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 wife and I knew we wanted a wedding that was equal parts fun and simple, something that everyone could enjoy. The more we talked about it though, the less simple it seemed to be. We could feel it starting to overwhelm us, so we put a moratorium on discussing it for a week while we regrouped. Sometime during that week she saw an ad for Key West, Florida and thought that might be the solution.
When she brought it up to me, we looked into everything the island had to offer. We realized that it was easy to get to in a variety of different ways, and there were plenty of different types of hotels and inns to choose from. With July being the slower season, rates would be lower and availability would be greater. Since we were having this discussion in January, we decided that gave everyone, including us, enough time to make plans.
The only thing we did before we chose the date and sent out the invitations was look through the Key West restaurants and decide which one we’d have the reception at. Once the day was picked, we were just like everyone else: looking for a great deal on hotel and airfare. Since there was almost no planning involved, it kind of felt like we were eloping. Even a couple of days before we left it almost hadn’t hit us that we were getting married. But when we showed up at the beach with the justice of the peace and one hundred invited guests, we knew we’d made the right decision.
One of the things that attracted me to my boyfriend at the time was the sense of adventure we both had. It was certainly something that brought us together and made for exciting times. When we decided to get married, we wanted our wedding to be an adventure as well. We were looking at all sorts of crazy ideas, but we both realized we were feeling the same thing: it wouldn’t be the same without our friends and family. We needed something that was bit of a compromise, and that was when we discovered Key West.
So much about it appeals to so many different people that we knew it would be the perfect choice. People who loved to spend time on the water would have plenty to do, as would those who enjoy history. There were coffee shops for early birds, bars and night clubs for night owls, and an amazing number of Key West restaurants for everyone to choose from.
Of course, we weren’t just concerned about our guests. We wanted to make sure our wedding was meaningful and special for us. We found a wedding planner who understood what we wanted and she helped us find the right location for the ceremony and a great restaurant that had an amazing reception menu of fresh seafood and crab cakes, not to mention a killer view. She even helped us violate one of the pre-wedding traditions that says a bride and groom aren’t supposed to see each other on their wedding day until the ceremony.
We spent that morning sky-diving.
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.
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.
My husband always wanted to get married in Key West. I always wanted a traditional church wedding in June. Much to the shock and surprise of our friends and family, we each got we wanted, and it turned out to be a magical time.
We had been on vacation to Key West a couple of times while dating when he brought up the idea of a tropical island destination wedding. We had started talking about marriage but not about our plans. Needless to say, this caught me off guard. I had imagined a big wedding in a church, followed by fun relaxed reception. I couldn’t possibly see myself abandoning all of that, but I didn’t think there would be much of a way to compromise. Instead of letting it blow up into something big, he proposed a compromise. Since it included a vacation, I was game.
We returned to Key West that June. We certainly did all the fun things we loved to do down there, but we also took the time to explore the life of the island. We even found our denomination’s church and talked to the pastor about having a wedding there. Discovering how easy it would be to arrange it was like the first domino falling. Soon everything else started falling into place.
The following summer we returned with 120 of our closest friends. The wedding was everything I had always pictured in my head with one stunning difference: a beautiful beachside tropical sunset that we took our pictures in front of before going off to the reception.
A group of friends and I work as teachers most of the year and spend our summers as counselors and program directors at overnight camps. Needless to say, this doesn’t allow for a lot of away time, so we try to make the most of it when we have it. A couple of years ago, we discovered Key West, and not only did we find so much to do, or not do, depending on our mood, we also got the most bang for our buck.
It was a hard sell for a couple of the guys, seeing as how the trip was planned for two weeks in August and we were going as far south as we could and still be in the country. To be honest, I think all of us felt a little trepidation, even though we had seen the weather charts and what the average temps were. We convinced ourselves that it wouldn’t be too bad, and if it was, there would be plenty of air conditioned Key West restaurants and bars we could duck into, and all of that beautiful cool ocean water to go swimming in.
Yeah, it was warm, but you know what? That might not have been the best thing. Keeping schedules as busy as we do makes it hard to just slow down and relax, but Key West coaxed us into that. We spent days the way you should on a tropical island vacation, lounging in the shade and sun feeling the tropical breezes, and nights that were filled with wonderful meals, exciting bars and great live music. This year will mark the third year we’ve made this trip, and nobody has even suggested we think about somewhere else.
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.
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.