Our 5 Best Florida Road Trips – Tales of Adventure & Luck
Last Updated April 18, 2026
We have lost track of how many road trips we have taken in Florida. They started four decades ago and continue very frequently.
Culling out the best Florida trips has taken some time, thought and subjective evaluation. The keyword “best” had to be defined. We chose to consider best in the terms of emotional attachment.
Our road trips in Florida are sometimes planned and quite often just get in the car and go. Florida is such a huge state that it is easy to find a new adventure in just about any direction. Living in Clearwater Beach means north, south or east – going west would mean getting a little wet!
How We Chose Our 5 Best Florida Road Trips
It was a process. We got the list to ten and then finally decided to use emotional attachment and chose a couple because we know they could never be completely repeated.
The ones below are in alphabetical order. All range from one to five days. Many you will know the names, but our experiences may be quite different. All have been repeated in one way or another over the years.
Travel along our scenic Florida roads with us from the Panhandle to the Florida Keys.
Amelia Island – With a Savanah Sojourn
If you are looking for a trip to escape Florida’s sweltering humidity and heat in the summer, the perfect relief is Amelia Island.
Located just north of Jacksonville and across the St. Mary’s River from Georgia, this regularly fought-over island has a clash of cultures. Between 1562 and 1865, the island flew the flags of no less than 8 sovereignties.
Today, this 13-mile-long island offers some of Florida’s best resorts along the east coast and the attractions of Fernandina on the east.
We love walking Centre Street. There are seven blocks of shops, historical buildings, restaurants and antique stores.
On the other side of the island is Fernandina Beach. Here you will find ritzy resorts, fun beach bars and long sandy Atlantic coastal beaches.
Things to do in Amelia Island include:
- Visiting Fort Clinch, the much-fought-over garrison protecting the island from invaders.
- For golfers, there are five golf courses for all skill levels.
- Bikers will enjoy bike paths among the hotels and resorts.
- Amelia Island State Park offers everything from horseback riding to shelling along the shore of some 200 acres.
- Visit the oldest bar in Florida, the Palace Saloon on Centre Street.
- Learn more things to do on Amelia Island.
Bonus Idea
This Florida road trip brings you within 2 hours of Savanah, Georgia. Amelia Island can be a base for the city that the Civil War General William Tecumseh Sherman said it was “too beautiful to burn” as the north marched south during the Civil War.
Savanah is enticing for historical reasons and the stately mansions that grace the streets date back generations. The walk along River Street is a lesson on how history can be converted into a boardwalk like no other.
Reverse course on W. Bay Street and see why Sherman refused to destroy the city. You will learn the reason “Southern charm” is still alive in south Georgia.
Getting to Amelia Island
There are only two roads into Amelia Island – one from the south across the Amelia River and one from the west across the river on State Route 200.
Amelia Island is less than 20 miles north of Jacksonville, and 3 hours north of Orlando (175 miles). Tallahassee is a little over 3 hours to the west (195 miles) and Gainesville is under 2 hours to the southwest (97 miles).
Recommended Hotels
We like to stay at the Hampton Inn & Suites on the river waterfront just a half block from Centre Street. If you prefer a luxurious Beachfront resort, we like the Omni Resort on the coast.
Final Thoughts on Amelia Island Road Trip
This is one of those trips you can adjust to the time you have. It could be overnight, a weekend getaway, or a week-long vacation to include Savannah.
Our last trip was 4 days. We spent two days on the island and two days in Savanah.
However, you plan your trip to Amelia Island, be prepared for a fun and informative road trip.
The Everglades – Loop Road
For years, we traveled across south Florida on the Tamiami Trail (Route 41). We preferred that route over Alligator Alley for many reasons you can find here.
Tamiami Trail was always adventurous with plenty of wildlife, old Indian villages and many airboat vendors across the Trail. That trip alone would be considered a great road trip on its own.
About three years ago, we heard about a historic old gravel road that cuts through the swamps off Tamiami Trail. It is called Loop Road. It gets its name because it loops from Mile Marker 59 south and then east back into Tamiami Trail some 25 miles later.
First, if you don’t like rustic old roads, this isn’t for you. If your transportation isn’t in good shape, don’t try this road trip. This gravel road is narrow skirting the swamp on each side of the road.
Why Loop Road is Unique
The Everglades is predictable. You plan on seeing alligators somewhere along the way. You will see the normal herons, egrets and hawks along the way. It is a great trip.
