Florida’s most historic and quaint small towns. Towns where you want to set your head down for the night in bed & breakfast and wake up to the sounds of wind rustling through trees and cows in the distance. You’ll find small town attractions and mom-n-pop restaurants. All in all, what could be more romantic than that?

Some of these road trips can even be day trips so put your road trip packing list to use, take your time, enjoy the journey, pack some road trip snacks, and revel in exploring a little of Old Florida.

Highway 98 (Pensacola to Apalachicola)

Starting in the relatively large town (for the Florida panhandle) of Pensacola, Highway 98 along this route passes through a number of beautiful Gulf coast towns, such as Gulf Breeze, Destin, and Rosemary Beach. Though you can make this trip in half a day, it’s much more enjoyable to stop and smell the sea breezes, see the sights, and take your sweet time exploring a few of the small towns along the way.

Total Trip Length: 176 miles. Approximately 3 hours 45 minutes if driven straight through.

Make this a two or three day trip. There are so many great restaurants, amazing sunset spots, beautiful beaches, and secluded nature trails to enjoy. Take your time! A two-day itinerary has you spending the night in Rosemary Beach or Panama City Beach while a three-day itinerary includes an overnight at one of the vacation rentals on Highway 30A, a highly-recommended side trip from Highway 98.

What to See on the Highway 98 Florida Road Trip

• Gulfarium Adventure Park
• Okaloosa Fishing Pier
• The Boardwalk, Okaloosa
• Big Kahuna Water Park
• Topsail Hill State Park
• Grayton State Park
• Constitution Convention Museum
• T.H. Stone Memorial St. Joseph Peninsula State Park

Overseas Highway (Key Largo to Key West)

The Florida Keys drive is one that many people have on their bucket lists and should be included on any South Florida itinerary. There’s just no place like the Florida Keys. Each of the islands has it’s own character. Some invite you to linger and play while others seem to just zip by with only a few residential neighborhoods on them. Along the way, you’ll drive past Pennekamp State Park, through Islamorada, and marvel at the views as you cross Seven Mile Bridge.

Total Trip Length: 104 miles. Approximately 2 hours 15 minutes.

Like our previous Florida road trip, this one deserves a couple of days to enjoy everything along the way. Why cut your romantic trip short? Linger in Key Largo and visit Pennekamp State Park, stop for a seafood lunch, and spend the night in Marathon. The next day, be sure to grab those Instagram photos from all of the photo op spots along Seven Mile Bridge, Pigeon Key, and Little Duck Key. End your road trip in Key West. Be sure to budget a few days here before heading back to Miami.

What to See on the Overseas Highway Road Trip in Florida

• John Pennekamp Coral Reef State Park
• Windley Key Fossil Reef Geological State Park
• Theater of the Sea
• Indian Key Historic State Park
• Florida Keys Overseas Heritage Trail
• Dolphin Research Center
• Florida Keys Aquarium Encounter
• Turtle Hospital
• Pigeon Key Foundation & Marine Science Center
• Bahia Honda State Park
• National Key Deer Refuge Nature Center
• Mote’s International Center for Coral Reef Research

Highway 41 (Brooksville to Dunnellon)

Brooksville, Dunnellon, and the towns in between are some of Florida’s lesser known little towns. You can choose a couple of different routes between the two towns. Highway 98 in this part of Florida takes you through tourist-favorites Crystal River and Homosassa Springs where you’ll find manatees congregating in the winter. Highway 41 runs further inland and passes through historic Floral City and Inverness.

Total Trip Length: 39 miles. Approximately 54 minutes.

This could be a one-day road trip. Or take one day to go up to Dunnellon, spend the night in one of the hotels or vacation rentals there and head back to the Tampa area via Highway 98. So many possibilities with this road trip in Florida!

What to See on the Highway 41 Florida Road Trip

• Big Pine Environmental Area
• Withlacoochee State Forest
• Floral City Heritage Museum
• Withlachoochee State Trail
• Fort Cooper State Park
• Inverness Flea Market
• Citrus County Speedway and Track
• Old Courthouse Heritage Museum

Highway 17 (Punta Gorda to Winter Haven)

US Highway 17 actually begins (or ends) at Punta Gorda and stretches through five states before reaching it’s northern terminus in Paris, Virginia. Along this romantic road trip in Florida, Highway 17 passes through historic Arcadia and Zolfo Springs while simultaneously showing off some of Florida’s interior country. Much of this area was historically cattle country or wetlands. The beautiful Peace River runs through this land, too.

Total Trip Length: 86 miles. Approximately 1 hour 40 minutes.

This romantic Florida road trip makes a good day trip or alternate route to get from the Charlotte Harbor area to the cute town called Winter Haven. If you’re headed to Orlando from the Charlotte Harbor area for a long weekend or romantic getaway, consider adding a day or two to your trip and take this romantic road trip in Florida. Take your time getting to Winter Haven, spend the night there, then let your inner child run free at Legoland or just continue on to Orlando the next day.

