The Reason For The Off Season in Key West

I’m not a fan of crowds, which can make going on vacation a little tricky. If I want to go somewhere during their slow season, I run the risk of places I want to visit not being open. It’s a trade-off I’ve been willing to make, but ever since I visited Key West, Florida, I realized it was one I didn’t have to worry about much anymore.

The busy time of the year down there runs basically from Christmas through Memorial Day, or so I’ve been told. I wouldn’t know from experience, but what I do know is that in July, I can walk into any of my favorite Key West restaurants for a great meal of fresh seafood. I can sit down at any of the bars I like to visit, get a seat up close to the live music, and probably end up getting to meet a local or two. I can pick my spot to watch the sunset without worrying about someone getting in my way, and I can take all the time in the world lounging by the pool with a good book, knowing nobody’s going to ask me if the seat next to me is taken.

It helps that, surprisingly enough, the weather there is not nearly as hot as you might think. When I compare the temperatures to other, much more crowded places where I could take my summer vacation, it turns out that many of them are just as hot if not hotter. So what if I don’t know what spring break in Key West is like? I know what summer vacation is like, and that suits me just fine.

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Once In a Lifetime Activities In Key West

There are certain things in this world that I want to make sure I experience at least once. They range from simple things, like dining in a Michelin starred restaurant, to scary things (skydiving, anyone?) to pretty big things. I want to see the running of the bulls in Pamplona, for instance. It seems like the more I do, the more things get added to that list, however. One of them is attending Fantasy Fest in Key West, Florida.

A month ago, I didn’t even know what that was. My buddies and I were on a golfing and fishing vacation in South Florida and that included a few days in Key West. We got to talking with one of the bartenders, and she mentioned how it was the busiest week of the year, full of absolute insanity, Key West’s version of Mardi Gras. When she heard us talking about maybe coming down, she advised us to start making plans now.

I thought she might be overstating the case a little but when we got home, I did some research and saw how right she was. I immediately booked a hotel room and made reservations at several Key West restaurants, including one for the night of the big parade that overlooks the parade route. Now I need to figure out just how many costumes I need to pack and what parties I am going to try to attend. People say the best plan for something that big is no plan at all, but I know that I want to make sure I do as much of it as I can, just in case it’s the only chance I get to do it.

Island Life One Week A Year In Key West

The first time I went to Key West was spring break my senior year of college. I immediately fell in love and tried to go back down every couple of years. Usually I went the same time of year, when the cold at home was too much to bear. A few years ago, I got a travel deal alert for a super cheap airfare. The trip was for late July and I thought it would be too hot, but the deal was too good to pass up on, so I booked it.

The heat ended up being a non-issue, partially because Key West in the summer isn’t as hot as you might think, and mostly because I was having way too much fun. I really got an understanding and feel for what life was like when it was much less crowded and the locals went on their own tropical vacation, or “staycations” as they like to be known. I got to do everything I always did when I went down there, including eat at my favorite Key West restaurants and spend a day fishing for tarpon, but what made it special was getting to know the people who call it home.

They’re the ones who explained how to handle the heat: simply do everything a little bit slower. Suddenly having plans wasn’t so important, hurrying to the next thing didn’t matter, and as long as I knew when it was happy hour where and what time the sunset was, I would be fine. My annual summer vacation is coming up next month, and I can’t wait to hurry up and do nothing.

High School Reunion Done Right In Key West

I was fortunate enough to attend a supplementary high school program my last two years. It was great because it helped me focus on my studies and the small size made everybody very close. At my traditional high school graduation, I marched with almost 200 students. At my other school, there were 26 of us. With a class that small, not only are we able to keep in better touch, we can also have more fun reunions. This year it was Key West, Florida.

We schedule one every five years and we have a small list of requirements. The location has to be relatively easy to get to. With an airport of its own and a highway back to the mainland, everyone had a simple time making arrangements. There has to be plenty of places to stay and eat. Key West just opened two new resorts and remodeled another four hotels, giving them the highest number of rooms they’ve ever had, and there are over 300 Key West restaurants to choose from. Finally, it had to be a place few if any of us had visited and be a destination vacation we wouldn’t normally think of on our own.

