Island Life One Week A Year In Key West

The first time I went to Key West was spring break my senior year of college. I immediately fell in love and tried to go back down every couple of years. Usually I went the same time of year, when the cold at home was too much to bear. A few years ago, I got a travel deal alert for a super cheap airfare. The trip was for late July and I thought it would be too hot, but the deal was too good to pass up on, so I booked it.

The heat ended up being a non-issue, partially because Key West in the summer isn’t as hot as you might think, and mostly because I was having way too much fun. I really got an understanding and feel for what life was like when it was much less crowded and the locals went on their own tropical vacation, or “staycations” as they like to be known. I got to do everything I always did when I went down there, including eat at my favorite Key West restaurants and spend a day fishing for tarpon, but what made it special was getting to know the people who call it home.

They’re the ones who explained how to handle the heat: simply do everything a little bit slower. Suddenly having plans wasn’t so important, hurrying to the next thing didn’t matter, and as long as I knew when it was happy hour where and what time the sunset was, I would be fine. My annual summer vacation is coming up next month, and I can’t wait to hurry up and do nothing.


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.

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.

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.

A Long Romantic Key West Weekend


Just like every year, I didn’t know what to get my husband for Valentine’s Day. There aren’t many gifts that scream “Romance” for a guy, and he can only own so many bottles of aftershave before it gets to be too much. So this year I decided to do something different. I gave us a gift: a romantic long weekend in Key West.

I gave it to him a day early, and we left for the airport first thing Friday morning. By 2pm, we were sitting at a waterfront bar, listening to live music and enjoying shrimp that had been swimming less than 24 hours earlier. The next day we were swimming in the same water, snorkeling on the reef and seeing some of the most beautiful fish I could imagine.

I scheduled us for a morning trip so we would have time to relax by the pool with a nap in the sun before joining the crowds to help celebrate the sunset. The best was we immediately afterwards found one of the amazing Key West restaurants I had been reading about. Sitting under the stars on a beautiful outdoor dining deck, we experienced what they call New Island Cuisine. Simply put, it was some of the best food we had ever eaten.

On the flight back home, I was already worried about what I could do next year for Valentine’s Day to possibly top it. Right before our plane took off, however, he turned to me and said, “Next year, we need to plan ahead and spend a week in Key West.” Looks like my gift is already in the bag.

Planning The Perfect Surprise Tropical Getaway to Key West, Florida


For our birthdays, my wife and I have agreed that, instead of exchanging presents, we each provide a surprise for the other at some point during the year. It could be a surprise party, a night on the town, a day at the spa, whatever. This year I wanted to really blow her socks off. It was a special birthday (I’m not allowed to say which one) and I wanted to take us on an island vacation.

The problem with planning a tropical trip is it’s hard to casually work “Is your passport up to date?” into a conversation. Luckily, the island I was most excited about visiting doesn’t require one. I have always wanted to visit Key West, especially after I heard about how exceptional the Key West restaurants are supposed to be. Of course, since this is a trip for her, I needed to do some research to know she would approve.

The restaurant reviews I read on Trip Advisor, Yelp and Yahoo all confirmed what I had already heard, about the great service, outdoor dining and casual elegance, which meant I could leave my suit at home. I also discovered Key West has great spas, where my wife and I could pamper ourselves with a couples massage. To her, the most important aspect of any vacation is relaxation, so I even scheduled her a second full day at the spa for a mud bath, facial, the whole works. The entire experience looks like it will be just long enough for me to sneak off for the golf course. I mean, after all, it is a vacation for both of us.

Traveling To The Tropics With The Family


My son is at that age where he knows everything and anything that he has to do with his family isn’t going to be cool enough. It’s hard to imagine that a 13 year old would be upset about taking a vacation, but when he found out we were going to Key West, he just rolled his eyes. Luckily, I know more about what Key West had to offer than he did.

The first day we were there, we went on an all-day water adventure that included snorkeling, kayaking and a trip around the island on jet skis. He quickly forgot to act cool and started telling me how cool it all was. The highlight was the look on his face after he came down from parasailing.

Once I knew I had him hooked on how much fun Key West was going to be, I knew we were free to do everything else, including visiting museums, spending time at the beach and enjoying some great meals at the amazing Key West restaurants. He got a chance to pet a shark, hold a real gold bar and watch a cat jump through a hoop, all on the same day.

My co-workers thought I was crazy to try to take a teenager on any vacation, much less one to a place that didn’t come with an amusement park attached. I think the only problem that I ran into by taking the family to Key West is now he won’t shut up asking when we can go back. My son wants to spend more time with his family? I’m okay with a problem like that.