Loop Road is less predictable. You can easily have to stop and let a ten-foot gator cross the road. You may see birds you have never seen before and only exist in these swamps. Turtles battle garfish in the sloughs for the fingerling fish.
Mother alligators alongside the road can be seen protecting their young. While we have never seen one, panthers roam the forests nearby.
On our first trip across Loop Road, it was almost too dangerous to get out of the car. Alligators lined the road on a mid-April warm day. In some spots it looked like they were having their own party with multiple gators massed together.
Above all, you knew you were in someplace not intended for humans. Literally, we always say, on Loop Road, there is something that wants to bite you, eat you or sting you.
The sounds of the swamp is an eerie deep humming. Creatures big and small moving by air and land with the occasional splash or grunt of an alligator.
The pictures we include here tell their own story, but you can learn a lot more in an article we wrote after our visit. See more pictures too!
Final Thoughts About Loop Road
Clearly, this is a road trip in Florida that not many have made. It is also one that many people would want to make.
Yet, there is something about being in a place that only Mother Nature can appreciate. The flora and fauna unique to The Everglades make you wonder how this road was built and the reasons anyone would need such a road.
We are just glad it exists to peak at what the swamps have been like for hundreds if not thousands of years. Its one of the few places man has not conquered.
Key West – Boat Races
Over the last 40 years, we have traveled the Florida Keys dozens of times. While each road trip to the Florida Keys was memorable, only one has turned into an annual trip.
About eight years ago we were in Key West meeting some other people there for a birthday celebration. The trip coincided with the Key West Super Boat Championships. The excitement around these powerful racing teams was infectious.
These multi-million dollar teams shared their insight and equipment on blocked streets lined with thousands of people. They paraded the boats down Duval and Greene Street (next to Sloppy Joe’s). Parked and allowed visitors to see these powerful machines up close.
The next day the power was exhibited in races along the waters shared with Mallory Square. The hard-fought competition was exhilarating and competitive, while drivers and throttle men risked everything for the chance to be champions of their class.
Since that time, the boat races, this year called the 45th Annual World Championships 2026, has found us on the waterfront watching these day-long heats and races.
What To Expect at the Key West Boat Races
Teams take over the Fort Zachary Taylor and Truman Annex. They come from all over the world. Set up their week-long villages for several days of competition. It becomes a city within a city that you can walk through and inspect their preparations.
Why do we go each year? Here are some of the reasons:
- The exhilaration of the competition spills over into the nightlife. Parades, parties and people watching spread through the island.
- Yes, the races bring people from hundreds of cities around the world where they co-mingle for fun times surrounding the races. It is 24 hour a day activity.
- From bands, street performers and headline talent, everyone is enjoying the entertainment that spills onto the streets,
- No issues, no trouble, no danger – few events in the world find thousands of people with one common purpose of enjoying the moment.
It is hard to describe the overflowing streets and the explosion of visitors that share these week-long activities.
Restaurants have special events, the waterfront is crowded with boats from around the state and every possible venue has a popular band playing – music is everywhere in Key West for this event.
Where to stay in Key West for the Races
If there is any negative associated with the boat races, it is the hotels who use the event to raise the room rates to ridiculous levels. The principles of supply and demand are in full force.
Our favorite hotel in the last couple of years has been the Opal Key West Resort. It is waterfront next to the boat race course. The Pier House is another great waterfront destination. If you want something that combines privacy and luxury, try the Casa Marina by Hilton, part of their Curio Collection.
Getting to Key West
There is only one way to take a road trip to Key West. You must travel the Overseas Highway from Key Largo the 106 miles.
Should you turn this road trip into another form of travel, there is the Key West Express from Fort Myers and Key West has a very busy airport with flights from every major city in Florida.
Final Thoughts on Our Key West Road Trip
Key West is always on our list of places to visit in Florida – even without the boat races. We get there two or three times a year.
The tropical weather, laid back vibe and quirky culture is always worth the visit.
Marathon – Jimmy Buffet Tribute Turns Stormy
As many people know, Jimmy Buffett passed away in September 2023. He was one of America’s best-known crooners who created a genre of music called “tropical rock”.
Jimmy sang about his days in the islands from Key West to the Caribbean. His music made people want to relive his songs whether it be from his days in Key West or on his sailboat in Jamaica. He was prolific in his writing and other ventures that created a billion-dollar legacy.
Jimmy’s ballads stretched across race, religion or political divide. He sang about love, fun and paradise. We doubt his achievements will ever be duplicated.
