Something For Everyone In Key West, Florida

My husband and I are part of a group of four couples that go on a vacation together every year. It can be hard to find something everyone agrees on, and some people are pretty insistent that we go back to the same place year after year. Thankfully, that doesn’t happen, but it doesn’t make the decision process any less awkward. This year was especially tense when somebody brought up Key West, Florida.

The loudest votes of dissent came from those who only knew of the island through the song “Margaritaville.” They had no interest in spending seven days on a bar crawl, which was how they described it. My husband was interested in the island, however, so he did some research and put together a five minute presentation that he emailed to everyone. When they all watched it, the decision became unanimous.

There was a day spent for golfing for some and shopping for others (and it didn’t break down the way you might think). For those who didn’t want to go fishing, sleeping in and a spa was on the agenda. We had a chance to visit art galleries, even see live theater and dine at several exceptional Key West restaurants.

I wouldn’t necessarily call it the highlight of the trip, but certainly a big layer of icing on the cake – or merengue on the key lime pie – was when we actually participated in a bar crawl, visiting several of the famous bars and hearing stories about their history. What made it especially gratifying was seeing how much fun the original dissenters had meeting other people on the crawl and having a blast.

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Long Weekend Getaways to Key West

My company is pretty laid back when it comes to summertime. We typically slow down, so as a bonus, the boss splits shifts each week, meaning every other workweek is only four days long. We don’t get paid for the day off, but it doesn’t count against our vacation time, so it works out okay. As soon as the schedule came out, my girlfriend and I put circles around all of my three day weekends so we could make plans. Most were local festivals or just getting away for a night, but the big one was a trip to Key West, Florida.

He had been once a couple years earlier, but that was only on a cruise and we knew we needed to see more of it. Granted, we didn’t think we’d see enough of Key West on a three day weekend, but we knew we could get the most out of our time. We actually left Thursday night, spending the night in Miami, so we could catch the first flight in the next morning. That meant by nine am on Friday we were debating which of the Key West restaurants we should be having breakfast at.

We spent the next three days loving our tropical island vacation. We made sure not to try and rush anything, but rather enjoy all that we were doing. That meant plenty of time spent at the beach, many hours listening to live original music, and visiting as many Key West restaurants as we could to get our fill of fresh seafood before we had to leave Monday evening. It was easily the best weekend of our summer.

Walking Through The History Of Key West

My wife and I, our idea of a fun vacation sounds a little dull to most people we know. We like to explore important locations in the country’s history. We still go out to nice restaurants and nightclubs while on vacation, but the original destination is chosen by wanting to learn more about its place in our country’s growth.

A few years ago, two items came to our attention that made us consider Key West as a possible destination vacation. One was the centennial celebration of Henry Flagler’s railroad across the ocean (now the Overseas Highway) and the second was the upcoming 500 year celebration of Ponce de Leon first discovering the Florida Keys. Neither my wife nor I knew much about Key West outside of its reputation as a party town, but the more research we did, the more we learned about its unique place in history.

For instance, even though Florida was a Confederate State, Key West managed to remain supportive of the Union. We also learned that at different times in its history, it was both the richest city in the country and one of the first to declare bankruptcy. It was home to some of the most influential artists and writers, and was one of the pioneering cities when it came to gay rights.

Seven days was not nearly enough to explore all of the history Key West had to offer. Part of that problem stemmed from all the great Key West restaurants we had to choose from, and their leisurely lunches and decadent dinners. In fact, much to the surprise of our friends, we’ve already booked a vacation back next year.

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.

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.

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.