Key West is such a cool city. Yes, it’s a city, it’s a small town, it’s its own republic. When you complete the Miami to Key West drive you are rewarded with one of the most beautiful communities in Florida. Yes, we love our lots of other Florida towns, like Saint Augustine, but Key West is equally beautiful in a different way. These are our picks for the most iconic things to do in Key West on a short trip.
While Key West was used by shippers and smugglers for a long time and shifted control over the years, the city wasn’t plotted or built up until the 1820s. Much of the iconic architecture was built in the 1880s and after. It’s a beautiful city to tour on foot, and if you don’t have a lot of time, just a weekend is plenty for all of these fun things to do.
We’ve picked what we think are the most iconic activities, for their cultural, Keys-ness and enjoyment factors. Add a few of these great things to do in Key West to your and you’ll have great memories for years to come. PS: if you’re traveling as a family, we have more recommendations for fun things to do with kids in Key West too! If you have any additional questions, send us a note and we’ll help you out as best and as quickly as possible!
Our 10 Picks for Iconic Key West Things to Do
Everyone has their favorite activities and sights to see that they think are iconic Key West, and so do we. No, the Southernmost Point buoy ISN’T on our like (seriously) but we have some other great activities and places to visit that truly capture the spirit of being in the Florida Keys and enjoying your time in Key West.
Bucket List: Dry Tortugas National Park
This is one of our absolute favorite things to do in Key West, and the journey itself is iconic. Taking the ferry out to Dry Tortugas National Park (a whole day adventure) and spending hours exploring old Fort Jefferson, snorkeling around the moat wall and walking the beaches is incredible. You need to read all about it to understand what a unique thing to do this trip is. If there’s one thing that is BUCKET LIST of Florida, and not just the Keys, it’s this adventure to one of the most remote National Parks in the USA!
Sand Bar Adventure Charter
Of all the tours we’ve done in all the places we’ve been, going out through the sandbars and mangrove islands with Island to Island Charters or Lazy Dog Adventures has been our favorite. Spending the day exploring the backwaters of Key West with the coolest captains is just remarkable. You get to swim and snorkel, see sharks and spotted eagle rays, and then, of course, hang out with dolphins if they’re around. It’s all amazing and all based on what sort of activities your family is interested in.
Hands down, this is the BEST experience for any family in the Florida Keys (and no, we get no commission from saying so.) If you’re visiting with another small family, this can be cost-effective if you can split it together!
Visit the Hemingway House Museum
The Hemingway House and Museum is on every list I make activities in the Keys, and when it comes to being iconic in Key West, this is it. Ernest Hemingway is such a part of Key West culture, and the polydactyl cats are such an attraction that you have to visit. The house is cool, the photos and the stories are just what you expect to hear, and the vibe on the property is very Hemingway. I love it and always recommend visiting this Key West icon.
Ride the Conch Trail (tour)
One of the best things to do in Key West is to ride the Conch Train. Operated by Historic Tours of America (they do one in Saint Augustine too!) it’s a comprehensive tour of the historic old town and neighborhoods of KW. You get to hear stories of the city, see some of the most famous sights in Key West (like the Southernmost Point), and you can get on and off in several places around town.
The Conch Train tour lasts about 75 minutes and covers a lot of ground. The best place to catch it is near Mallory Square and the KW Aquarium. For the many tours we’ve done in many cities across the USA, the Conch Train is my favorite.
Book the Conch Train Tour here!
Eco-tour to Key West National Wildlife Refuge
Eco-tourism is becoming increasingly important as more and more people travel to new places. Add a jaunt with either Key West Ecotours or with Honest Ecotours to your Florida Keys road trip. We really like Honest Ecotours for a few reasons:
- The naturalists are well educated and deeply care
- The Java Cat is small and agile (Key West Eco tours) or Honest Eco’s boat, the Squid, is fully eco-friendly (including solar power)
- The tour route and snorkeling is awesome
- Dolphins are HIGHLY likely
Honest Eco and Key West Ecotours really do a wonderful job with kids and adults alike. They provide healthy, fresh snacks and are well prepared for even inclement weather days. Honest Eco also does sunset cruises (we did a Pride sailing) and private voyages.
Explore the Historic Key West Town
The cheapest thing to do in Key West is to wander the historic town area. It’s beautiful and there are chickens everywhere. Parking downtown is a little expensive, but it’s worth it for the time you save and the ease of finding a spot. Once parked, enjoy the Mallory Square area, then walk through the Truman White House complex towards the Key West Lighthouse.
