Many fun Florida road trip stops are waiting to be explored and discovered. What are your favorites Florida road trip stops?

8 Great Fun Florida Road Trip Stops

Continuing the current theme of Florida Road Trips from a previous article (Road Trip Habits), here are some Florida road trip stops to entertain (and hopefully inform) you.

McCool Travel tip: When possible, stay off the major roads. Seeing Florida from smaller roads is much more fun than from the highways.

Since learning to drive 30 years ago in South Florida, I have found some wonderful scenic drives. Here are 8 great scenic drives in South Florida.

8 Great Fun Florida Road Trip Stops

1. Cemetery Humor

Residents of Key West, locally called The Conch Republic, celebrate life every day and, as I found out, even spin a humorous slant to death.

Here are just two humorous examples I found in the Key West Cemetery.

Many fun Florida road trip stops are waiting to be explored and discovered. What are your favorites Florida road trip stops?

Florida Road Trip stops: Key West Cemetery humor

Many fun Florida road trip stops are waiting to be explored and discovered. What are your favorites Florida road trip stops?

fun Florida road trip stops: Key West Cemetery

Other historic cemeteries, not necessarily humorous, in Florida include three Florida National Cemetery locations (Bushnell, Jacksonville, and Lake Worth) and the Coconut Grove Bahamian Settlers Cemetery (where Michael Jackson’s Thriller video was filmed).

Many fun Florida road trip stops are waiting to be explored and discovered. What are your favorites Florida road trip stops?

Florida Road Trips Stops: Coconut Grove Bahamian Cemetery

>>> Read the McCool Travel article: 8 Great Spots to Visit in the Florida Keys.

2. Beach Scenes

Although there are so many fun Florida road trip stops all over the state, I certainly hope you incorporate some beach time into your next Florida road trip. Perhaps you will see some of Florida’s colorful lifeguard stands, amazing beaches, or kitschy fun decorations.

Miami Beach lifeguard stand, Scenic Drives of South Florida

Miami Beach lifeguard stand

Many fun Florida road trip stops are waiting to be explored and discovered. What are your favorites Florida road trip stops?

Florida Road Trip Stops: Anna Maria Island beach

The area near the Daytona Beach boardwalk retains yesteryear charm. The Jantzen lady is just one of the old school discoveries you will find.

Many fun Florida road trip stops are waiting to be explored and discovered. What are your favorites Florida road trip stops?

Florida Road Trip Stops: Jantzen diving woman in Daytona Beach

Perhaps you will also witness an exploding sunrise.

Many fun Florida road trip stops are waiting to be explored and discovered. What are your favorites Florida road trip stops?

Florida Road Trip Stops: glorious sunrises

3. Fun Mailboxes

Many fun Florida road trip stops are waiting to be explored and discovered. What are your favorites Florida road trip stops?

Quirky South Florida: Artsy mailbox on Star Island, Miami Beach

Many fun Florida road trip stops are waiting to be explored and discovered. What are your favorites Florida road trip stops?

Florida Road Trip Stops: manatee mailbox in Florida Keys

>>> Read the McCool Travel article: Road Trip Sights: Manatee Mailboxes

4. Smallest Post Office

Along Tamiami Trail—the road between Tampa and Miami (thus, its name Tamiami)—in the middle of the Everglades, is the world’s smallest post office. It is located in the small village of Ochopee. By the way, my grandparents lived a mile from this post office for about 25 years, so my cards and letters went through this building.

Many fun Florida road trip stops are waiting to be explored and discovered. What are your favorites Florida road trip stops?

Florida Road Trip Stops: smallest US Post Office, Ochopee Florida

>>> Read the McCool Travel article: 7 Fun Scenic Drives in Florida.

5. Funky Buildings

In addition to the smallest post office, Florida is home to the oldest building in the Western Hemisphere and countless other quirky, funky, fun buildings.

Many fun Florida road trip stops are waiting to be explored and discovered. What are your favorites Florida road trip stops?

Florida Road Trip Stops: pink house on canal

Little pink houses for you and me!

Many fun Florida road trip stops are waiting to be explored and discovered. What are your favorites Florida road trip stops?

Florida Road Trip Stops: Anna Maria Island stone house

I like to call the above house, The Flintstone House? So many houses in Florida were constructed with a miss-mash of whatever stones they could find. Interesting, right?

