The Florida Keys is one of the best (and only) trips you can take to a tropical island by car from the continental US. With roughly 1700 islands making up this archipelago off of the US, there is no shortage of fun adventures to have, both on land and in the ocean! Keep reading for the ultimate Florida Keys travel guide, from Key Largo down to Key West!
The Keys are split into a few main areas, with multiple islands often making up each “region.” Each island has its own unique experience, so it’s best to see the Keys over a few days (at least). Many people forego the upper keys and head straight to Key West, but you could be missing an experience or memory that could be the highlight of your trip! For this guide, we’re going to go through the Florida Keys as if you were driving on your own road trip!
Hey there! Some of the links in this post may be affiliate links. This means I make a small commission if you make a purchase, at no cost to you, which helps support the blog and guides for you in the future!
On your drive from mainland Florida, the first island that you will come to will be Key Largo. This Key is known as the “Diving Capital of the World” and is a great spot for some underwater adventures!
Activities in key largo
Key Largo is home to numerous dive shops, as is expected with a reputation like that! Try your hand at getting dive certified (if you’re not already) or go on an exciting reef dive adventure. Not up for a dive adventure? Check out John Pennycamp for an underwater sculpture and coral park! Its a great way to get under the water and experience the magic of the sea without having a dive certification!
where to eat
After your long day of exploring in the ocean, you’ll probably be hungry! Here’s 3 great spots in Key Largo to check out for a great meal:
- This resort and marina is going to be the first resort you pass right when pulling into the Keys. They have fun beachside tables, tiki bars, and the BEST piña colada I’ve ever had. Don’t be surprised if parking fills up right before sunset, it’s a great spot to watch the sunset while you sip on your Pina colada and snack on a delicious Mahi grilled cheese!
- Mrs. Mac’s Kitchen
- This little diner has been around for ages, and is your old time-y diner with great comfort food and a delicious breakfast! There are two locations, make sure to go to the original (on the right side of the road if you’re heading south on US1). They’ve got a great champagne breakfast deal, if you order any of their specials your Mimosa (with fresh squeezed orange juice) is complimentary, or just $2 with any other breakfast meal! Definitely a steal and the fun, family-ran type place that you won’t find at the big resorts.
- Alabama Jack’s
- While a little off the beaten path, this roadside dive bar and restaurant has some delicious conch fritters and rum punch! You’ll have to drive down a toll road to get there, but once at the restaurant, try and sit by the water - you’re likely to see tons of manatees swim by! Not only is their rum punch incredible, try their Bloody Mary! It’s small but packs a flavor blast that I was not expecting from a little spot on the side of the road! While you’re there, look out for a big American Bulldog named Blue - he’s got his own seat at the bar and is a regular!
A couple days in Key Largo mean you’ll need a place to stay during your Florida Keys trip, and Drift Hotel is one that is budget friendly while offering a bit more luxury than your typical budget spot. A modern, waterfront hotel with paddle board and kayak rentals, bikes to cruise Key Largo on, and the cutest rooms for a comfortable stay - you can’t beat a little spot like Drift Hotel and is where I would have stayed if I wasn’t onboard a boat! You can book your stay here!
Once you leave the main island of Key Largo, Tavernier is the next little part of the Florida Keys that you will come across. I believe it is still considered to be part of Key Largo but definitely feels like a separate area! It’s a super small island, and seems to be pretty residential, but I’ve still got two recommendations for you!
Harry Harris Park is one of the places that you can swim right off the beach. There is a little tidal lagoon that makes for a calm swimming area when the tide is up! There is a $5 entrance per person, but there are volleyball courts, picnic tables, the lagoon, and a great family environment and a fun place to relax!
While we didn’t eat on Tavernier, my parents actually lived in the Keys for four years and were raving about the Sunrise Cuban Market! My mom recommends the roasted Cuban chicken, while my dad says they have the best Cuban sandwich in all of the Keys! Unfortunately, I’m not a meat eater, so if you try either of these, you’ve got to let me know if they really are the best of the Keys!
Islamorada is best known as the sport fishing capital of the world, but if you’re not a fisherman, don’t worry, there are plenty of other super fun things to do on this little string of Keys! In fact, Islamorada is made up of 6 individual islands, Plantation, Windley, Upper and Lower Matecumbe, and 2 islands offshore called Indian Key and Lignumvitae Key. Since this string of islands is so extensive, and each offers so much, I’ve decided to lump them all under Islamorada for simplicity’s sake.