Stop into Ernest Hemmingway’s House (and museum) and then enjoy a stroll past banyan trees and historic homes as you make your way to First Flight (brewery and restaurant) where the first PanAm Airways office was. Visit the Audubon House and Tropical Gardens, hit up a few museums in the historic quarter and you’re done.
There are tons of wonderful stops to make along the way, and lots of key lime pie and martinis to enjoy as well. Walking Key West on foot is a great all day or afternoon activity and it’s the best way to see the city at your own pace.
Book a Private Guided Walking Tour!
The Vintage Key West Aquarium
I’ll admit that the admission to the very small Key West Aquarium might not seem worth it initially, but it’s such a cool place. The interior feels like you’ve stepped onto Captain Nemo’s Nautilus, and the sharks in the middle of the aquarium are really cool.
Being a very old attraction, some of the features and design look like they’re from another time… which they are. It’s all very vintage. Pop outside for a wonderful living mangrove exhibit and enjoy the view from above. This is great with kids, but if you’re looking to take a break from the sun AND want to do a little learning about the wildlife in the Florida Keys, this is a great spot!
Night Kayaking in Key West
We do a lot of kayaking tours and paddling on our own, but Night Kayaking KW is a must-do, experienced kayaker or not. Heading through the mangrove tunnels and shallow coves around KW, Night Kayaking gives you a totally new view of nature.
The kayaks have a plexiglass bottom and are outfitted with LED lights to see underwater. We saw sharks, lobsters, tarpon, sea hares and more. It was really a memorable experience and one of the most unique things to do in KW.
Visit the Key West Lighthouse
I am such a sucker for lighthouses and the KW Lighthouse is one of the prettiest. It’s one of the best things to do in Key West both as a sight and as a unique activity.
There is a museum on sight about Key West’s nautical history, and then you can climb the lighthouse tower as well. I love it! You’ll also find some great lighthouse exhibits, a gigantic banyan tree and more. Spending an hour or two here is one of the best things to do in Key West!
Beaches in Key West
As I mentioned before, there aren’t a ton of beaches in the Florida Keys to visit on your road trip, but Key West has a few beach spots. The following are the easiest beaches to access with the best surroundings. They aren’t all-natural, so it’s a mixed bag when it comes to sand and obstacles, but they serve the purpose of cooling off and relaxing when you visit KW.
These are the best beaches IN Key West for relaxing or swimming:
- Rest Beach / Higgs Beach – right next to each other, south end of Key West
- Fort Zachary Taylor State Park – good beach for relaxing and snorkeling
- Smathers Beach – southeastern end
If you spend time at Rest Beach, there is a really cool pier that goes pretty far out into the water. The views are beautiful and there’s a fair amount of wildlife living along the pier structure. Check it out!
Doing a Florida Keys road trip isn’t typically a beach trip, but it’s all about the culture and other natural sights. Enjoy what you like, but we don’t recommend the Keys if you truly want a beach destination.
More Fun Things to do in Key West
Key West is many people’s favorite destination in the Florida Keys. You can’t blame them; there are so many wonderful things to do, historic sites, so much wildlife and great food. If you know you’re coming to Key West and need some ideas to add to your itinerary or travel plan, take a look at some of our favorite things to do. You can always just play it by ear, walking from neighborhood to neighborhood, but I like to always have at least a loose plan.
Where to Stay in Key West
If you haven’t planned where to stay in Key West yet, of course we have recommendations. We’ve stayed many place, from luxury resorts to family friendly hotels, cute stays in the historic center to spacious condos on the end of town. There’s the right type of accommodation for any type of traveler in Key West. Keep in mind that with so many things to do and beautiful places to just explore on foot, you may not have a ton of time in your hotel room, so you might not need a ton of space and lots of amenities. Also, Key West is pretty costly for accommodations. As you look for where to stay, balance out your budget by considering hotels that AREN’T directly downtown.
Here are some of our recommendations for where to stay in Key West. We’ll keep adding to this list as we enjoy more wonderful hotels and resorts.
This is just a quick hits list of the best thing to do in Key West. Really, you can easily spend a whole week in Key West and have a different adventure every day. Be sure to check out our other Florida Keys travel ideas. We spend so much time in the Keys that we always have more to share. Please be sure to leave a comment or send us a note if you have any additional tips or questions about Key West and the rest of the islands!
