The Key West Mystique

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Camping at Fort Jefferson

Key West vacation: What I learned on my 10-day island escape

By Linda Grist Cunningham, editor and proprietor

Linda Grist Cunningham is editor and proprietor of Key West Island News and KeyWestWatch Media LLC. She and her husband, a park ranger at Fort Zach, live in Key West with their Cat 5s.


Well, that was fun. Ranger Ed was off the island the past two weeks, skiing in Utah. I hate the whole idea of sliding breakneck fast down the side of a mountain, in the cold, strapped to two slats about as wide as a Venetian blind. So I did what I haven’t done for 10 years: I took a Key West vacation.

Well, sort of a vacation. Living in Key West and vacationing in Key West aren’t remotely the same. I still had to scoop the Cat 5 litter boxes, clean the house, wash the laundry, go to the grocery store, sweep the garden and take out the trash.

Anyway, back to the point. If you’re working with a 2019 “here’s what to do in Key West” list, you ought to toss it, because you’re going to find Key West vacation planning has changed since our Covid-19 lock down ended June 1, 2020. Without an updated list, you might find yourself mightily disappointed.

What’s a Key West vacation like now?

Spontaneous is out. Reservations are in

Don’t even think of arriving on the island with the idea you can decide once you get here what you want to do.

Especially if your top 10 list includes things like taking the Key West Express to Fort Jefferson in the Dry Tortugas. Right now, May is the earliest you can grab a seat. (Although, I did find two seats for March 11; someone must have canceled.) Think you can just book a charter flight if the ferry is sold out? Nah. One not even taking reservations again until April 28.

Key West vacation Ranger Ed Jefferson
Key West vacation: Make reservations at least six months ahead if you want to camp at Fort Jefferson.

If you want to camp at Fort Jefferson, plan six months to a year in advance. If you’re local and flexible, you might luck out. I grabbed three nights for four people in mid-June (the perfect time) because there’d been a cancellation right before I called. I’m still grinning about that.

Even the ubiquitous sunset sails, snorkeling trips, dolphin watches and kayaking are best done with reservations. You might grab one at the last minute, but if you’re particular about your ship, have a group bigger than two or are committed to a specific day, don’t wait.

Same with Key West’s iconic restaurants, especially the ones with cloth napkins and water views. Reservations are a must for lunch and dinner and some are booked deep into May. You might find a breakfast slot or maybe a 9 p.m., dinner spot in April, but for tonight? Options will be limited.

You’ll need tickets in hand for things like theater performances, events at the Truman Waterfront Park Amphitheater and concerts. Many sell out days, if not weeks, in advance, so getting tickets after you arrive can be dicey.

Expect to wait

Not everything requires reservations, of course; some places don’t take them; and, even with them, lines can be, shall we say, long.

Key West has long had lines at popular places, especially in season. Since Covid-19, season stretches through the entire year and hundreds of thousands of visitors with few other places to go for a tropical vacation descended on Key West. That means waiting in line for pretty much everything from a happy hour drink at the bar to wandering through museums and galleries.

It doesn’t help matters that the whole island is short-staffed. Everything takes longer. Staff are often covering for vacancies (or for the Covid sick during the spikes). There simply are not enough workers to ensure consistent, top-notch service. No one is deliberately trying to make your vacation unpleasant.

Keep your groups small

This applied before Covid and it’s more important now. Pretty much nowhere in Key West easily accommodates groups with more than six and that’s often a stretch. Ditto if you have kids under 18 along. Heading out for dinner with you and a dozen of your friends without reservations? Plus two emotional support dogs and three strollers and the three toddlers? Just don’t.

Would I do it again?

But the most important thing I learned? A Key West vacation stays on the to-do list. Because the best thing one can do in Key West is sit on a bench on the White Street Pier and watch the shifting water and sky dance toward the horizon. Even if one must occasionally overlook the early morning “this is our bench” crowd.

Want to plan your Key West vacation? These links can get you started


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