I love spending time in the Florida Keys and for so many people it’s something they have only dreamed of. We were chatting in our household and put together a list of the most frequently asked questions about planning a trip to the Florida Keys, including where to stay, things to do, and when to visit. If we’ve missed a question, please tell us, but I think this is a solid place to start when it comes to understanding the adventure ahead.
What’s Surprising about the Florida Keys?
And let’s be honest, some visitors may be disappointed by the level of development and commercialization in some areas of the Keys, as it may not align with their expectations of a “tropical paradise.” However, because the Florida Keys are an actual living community there is a unique culture. Pair that with beautiful natural surroundings and abundant recreational opportunities more than make up for any minor inconveniences. I think a lot of people who come down to the Keys are expecting it to be just a bunch of coconut shacks and old boat captains. Not the case. There aren’t a lot of towns in the Florida Keys, but there are lots of communities.
Something else that surprises a lot of first time visitors to the Florida Keys is how few beaches there are. When you look at a map, you see this epic island chain surrounded by nearly imaginary turquoise waters. Surely this must be a beach-goer’s paradise. Not hardly. Yes, there are some beaches, but most of them are either manmade or only have the smallest amount of sand. Florida Keys beaches typically are areas of water access, often with a grassy flat just ahead of the shorebreak or just tons of rocks and old coral. There are a few really good, sandy beaches in the Florida Keys, but they are few and far between.
One last thing that surprises people when they come down here is how boat-centered visiting the Florida Keys is. That doesn’t mean that you have to show up with your own boat, but that you can rent boats or charter every type of on-the-water activity from Key Largo to Key West. Want to enjoy a nice swim? Charter a sandbar boat trip. Want to go fishing? Charter a fishing trip or rent a boat to get yourself into the right waters. In the mood for wine and sunset? Jump on one of the many catamarans to watch the sun go down. Boating is central to visiting the Florida Keys.
When is the best time to visit the Florida Keys?
Having brought family and friends to the Florida Keys in each season, I will say that springtime is my absolute favorite time down here for myriad reasons. If you’ve been to the Florida Keys in summer, you know that it feels like you’re in hell and that Satan left the steamy shower going. I love the humidity but even I struggle to find happiness here in July and August.
Winter in the Keys is nice and it’s much cooler, but also there are random cold days that make things like snorkeling or fishing not quite as enjoyable. I remember one time in December we were out with our kids on the Squid (Honest Eco Tours) and were doing a snorkeling trip in the Key West National Wildlife Refuge, and we wore wetsuits but were still too cold to snorkel. You have to think about both the air and the water being cold, so depending on the sort of activities you plan on doing, either of those factors can impact you.
Fall temperatures are great, but this is also peak time for hurricanes (see below). I don’t like to risk storms, so I typically discourage visiting in September and October, but this is also when you can get some of the best deals because of how people like me think. Ultimately, spring is the best time to visit because it’s perfectly warm, the water is warm, the birds are mid-migration and if you can plan between local spring breaks, you can find some good hotel deals.
Is it okay to visit in Hurricane Season?
While fall can be nice because it’s starting to cool off in the Keys, it’s also still prime hurricane season. The Atlantic Hurricane Season runs from June 1 to November 30, and while that doesn’t mean there are storms constantly, this is the time that a hurricane is more likely. Modern weather tracking means that there is ample time to get out of the Keys if there’s a storm approaching, but because a lot of people have been conditioned to not worry about each potential storm, sometimes the traffic on the Overseas Highway is horrifying and that delays evacuating.
So should you NOT visit the Florida Keys in hurricane season? No, it’s still fine, but you just need to be aware of the storm reports (I like to check NOAA every few days) and be ready to change your plans. I recommend travel insurance if you’re feeling like it’s a bit risky, but like I said, the chances of actually being in the Keys when a named storm comes through are very unlikely.
What is the weather like in the Florida Keys?
