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.

Bush Key in the Dry Tortugas National Park

Seeing All Of South Florida – Make Sure to Visit Key West

My wife grew up in South Florida before moving north for college. We had gone back a couple of times but her parents reversed the trend and moved up this way after they retired so they could be closer to their grandkids. When it came time for her 25th high school reunion, we figured it was worth the trip, seeing as how it had been at least a decade since we had visited. But I wanted to make sure we really got our money’s worth, so after the weekend in Fort Lauderdale was over, I booked us a few extra days in Key West.

I had never been there, and the last time she visited, the big thrill for someone her age was riding the Conch Tour train, so it was a brand new experience for both of us. We took part in some of the required activities – watching the sunset, going on a snorkel trip, doing the Duval crawl – and we were fortunate enough to discover some of the great Key West restaurants. Even though the island is surrounded by some of the greatest fishing grounds in the world, I guess both of us just expected to find typical tourist island seafood dining options. Instead, we had some of the best meals of our lives.

Having a chance to get away from it all for a few days reminded us that we need to take more advantage of or vacation time. The kids are old enough to be on their own, and already we are looking to come back down later this summer to try some more of that great seafood.

My Southernmost Wedding Ceremony In Key West

Pretty much from the first date, my husband and I knew how to compromise on almost everything so we would both enjoy what we were doing. Still, I was a little nervous when we started talking wedding plans. I always envisioned a traditional ceremony and reception, while he wanted a tropical island wedding. I wasn’t sure how it was going to work out until we discovered Key West.

We went down on an early scouting trip even before we knew much about it, and almost right away, many of my fears were put at ease. There were several churches to choose from, and many Key West restaurants had the menu, style and décor that I was looking for, but then a strange thing started to happen to me.

The more I thought about our time down there, the more I realized I didn’t want to have the same wedding I could back home. We started looking at some of the different options, including getting married on a boat at sunset, or at a historic fort on the beach, and I realized how much fun and how memorable that could be.

My husband was so excited about my change of mind that he blindsided me and found the perfect reception spot that was everything I could have hoped for. There were beautiful outdoor dining decks, some of the best seafood I ever had, and a casual elegance to the whole evening that was fancy enough to make the event special but relaxed enough so everyone had a great time. And when the reception was over, we didn’t even have to pack for the honeymoon.

Southernmost Wedding Ceremony in Key West, Florida

A cousin of mine was getting married this winter in Key West and I was invited. Naturally, I wanted to go, but I was afraid that I wouldn’t be able to get the time off from work, much less be able to afford it. I didn’t know much about the island and so I thought it was like the rest of the Caribbean islands: far away, hard to get to and overpriced. Luckily, my wife is a little smarter than I am and she made the trip work.

First, she found us a direct flight into Fort Lauderdale and a rental car. Before I could ask her what good that was, she showed me pictures of the Overseas Highway and the iconic 7 mile bridge. She found us a flight that left at 6am (ugh) but that meant I would only have to miss two days of work. Then she lined up several different hotel options, all of them well within our budget. We settled on an inn in a restored mansion that seemed close enough to where everything was happening.

Everything was perfect. The wedding was beautiful, the weather was gorgeous, and I even got the chance to go snorkeling for the first time. We had such a great time in Key West that my only regret was having to leave around noon on Sunday to drive back to the mainland, but even that was tempered by the chance to take that beautiful ride. My wife even drove so I could take in all of the scenery. Now that we know how convenient and affordable it is, we will definitely be back again and 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.