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.
My buddies and I try to get away for a fishing trip once a year. Our wives are all pretty understanding (I think some of them secretly look forward to it) and we try to make it as much fun of an adventure as we can. Part of that comes from trying some place new every year. Typically, it’s a cabin on a lake or nearby a river, but this year we decided to really mix it up by heading down to Key West to do some fishing there.
Before we left, I did a little research to see what kind of fishing we could do. Five minutes later I discovered it might be shorter to list what we couldn’t do. There were private all day charters that went out to deep water, party boats they stayed closer to shore, and even flats fishing, regarded by some as the pinnacle in sport fishing. Naturally, we tried them all.
Over the week, we saw more fish then we could imagine, and the stories of the ones that got away were amazing. Some of the fish was catch and release, but we made sure to get plenty of photographic proof, so our wives knew we actually fished and didn’t spend the whole time walking up and down Duval Street. And the fish we could keep, it turns out, we could take to several Key West restaurants where they’d make us dinner with it. It’s a great feeling to be on an outdoor dining patio, palm trees overhead, laughing and joking with some of your best friends eating fish you caught earlier that day.
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.
For years I have always been taking the same summer vacation. Problem is, so has apparently everyone else, and they all want to be there at the same time. The moments of relaxation have become so few and far between as the crowds have grown that it just hasn’t been worth it the last few years. This year I decided to do something radically different. Instead of heading north into the mountains, I decided to go south to Key West. I so made the right decision.
From the moment I switched planes and saw only a dozen other people flying to the southernmost island I knew I was in for a treat. Sure enough, when I checked in, the hotel clerk told me they were only at about half capacity. That meant I got to sit by the pool and not be bothered, have my choice of any of the Key West restaurants and not have to wait for a table, and got to know all of my bartenders on a first name basis in about two days’ time.
Naturally, when I got back to work and people asked where I went, they all said I must be crazy to go to Key West in the summertime. That was when I pointed out the average temperature down there had actually been less than what it was the same week at the resort I used to visit every year. Of course, now I wonder if I shouldn’t have told them that. I don’t want them crowding up Key West next year.
One of the toughest challenges my wife and I had was planning our wedding. I’m not kidding. It got heated from time to time, and what made it worse was it wasn’t us putting the pressure on ourselves. It was everyone else. As the first child to get married in each family, everybody had an opinion on what we should do and nobody was shy about sharing them. It got to the point where we almost eloped, but then we did the next best thing: we decided to get married in Key West, Florida.
We invited everybody that we had planned on, told them all that is was going to be a very simple beachfront ceremony, and that if they wanted to come to the reception, we needed to know a month in advance. Once we had our number, we then scrambled to pick from the Key West restaurants to find the perfect place. We wanted a combination of fresh seafood on the reception menu and outdoor patio areas so we could dine and dance under the stars. We were lucky enough to get a booking at our first choice, and after that, the planning was basically done.
My cousin thought it was the coolest idea ever, so he got his certification online so he could marry us. Most of the people who had shared an opinion agreed that we had managed to throw one heck of a wedding, and as the two of us danced to our first song, both in our flip flops, we knew that we had made the right decision as well…so much so that we booked our one year anniversary trip even before we left 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.
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.
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.
When I found out my niece was planning a tropical wedding, I assumed that meant no invitation. Not because she wouldn’t want me there, but because there’d be no way she could afford a large number of guests. When my wife and I got the invitation, I assumed that meant we wouldn’t be able to make it because it would cost too much and be too difficult to get there. When my wife showed me just how easy and affordable it would be, I realized I needed to stop making assumptions and start paying attention.
She picked Key West as the tropical island for her destination wedding, and I could see that, in many ways, it was no different (and therefore probably not more expensive) than a wedding back home would have been. She wasn’t stuck using a specific wedding package from a resort but instead could create her own ceremony and reception, hire her own entertainment and work within her budget.
Key West also meant there were dozens of hotels to choose from and several different travel options, which helped keep the costs low for her guests. Many of the family members I talked to at the reception remarked on the same thing I had thought, that once they heard about it they wouldn’t be able to make it. Instead, some of them had the opportunity not only to see her get married but also take their first vacation to the tropics. My own daughter has a few years to go before she’s marrying age (thank God) but at least I can now say I won’t be too worried if she says she wants an island wedding as well.
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.