The daily weather in the Florida Keys is pretty wonderful, even when it’s the blazing summer. You’ve typically got a nice breeze keeping things a bit cool out on the water or at the beach, and at least once a day a little cloud cover rolls through, often doing a short downpour that helps cool things off. The sunniest, clearest weather is typically in March or April before the summer storms start their daily cycles, but you can also get some gorgeous, clear days in the winter. The trick to enjoying the weather in the Florida Keys is to plan for rain and then be delighted if it misses you.
How long should I plan to stay in the Florida Keys?
The length of a Florida Keys trip is going to vary for everyone depending on their budget and travel style. Some people like to come down for two weeks and spend a lot of time fishing or just relaxing. Others like to do all the touristy or adventuresome activities and wear themselves out after about five days. I think a 5-8 day trip through the Keys is just perfect, but again, it depends on what you want to do during your visit.
If you’re planning on a Key West vacation vs doing the whole of the Florida Keys, 3-5 days is ideal. There is so much to do and see in the town, and then if you want to enjoy time on the water as well, you should be able to do Key West in less than a week.
How do I get around the Florida Keys?
You know, there aren’t a ton of options for getting around in the Florida Keys. When you’re in Key West there are lots of taxis and Ubers, and you can easily bike everywhere, but in general you cannot easily hop on public transit or enjoy a day trip from Key Largo to Marathon. You do need to have your own car. There are some services, such as Freebee and Conch Connect (both are ride-share apps), that make it easy to not have to drive within a destination, but in general going between towns requires personal transportation.
You can take the Greyhound Bus from Miami to Key West (stops along the way) if you like (less than $30 one way), but this is really only an option if you’re car-free and plan on having a trip based in one area.
Note: in emergencies (hurricane evacuation) there are services to get people out of the Keys, but again, they’re limited and time is of the essence.
Biking the Overseas Highway is very popular for the hardcore road cyclist. I haven’t done this myself, but I have ridden on the same trail that mimics the highway route and it’s pretty easy (level). If you’re biking in the Florida Keys you need to keep in mind the heat and humidity to ensure you have a safe bike trip, and plan your travel days so that you can arrive safely each evening.
What are the best places to stay in the Florida Keys?
When I’m helping friends plan trips to the Florida Keys, I usually recommend splitting the time between two or three destinations. Key Largo is a great place for a first and last night if you’re doing a road trip from Florida or Georgia, but it’s also a good 2-3 night destination. Islamorada is my favorite part of the Keys to stay for a relaxing trip. I like that staying here provides both active opportunities and plenty of resorts that are all about relaxation. Islamorada also has some of my favorite restaurants and cocktail spots in the Keys.
Top Upper Keys picks: Baker’s Cay Resort OR Casa Morada Resort (favorite!)
Marathon is another destination that’s good for 2-3 nights. I consider Marathon and Grassy Key as the quiet part of the Florida Keys. Whether you’re checking into the Faro Blanco for a spa trip with afternoon pool sessions or if you’re looking to kayak through the quiet mangroves at the north end of Marathon, you can plan a stay here that varies the pace each day.
Top Middle Keys picks: Faro Blanco Resort OR Grassy Flats Resort OR Hawks Cay Resort
Key West can totally be its own trip or a part of a bigger Keys vacation. More than 5 days in Key West is too much for me because I love being in the Middle Keys so much, but in general, a 5 day stretch in Key West offers you plenty of time to explore the town, do tours through the backwaters and wildlife refuge, and even make it out to Dry Tortugas National Park. 5 days is the perfect Key West vacation length.
Top picks in Key West: either the Perry Hotel and Marina OR Hotel Laureate
What are the best activities in the Florida Keys?
