Sneaking In A Family Getaway to Key West, Florida

The joke at our house is that our front door should be a revolving one. Both my husband and I have busy careers, plus we volunteer in our community. Our children are active as well, playing sports and joining clubs, and it is not uncommon that even in the summertime, we will go from early in the morning until late at night when all four of us will see each other at the same time.

Planning a family vacation around such chaos can be hectic, but that is why I try and stay on top of it with email alerts for travel deals. Additionally, I sneak in some research when I can on where good, unique destinations are. I figure if we only get a few days to travel as a family, I want to make sure it is something that can’t be replicated just anywhere. That was how we ended up on our first trip to Key West.

The stars aligned and there was a four day period my kids didn’t have anything planned and my husband I could take off a couple of days. It was a very early morning drive to the airport, but that meant we were choosing from several Key West restaurants for lunch that day. When we weren’t enjoying the fresh seafood, we were out on the water watching it swim around, and we got to spend a few stress-free days as a family.

I’m not sure when we’ll be lucky enough to have time to travel together again, but I was glad to discover that we could make a quick getaway to Key West, and I know for a fact that we’ll make it happen again.

Island Wedding Reeption

A Tropical Dream Wedding Renewal In Key West

When my wife and I got married, we were both fresh out of college and just starting our careers, so money and time was tight. We had a simple ceremony followed by a reception in her parent’s back yard, and our honeymoon was a weekend getaway. Although we never regretted having something so small, we talked from time to time about what we would have done differently if we could have.

Flash forward about twenty years and our upcoming anniversary. We wanted to do something special so we decided to renew our vows. This time, we were going to do it the way we wanted, and that meant by making it happen in Key West. That had been our dream honeymoon destination back then, and we had been fortunate enough to vacation there a few times over the years.

Even though we were already married (obviously), we still hired a wedding planner to take care of the logistics. Then we went through our old guest list and re-invited everyone who had been there the first time, plus some new friends we had made over the years. I’m not sure if it was because they wanted to support us or just wanted a tropical island vacation, but most of them said yes.

We had a blast. We got to say “I do” on the beach as the sun set, we took our friends to several of our favorite Key West restaurants, and we even got to spend the night in a honeymoon suite. We may have been one of the older couples having a tropical island wedding that weekend, but we felt like newlyweds all over again.

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Class Reunion On A Tropical Island Named Key West

I’ve got a group of friends from college that have tried to stay pretty close even though we’ve all moved to various parts of the country. Social media and video chats help, but there’s nothing like spending time together, so every couple of years we try to plan a vacation together. More often than not, we end up making that vacation in Key West, Florida.

Surprisingly, it is pretty easy place to get to. Several different airlines fly there, and there is always the option of driving down from the mainland as well. There is also plenty to choose from when it comes to where to stay. The first couple of times, most of us ended up in hotels or resorts, but lately we’ve been renting out houses or condos. That way, we save a little money and have the comforts of home, including a kitchen. Of course, nobody really likes to cook (and clean) while on vacation, so thankfully there are plenty of Key West restaurants to choose from. No matter what our mood is at the time, or even if we are in different moods, there is always the perfect spot. That goes for our last night, when we have a big blowout final meal.

There is nothing like sitting around on an outdoor dining deck, watching the stars while enjoying fresh seafood, with some of your best friends in the world. At some point during the week, inevitably a few people will say, “Hey maybe next time we should go to…” but by the end of the trip, everyone agrees that the next time, we’ll be coming back to Key West.

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.

Peace, Love And Sandy Wedding Vows at Key West

I wish I could say I was carefree enough to live on a tropical island, but there is just too much practicality in me. At least I try to always live in a relaxed manner and spend as much time as I can getting away and enjoying life. Needless to say, when it came time to getting married, there was no doubt it was going to be a tropical island wedding.

I had visited Key West once, years ago, and my fiancé had been there a couple of times more recently, and we pretty quickly picked up that it would be the perfect place. There were so many beautiful locations to choose from for the ceremony, several dozen great Key West restaurants for us to have our reception at, and plenty of hotels and resorts to choose from so we didn’t have to worry about limiting our guest list. We met with a terrific wedding planner who helped us every step of the way, and two weeks ago, we tied the knot.

I can’t even say it was all I hoped for, because it was so much more than that. The weather was epic, the whole experience was wonderful, but the highlight was just how beautiful it felt to be standing barefoot on a Key West beach, sand in our toes, telling each other we were going to love each other forever while the sun set in the background. We both know it’s not even a matter of if we’ll go back, but only a question of how soon.

Island Vacations

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.

Married To A Beautiful Island – Key West, Florida

My fiancé and I wanted to have a special destination wedding. We felt it was important to start our marriage together in a meaningful place. We both love to travel, and between the two of us, have visited most of the states and about a dozen countries, but neither of us had ever been to Key West.

At first we kind of dismissed it, mostly because all we knew about it was its reputation as a party town. But we decided that the place we chose should be new to both of us, so our first memories of it could be together, so we bought a couple of plane tickets and headed down for a week to see if it would be our tropical island wedding.

It turned out to be far more than that. We immediately fell in love with the beautiful weather, the warmth of the people and the laid back island lifestyle. We understood the reason why so many people we met told us stories of having come down for a week ten years ago. We knew we couldn’t quite do that – we each had responsibilities back home and there was still a wedding to plan – but we decided to do the next best thing.

We still had a destination wedding. We had a beautiful oceanfront ceremony and chose among our favorite new Key West restaurants for our reception. The only thing that made our wedding different than most was that when everything was over, all of our guests went back, and we stayed in our beautiful new island home.