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24 Hour Roadtrip: Miami to Key West in a Convertible

a woman in a convertible car

For several years I’ve had a hankering to rent a convertible and drive down the Florida Keys from Miami. So when I wound up with an unexpected free day this week, I found a cheap ticket for a 26 hour trip and went for it. AutoSlash helped me get a great price on a one-way convertible rental and the weather in DC improved enough that my flight was able to get out.

a red car with a black top

I hopped in my cherry red Ford Mustang and decided to make my first stop Alabama Jack’s about an hour down the road at the north tip of the Keys. My flight was late getting in, so it would be lunchtime when I got there and they were reported to have some amazing Conch Fritters a dish I was eager to try at the recommendation of reader Erik.

a fence with a gate and flowers

a group of people sitting at tables

$10 gets you a small bowl overflowing with 3 gigantic fritters. I picked a seat in back of the kitchen directly on the water. It was a little quieter than the main area, though if I went back I would head for one of the corner waterfront tables to the far left of the bar.

a plate of fried food with two forks

The fritters were good — crispy, chunks of Conch, but a little bit too much sweetened batter. Service was good but not fast so it was an hour before I was back in the car again. Then you go through one of the few non SunPass toll booths ($1) and you’re on a rather boring road through mangroves to connect back up with Hwy 1.

a car driving on a road

I had this glamorous vision of a 3 hour drive with nothing but long vistas of beautiful blue waters and beaches occasionally interspersed with small Americana towns. In reality, more than 2/3 of the drive was a road through dense foliage and uninspiring store fronts.

a car driving on a road

Originally the plan was to stop at Robbie’s to do the cheesy (but probably fun) Tarpon feeding, but I was behind schedule with the flight delay and wanted to leave time to kayak at Bahia Honda State Park. As I got closer I was finally rewarded by the long bridges and gorgeous views though the necessary guard rails made it difficult to take pictures.

a sign board with a logo on it

I arrived at Bahia Honda late in the afternoon with a darkening sky, only to discover there were no kayak rentals that day. I was really really disappointed but I understood. The water was not a beautiful teal pool from which to view sea life, it was a choppy blue green pudding.

a group of kayaks on a wood rack
a small island in the middle of a body of water

So I parked near the main beach and nature center and forlornly walked the paths, trying to take “artistic” pictures of the old bridge.

a metal bridge with a pipe

It all worked out for the best though, because as I was heading back to the car after a half hour or so, the heavens opened up and the driving rain and high winds started.

water droplets on a window

a road with palm trees and trees in the background

And I was reminded of how convertibles are a lot less comfortable with the top up. But it was what it was, so I got myself back on the road to try to get to Key West as quickly as possible.

When I checked in at the Hyatt Key West around 5:45 they let me know that Mallory Square just a few blocks away was the best sunset viewing point. Sunset was at 6PM so I dropped off my stuff and sped over to the square with a few minutes to spare.

a large cruise ship in a harbor

To discover that a cruise ship had called dibs on the best place to see the sunset…a peak around its far end revealed that there wasn’t much of a sunset that night so at least I wasn’t missing out too much.

a large ship in the water

I wandered around the area a little bit taking in the sites and decided to take advantage of happy hour wings at Kelly’s Caribbean Bar Grill & Brewery. It had originally been the offices of Pan Am, so it seemed perfect for me. A little after 6 it was hopping with live music (until the rain started again), and the local golden Ale and wings were quite good.

a building with a sign and plants

a plate of fried food with sauce and celery

While I love wine, I’m not big on all night drinking so I decided to head back to the hotel and catch up on a day’s worth of work email. Opening the curtainsto my partial view balcony and enjoying my Diamond amenity of wine and cheese.a plate of food and a wine bottle

The next morning I was up early, breakfasting outside overlooking the harbor and then setting out on a walk around the town. At 8AM it was pretty quiet — some tourists, but not a lot — and the overcast weather made for some balmy breezes.

a street with houses and trees

I walked to length of Duval, taking in the stores and galleries and checked out the Southernmost beach which was beautiful, even in strong winds and the beginning of rain.

a building on the beach

A short hop down to the Southernmost point, where selfie takers (like myself) were in danger of getting wet from a particularly big wave coming up behind (would make for a great photo though!).

a sign on a stone wall with Southernmost point buoy in the background

And then I strolled back to the hotel in the light rain via Whitehead St which passes many of the historic places like Hemingway’s home (no credit cards!), the Audubon House, and others.

a building with a fence and palm trees

I wanted to swing by the the Florida Keys Eco-Discovery Center which offers free admission and insights into the plants, animals, and marine life in the area, but was running out of time to check out and get my car to the airport in my 24 hour window.

a yellow taxi cab outside of a building

The downpour started almost as soon as I got there, so again, I think the timing all worked out for the best. I headed to the adorable Key West Airport, where access to the terminal is at the top of the parking garage, and wound up hanging out at the nation’s only airport beach bar longer than expected as more storms ripped through the area, slowing things down.

a sign on a wall

people walking around an airplane

It was a race through the Miami airport to catch my connection, but I made it, arriving in DC a little underdressed and with a tiny bit of color to hint at my advetures.

This trip accomplished what I wanted so I have no regrets– I got sunshine, beautiful views, and much needed warmth, but it wasn’t as ideal for a 24 hour trip as I had originally thought. If/when I go back I’m going to give myself 2-3 days.

At least a day, possibly a night, to get down to the Keys with plenty of time to mosey, stop in the small towns, and spend time in the state parks kayaking, swimming, or hiking. Then a day to wander through the historical points of interest in Key West and eat at all the reader recommended restaurants, possibly even time to do the sunset wine tasting cruise. With an extra day I might take the ferry to Dry Tortugas or something similar.

Full Disclosure: I may receive affiliate credit from links in this post or on this site which will help fund my travels. Thank you for your support!

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3 Comments

  1. There aren’t many things to see close to shore in the keys, the water tends to be murky, and the beaches are sharp small coral and rough on the feet. That isn’t to say that there aren’t ways to have fun in the Keys in the water. If you want to see the sea life take a glass bottom boat tour or a snorkeling tour out of John Pennekamp Coral Reef State Park in Key Largo. One other thing to consider doing in Key Largo is to take a ride on the “African Queen” located next to the Holiday Inn. Someone purchased and restored the boat used in the movie and they offer trips on this boat through the canals and out to the Atlantic Ocean.

    You may be able to purchase tickets to the Hemingway house with a credit card, however not at the home itself. Several companies that provide tours of Key Largo sell tickets to the home and accept credit cards.

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