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.

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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.

Flying The Tropical Airways to Key West, Florida

My wife and I have a lot in common (they say that helps when you get married), but one thing that freaks her out as much as I love it is flying. It doesn’t matter how big the plane is, she is holding on for dear life while I have my face plastered to the window. Naturally, this makes certain vacations off limits, including most tropical islands. Thankfully, that list doesn’t include Key West.

Whenever I went in the past, I would fly directly into the airport, not only because I enjoyed seeing Key West from the sky but also because a car is unnecessary on an island so small. Naturally, I knew my wife would want none of that, but what we could do is fly into one of the mainland airports and enjoy the drive down the Keys highway. From the first time I took her, she enjoyed the Key West restaurants and island vibe as much as I did, and soon we were going twice a year.

It was when she brought up wanting to go away for a long weekend that I finally made the move. I showed her that a couple of airlines flew in on a 737, the same planes we fly on almost everywhere else. By not having to worry about the drive, we could make it back and forth to Key West and still enjoy all three days.

Her desire for a tropical getaway outweighed her fear and we made the trip. I don’t think it will ever be her favorite airport in the world, but it is certainly her favorite island.

Driving To A Paradise Named Key West

My wife has a business convention every year, and every year she asks me if I want to go with her. The fact that it typically happens in March in cities like Indianapolis and Chicago make me say no pretty quickly, but this year the travel gods were smiling on us. The trip was to Miami and I couldn’t say yes fast enough. I wasn’t too interested in Miami itself, but I was excited to take a few extra days to drive down the Overseas Highway and check out Key West.

My friends said that the total flight from Miami would take less than an hour (and most of that was taxiing), but ever since I heard about that drive, I had always wanted to experience it. I was not disappointed. There is nothing else like being in the middle of a seven mile bridge looking out and seeing nothing but crystal clear blue water and lush green islands for miles. We took some extra time to poke into the little towns along the way, but the closer we got, the quicker we wanted to get there.

Key West was everything we hoped it would be. The legendary sunset was beautiful, the nightlife was fun filled and overwhelming, and the Key West restaurants left us so happily stuffed that it was all we could do to lounge by the pool and order another round of margaritas. We decided that it didn’t matter where next year’s convention was: as soon as it was over, we’d be hopping a flight to Miami and taking that drive again.

Seeing The World On One Small Island Called Key West

I would love to be able to see the world. Unfortunately, my boss doesn’t see that happening anytime soon, and if he fired me so I’d have the time, it would severely limit the money I had. A few years ago, I discovered the next best thing. If I couldn’t see all of the world, then I would go somewhere that a lot of the world has seen: Key West, Florida.

Key West has a recorded history that goes back almost five centuries, meaning that when the United States finally became a country, people had been calling Key West home for 150 years. These people first were the explorers from Europe, followed by fisherman and sailors from New England and the Bahamas, sponge divers from Italy, cigar makers from Cuba, and artists, musicians, writers and chefs from all around the globe.

This influence can be seen on every block, and each time I go back, I try to discover a little more of it. There are walking tours that point out the architecture, museums that celebrate the various influences, brightly colored paintings hanging in the galleries, and so many Key West restaurants with menus that make you think you’ve visited a hundred different places.

Before I go, I decide what I want to explore when I get there, and by the time I’m done, I have several new ideas for my next trip. At the rate I’m going, I’m going to have to quit my job just so I have time to get it all done in my lifetime.

Taking The Ultimate Family Vacation to Key West, Florida

I wanted to do something special for the family vacation this year. Kids being kids, it can be hard to find something for everyone. One unbreakable rule is that no matter where we go, there has to be at least a pool and preferably a beach as well, so if someone is just too sullen to have fun with the rest of us, they can hang out there with one parent while the other plays tour guide. Kids also being kids, they thought there was nothing we could do to surprise them, so we decided to go somewhere they had never heard of before: Key West, Florida.

They tried hard to play it cool, but that vanished when we were checking into the hotel and a chicken ran right in front of us. They were excited and told the manager, who shocked them even more when he told them the chicken’s name and warned them that he – the rooster, not the manager – would probably be waking us up every morning around five. Sure enough, the next morning he was up before the sun. More surprisingly, the kids were up with him, watching him strut around the courtyard.

Everything we did after that in Key West was one surprise after another. They had never been to a tropical island before and were overwhelmed by all of the plants and flowers. Their picky eating habits disappeared and they tried key lime pie, fresh seafood and even conch fritters. And the only time anyone went to the beach was when we all did, so they could go snorkeling and see if they could find any of the buried treasure that helped make Key West famous.