In hindsight, what made Key West the best choice was not anything on that list, but the wide range of activities to choose from. Between all the ocean activities, the history, the arts and entertainment and the beaches, we didn’t feel the pressure to do everything together. We could all do our own thing and still get together every night for a meal to catch up. We vowed we’d never repeat a locale, but five years from now, we may have to rethink that rule.

Enjoying The Island Style Of Dining in Key West

I’ve been working as a server in Key West for a few years now. One customer that stands out in my mind came in a couple of years ago for lunch. He and his wife were on a cruise and point blank asked me what the quickest item on the menu was. We offered a slow simmering Cuban style stew that could be out in just a couple of minutes. He said, “We’ll take two, two waters and the check.” He did manage to find enough time to explain that since they were on the cruise, they wanted to see as much as they could in the little time they were here.

I was talking with some of my fellow restaurant working friends that night over beers and we all agreed they were missing out on what Key West had to offer. Part of the joy of coming here is to be able to relax and enjoy the laid back atmosphere. I understand a cruise only offers a limited amount of time to see everything a tropical island vacation has to offer, but how much of it are you going to remember when you simply try to rush through it all?

A few nights ago, I was at work and this couple came in for dinner. They relaxed, took their time and we got talking about all the different Key West restaurants they had visited during their stay. That was when they told me about their first visit: it was the same couple! We laughed about it, and they admitted that the only thing they really remember from their first visit was realizing they needed to come back when they could really enjoy Key West.

Creating Some Father And Son Time In Key West

When I was a kid, my dad would take my brother and I fishing a few times a year. Neither of us were that good (or that interested) but my dad tried anyway. I’ll give him credit for being smart enough to save his real fishing trips for when he would go out with his buddies,. Looking back, I realized that it was less about the fishing and more about just being sure that he had time alone with his sons. I was thinking about that when I made plans for his Father’s Day present this year and a trip to Key West.

Even though he’s talked about wanting to go deep sea fishing or try something else, he’s never done anything other than the lakes and rivers back home. The first thing I did after booking our flight and hotel was to start looking into some fishing charters. I read as many online reviews as I could find and ended up arranging a few different trips. We’ll be going deep sea fishing, another trip takes us to the reef and we’ll also spend some time fishing the flats.

Another good thing I discovered was that Key West is more than just a bar and party town at night. There are several great Key West restaurants we can choose from, a walking ghost tour that I think he will like and both a jazz club and a blues club where we can enjoy a good cigar with some live music. I just hope the trip to Key West won’t disappoint him too much: for all I know he could be looking forward to the annual bottle of aftershave I give him.

Sneaking In A Family Getaway to Key West, Florida

The joke at our house is that our front door should be a revolving one. Both my husband and I have busy careers, plus we volunteer in our community. Our children are active as well, playing sports and joining clubs, and it is not uncommon that even in the summertime, we will go from early in the morning until late at night when all four of us will see each other at the same time.

Planning a family vacation around such chaos can be hectic, but that is why I try and stay on top of it with email alerts for travel deals. Additionally, I sneak in some research when I can on where good, unique destinations are. I figure if we only get a few days to travel as a family, I want to make sure it is something that can’t be replicated just anywhere. That was how we ended up on our first trip to Key West.

The stars aligned and there was a four day period my kids didn’t have anything planned and my husband I could take off a couple of days. It was a very early morning drive to the airport, but that meant we were choosing from several Key West restaurants for lunch that day. When we weren’t enjoying the fresh seafood, we were out on the water watching it swim around, and we got to spend a few stress-free days as a family.

I’m not sure when we’ll be lucky enough to have time to travel together again, but I was glad to discover that we could make a quick getaway to Key West, and I know for a fact that we’ll make it happen again.