Many fun Florida road trip stops are waiting to be explored and discovered. What are your favorites Florida road trip stops?

Florida Road Trips Stops: Opa Locka

Explore the Arabian themed architecture in Opa Locka, Florida (but read my warnings first!).

Many fun Florida road trip stops are waiting to be explored and discovered. What are your favorites Florida road trip stops?

Florida Road Trip Stops: oldest building, complete in 1141

Can you believe there is a building in Florida that was built in the year 1141? Read the amazing story about the oldest building in the Western Hemisphere

6. Mossy Streets

Exploring smaller roads in North Florida will present you with many opportunities to see Spanish moss hanging from oak and cypress trees.

Many fun Florida road trip stops are waiting to be explored and discovered. What are your favorites Florida road trip stops?

Florida Road Trip Stops: Spanish moss in Florida

Many fun Florida road trip stops are waiting to be explored and discovered. What are your favorites Florida road trip stops?

Florida Road Trips Stops: Spanish moss in Florida

7. Dirt Roads

If your Florida road trip experience has only been on I-95, I-75, and the Turnpikes, then you will be surprised (pleasantly, I hope) to learn that there are plenty of opportunities to drive on unpaved roads.

Many fun Florida road trip stops are waiting to be explored and discovered. What are your favorites Florida road trip stops?

Florida Road Trips Stops: white dirt road

Many fun Florida road trip stops are waiting to be explored and discovered. What are your favorites Florida road trip stops?

Florida Road Trips Stops: red dirt road through citrus grove

Some beaches allow for beach driving. Daytona Beach is perhaps most well known and has 13 miles of drivable beach.

Many fun Florida road trip stops are waiting to be explored and discovered. What are your favorites Florida road trip stops?

Florida Road Trips Stops: drive on Daytona Beach

>>> Read the McCool Travel article: 8 Great Scenic Drives in South Florida.

8. Drive Thrus

The state of Florida has ample opportunity to shop, worship, and more from your car. Good thing we are on a road trip!

Farm Stores are a staple of South Florida living.

Many fun Florida road trip stops are waiting to be explored and discovered. What are your favorites Florida road trip stops?

Florida Road Trip Stops: Farm Stores Drive Thru

Drive thru liquor stores are all over Florida. Big Daddy’s is the most weep-established and oldest brand, so there are knock offs with cutesy names like Happy Pappy’s.

Many fun Florida road trip stops are waiting to be explored and discovered. What are your favorites Florida road trip stops?

Florida Road Trip Stops: Drive Thru liquor stores

Alas, this location was closed so I could not cure my “eat catfish while driving” jones.

Many fun Florida road trip stops are waiting to be explored and discovered. What are your favorites Florida road trip stops?

Florida Road Trip Stops: drive thru Catfish Shack

And, yes, Florida has at least one drive in church. The Daytona Beach Drive In Christian Church has two services on Sundays. They serve snacks in the Friendship Hall but I wonder how many bring their own to eat in their vehicles.

Many fun Florida road trip stops are waiting to be explored and discovered. What are your favorites Florida road trip stops?

Florida Road Trip Stops: drive in church, photo by driveinchurch.net

Some of the other fun Florida road trip stops categories I left off this list include hills, local food and drink, signs, favorites, and attractions.

Do you have any favorite Florida road trip stops?


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Many fun Florida road trip stops are waiting to be explored and discovered.

8 Great Florida Road Trip Stops was first published on McCool Travel in June 2016.

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34 Responses to “8 Great Fun Florida Road Trip Stops”

  1. Melody Pittman (@melodytravels) December 14, 2016 at 10:04 pm #

    Interesting choices. I’ve seen quite a few of these since living in Florida. I like visiting all of our great rest areas myself. 😉 The manatee mailboxes are all along US1 and A1A.

    • McCool Travel December 14, 2016 at 10:17 pm #

      A1A has all kind of critter mailboxes: dolphins, gators, and so many manatees. Keep on enjoying the Sunshine State.

  2. Carrie @Frugal Foodie Mama December 14, 2016 at 9:21 pm #

    What fun Florida road trip ideas! 🙂 I have pretty much drove the entire length of Florida a couple of times when we used to vacation in Key West. There is definitely so much to see and do along the way.

