The Key West Mystique

Key West Island News


Key West Island News connects Key West residents and friends of the island, fosters our One Human Family culture and advances understanding of shared goals for our island community

Key West winter week

A chilly Key West winter week | Best things to do

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.


Chances are pretty good if you’re in Key West between Christmas and New Year’s you won’t encounter much rain (or snow, come to think of it.) But there are those gloomy days when it’s chilly and windy and just not what you’d planned for your winter escape.

So what does one do during a Key West winter week when it rains or it’s so chilly that you need to get out the fleece? Depends on whether you’re local or visiting. Let’s start with local.

Locals keep doing what they were doing before except they might wear a raincoat, carry an umbrella or replace flip flops with boots. Or not. You can tell locals from visitors because locals aren’t the ones in yellow, see-through ponchos. Locals know better than to step off curbs in flooded streets without boots.

Locals are the ones with the hats, coats and gloves when visitors are in shorts and T-shirts. I mean, we’re freezing and complaining like it’s a Chicago winter — and the temp is 72.

Other than that? Just another day. We go to work, school and errands on bikes and scooters. Keep a change of clothes in a dry bag. Might take a book to work with us since things are almost guaranteed to be slow. Except in the bars where an adult beverage or two and some live music can make for one great afternoon.

Which brings us to visitors. Visitors come down here all prepared for sun, sand, water sports, sunset sails, fishing and a week in paradise. You get rain. Buckets of it for which you are, of course, paying buckets of money.

Key West winter week

9 things to do during a Key West winter week

Conch Train: That sucker keeps on rolling around the island come rain or shine. Ditto the trolleys. Climb aboard and relax for the history tour. And, this time, take the whole thing, not just the first half before the store stop.

Go to the beach: Seriously. Grab some rain gear and an umbrella and wander the deserted sand of Smathers, Higgs, South and Fort Zach. It’s not cold, overcast and rainy makes for a contemplative way to enjoy a cafe con leche along the way. Walk the White Street Pier, too. Same reasons.

Take the kids to the splash pad and playground at Truman Waterfront Park: Kids love splashing in the rain; they’re already wet. (We took our grandson recently in the rain and he had the place to himself.)

Catch a movie at the Tropic Cinema: First-run movies and art films, the best popcorn ever and beer and wine to go with. Make it an afternoon for grownups or bring the kids. The Tropic is an experience you won’t get back home — and who goes to the movies on a sunny vacation day?

Do the history stuff: From Hemingway House to the Key West Butterfly and Nature Conservatory, the Eco Discovery Center, the Shipwreck Museum and the Custom House, these are great places to explore on a rainy day — and the free Duval Loop bus will take you around if you can’t bear to get your hair wet. Just wear a rain coat, pull up the hood and dash for the door. On a rainy day you’ll have time to wander, not just tick off a checklist and split for the next place on the list.

Art galleries: Ditto. See above. And, if you see something you love and have to have? Most of the galleries will ship right to your door back home.

Go sailing: Sure the marketing pictures show clear water and brilliant sun. But a day on the water under cloudy skies and decent winds ensures you see Key West in a different way. Experienced captains won’t take you out if it’s dangerous, so don’t let the rain or cloudy skies stop you. (PS: Same with kayaking.)

Grab some art supplies, some cards or a board game: Nothing says you can’t sit by the pool or on the porch and simply let the hours slip by in casual conversation with friends and family. Oh, and put away the electronics.

Just chill: Sleep a little later. Savor a second cup of coffee. Put on some music or drop into a venue. And know that despite the forecast, the chances are darn good that somewhere today the clouds will break and there will be some sun. It’s Key West.

1 Comment

  1. Esmond G

    I love the image of hats, coats, gloves and complaining like it’s a Chicago winter for the locals at 72*.…


Submit a Comment

Your email address will not be published. Required fields are marked *

This site uses Akismet to reduce spam. Learn how your comment data is processed.

Related Posts

Pin It on Pinterest