What to See on the Punta Gorda Road Trip in Florida

• Howard and Velma Melton Historical Research Library
• Ingraham Seed House
• Desoto Veterans Memorial Park
• Arcadia Historic District
• Creation Adventures Museum
• Pioneer Park
• Cracker Trail Museum
• Paynes Creek Historic State Park
• Homeland Heritage Park
• Wonder House

Highway 441 (Ocala to High Springs)

Ocala is best known as Florida’s horse country. This part of Florida has beautiful rolling hills and is one of only six places in the world with exceptional nutrients in it’s grass which is perfect for raising horses. High Springs is a very little known town, best known to locals as an historic sleepy town with not a whole lot going on. This Florida road trip will bring you close to historic sites and amazing nature as it passes through McIntosh, Micanopy, Gainesville (University of Florida), and Alachua.

Total Trip Length: 59 miles. Approximately 1 hour 13 minutes.

Like our other romantic road trips in Florida, this one can be done in one day. If you love antiquing, this is a very viable option. With Ocala as a home base, spend a couple of hours in Micanopy, lunch time in Gainesville, explore High Springs, then head back to Ocala. It can easily be done in one day.

For a romantic weekend, however, definitely take your time! Along the way, enjoy the nature and history of several parks and some of the oldest towns in Florida, spend the night in Gainesville, then continue on to High Springs the next day. From High Springs, all of north central Florida is open to you. Go see the freshwater springs. Head back to Ocala via I-75. Travel east to see more of the area’s small towns, like Hawthorne. This part of Florida really offers endless possibilities for fun and romantic things to do.

What to See on the Ocala Florida Road Trip

• The Canyons Zipline and Adventure Park
• Historic McIntosh
• Micanopy
• Paynes Prairie Preserve State Park
• Florida Museum of Natural History
• Devil’s Millhopper Geological State Park
• San Felasco State Park

Highway A1A (St. Augustine to Fernandina Beach)

Highway A1A has been Florida’s favorite coastal highway since mid last century. Before Orlando became the theme park capital of the world and interstates made travel fast and faceless, the coastal towns along A1A welcomed visitors to their seaside motels. These days those towns are filled with beachfront mansions and vacation rentals, but Highway A1A remains an iconic road trip in Florida.

Total Trip Length: 58 miles. Approximately 1 hour 30 minutes.

It’s hard to get much more romantic than St. Augustine and Amelia Island, the two end points on this Florida road trip. Starting in St. Augustine (be sure to spend a few days there first!), cross the river and take the slow-traveling A1A north. Along the way you’ll see beautiful views of the Atlantic, take a car ferry, and wind through the salt marshes and state parks of St. George Island. Spend a day or two at Fernandina Beach to see the beach, parks, and all of the history of this wonderful town.

What to See on the Amelia Island Road Trip in Florida

• Guana River Dam
• Beaches Museum
• Mayport Ferry
• Kingsley Plantation
• Blackrock Beach
• Boneyard Beach
• Kelly Seahorse Ranch
• American Beach Museum
• Fort Clinch State Park
• Amelia Island Lighthouse

Highway 44 (New Smyrna Beach to Mount Dora)

Highway 44 roughly mirrors I-4’s route. Without the traffic and crazy accidents. This part of Florida goes from wetlands and lagoons to forest pretty quickly. Expect to see a variety of landscapes when you take this romantic road trip in Florida. The highway winds nature preserves before passing through Deland then turning south over the historic St. John’s River and through more wetlands and forests. It’s a quiet yet interesting drive.

Total Trip Length: 54 miles. Approximately 1 hour 6 minutes

If you’re in the New Smyrna Beach area, this road trip makes sense for you, especially when you consider that Mount Dora is one of the cutest, most romantic towns in Florida. Though the trip can be short, there are plenty of places to stop for photos or just to explore. In Deland, for example, you can explore the area’s history then eat lunch downtown or drive over to the river for a waterfront lunch. With several parks on this route, you can also get a little hiking in and enjoy a few hours in nature.

What to See on the Mt. Dora Florida Road Trip

• Xplex Paintball and Airsoft
• Long Leaf Preserve
• African American Museum of the Arts
• Deland House Museum
• Stetson Mansion
• Seminole State Forest

Final Thoughts on Romantic Road Trips in Florida

Florida is filled with so many great little highways and towns to explore. It’s always been a passion of mine to take the country roads and see where they lead, sometimes getting lost along the way, often finding a little-known treasure. These romantic road trips in Florida invite you and your significant other to relax and take a laid back journey from Point A to Point B. The beauty of road trips like these is that you can do this with any small highway, in Florida or elsewhere.

This February, explore your local iconic highways a little. Get lost in the magic of not knowing exactly where the road will lead you. Go explore the park on the road sign. And take someone you love with you to share all of the memories and laughter!