  3. erinklema December 14, 2016 at 1:39 pm #

    A drive-in church? That’s something I’ve never seen! Florida is definitely full of some quirky sights and road-side attractions.

  4. Carolina Colborn December 14, 2016 at 10:01 am #

    Fun way to look at Florida. Must’ve spent six months there in two winters. Brought back great memories!

    • McCool Travel December 14, 2016 at 10:07 am #

      Thank you, Carolina. Fun indeed. That is how I like to think about road trips in Florida.

  5. Rachel @ www.theworldinaweekend.com June 13, 2016 at 6:17 am #

    Loved this! One of my favourite things about Daytona is the “yesteryear charm” you mention! Great article

  6. Vicki Louise June 12, 2016 at 9:40 am #

    Great ideas for roadtrip stops – and great images! From reading those first two headstones, it looks like Disney took inspiration from Key West Cemetery for their Haunted Mansion graveyard!

    • McCool Travel June 13, 2016 at 11:18 am #

      Good one, Vicki. I wonder if Walt Disney visited Key West cemetery and was inspired?

  7. Aperture Of My Soul June 12, 2016 at 9:18 am #

    Great road trip stops!! I would love the humorous cemetery gravestones! I’ve never made it as far south as Key West, so I’ll keep that stop in mind. The history in Florida always amazes me. St Augustine is one of my fav cities. Would love to see some of Opa Locka one day. Great post! Thanks for sharing!

  8. Holly June 11, 2016 at 12:28 pm #

    I need to explore more of Florida. I would love to see the cool mailboxes.

    • McCool Travel June 13, 2016 at 11:20 am #

      Thank you for the note, Holly. The funky mailboxes are just another wacky Florida attraction.

  9. Sarah Fazendin June 11, 2016 at 10:14 am #

    I love a good road trip!! I’ve been watching Bloodline, some of these shots remind me of that show!

    • McCool Travel June 11, 2016 at 12:26 pm #

      Ooooh, Bloodline sounds like something I should watch.

  10. Patti Morrow June 9, 2016 at 7:56 pm #

    How fun! I’ve always loved Florida’s colorful lifeguard stands, but the diving woman at Daytona Beach takes the cake!

    • McCool Travel June 11, 2016 at 12:27 pm #

      I know! That diving woman figure is so retro!

  11. Wendy June 9, 2016 at 1:03 pm #

    We did the trip twice. Our favorite stops were St. Augustine the town and Vilano Beach, St. Pete – Dali Museum, Alligator Alley for the airboat rides, Nokomis – the beach, and a stop for Indian River Grapefruits near the northern border of Florida.

  12. Love the mailboxes! We took a long road trip through the US last summer (approximately 6,000 miles zig-zagging about) which included part of Florida’s western coast and plan to do some more driving when we visit again in August. So fun to see the US from the road! Anita

    • McCool Travel June 11, 2016 at 12:29 pm #

      Thank you for the note, Anita. Happy travels!

  13. Lyn aka TheTravellingLindfields June 6, 2016 at 7:31 pm #

    I love the fun things you see by the side of the road. I wish I had kept a separate file of photos just labelled ‘roadside nonsense.’ BTW ‘I told you I was sick’ is also the epithet on Spike Milligan’s grave except the church authorities required it to be printed in Gaelic because it looked irreverent.

    • McCool Travel June 11, 2016 at 12:30 pm #

      Love that trivia! Roadside Nonsense is a great idea! Time for a collaboration post!?!

  14. A Taste for Travel (@atastefortravel) June 6, 2016 at 6:11 am #

    What a great round-up and reminder of why I love Florida. From quirky sights to natural beauty ( love that Spanish moss!), it’s a one of a kind place.

  15. Jack Moscrop June 3, 2016 at 4:00 am #

    So quirky! Love it 🙂

    • Sue Reddel June 9, 2016 at 2:04 pm #

      Drive thru churches that’s a first for me! I was always taken a bit aback by the drive thru liquor stores, that just seems like such a bad idea.

      • McCool Travel June 11, 2016 at 12:27 pm #

        Really, what could go wrong with drive thru liquor stores and gun crazy populace?

    • McCool Travel June 11, 2016 at 12:40 pm #

      Thank you, Jack!

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