I had planned our 7-day Caribbean cruise several months ago and ended up taking the ship out of Miami instead of the local port here at Port Canaveral. The reason was a good deal through our agent Mindy, plus a chance to cruise on the mega ship, Oasis. Well, we were already halfway to Key West, Florida so it was just too tempting not to add a little three day surprise visit!
Prior Key West Vacations
I booked this little 3-day trip a few weeks ago for a Sunday through Tuesday nights, leaving Wednesday morning. And was able to keep it a secret from Trish for quite some time. I prefer the weekdays in Key West as the weekends can be very crowded and crazy.
We had come to the keys for several vacations back in the years when I was working. It was great to come to Florida and see my aging parents for a few days and then work in a cruise or else a drive to the keys.
I always really enjoyed our trip to this quirky small town. Yeah, the costs are crazy high, parking is ridiculous to find, the streets are very narrow, and at times there can be way too many tourists. But, we kept coming back.
How to describe the attractions? Well, it is like being on a Caribbean island, but still in the good old US. It is very tropical with lush plants and palm trees everywhere. And the Old Town of Key West is the most walkable tourist city that I have ever seen. I park the car, when I finally find an open spot, then never touch the car until it is time to pack up and head back home.
I really like the architecture of the old homes that are still here after countless hurricanes have tried to blow them away. There are also many, many good restaurants and bars. And I love some good seafood.
Key West still has the reputation of being quirky, artistic and free spirited.
Arrival and First Impressions
The drive south on US1 went fine. Traffic moved smoothly and the view from the 7-mile bridge is awesome. That is actually one of my highlights when driving down. The beautiful aqua blue-green water as far as you can see.
We arrived and got parked by 1pm, got checked into the B&B, then headed over to Conch Republic for lunch. I had the catch of the day and Pat enjoyed their smokehouse burger without the bun to stay keto friendly.
The town still has a plethora of tacky $5 t-shirts that I cannot imagine who would wear them. But they stay in business somehow.
We mainly walked around the first day. Stopping in some art galleries. Attending Tracy’s (B&B) happy hour at 4pm. She is a delight to chat with. There were several visitors from out of the US. Europe and China. Although, there was one couple from Ohio that we met.
Then we walked down to the required sunset celebration at Mallory Square. It was kind of a dud due to heavy clouds but all the strange people were out and about. Some entertainment there I suppose. We stopped for some live music on the way home at the Smokin’ Tuna.
This guy has a trained cat. Must be a rarity. 
Another popular street performer.
I don’t know, but perhaps the newness has worn off the quirky town for me. Maybe it is all that we have seen over the last 2.5 years of RV travels that has overshadowed our old go-to vacation place. Maybe, in prior visits, I was still working, and the time in KW was the relaxing and de-stressing that I was seeking. That has certainly changed.
THey still had Christmas decorations up! 
But, for whatever reason, the attraction to the offbeat and quirky has been kind of dulled. Yep, still enjoyed the food and walking around. But, it was just not quite the same.
Key West Harbor Inn B&B
Tracy, the manager of the Key West Harbor Inn, has perhaps 10-12 rooms in this 1800’s caribbean style mansion. It is always booked up, as is most everyplace else in this town. They have a free breakfast and happy hour and a heated pool. We love this place and just hanging out by the pool.
Me at the pool. 
Pat and Tracy.
Wrap Up
The weather was absolutely perfect for our stay. No rain and 80 degrees every day. Wake up in the morning. Walk a block to the Cuban coffee place. Then walk the historic harbor for awhile before making our way back to the B&B for the breakfast.
The required Key West rooster photo. 
We are currently in Cocoa Florida and leave tomorrow for Clermont Florida. Thanks for following along! Take care and God Bless.
Lot’s of great memories of our vacations together at Key West over the years. Glad you guys had a fun time there!
Tom
Yes, many great memories of the Southernmost City!