This Florida roadtrip itinerary is designed for high energy travelers who want to pack alot of sight-seeing into a relatively short period of time. I also like to prioritize checking out national park units and exploring novel environments as I move around. This itinerary can be easily adjusted if you have more time, but will generally excite roadtrippers who love getting a dose of nature and history when they travel.

Day One: Get a Taste of History in Jacksonville

(1) Arrival

Plan on arriving into Jacksonville as early on this day as you can manage. This will give you more time to explore if you are strapped for time. If you can afford to make your itinerary a day longer, you might also consider giving yourself two days here. One to arrive and one to explore the city a little. Jacksonville is surprisingly vibrant and large for those unfamiliar with the area.

(2) Visit Fort Caroline National Monument/Timucuan Preserve

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The Fort Caroline National Monument and Timucuan Preserve in combination will give you the opportunity to learn more about the history and ecology of the northern, coastal area of Florida. You should start at the visitor center, which can be found at 12713 Fort Caroline Road, Jacksonville, FL 32225. They are open seven days a week from 9:00A-5:00P and entrance to both parks is FREE.

The star of the Fort Caroline show is, of course, the fort itself. This is a particularly unique place in respect to the other forts of the Caribbean region (and there are many), because Fort Caroline is a simple, wooden fort. It harkens back to an earlier colonial time than most of its cousins. Fort Caroline will give you insight into some of the deeper past of the region than you can get elsewhere. This National Monument also has some information on the local indigenous people that inhabited this area at the time that European immigrants first started arriving. The long human use for the Jacksonville area was a poignant indicator for me of just how important this area has been for people over time. It’s rivers, shores, and forests have long served as sources of wealth, places of transportation and trade, and shelter from the oft-stormy waters of the Caribbean and Atlantic.

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With these things in mind, the Timucuan Preserve serves as a great partner to Fort Caroline on your Florida roadtrip as visiting here will give you the opportunity to explore and experience some of Florida’s beautiful natural landscapes. This is something that people often overlook in this state, north of the Everglades, but the forests are a strange and unique mix of tropical, coastal and dryland plants. They should not be missed by any hikers, birders, or nature-lovers among you. There is also a nice selection of trails in this area, allowing for a range of trips from short walks to easy day hikes.

Essential Information:

Address: 12713 Fort Caroline Road, Jacksonville, FL 32225

Hours: 9:00A-5:00P

Entrance Fee: None

Bathrooms: Yes

(3) Stay in Jacksonville or Saint Augustine

Depending on your Florida roadtrip schedule select either Jacksonville or Saint Augustine as your camp for the night. Jacksonville will be better for people coming in on the same day that they explore the National Park Units. For those of you tacking on an extra day to explore the area, head on down to Saint Augustine after dinner so you can make a little distance on your longer drive for tomorrow.

Day Two: Driving the Eastern Coast

DRIVE TIME: About 7 hours

(1) See Fort Evolution and Spanish Colonial Culture at Castillo de San Marcos

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Start your day off with Castillo de San Marcos in Saint Augustine, Florida. The visitor center opens as early as 8:45a, so this allows you to get a nice, early start on this long day of your Florida roadtrip. This NP will also give you fairly convenient access to the historic area of Saint Augustine, so don’t worry if you have to pay for parking. You can park once and explore both. The cost for entry to the fort is $10.00 and the visitor center address is 11 South Castillo Drive, Saint Augustine, FL 32084.

This fort has been beautifully maintained by the National Park Service so that you can really get the feel for what life in the installation was like during its relevant era. It will be a really stark contrast to everything that you saw previously at Fort Caroline. If you have visited other forts in the Caribbean, however, the architecture will feel a little more familiar.

Castillo San Marcos was a Spanish-built fort, and this history will be apparent to anyone familiar with their colonial architecture. Visiting the site will give you a good taste of the long and varied history of this place, as it passed hands from the hands of indigenous people, to the Spanish, and finally to the United States. While Florida isn’t often acknowledged as a major player in American history, it has played an integral role in the region and certainly forms a cultural and historic bridge between the Caribbean and the mainland North American continent.

Essential Information:

Address: 11 South Castillo Drive, Saint Augustine, FL 32084

Hours: 8:45A-5:00P

Entrance Fee: $10.00

Bathrooms: Yes

(2) Experience Saint Augustine the Oldest Continually Inhabited Town in the US

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Once you are done at the Castillo, take a short walk over to the cobbled streets of Saint Augustine’s historic district. This is a great place to explore; there are plenty of restaurants for all tastes and time of day, as well as souvenir shops. My favorite thing about this area is the really lovely atmosphere. The buildings are mostly one-story cottages, many of the roads have a well-worn, cobbled quality to them. There are bright pops of color everywhere, and the fresh sea air seems to settle along the streets, making everything fresh and vivid.

Saint Augustine is the perfect place to spend a little bit of restful time enjoying the culture and long-history of this iconic little town. It’s also perfect for people watching as well!

