Fun & Weird

24 Hour Roadtrip: Miami to Key West in a Convertible

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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.

convertible car rental miami

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.

alabama jacks key largo entrance

alabama jacks bar interior

$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.

alabama jacks key largo conch fritters

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.

miami to key largo card sound 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.

miami to key west drive key largo

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.

bahia honda state park sign

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.

bahia honda park kayak rentals
bahia honda state park island

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

bahia honda state park bridge (2)

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.

miami to keywest rain

bahia honda state park downpour

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.

key west mallory square sunset cruise ship

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.

key west sunset cruise ship

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.

kelly's bar grill key west florida

kellys bar grill wings key west

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 key west cheese plate

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.

key west florida street

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.

keywest southernmost beach key west

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!).

southernmost point Florida

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.

hemingway house entrance key west florida

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.

key west airport florida

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.

key west airport beach bar

key west airport american airline boarding

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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