When our Virgin Voyages ship pulled into Key West, I imagined sunshine. I also thought I would be eating my way through the city or at least making a couple of stops. I had an entire list on my phone of places depending on where we ended up.
Instead, we woke up to a torrential downpour. I know that rain comes and goes, but the question was when would it end? We went to The Galley to get some breakfast while we watched the rain comes down in sheets. Once it cleared enough for us to get off, we were ready to go.
Flooded Streets and a Quick Reality Check
When we finally stepped onto Key West, it was bright and sunny. We walked away from the port trying to figure out where we should go. We saw people renting golf carts and vespas. There was a bunch of large puddles all around the streets. My friend was ready to rent vespas, but I was skeptical about that. A gentleman riding around in a golf cart told us we could rent from his company. So we hopped in his golf cart and rode over to A&M Rentals.
I had never been on a vespa before and I was nervous to even try. So my friend talked me into renting bicycles. We rode to the Southern Most Point to take some photos. The streets were pretty flooded. Trying to navigate that and avoiding cars was making the bike ride a little stressful. Not to mention trying to use our phones for directions. We stumbled across the second A&M Rentals location and they drove us and the bikes back to the main location. We ended up renting a golf cart instead.
The Southernmost Point
I heard the lines can get long at Southernmost Point Buoy. So this was the first place we headed to. Luckily, there weren’t too many people there. There was a gentleman there to help people get the best photos for you. It is defiantly a touristy spot, but I had always wanted that picture.
Cuban Coffee, Key Lime Pie, and Roosters
I really wanted to try some key lime pie while in Key West. If you didn’t know Key Lime Pie originated in Key West. We stopped at the Clinton Square location of Cuban Coffee Queen to grab coffee for my family and get some pie. We sat outside, my friend got a smoothie and me some pie. We were talking to some other tourists and some roosters joined us.
If you have never been to Key West, the roosters are part of the daily life there. They roam freely and are protected by locals. Their lineage traces back to Cuban settlers who brought livestock generations ago, and now they just wander around town. The coffee ended up being a hit when I brought it home, so I highly recommend stopping by if you are in the area. They have multiple locations across the island, which makes it easy to grab something quickly during a port stop.
Wandering Mallory Square and the Waterfront
After coffee, we walked through Mallory Square and along the waterfront. We popped in and out of small artisan shops filled with handmade jewelry, island art, and colorful décor that feels like it belongs exactly where you found it.
Key West has a ton of bars. Even in the middle of the day, we saw people funneling in and out of them. There is definitely a nightlife energy that starts early. We did not go into a single bar, but it was clear that for many people, that is the main event.
Duval Street, Mile 0, and Island Icons
We drove down Duval Street, the famous 1.25 mile stretch that serves as the main drag. Duval is packed with historic sites, bars, restaurants, shops, and nightlife. That is where many people were.
We also stopped at the Mile 0 sign for U.S. Route 1. It is that iconic green and white road sign marking the southern end of the 2,369 mile highway that stretches all the way to Maine. I thought it was pretty cool and had to grab a photo with the sign. As we continued driving around, we passed the home of Ernest Hemingway. Even from the outside, it is one of those places that reminds you how much history and interesting places there are in Key West.
As we continued driving, I spotted something that made me immediately ask my friend to pull over. Pralines. So we stopped so I could run into River Street Sweets on Duval Street. If you love pralines, you understand. I had no problem bringing them back onto the ship either.
Calling It Early and Heading Back
Between the heat, the humidity, driving around to see as much as we could, and just being tired, we ended up cutting our Key West day shorter than planned. A&M Rentals has a van that will take you back to the port which is really nice. Cruise stops always come with a time limit, and instead of pushing ourselves to squeeze in more, we headed back to the ship. We figured most passengers were still in port, which made it the perfect time to check out the spa.
Would I Go Back
I definitely would. There were restaurants on my list I did not get to try. Historic spots we only passed by. Bars and nightlife we skipped entirely. Key West deserves more than a few compressed hours between ship schedules and weather delays. Even with the rain, the flooded streets, and the bike fail, I am glad we were able to explore a little.
