Miami, Key West, and Disney..Oh My! The January 2024 Girls Trip – Day 3 – Key West
Once again, for a little recap, if you missed Part 1, This trip came about because a little over a year ago, my cousin, Cara, asked me if I wanted to join her in Key West to complete a half marathon. We flew into Miami, spent two nights exploring the South Beach area, and then headed to Key West for the next portion of our trip and the race. To catch up or reread about Miami, read this post.
Jan 12, 2024 – We packed up our rental car, checked out of our Airbnb, and hit the road. When we originally planned this trip, we thought about flying directly into Key West but decided to drive through the keys, so we booked the first two nights in Miami. We got on the road around 9 am. The first hour was boring, but once we got to Key Largo, the scenery changed, making the drive much more enjoyable. The drive from Miami to Key West is only around 160 miles, and if you drove straight through, you could make it in 3-4 hours, but there are so many fun places to stop along the way that you could easily spend days just exploring the Keys. Since we only had half a day, we decided to stop in Islamorada to visit the Rain Barrel Village and have lunch at Florida Keys Brewing Co.
Our first stop on the north edge of Islamorada was at the Rain Barrel Village. This fun little roadside stop is full of artist’s galleries, specialty shops, and boutiques. (as always, click on pictures for full size)
After checking out the Rain Barrel Village, we headed down the street to the Florida Keys Brewing Co. to try some of their brews and have lunch. This was a great stop. There was a taco food truck right outside and plenty of seating in the beer garden behind the building to sit in the shade and enjoy our lunch and beer.
After our lunch stop, we got back on the road. After passing through several more small keys, we went through the town of Marathon, the last land mass, before crossing the seven-mile bridge. Driving along the bridge was a neat experience, and I highly recommend it if you ever get the chance.
Before we knew it, we were coming into the north side of Key West, where we made our way to Duval Street to find our rental for the next three nights at Casa 325. Our rental had a living room, full kitchen, dining table, and a separate bedroom and bathroom.
After settling in and parking our car, we headed out to have dinner at Sloppy Joe’s Bar. This historic bar is a must if you are in Key West, especially if you are a Hemmingway fan, as it was one of his favorite places during his time on the island.
Fun Fact: Sloppy Joe’s was established in 1933 and was originally located about a block from its current location until 1937 when the landlord raised the rent. Angry about this increase, the owner, Joe Russell, decided to move, but a clause in his contract prevented him from taking any of the furnishings or other items from the bar. Luckily, at this same time, the former Victoria Restaurant, built in 1917, was vacant, and Russell quietly paid the owner $2500 for the building. Then, when the lease expired while the landlord was overseas on a business trip, Russell recruited a pack of midnight drinkers to help him haul everything out of the original building and move it to its new location down the street.
We all ordered the Sloppy Joe. It came served on a hamburger bun, with a slice of American Cheese and pickles on the side. We were also seated at a table with a view of the stage, where live music was playing. It was a fun atmosphere; the Sloppy Joe was good. It was nothing spectacular and a little bit expensive for what you got, but it was still good, and the beer was refreshing. It was a good choice for dinner, and I would return here in the future.
After dinner, we visited Mallory Square Market. Then, Cara returned to the rental to decompress while Sara and I watched the sunset.
After the sunset, we returned to our apartment to relax for a while before heading out again. We stopped for drinks at First Flight Brewery, located in the building that housed Pan American World Airways’s first office. None of us were super impressed with their beer, and I probably would not go there again, but the atmosphere of the place was nice.
After our drinks, Sara and I went on a ghost tour while Cexploredring on her own. The tour was very interesting, and we learned a lot about the history of Key West—a couple of the haunted locations.
After the tour, we slowly walked back, stopping at Kermit’s to pick up a slice of Key Lime pie. Then, we returned to the rental to relax on our porch before calling it a night.
To Jump To Related Posts, Click Below
- Days 1&2 Miami Beach
- Day 4 Key West
- Day 5 Key West
- Day 6 Disney World
- Day 7 Disney World
- Day 8 Disney World
- Day 9 Disney World
- Day 10 Universal Studios
- Day 11 Disney Springs and Departure