What to do: Islamorada guide
If you’re in search of beaches, there’s a couple to look out for. Founder’s Park is one of the only natural beaches around. Similar to Harry Harris Park in Key Largo, there is a $5 entrance. This park actually has a bit more to offer including a baseball field and playground! Another beach to visit is Anne’s Beach, which has no cover fee, but is located right off of the highway. There is a shallow swimming area, but space may be limited due to the size of this small beach. It’s a great place to enjoy the beautiful Keys water in Islamorada though!
Are you a fan of of local arts and crafts? Head to the Rain Barrel Village. From the road, it may look like your typical tourist trap with the gigantic spiny lobster calling you in, but the village is full of galleries and artist’s work wound through overarching trees and a winding path! You can even see glass blowing live if the artist is in, which was something I had never seen before! Don’t miss the hidden tiki bar in the shop closest to the road for your ultimate Florida Keys experience!
There are more arts located at the Morada Way Arts District, which is where the next stop you don’t want to miss on your Florida Keys trip is! Maybe you need a little afternoon cool down and want to try some local brews. If that’s the case, then you’ve got to visit the Florida Keys Brewing Company! Their brewery offers a tasting room, tropical beer garden, live music, and food trucks to be my favorite brewery that I’ve ever visited! My favorite of their brews is their Iguana Bait, and is the local favorite as well! With a courtyard this cute, how can you resist visiting? Plus, you can still the art district and see some amazing galleries and meet some fun locals!
It’s not a visit to Islamorada without some kind of fish interaction, even if offshore sport fishing isn’t your thing. Get your hands wet with a trip to Robbie’s to feed the tarpon by hand! Just a couple dollars for an entrance, and a few for a bucket of fish, you’re bound to have a great time! Watch out for the pelicans, they are all over, but they are no joke! They'll steal fish right out of your bucket, and aren't afraid to give you a bite if you get too close (my camera took a bit of a chomp by this guy below - but at least I got a gorgeous shot!) Also keep your eyes out for manatee! They will hang around the docks, but be sure not to feed them, as they are protected!
foodie guide to the keys - the best spots in islamorada
Looking for something delicious to eat while on Islamorada? Head to Lazy Days for lunch with a view of the gorgeous Atlantic Ocean! Sit upstairs and try to get an outside seat, and you can watch the boats and birds come in and out of the harbor. The water is nothing short of incredible from up on the balcony of the restaurant and the food is the delicious Florida Keys seafood you can hope for! If they’re serving hogfish, get the fish sandwich, it’s incredible!
Hands down, the best place for a key lime pie in the Florida Keys is Lorelei’s. Many other restaurants will argue that theirs is the best, but having a slice from Lorelei’s will make you spoiled for the rest of your life. Not only can you enjoy the best pie you’ve ever had, but Lorelei’s also has incredible sunsets to watch. One of my favorite spots in the Florida Keys, we make sure to visit every time we go!
After a long day of exploring the Keys of Islamorada, you’ll need a place to relax and enjoy the night. The Cheeca Lodge & Spa has the Florida Keys look that you hope for, but wrapped up in luxury. There’s a full golf course, spa, beautiful grounds, and a huge stretch of beach dotted with coconut palms.
Marathon covers a huge part of the Florida Keys, stretching all the way from Boot Key down to Grassy Key. This huge stretch of islands is known as the “Heart of the Florida Keys” and has so much to offer. A lot of what there is to enjoy on these keys is natural beauty, so don’t be afraid to go off the beaten path to find an amazing experience!
The best place to stay in the florida keys
By far the best place to stay in Marathon (and arguably the Keys) is Hawk’s Cay Resort. The resort has a place to stay for everyone, from those looking for a resort room, to families and groups looking for a vacation rental home with a dock on the canal. There’s a boat ramp, pools, beaches, and tons of villages outside the main resort to explore. Definitely the ultimate place to stay if you want a central location in the Keys for your trip! The last time I stayed there, we stayed in one of the home rental villages, and it was like a complete secluded paradise!
