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.

A Spring Break Tropical Wedding in Key West, Florida

Anyone who has gone on a spring break trip usually has a story about some crazy romance that lasted just as long as the vacation did. We all thought that happened to one of our friends when we went down to Key West for spring break several years ago. Little did we know that the two of them stayed in touch, made the long distance relationship work, and even took a couple of vacations on their own back to Key West.

Naturally, when it came time for their wedding, they first thought of honeymooning in Key West. Then they decided to have an island wedding as well. Since they had met during spring break, and many of the people whom they would be inviting had been on that same trip with them, they decided to have the wedding the same calendar week. Talk about a trip down memory lane.

We tried to do as many of the same silly things we had done back then – late night karaoke followed by an early morning Jet Ski tour – but found we didn’t bounce back the way we used to. Luckily, calmer heads prevailed and this time, we spent doing things we hadn’t thought of all those years earlier. This included visiting some of the Key West restaurants and having the best meals of our lives.

They got married on a sailboat right as the sun was setting, and we sailed back into the harbor under the starlight. As they went off to start their honeymoon, the rest of us tried to do the Duval crawl one last time. We were all in bed long before last call!

Springing a Break On My Husband to Key West, Florida

This winter has been horrible. I know that living in Connecticut means I shouldn’t complain when it snows during the winter, but this was particularly a rough one. I finally couldn’t take it anymore and decided to surprise my husband with an early anniversary present: a quick trip to Key West.

I found us a great deal on a flight right into the island, and seven hours after we left the ground, we were having lunch at one of our favorite Key West restaurants. We spent most of that first day joking about what that big yellow thing in the sky was and hoping we wouldn’t get sunburnt, the whole time eating our share (and then some) of fresh seafood, shrimp and crab cakes and of course, the best key lime pie on the planet.

We only had a few days to spend exploring the island, but it seems like we weren’t the only people who had the same frame of mind. Everywhere we went, we met other people from somewhere up north. All of them had a similar story about running from the snow and cold, and everyone agreed the best cure for a lousy winter was time spent in the Key West sun.

When we got back home, it was to find out another late season storm was on the way. I thought the prospect of another two days of shoveling and snow blowing would kill him, but my husband said he was so refreshed from the trip, he wouldn’t mind if it snowed ten more times this season. I really hope I don’t have to find out if that’s true. 

An Island Vacation Spring Break Destination – Key West, Florida

This is my senior year of college and my friends and I wanted to do something special. We’ve done spring break trips to destination vacation spots the last few years, but this year, as seniors, we wanted to do something extra special. That was when we decided on Key West, Florida.

It had everything that we would normally want in a spring break vacation. We could spend the days hanging out on the water. That meant both if we felt active and could snorkel on the reef or we were feeling a little more relaxed. Those days we could just lay down on the beach. Volleyball was there if we wanted to join, but if not, we could just sleep off the night before.

Something that made Key West stand out opposed to other Caribbean island vacations was the level of quality found at the Key West restaurants. We knew this would be one of the last chances we’d all be together until graduation, and then after that, who knows when we would see each other again. That made it important to us to have one night together having a dinner that was important.

Turns out we found such a great island we did the dinner three times. None of them were as heavy as the first, mostly because it took us very little to feel how great spring break in Key West Florida can be. Everyone we met was so warm and engaging that when we were out celebrating, we found plenty of people willing to celebrate with us.

Bush Key in the Dry Tortugas National Park

Seeing All Of South Florida – Key West

I’m lucky enough that if one of my wife’s frequent business trips is to some place I would like to visit, I can usually arrange for a few days off and “working from home” to accompany her. Not too long ago, she had a weeklong conference in Miami. I’d been there enough times to know I didn’t need to go back, but where I’d never been was Key West and the Florida Keys. I thought this would be the perfect opportunity.

My wife knew very little about that part of South Florida. So little, in fact, that her first reaction was the amount of money it would cost to fly to Key West from Miami. I pointed out that there was the overseas highway that connected the Florida Keys to the mainland, and if we timed our trip right, it would only take a few hours to make the whole drive. Once she saw this was a possibility, she really began to look into it and soon became our tour planner for the bonus vacation.

Turns out it took us far longer than three hours, but that was because we kept finding cute little stores and unique restaurants to check out along the way. We didn’t get into Key West until late in the night, but were excited to see that the town was still wide awake. We dropped off our bags and quickly grabbed a margarita.

By the time Sunday rolled around, we knew we were going to need a lot more than just 48 hours to explore the Florida Keys. As I drove us back to Miami, my wife spent the time planning our tenth anniversary trip back to the southernmost city for later in the year.

way to the beach

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.

Professional Planning Of Island Weddings In Key West, Florida


My son is getting married later this year, and in a move that flipped a lot of wedding traditions on its ear, he was the insistent one on where and how it would happen. He has always had a love for tropical paradises ever since I first read him “Treasure Island,” and when he proposed to his fiancé, he did it with the caveat they would get married on a beach with a palm tree blowing in the background. She said yes with a caveat of her own: it better not include any more work than planning a wedding at home would be.

Luckily for both of them, he did his work ahead of time and knew that Key West, Florida was going to be the perfect location. It offered multiple choices for every aspect, from how to get there and where to stay to where to hold it and what kind of food to serve at the wedding reception. Best of all was the number of full-time professional wedding planners living and working on the island. He and his fiancé had a chance to meet with several of them to choose the one that they felt most comfortable working with and thought could help make their dreams – okay, his dream – come true.

Already, the wedding planner has proven her worth by setting up tasting meals at several of the finest Key West restaurants to help them choose the reception menu. She checks in by phone and email constantly to keep them up to date and responds promptly whenever they have a question or concern. I’m just worried my son is setting a dangerous precedent of efficiency for the rest of his marriage.