In the fall of 2024, the Florida Keys put together a tribute to Jimmy Buffett to be held at the famous Hawks Cay Resort near Marathon. The headline entertainment was long-time members of Jimmy’s Coral Reefer Band.
Since we knew we liked Hawks Cay from previous visits, we planned a road trip to join this tribute to an entertainer who meant so much to the values we enjoyed over the years.
That trip alone is a memorable excursion to the Keys. Little did we know, it was going to turn out better than we ever expected.
On the first night of the show, the grounds had been set up with several hundred seats, many food vendors and portable bars to handle the crowd. The band came on as expected and the skies opened up.
It’s Florida! When the sky turns dark and rain starts to fall, it can ruin the best of outdoor parties. The weather looked to be set in for the evening. We headed inside to the lobby bar that bordered the doors to the patio and pool.
Seated in the first couple of seats, we had a view of the weather and the lobby entrance. In 20 minutes, sound people, band members, and singers who were just on the outdoor stage began to show up. They started to bring in equipment, instruments and lights.
Within another 20 minutes, the show was back together. Hundreds of people packed the small lobby. Soon, the performers were next to us, telling stories about Jimmy Buffett and performing many of his hits along with songs they wrote for him.
The show was electric. Many performers would have walked away under the conditions. Not these guys who were used to putting on a show – just the way Jimmy did it.
Tales from guys who traveled with Jimmy Buffet for years, hearing the music he loved so much, and the weather-created cozy conditions, was an experience that was well beyond expectations.
Getting to Hawks Cay Resort and Marathon Florida
While creating the experience we had at the Buffet tribute is very unlikely, heading to Hawks Cay and Marathon is easily duplicated. Marathon is one of the most popular Keys in Florida and is located about halfway between Key Largo and Key West.
Road trips to the Florida Keys are notoriously memorable with so much to see and do. Hawks Cay is one of our favorite resorts well known for their exploits from TV fishing shows that are based there.
The resort is large enough to hold events and offer accommodations that large families will love.
Pensacola Naval Air Museum and The Blue Angels
Sometimes you just get lucky! We had made plans to see the much-heralded National Naval Air Museum in Pensacola. This particular road trip had started in Destin, Florida with a second day planned in Pensacola.
We were looking forward to seeing the history of flight from the perspective of the Navy’s participation. The museum is well worth the trip.
On this day, we approached the well-guarded naval base to make entry to the museum. As we handed our identification (and money) to the guard, out of nowhere a jet roared over our heads, seemingly low enough to see the rivets holding this jet together.
Immediately, I asked the guard, what in the world was that? Oh, he says, that’s the Blue Angels doing an unscheduled practice. They didn’t inform us like they normally do; he went on as if they didn’t inform him about a lot of things.
Blue Angels Impromptu Show
For the next 20 to 30 minutes as we entered the massive grounds of the Air Museum, a half dozen of the famous Blue Angels performed stunts over our heads. It was stunning, loud and everything on the ground just stopped to see this unbelievable show.
The wing-to-wing precision and speed was spellbinding. It is hard to believe jets traveling up to 700 MPH can move in predetermined formations just inches apart from each other.
While the Blue Angels’ show left us in amazement, it did not lessen our original goal – the Naval Air Museum is a must-visit in the Panhandle.
A half dozen large buildings house planes and supporting equipment. Since 1911 Naval Aviation has been a significant part of our defenses. The historic development from land-based craft to aircraft carriers is part of this museum’s interactive displays.
Other things to do in Pensacola include:
- Famous for its sugar-white sands and emerald-green waters, Pensacola Beach is perfect for swimming, sunbathing, and water sports.
- Visit the lighthouse directly across the road from the Naval Air Museum.
- Tour the historic 19th-century Fort Pickens that played a role in the Civil War. Enjoy pristine beaches, nature trails, and spectacular sunset views.
- Visit the Pensacola Beach Boardwalk. The boardwalk is lined with lively restaurants. Try local favorites like Grouper Sandwiches or Shrimp Po’boys at places like The Grand Marlin or Crabs on the Beach.
- Not far away is the famous Flora-Bama. The beach bar half in Florida and half in Alabama.
Final Thoughts on Our Florida Road Trip to the Naval Air Museum
The Blue Angels do have planned practice sessions. We were fortunate enough to see what we were told one of their unplanned shows that highlight new maneuvers and unique flyovers.
We were lucky to turn a normal, fun road trip into a spectacular event most people never see.