I love wildlife so much, and the wildlife of the Florida Keys is some of my favorite in the USA. Going from Key Largo, Marathon and Key West, you’ll find countless opportunities to be on boats for wildlife watching, dolphin cruises, snorkeling trips, and birdwatching with a naturalist. Snorkeling and kayaking tours in the Lower Keys and Key West are, I think, the absolute best way to experience the magic of the Florida Keys. Kayaking at Geiger Key is amazing!
When you’re in Key West, there are tons of museums to visit, and most are pretty interesting. If you’re a Hemingway fan, touring his home and enjoying the Hemingway Social Club are both fun things to do. If you like history, there are ghost tours and guided walks that will tell the story of Key West, from founding to today. There’s never a dull moment or lack of things to do in KW.
In the Middle and Upper Keys, it’s all about the fishing, snorkeling and kayaking. There are quite a few marinas to launch from on each island so you’re never far from fun. With several state parks in the Keys, kayaking and SUP are favorite activities, and there are plenty of tour or rental opportunities if you’re not traveling with your own gear.
What are the best beaches in the Florida Keys?
This is like asking “Where is the best sushi in Omaha?” Yes, there are beaches but they aren’t epic like the rest of Florida. There are a few nice spots though and you can easily plan some time to lay out as you make your way through the Keys. Here are our picks:
- Pennekamp State Park – big enough beach to enjoy, good swimming
- Harry Harris Beach Park – it’s a good park and there is a calm swimming area, but it’s not epic or beautiful
- Sombrero Beach or Coco Plum Beach – I think these are the two best beaches in the Florida Keys
- Long Key State Park – there are rocks but also plenty of waterfront areas to enjoy the view
- Bahia Honda State Park – there are a few different beach spots here, but the current can be really strong if you’re looking to swim
- Key West’s Smather’s Beach or Higgs Beach – these are both pretty okay beaches with good swimming
- Fort Zachary Taylor State Park – this is our preferred Key West beach
If you’re looking for a Florida Beach vacation, I would aim for Fort Myers Beach, Sanibel, Longboat Key or Madeira Beach, and then once you go north around the Big Bend, you’ll have endless Florida beach opportunities.
What are the top attractions to visit in the Florida Keys?
If I had to pick the two top attractions in the Florida Keys I would assign Key West’s old town and the underwater reef system. Key West is such a wonderful, unique city and it’s so much fun to explore or relax in. No matter how much time we spend here, we still love it and never tire of the Key West life. From the famous Conch Train Tour to the Key West Lighthouse, there are attractions here that suit any number of interests. You can learn so much… or just walk around trying cocktails. Do your thing!
When it comes to the reef system that borders the Caribbean side of the Florida Keys, it’s absolutely amazing. The snorkeling at Sombrero Reef and Molasses Reef is some of my favorite. Stretching to Key West, the protection the reefs offer to the Key West National Wildlife Refuge make it an immensely beautiful and unique place to observe wildlife. Without the reefs, the Keys wouldn’t be as magical and beautiful as they are.
How can I save money on my Florida Keys vacation?
One of the most common complaints about visiting the Florida Keys is the cost of accommodations and activities. The Florida Keys is a popular tourist destination, and as such, prices for hotels, restaurants, and attractions can be quite high. Visitors may also find that some areas of the Florida Keys can become overcrowded during peak travel seasons, which can detract from the overall experience. It’s true, but it doesn’t have to ruin your trip!
If you’re okay traveling outside of peak season (including visiting during summer) you can save quite a bit on accommodations. While tourist attractions and activities don’t tend to fluctuate their prices, hotels and resorts do. If you keep your eyes peeled on the different properties or destinations in the Keys that you’re most interested in, when they offer deals on stays or if you see a price drop, book it and then plan your Florida Keys trip around the deal you find.
I hope this is helpful as you work on planning your trip to the Florida Keys. It’s a very special destination, but it does take some research and planning to put together just the perfect trip for you and your travel buddies. If you have any questions about planning or activities, please send us a note or leave a comment. We’re always happy to share more and help YOU plan a wonderful trip to explore the Keys!