Where to eat
A little off the beaten path, you’ll find a delicious little restaurant that is definitely more than meets the eye. While not the most glamorous restaurant, the food is absolutely delicious. Keys Fisheries is known for their lobster reuben, and have sold over 381,000! Personally, I usually go for the lobster roll, since it’s a bit smaller. Their fish tacos are delicious too, while not the most picturesque spot in the Keys, it will definitely amaze you with their food, friendly service, and is right on the waterfront!
What to do in Marathon
Even though Islamorada is known for it’s great fishing, in my opinion, Marathon is just as incredible, if not even a little more untouched! Driving though Marathon, you can definitely tell how much of a fishing town it is. If you are up for it, try to find a fishing charter! I personally haven’t taken a charter with any of the companies in the Keys because my dad has brought us fishing in the past, but its definitely a fun sport to try out, even better if you cook your catch for dinner! (P.S. This wasn't a fish I caught, scroll down to see the one I reeled in!
Want a little interaction with some of the Florida Keys residents? Head over the the Dolphin Research Center, where you can meet some of the dolphins that live in their natural lagoon. These dolphins act as ambassadors for their ocean counterparts, but could leave if they wanted to (who wants to leave free food though). Getting up close and personal to these amazing animals helps to build a bond and a passion to protect them, and DRC is one of the best places to get an experience up close with a dolphin while you’re in the Florida Keys!
One of the most famous bridges in the US has to be the Seven Mile Bridge. Spanning between Marathon and Bahia Honda Key, the bridge drives over the gorgeous blue waters of the Keys. While you can’t get out and stop, you’ve got a nice long drive over the bridge to enjoy the scenery, and is definitely something you don’t want to miss on your trip to the Florida Keys!
Once over the bridge, you’ll find yourself at Bahia Honda Key, a Florida State Park with gorgeous water to swim in, a historic railroad bridge built by Henry Flagler, and complete natural beauty. Pack a picnic and head over to enjoy one of the most beautiful beaches in the area, or bring your snorkel gear and swim off the shore to see some marine life, you won’t be disappointed!
Another animal you may want to see while in Marathon is the endangered Keys deer! On Big Pine Key, there is a refuge for these little deer to live safely and help to build the population back up. These little guys are the smallest of North American deer, and are definitely adorable! You can learn more about the Keys Deer, and how you can help them here!
Last but not least, you can’t forego Key West on your trip to the Florida Keys! While some people stay in Key West for the majority of their vacation, it definitely has more of a city feel than the other Keys, so keep that in mind. There’s lots to do, so here’s some that you definitely don’t want to miss!
Things to do for your trip to Key West
Something on my bucket list is to take a ride in a seaplane, and you can do just that on a trip from Key West to the nearby National Park of the Dry Tortugas. This national park is only accessible via air or water, but a seaplane is definitely the most unique way to do it! Seaplane Adventures offers a 1/2 day adventure that would be a memory you definitely would be talking about for ages! If you’re searching for something a little more budget-friendly, you can check out the various boat tours to the Dry Tortugas as well!
Now if you want a beach in Key West, Smather’s Beach is the place to visit. It’s one of the only public beaches on the island, and definitely the most accessible. Lined with palm trees and a nice shoreline, you can spend a day enjoying the beach here. Just be aware that it can get crowded very quickly, so don’t plan to leave with the hopes that your spot will still be there!
On a trip to Key West, you’ve got to visit the famous Kinos Factory. No trip to the Florida Keys is complete without taking your own pair of homemade sandals home! The Kinos Factory and sandal shop has been making sandals since 1966 and are some of my favorite sandals to wear! Affordable, comfortable, and cute, you definitely can’t miss a pair!
Most people visit Key West with the hopes of seeing two famous landmarks: The Southernmost Point and Mile Marker 0. Both are located on Whitehead Street, with the Southernmost point being at the corner of Whitehead and South Street, and the Mile Marker being about 9 blocks north. Definitely walking distance! The Southernmost point may be busy mid-day, so try to visit early so you can get a picture without waiting for a bunch of people! Mile Marker 0 is where US1 officially ends, and is propped up on a street sign. Keep an eye out or you may miss it, it’s not quite as obvious of a landmark as the Southernmost Point is!
Also located on Whitehead street is the Hemingway House. The gardens and property are fun to walk around, especially if you’re a history or literature fan, but the big attraction for most are the cats that roam around! The Hemingway cat, as they’re known, all have 6 (or more!) toes on their feet! They roam the property and definitely have adorable toes!
