Not a fan of the cold? Prefer to chase summer year-round like me? Consider Key West as a winter vacation destination in 2024 than!
Key West is much more than just an endless Happy Hour where it’s always “5 o’clock somewhere”! There’s a ton of rich history, beautiful nature, and even a couple of National Parks! This Key West Winter Vacation Guide will give you a full list of best things to see and do, as well as how to plan your logistics!
Covid Disclaimer: If you choose to travel, please do so responsibly and safely. The Florida Keys currently has a mandatory mask rule in place, and encourages social distancing and frequent hand washing.
Disclaimer: This post is in collaboration with Hotels.com, however all writing and opinions are my own!
The Florida Keys have over 800 keys stretching over 180 miles! Key West is the most populated key, and also furthest south key, which means it takes quite a while to reach it.
Not to worry though, it’s a beautiful drive across over 40 bridges! You’ll definitely want to leave as early as possible in the morning to avoid traffic, and plan a couple rest stops!
Getting there is easy because it’s a straight shot from South Florida’s mainland. If you’re already in Florida, just keep driving south on I-95 or the Turnpike, and it will eventually turn into the road to Key West.
If you’re flying in from a farther location, you can actually fly straight into Key West International Airport! Or if it’s cheaper, you can fly into Miami International, rent a car, and drive about 4-5 hours to get there.
Most of the hotels are located in the Historic District. As you can probably guess, that’s where pretty much everything is going on, so it’s the perfect place to stay! Hotels book up very quickly though, so try to grab something as soon as you can!
If you want something a little quieter and cheaper, you could consider staying in New Town or near the airport. However, since there’s a good chance you’ll be drinking, and cabs are expensive, you might as well pay extra to stay in the Historic District!
From activities to photo spots, here are all of the best things to see and do in Key West!
Arguably the most famous street in The Keys and notorious for it’s many bars and pubs! When you go to Key West, you will definitely be spending a lot of time on Duval Street!
Meander into smaller lesser-known venues, or check out one of the most famous ones, like Sloppy Joe’s! OR! You can even do a Pub Crawl tour, sometimes with ghosts involved!
In case it’s not obvious, Key West is the southernmost city in the U.S.! It’s actually so far south, that it’s closer to Cuba than it is to Miami! To commemorate this feat, there is a massive Southernmost Point marker at the very tip of the island that is a must for photos!
Ernest Hemmingway was a huge fan of Cuba, and thus Key West as well! Therefore it’s no surprise that he had a house there, which you can visit today as a museum! It’s said that the house is also home to several cats!
Since you are at the southernmost tip of Florida, you have the advantage of seeing both the sunrise, and the sunset! And nothing is more beautiful than a sunset over tropical waters! Take a sunset sail cruise one of your nights on the gorgeous island, and prepare yourself, because most of them are all-you-can-drink!
In the morning or afternoon, either head to the beach or book a boat tour to one of the many coral reefs around the island!
There are tons of natural coral reefs, and also artificial ones created by the many sunken ships!
Did you know that Key West is known to be haunted? Whether it’s because of the many shipwrecks right off the coast, or the indigenous Indians that were driven out by Spaniards, you’ll definitely feel spooked if you take a Ghost Tour!
One is also a “Ghost Tour and Pub Crawl” and will take you to the most eerie bars in Old Town, located in two haunted mansions, and a repurposed morgue. Eek!
You can’t go to Keys without trying Key Lime Pie! And Ohhhhh how delicious it is! You can find it at almost any restaurant or you can seek out the places with the best reviews!
There’s Key West Key Lime Pie Co., Kermit’s Key West Key Lime Shoppe (with vegan pies!), and Key Lime Bakery!
Did you know that there is a National Park off the coast of Key West? It’s called Dry Torugas National Park, and it’s about 67 miles south, so would require an entire day to see it.
Here is where the U.S. benefited from a natural defense barrier against smugglers, pirates, and invaders. In fact, it is said that at least one ship would wreck here per week due to the coral reefs!
Now of course it is an ideal place to snorkel and scuba dive, and definitely worth the adventure if you have time!
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Thank you for sharing this amazing piece of content with us. I reach out to this post after many hours of research on the web to find where can I stay in Key West This Winter and this valuable post save me a lot of research.
I just Have a question if it is safe to spend this winter out there this year because of Covid-19.
thanks in advance for your help.
Aw I'm glad it can help!! To be honest, I think everywhere is a bit risky for covid right now in the U.S., however Key West has a mandatory mask rule, so I think that will help a lot to keep everyone safe :) Maybe I will see you there, we are going in December as well!
I think this Winter I will only read about the vacations... Thank you for the informative post.
Haha sounds like a great idea!
Thank You for the article, I was badly looking for the winter vacation since I'm fed-up with this covid issue. But do you think it's possible to travel in December? How about visa procedure since I have to travel from UK?
Hello! I'm not familiar with the current rules in UK, I thought it went back in lockdown, so I'm not sure if they are allowing citizens to leave, or maybe if there would be a problem coming back in? I do know that there's an enhanced, and thus much longer process for visas to enter the US right now as a foreigner :/ To be honest, it would be easier to do a vacation in Mexico!