(3) Relax on the beach at Canaveral National Seashore

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After you grab some food in Saint Augustine, and maybe a memento or two, it’s time to continue the journey south.

Along this leg of your Florida roadtrip, I’d suggest taking a break at Canaveral National Seashore. This national park unit can serve a variety of recreational activities, including boating, birding, fishing, and some very limited hiking. Of course, beach-going is on the menu here as well, as the name would suggest. The visitor center is as 7611 S. Atlantic Avenue, New Smyrna Beach, Florida. The vehicle entry fee is $15.00 and is valid for 7 days.

If you are feeling short on time, be sure to stop by some of the boardwalks and beaches in the area. You will need the fresh air on this long driving day and explore more of Florida’s natural beauty. You might even catch sight of some local wildlife if you keep your eyes peeled!

If you are less worried about the drive ahead, take some time to nestle up on the beach with a good book and a camera. Canaveral is a very peaceful place and the coast is absolutely stunning.

The Canaveral National Seashore is close to NASA’s launch site, so it may close at certain times. You should also be aware that rip currents and tidal forces can be strong along the seashore. Follow all signs and don’t swim alone!

Essential Information:

Visitor Center Address: 7611 S. Atlantic Avenue, New Smyrna Beach, Florida

Hours: 9:00A-5:00P

Entrance Fee: $15.00

Bathrooms: Yes

(4) Drive down to Homestead, FL

The final step of today is the tail end of your long drive. You will need to make it south, past Miami so that you can take your time exploring the Florida Keys tomorrow. Plan ahead so you don’t get too tired on your way. I stopped in Miami for dinner in order to stretch my legs and to make sure that I didn’t get too sleepy.

Also be prepared for toll roads to come into play as you get into the Miami area. I avoided them, but ended up hitting more traffic and having to take longer routes in order to do that.

(5) Stay in Homestead, FL

Stay tonight in the Homestead area, so that you can be as close to the Florida Keys as possible for tomorrow’s section of your Florida roadtrip.

Day Three: The Overseas Highway and the Florida Keys

Drive to Key West from Homestead is around 3 hours. Unfortunately, depending on the time of year that you visit the Florida Keys, there might be a considerable amount of traffic, so be mentally prepared.

(1) Biscayne National Park

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You can make your stop at Biscayne as long or as short as you’d like- in fact, unsurprisingly, this could make for a great full day adventure. I would suggest doing some research before you finalize your Florida roadtrip itinerary here.

If you want to just stop by Biscayne NP before heading out to the Keys, stop by the Visitor Center. They have a lovely little museum that will fill you in on the coastal ecosystem, and there are also some very nice boardwalks where you can explore coastal mangroves.

If you’d like a shorter excursion, but want to do some exploring, consider organizing a rental kayak. You can paddle along some of the mangrove forests to enjoy the lush, tropical setting.

For a full day experience, I would highly encourage you to buy an organized trip out to one of the islands that live within the park. The Biscayne National Park Institute ( has some great excursion options that you can check out.

Essential Information:

Dante Fascell Visitor Center Address: 9700 SW 328th Street, Sir Lancelot Jones Way, Homestead, FL 33033

Visitor Center Hours: 9 a.m. to 5 p.m.

Entrance Fee: Free

Bathrooms: Yes

(2) Florida Keys State Parks (Windly Key Fossil Reef Geological Area State Park)

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For the most part, the drive down the Overseas Highway wasn’t what I had been sold in movies and TV. There was no cruising over the massive ocean bridges with the wind in my hair because I was literally stuck in a traffic jam the entire journey. I’m sure this is seasonal, but set your expectations so that they can be exceeded!

In any case, there is some hiking hidden among the different islands, so you can stop along the way as you head out towards Key West. My favorite spot for this was the Windly Key Fossil Geological Area. As the name suggests, there were tons of fossils here, and a nice mix of industrial history and rebounding nature. You can hike through the forest here, and enjoy the odd wonders of an old quarry.

I’d also suggest stopping at some of the bridges along the way that have safe places for pedestrians. You can pick some of these ad hoc places out as you drive when you see other people parked at the end of a bridge.

(3) Key West

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Of course, the real star of today’s Florida roadtrip show is Key West, which has a little bit of that Caribbean charm that I was looking for when I set off across the Overseas Highway. And yes, I would suggest checking out the little touristy things in this area too.

If you have time for nothing else, check out the Southern most spot in the continental US. This is a great place to take a picture and enjoy the warm ocean air. The Ernest Hemingway Home is another essential place to visit in Key West. It’s a historic gem and obviously the best way to learn more about the late author. Finally, check out Duval street for food, shopping, and some lovely buildings.

Accommodation: Seashell Motel and Key West Hostel; You can also save some $$ by staying elsewhere in the Keys.


This itinerary is only meant to be a travel planning tool. You should adjust this to be as safe as possible, and to fit your energy level.

Remember, your safety is your own responsibility.

You should never drive when you are tired.

Check out Part Two for the second half of this itinerary.

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