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.

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.

Business And Pleasure In Key West

Every year for work, I have to attend several different conferences. Most of these happen in large stale convention centers in Midwestern towns or hotel complexes conveniently located next to an airport. I’m not sure who thought having a conference in Key West was a good idea, but I was not about to look a gift horse in the mouth.

When I posted on social media that I would be going, many people who had been there before started telling me all the places I should go. I made up a list of the most recommended places, and when I had free time I went to check them out. I expected to enjoy myself while I was there, but what I didn’t expect was how amazing the dining experiences were.

In my mind (thanks to several childhood vacations to beachside tourist towns in New England) I expected every restaurant to offer their own version of deep fried seafood and that would be about it. I was blown away by the level of creativity and flavor that some of these Key West restaurants had come up with. Needless to say the seafood was as fresh as could be, I had some amazing crab cakes and, of course, I had to try what each place claimed was the best key lime pie on the island.

My husband wasn’t able to make the trip with me, but as soon as I got home, I told him to start planning some vacation time. I can’t wait to go back and try all the places I missed while revisiting those that are already my new favorite.

Summertime Tropical Fun In Key West, Florida

My friends think my wife and I are crazy to go to a tropical island in the summertime. When I point out to them that they go north to the mountains in winter, of course, they say that’s because of all they can do. They can spend the day skiing and snowboarding, or they can lounge by the fireplace with a book. Well, that’s exactly why we go to Key West every summer.

Every morning, we decide on a scale of 1 to 10 how active we are feeling. A 1 means we are probably going to spend the day lounging by the pool, napping in the hammock, and finding one our favorite Key West restaurants for a long leisurely dinner. A 5 means we are going to head out and take a walk around the historic neighborhoods, enjoying the architecture, head down some streets we’ve never been on before, maybe spend the afternoon on a snorkel trip, and of course, enjoy a margarita or two.

Any day that’s a 9 usually starts with a swim in the ocean, followed by renting a paddle board for a few hours and then taking a kayak tour of the mangroves, where we can see some of the nature while getting in a great work out. That’s what we love about Key West. No matter what we wake up in the mood to do, it is there for us to do. I will say this. We’ve never had a day that we thought was a 10, and I’m not sure what we would do fulfill it, but I know for sure the next day would be a massage filled sundrenched lazy 1.

Last Minute Key West Spring Break

I love to travel whenever I can, so I’ve set up a few different notifications with various travel websites. Last week I got a deal on airfare and a hotel in Key West for a quick four day getaway, and I figured why not? The hotel had free Wi-Fi, which is all I need for work (ah, the joys of the telecommute!) so I dug out my spring clothes, packed a bag and headed off to the airport.

The trip was everything I needed to recharge my batteries after a long, cold winter. After sleeping in, I would take my computer down to the pool so I could enjoy the warm weather and my breakfast while I finished that day’s assignments. The lull of getting out to walk the streets, listen to live music and experience the fresh seafood and key lime pie at some of the Key West restaurants was motivation enough to make sure I worked quickly. With each last email sent, I was free to explore.

What really made the trip more special than other island vacations I’ve been on is the sense that this island is not just a man-made destination but a vibrant city with hundreds of years of history. I got a chance to meet a few locals and find out more about where they call home, and even indulged my inner child by going to the aquarium where I got to pet a live shark. The first thing I did when I got home was look at my calendar to see when I can go back there for more than just a few days.

The Surprises From A Key West Wedding

My niece decided to have a destination wedding in Key West, Florida. My wife and I were invited but were on the fence about going. We wanted to be there, but we both work full-time and getting time off might be a challenge. Plus, we both thought that maybe we were too old to go there. It seemed to us to be a younger person’s island. But we love our niece so we decided to look into it.

The first surprise was finding a flight that got us directly into Key West and only involved us taking two vacation days. The second surprise was discovering the number of quirky little inns to choose from. Based on the recommendations and reviews we read online, we chose one that was close to where everything would be happening but far enough away that it would be quiet at night (the third surprise was actually getting there and discovering that the reviews were true. The place was beautiful, relaxing, and, yes, quiet).