Need a quick drink to cool down while you’re cruising down Whitehead Street? Check out the Green Parrot, a little bar that’s more of a local’s hangout than some you may find in other areas. You’ll find no shortage of Florida Keys vibes here, with unique decor and lots of unique stories to share!
lots to do on Duval Street
Just one street in from Whitehead and you’ll find the most action in Key West on Duval Street. From shops to restaurants, hotels, bars, and chicken roaming, there’s no way I could cover everything without taking up all of your time. Some great spots to hit are:
- Captain Tony’s Saloon - Opened in 1851, Captain Tony’s is a famous bar that has been the spot for many celebrities to sip on a cold drink in the Florida heat, including Jimmy Buffet and Ernest Hemingway! Inside the bar, you may find dollar bills and bras hanging from the ceiling, so it may not be super kid-friendly. If you’re feeling lucky, try and toss a quarter into the fish’s mouth outside the entrance. If you’re successful, it’s said that you’ll have good luck for the rest of your time on the island!
- Sloppy Joe’s - Opening on the day Prohibition ended in 1933, Sloppy Joe’s has since become a “Key West Tradition.” Like Captain Tony’s, the bar holds a great amount of history, but provides entertainment, drinks, and food for us travelers today.
- Bull & Whistle - Standing three stories high, the Bull and Whistle bar(s) offer lots in terms of cocktails and entertainment, but the third floor brings more curiosities than the lower levels. Known as the Garden of Eden, the third floor is Duval Street’s only clothing optional bar. While I’ve never personally been, I would venture to say that you’ll have to muster up a bit of courage to visit and partake on the third floor.
- Drag Shows - Key West has a rich culture that celebrates the LGBTQ+ community, and a fun way to experience a myriad of people is venturing down to see the Drag Shows. They’re not too hard to find off of Duval street when you see a queen strutting towards you looking fabulous! Drag shows are so much fun, and you’ll definitely want to visit one in Key West!
- Margaritaville - Most Jimmy Buffet Fans will already know about the famous song, but there is a restaurant that you can visit as well! Definitely worth checking out if you’re a fan, when I used to eat meat I loved their “Cheeseburger in Paradise,” but there are so many options! Don’t forget to grab one of his famous boat drinks like the Island Sunrise or the Fins Up!
Another spot to eat, if you haven’t gotten your fill from Duval Street is Blue Heaven. So many people rave about this place, and it’s just the cutest little spot for sure! Oh and did I mention it’s pet friendly? Brunch, live music, dogs, as well as a gorgeous spot to eat in the courtyard? Count me in!
On the outskirts of Key West is Stock Island, and you’ll want to check out Hogfish Bar and Grill. A local seafood spot that’s a bit removed from the bustle of the tourist area, Hogfish Bar & Grill is everything you could hope for in a Florida Keys restaurant, from the tiki style building, banana palms in the parking lot, brightly painted stools, and plenty of seafood, it’s a little sliver of paradise!
The Best of florida Keys Sunsets
If you know me, you’ll know that I’m a sailor, and wish I could take everyone sailing with me! While you may not be learning all that you can about a big multi-day sailing trip, you can enjoy a day on the water while you’re on your trip to the Florida Keys! In Key West, there are a lot of options to choose from, but check out Danger Charters for one of their sails! They have a Wind and Wine Sunset Sail that is a great way to enjoy a romantic evening on the water! Not a fan of wine or have other plans for sunset? They also offer day sails, snorkel trips, and specialty sails as well!
But aside from sailing, by far my favorite place in the Keys to watch the Sunset is Mallory Square. With tons of live entertainment, street performers, vendors, and a killer sunset, you can’t beat the Mallory Square Sunset party! It is free to enjoy, but most performers and vendors have tip jars. Bring some cash to support the local artist and catch a coconut drink while you walk around. If you get there on time, you may be able to catch a seat at one of the nearby restaurants, but Mallory Square is an amazing way to end the day of exploring Key West!
As you can see, there's so much to see and do in the Florida Keys, it's definitely a major bucket list destination! Did I happen to miss something that you've loved in the Keys? Have you experienced any of these bucket list items down in the Keys? Let me know, I'd love to chat!