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.

Advertisements

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.

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.

Traditional Wedding In Tropical Attire in Key West

My husband and I are perfect examples of opposites that attract. Luckily, we’ve always been able to compromise. He teaches art and sculpture at the local college while I commute to the city for my finance job. I own at least two dozen professional outfits and I think he has one suit and maybe two ties. When it came to our wedding, I wanted a traditional church service and he wanted a tropical island celebration. Key West offered us the perfect solution.

We told the local Key West wedding planner we hired what all of our concerns were and she helped us arrange the perfect destination wedding. We found a beautiful church to hold the ceremony at, and she took us to several different Key West restaurants to look at for the reception venue. We got to sample some of the fresh seafood and key lime pie that would be part of the menu, and found a beautiful location with outdoor patios and plenty of room for dancing.

Most of the guests on my side were a bit surprised when they saw the invite for a tropical wedding, knowing as they did my traditional wedding dreams. I’ll admit, I was skeptical at first, too. Much of that was due to how little people know about Key West beyond its reputation as a partying resort town. Everyone thanked us afterwards not only for having such a beautiful wedding, but also for introducing them to a great new vacation destination. Every time someone said that, my husband just gave me a wink. He was too polite to take credit himself, but if not for him, I never would have learned how beautiful Key West is.

A Foodie’s Tropical Vacation to Key West

My husband and I plan a big trip every five years for our anniversary. We both like to eat and drink, so some of our previous trips have been to California wine country and Paris and the French countryside. This year was the second brutal winter in a row, so I decided that it would be nice if we went somewhere where not only would we love the food, we’d appreciate the weather as well. My husband thought I meant Miami, but I was thinking a little farther south.

Thanks to websites like Yelp and Trip Advisor, I learned about how popular and exciting the Key West restaurants were. Even places that were described as run down and weather beaten still had amazing reviews when it came to the food and the service. I read as many reviews as I could and made a few reservations ahead of time to be sure we could get in to some of the more exciting sounding places.

We were both blown away by how good the food was. The chef at one of our now favorite restaurants came out to tell us about what they call New Island Cuisine: local food, such as seafood, fruits and spices, prepared with traditional cooking methods. The results were astounding, and surprisingly, many of the restaurants we went to not only had such great food, they also had extensive well thought out wine lists. During each meal, we managed to find several excellent choices to pair with our food.

We have five years to think of our next destination, but if winters keep being the way they have, I’m sure we’re going to end up back in Key West. We might not even wait five years.

A Long Weekend Getaway in Key West, Florida

Last year, between the two of us, my wife and I had to give up almost three weeks of vacation days. We had been accruing a lot of time and never seemed to know when to use it, but after cashing out what we could and rolling over some more, when we saw how much we had to sacrifice, we decided that wasn’t going to happen again. We switched up our focus from trying to find a week or two to take a big trip and instead, looked for weekend trips with an extra day or two. The beauty of that is so far this year is that we’ve made three trips to Key West.

We can fly right into the island and be poolside at our hotel by two in the afternoon. There are several different Key West restaurants all within walking distance for us to explore. If we feel like going out on a sunset sail or a snorkel trip, we can do that, or we can just spend the day lounging on the beach before checking out the nightlife on the world famous Duval Street.

A couple of friends give us grief that we keep going back to the same place, but we look at it this way: why mess with a good thing? We don’t need passports, we are already getting to know our way around, and we don’t have to worry about choosing some place new that doesn’t live up to our expectations. We know that we can spend the whole extended weekend in Key West just relaxing and getting the most out of our vacation time.

Planning Our Summer Vacation to Key West, Florida

We live in Ithaca, New York, and this past winter, our town achieved fifteen minutes of internet fame when our board of tourism replaced its typical web pages with links to the Florida Keys tourism board. When you’re buried under six feet of snow and the temperature is hovering in single digits, it’s pretty obvious that Key West is a better vacation spot than upstate New York.

As much as we would have liked to get away during this horrendous winter, between our kids being in school (when it wasn’t closed) and the airport being buried, we could do nothing but dream. That didn’t stop my husband from looking into what a vacation in Key West would be like. He was smart enough to look at times when all four of us could go, and that was when he made some surprising discoveries.

Discovery one was that there was plenty to do for everybody. Key West has a reputation as a party town, but we found several different activities that would keep us all busy. And when we didn’t want to be busy, there was always a beach to go to. Discovery two was that the average summer temperature in Key West is lower than other more “touristy” locations in Florida. We all talked about it and decided we would try something new this year.

We’re still undecided about flying in or driving down on the Overseas Highway, but no matter how we get there, we are already looking into planning our summer vacation by letting everyone pick one day where they get to choose what it is we do. With so much to choose from, we’re going to run out of days before we run out of options.