As a North Carolinian, where we do have winter (although I realize it's all relative!) I always thought of the Keys, and Key West in particular, as a winter or early spring destination. Before we bought our house we usually came to Key West to celebrate my birthday in early September, and it is definitely not crowded then and I assumed that to be true for the summer as well. Imagine my surprise when I came to Key West in June and July and realized that it's not only a popular summer destination but there's just the right balance between too many people in town and not enough people in town. Actually, "not enough people in town" never happens in Key West!
The first summer we owned the house, 2015, we scheduled the installation of the pool. Ground-breaking, literally, was set for the first week of June. Bill and I both traveled down to stay for a week and celebrate our anniversary while overseeing the beginning of construction. As an aside, it was a good thing we came down to oversee-the crew did not have access to the house, obviously, and the patio furniture all needed to come inside to avoid possible damage during construction. But our plans to have the restaurants and town to ourselves were not to be! It was wonderful, though, to enjoy summer in Key West. The boating is better since the north winds die away. We rented a boat for the day and explored the Atlantic side of Key West, including several snorkeling spots and the small keys that stretch away from Key West to the west toward the Marquesas and the Dry Tortugas. We chartered a fishing boat at the Hurricane Hole for the day and learned the ropes of fishing in the Keys-I can't remember what we caught other than sharks at the end. I don't think we kept anything (especially the sharks!) but we learned a lot. In fact, this was when we realized that we needed a small boat of our own to keep at our house and Bill started checking in for boats on craigslist. We were thrilled to find that the Mallory Square sunset Celebration was still going strong every day-we really enjoy going to watch the sunset and chat with the local vendors. We've met some fun locals that way. We also thought it would be a good time to take the seaplane trip to the Dry Tortugas since we didn't have the dogs along-no worries about leaving them at home for hours and hours. That turned out to be impossible; they were already booked every day for the 5 days we were in town! We did notice though that there are very few cruise ships that come in to Key West during the summer.
Our experience with the pool-building crew while were in town in June indicated that a return visit was going to be necessary to make sure everything stayed on schedule. The pool was supposed to be finished at the end of July so I flew down alone the last week, hoping for the best. No surprise, the pool wasn't finished, but they did move things along once I arrived and I was able to fill the pool up the night before I left. No pool decking but at least I could verify I had a functioning pool! I also learned about the "mini-lobster season". Several people assumed I had come down for mini-lobster season. Almost every home on our lagoon had a boat that had never been there before, or they had extra boats at their docks, and all those boats went out every morning for 3 days. The island was packed! Turns out the "mini" in "mini lobster season" means just three days that you can catch lobster. The dates are in late July every year, it seems. There's a limit per boat; thus the proliferation of boats. More boats going out means more lobster you can bring home. If I remember correctly, the three days of lobster season in 2015 were a Wednesday, Thursday and Friday. I was scheduled to fly home from Fort Lauderdale at 6 pm on Saturday. My main thought was that the season wouldn't impact my travel back up the Overseas Highway. Wrong. Fortunately I left early to get the rental car back on time (4 hours early). I needed all that time as the exodus of trucks and cars with boats on trailers was a traffic jam in the making. Add to that a fender bender somewhere north of Marathon and a big seafood festival in Key Largo and just general vacation traffic headed north and that meant it took almost 7 hours to get to Fort Lauderdale (instead of 4). I barely made it to the airport in time. So much for "not busy in the summer"!
So I survived "mini lobster season" but I've yet to experience the Hemingway Days Festival. I keep up with it via the local paper (The Keys-Citizen) and it's on my list of things I want to do in Key West one day. It happens in July and lasts a week, culminating in the Hemingway look-alike contest. That definitely looks like a fun week in Key West! Now I know not to fly out of Miami or Lauderdale though!
Late August and September are definitely slower. The sunset celebration still happens but there are limited vendors and performance artists. The traffic is definitely not as bad on the Overseas Highway. The restaurants offer great specials (and even better deals for locals). It's easier to get on the tour boats. It's easier to bike around town. I actually love to be in Key West in September. A good thing since our house is a popular rental in the summer-and at least we know why! Summer in Key West is just as fun as winter in Key West!