Planning A Super Summer Vacation to Key West

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.

Advertisements

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.

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.