Bargain Shopping For Summer in Key West

My husband jokes that I could be the star of my own reality show regarding the lengths I go to when it comes to saving money. But he certainly appreciates when we take all that money I save us and spend it on a destination vacation. Of course, me being me, I can’t book us a trip without making sure we’re saving money in the process. That’s why we’ve been going to Key West for our summer vacation the last few years.

Part of the reason we manage to save so much money on the trip is because a lot of people seem to think like our friends do: “Isn’t it hot there in the summer?” Well, yes and no. I mean it’s summer, so it’s hot everywhere, but Key West is actually cooler, by as much as ten degrees or more, than most of Florida, including many of the destination vacation spots. Plus, it’s cooler in a lot of other ways.

There is no place quite like Key West. If we want to spend an action packed day doing all sorts of activities, we can, and we can just as easily spend a quiet day walking the streets looking at the old houses or sitting by the pool with a book. The good thing about people thinking it’s too hot to visit means that rates are lower and lines are shorter, so not only do we save money over what that trip would cost us in February, we also get to enjoy more of it by not having to worry about crowds.

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Pomp And Circumstance And Sunset in Key West, Florida

My son is graduating from college this spring, and he is fortunate enough to have a job waiting for him almost immediately after graduating. When he started interviewing, I told him to tell his prospective employers that he would need a couple of weeks between school and the real world. He thought it was so he could move. I knew it was so he could go to Key West.

I wanted to give him a graduation present that was something special and long lasting. I know that a vacation may not sound like something that lasts more than a week, but I knew that spending time in Key West, Florida would give him memories that would last a lifetime. I knew some of it was my own projection and remembering the effect it had on me when I first went there. I’m sure some of the Key West restaurants are different but I bet the seafood is just as fresh, the water is just as blue and the sunset is just as beautiful.

Of course, I want to make sure he has the chance to make those memories on his own, so that is why his mother and I will only be there for the first half of the trip. Besides, I’m sure some things have not changed about Key West, and a young man of 22 will find it a lot easier to have fun and enjoy his tropical island vacation if he knows his parents aren’t right around the corner. I just hope he doesn’t fall too much in love with the island and forget to come home for his new job.

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.

Seeing The World On One Small Island Called Key West

I would love to be able to see the world. Unfortunately, my boss doesn’t see that happening anytime soon, and if he fired me so I’d have the time, it would severely limit the money I had. A few years ago, I discovered the next best thing. If I couldn’t see all of the world, then I would go somewhere that a lot of the world has seen: Key West, Florida.

Key West has a recorded history that goes back almost five centuries, meaning that when the United States finally became a country, people had been calling Key West home for 150 years. These people first were the explorers from Europe, followed by fisherman and sailors from New England and the Bahamas, sponge divers from Italy, cigar makers from Cuba, and artists, musicians, writers and chefs from all around the globe.

This influence can be seen on every block, and each time I go back, I try to discover a little more of it. There are walking tours that point out the architecture, museums that celebrate the various influences, brightly colored paintings hanging in the galleries, and so many Key West restaurants with menus that make you think you’ve visited a hundred different places.

Before I go, I decide what I want to explore when I get there, and by the time I’m done, I have several new ideas for my next trip. At the rate I’m going, I’m going to have to quit my job just so I have time to get it all done in my lifetime.

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.

Planning A Summer South Florida Vacation to Key West, Florida

The good thing about having kids that are actively involved with their school is that it keeps them occupied. The bad thing is that it makes it hard to plan a vacation during one of their vacations. We were hoping to visit Florida this year, but we couldn’t pull it off during spring break and I figured the summer would be too hot. Certainly it would be cheaper and less crowded, but would that make up for the heat?

My husband started doing some investigating and discovered that if we went farther south, it might actually be a little bit cooler. Key West may be the southernmost city in the country, but thanks to its location and the trade winds that are usually blowing, it is one of the cooler spots in all of Florida. Of course, weather isn’t the only consideration, so I decided to look into how family friendly a vacation it would be.

Turns out we might not even be able to fit everything in. We decided to fly in and out of Miami and spend the first couple of days on the mainland before heading down. Now that I’m seeing everything that we could possibly do – swimming with dolphins, camping overnight at a National Park 70 miles from the nearest island, jet skiing, parasailing – we might just skip the mainland all together. We have plenty of time to make up our minds, but if the kids are half as excited as we are about going to Key West, that may be the only stop we make this summer.

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!