Key West Keeps Calling Me Back

I’m really not someone who likes to return to a vacation spot time and again. Although I can certainly understand the attraction of predictability with restaurants, accommodations, and attractions, I’m typically more into the thrill of first-time discovery.

The exception to that rule, at least for me, seems to be Key West.


Last summer, Angela and I returned to the Conch Republic for the fourth time as a couple. We had visited twice before during cruise stops and once before during our first big dive trip with the boys. This time we returned to the island to acquire our Advanced Open Water diving certifications. And it didn’t hurt that Angela found a super cheap flight so we could avoid the 17-hour drive on this trip.

I had already visited Key West four times during my youth. But those were mostly blurry, drunken affairs that ended with regrettable consequences unworthy of mention here. Save one, which I will perhaps share in a later post …

While the youngster in me once enjoyed the debauchery of Key West, the middle-aged man has learned to appreciate the culture, the cuisine, and the very tangible curiosity that exists in this fiercely independent town.


My first-ever pedicab ride

It was my first time flying into Key West, which is a breathtaking experience in itself. Being without a car and wanting to take advantage of the the easy walkability of the island, we stayed on the quieter end of Duval Street at the Avalon Bed and Breakfast. It is far enough removed from the cruise port and tourist bars to be blissfully calm at night, yet close enough to walk if you feel like tying one on. The accommodations were clean and charming, the staff were friendly, and the breakfast was citrus perfection, served in the cozy dining space or on the welcoming front porch.


Avalon also hosts an afternoon cookie break, with a delectable assortment of free freshly-baked cookies and happy hour deals on beer and wine. The perfect option for bridging the gap between beach drinking and dinner drinking.

Even bad weather can be spectacular in Key West. A late evening thunderstorm rolled by the island, just as the last of the sunset glow was disappearing beneath the gulf. Angela and I braved the quickening wind and walked to the end of the pier at the Southernmost Beach Resort. The storm raged just a few miles off coast, and the lightning was fantastic, crackling between clouds and striking the tops of white-crested waves.

For our Advanced Open Water (AOW) diving certification, we enlisted the expertise of the Captain’s Corner Dive Center. In an upcoming post, you can read all about those amazing dives, which included a wreck dive to the U.S.S. Vandenberg.


An American flag adorns the wreck site of the U.S.S. Vandenberg

This trip makes my eighth time visiting Key West, a vacation destination record for me. And, according to the locals with whom I shared that knowledge, a number that would almost certainly guarantee I would pull up roots in Tennessee and stay on the island forever. A prediction that sounded a bit like the Eagles song, Hotel California.

But those locals didn’t know that I was already searching the world over for the place I would next call home. You’ve certainly got some stiff competition, Key West. And yet, while writing this, I still feel the powerful pull of this most magical place.


Since we will inevitably return to Key West in the near future, Angela and I are already planning the trip. On our short list, Angela wants to visit the Key West Tropical Forest & Botanical Garden and the Key West Butterfly & Nature Conservancy, while I’m all about getting to the Dry Tortugas for both the history and the epic snorkeling.

There are also some incredible Key West restaurants we’d love to visit again. Check our next post for details on these amazing meals!