Great Road Tips in Florida That Didin’t Make the Cut
You may be wondering about which road trips we left on the editing board. Here they are:
- The Christmas trip we have taken for the last two years to the World Equestrian Center near Ocala, Florida. Each year, these people spend over a million dollars on holiday decorations that are unique, colorful and many are interactive. Add a 5-star hotel and daily horse jumping events in the arena and you have a fun trip.
- While we generally go for headliner entertainment like The Beach Boys, George Thorogood and others, The Villages St. Patrick’s Day Parade was memorable. Rarely do you find an entertaining parade that lasted almost 60 minutes. Colorful and entertaining, we loved the trip.
- The Space Coast road trip that included Cocoa Beach found us watching a rocket launch on the beach and exploring NASA’s massive grounds, exhibiting our journey into space.
Florida is a state that is always ripe for discovering new adventures and revisiting places that constantly change. Pack your overnight bag and see what you can find.
FAQs About Florida Road Trips
What are some of the best Florida road trips?
Some of the best Florida road trips combine very different experiences, including Amelia Island, the Everglades Loop Road, Key West via the Overseas Highway, Marathon in the Florida Keys, and Pensacola with the Naval Air Museum.
How long should a Florida road trip be?
A Florida road trip can be as short as an overnight getaway or as long as five days, depending on the route, stops, and whether you turn it into a weekend or multi-day vacation
What makes Florida road trips unique?
Florida road trips stand out because they can include beaches, wildlife, historic towns, island drives, aviation history, and special events all in one state, from the Panhandle to the Florida Keys.
Is the drive to Key West worth it?
Yes. The drive to Key West is one of Florida’s most memorable road trips because you travel the 106-mile Overseas Highway from Key Largo and end up in a destination known for its tropical feel, laid-back vibe, and quirky culture.
Are Florida road trips good for weekend getaways?
Yes. Many Florida road trips work well as weekend escapes because they can be adjusted to the time you have, from a quick overnight trip to a longer stay with added side stops.
What should you expect on a Florida road trip?
You can expect variety. Some routes are relaxing and scenic, while others are more adventurous, with wildlife sightings, historic attractions, museums, beach stops, live events, and weather that can quickly change your plans.
Sign up for our monthly updates and news about Florida travel. Join 21,000 other travelers!
Can’t Find It? Search Florida Travel Blog
Florida Travel Blog is an Amazon Associate and other programs. Should you purchase something from a link, we earn a very small commission at no cost to you.
Latest Posts
Where Is Chattahoochee Florida? A Complete Local Guide
Last Updated September 9, 2026 Chattahoochee, Florida sits in the far northwestern corner of the state, in Gadsden County, just a few miles south of the
What are the Best Beach Destinations in Florida for Families?
We have been traveling Florida for over 40 years. Here are our 24 best beach destinations in Florida. From the far reaches of the Panhandle
Best Beaches on Florida’s West Coast: 21 Gulf Coast Picks (2026)
We’ve visited every beach on this list. Here are the 21 best beaches on Florida’s west coast — from Clearwater south to Marco Island — with parking, tips, and what makes each one worth the trip.
Marco Island, Florida: The Complete Travel Guide
They call it the “Hawaii of the East,” and once you arrive, the nickname makes perfect sense. Marco Island sits at the southern tip of
Florida Travel Guides
Key Largo to Key West Florida Mile By Mile Guide
Key Takeaways Top 10 Stops – Key Largo to Key West John Pennekamp State Park Florida Keys Wild Bird Center Theater of the Sea ROBBIE’S
Best Places in Florida for Young Adults to Vacation (2026 Guide)
Florida isn’t just theme parks and family trips—it’s beaches with a pulse, neighborhoods with art and music until late, and water adventures you can’t get
Clearwater Beach Visitors Guide – Unwind in Paradise
Last Updated April 18, 2026 Clearwater Beach delivers powder-soft sand, calm Gulf water, a walkable marina-to-pier strip, and nightly sunset vibes. As Tampa Bay locals,
Interesting Facts About the Florida Everglades – 100 Of Them!
Our Number One Fact About The Everglades — “The Florida Everglades is one of the most extraordinary ecosystems on Earth! An immense subtropical wetland famous
Guide To Florida Keys: Resident’s Essential Tips
You are about to embark on a journey through the most beautiful tropical islands in the world. This guide to the Florida Keys is a
Florida Travel Blog is an Amazon Associate. Should you purchase something from a link, we earn a very small commission at no cost to you.