Since we had had so much luck trusting anonymous reviews for where to stay, we decided to try our luck again when it came to the Key West restaurants. We went online and found several places that had received great recommendations, so we checked them out. We were blown away by not only how amazing the food was, but also the level of service and the beauty of the outdoor dining.

We had such a great time that after the reception was over and some of the younger people were going out, we decided to join them. We may not have stayed up as late as they did, but we discovered Key West is perfect for just about everyone.

An Unexpected Key West Highlight

My wife and I were looking over the holidays to plan a trip somewhere warm and tropical for March. We knew it was going to be another nasty winter and wanted to escape it for just a bit. Both of us wanted to visit someplace new, so we took the recommendation of friends and booked a trip for Key West, Florida.

We went in with pretty high expectations, and I have to say that not only were they met, most were exceeded, but none more than our experiences at the Key West restaurants. I guess we just figured that an island basically in the middle of the ocean that caters primarily to tourists would have serviceable predictable meals. Boy were we wrong! On multiple nights, we found ourselves having exceptional dining experiences. The menus were fresh and inventive, the seafood was some of the best I’d ever tasted, and the atmosphere, even in the nicest of restaurants, could be best described as “casual elegance.”

Just as surprising was the number of great meals we had at places that we’d least expect. Several times, we stopped in harbor side restaurants or little hole in the wall joints just to grab a quick bite to eat. Even in these places, it was evident that everyone took pride in what they were doing. Before the week was half over, we were already struggling, trying to decide if we should continue to visit new places or return to those that had already become our favorites. We settled for going to new places, but with promises to return to Key West as soon as we can.

Count On Key West For Best Birthday Ever

My husband’s birthday was last weekend so I decided to surprise him with something special. With the winter we’ve been having, anything that wasn’t snow covered would be special, but I was looking for something more than that, but that could also be squeezed into a three day weekend. Luckily, I was able to get us to Key West, although I had to convince him to take a half-day on Friday.

Our first plane took off just after lunch and, after switching planes once, we touched down right on the island and immediately went to one of our favorite Key West restaurants. We had our favorites, conch chowder and crab cakes, and we were sure to end the meal with a couple of slices of the best key lime pie. A leisurely walk through the historic neighborhood (with no piles of snow to step around!) brought us to the quiet inn I had chosen for our weekend getaway.

Quiet seemed to become the theme word for the whole time we were there. Even though Key West is known for having a bustling night life full of bars and live entertainment, we spent most of the time lounging by the pool, napping in a hammock or taking long walks on the beaches and through the museums. We stretched our Key West getaway as long as we could, not getting back home until late Monday night. We both knew getting up for work the next day was going to be tough, but we both knew it would be worth it. He told me that night, as well as almost every minute we were there, that it was his best birthday ever.

Shoveling Sand Instead Of Snow – Visiting Key West, Florida


You know when your own Northern New York town officially calls it quits on its tourism page and tells you to head to Key West instead, it might be a sign that this winter is just too much. That is just what my hometown of Ithaca, New York did this past week. Normally, I’m not one to be susceptible to such enticements, but as I cleared three more feet of snow off my driveway and the weatherman said three more was coming next week, I decided maybe it was time to look into this tropical island paradise.

Everything I knew about Key West came from a three minute pop song that was over 30 years old, so I started doing some research. My first happy discovery was that I only had to change planes once to get there, and I could even drive if I wanted to. I never imagined crossing a seven mile bridge, but immediately decided that might be the best way to get into Key West. I found over a hundred different accommodations to choose from, from five star full service resorts to quirky inns in homes that were over 100 years old.

I made reservations at several Key West restaurants, scheduled a day on a fishing charter and an afternoon on the golf course, and also made sure I left plenty of time to visit the world famous bars and lay on the beach. My plane takes off about a day before the next storm comes in, which doesn’t give me much time to remember where in the basement I packed away all of my shorts, bathing suits and other summer clothes. But I’ll find them…..that’s a 100% guarantee.