Road tripping the Florida Keys – my favorite places to see and things to do

We have recently visited South Florida and I have described the experience in a three piece article series. The first one presents the reasons why I am drawn to South Florida and why I consider it to be a great family destination. This one focuses on the Florida Keys and lists my favorite places to see and things to do there. Finally, in the third article I go through the aspects of the United States that annoy me :-).

From what I have read and experienced, for us Europeans the Florida Keys are a relatively unknown destination. I am not sure why this is the case. I remember I had discovered them some ten years ago when I was browsing the map of Florida in Google Earth. I was fascinated by this group of small islands stretching some 150 kilometers into the Atlantic ocean from the Florida mainland, all connected with bridges. The more I read about them, the more I was fascinated. I knew I had to have a road trip there at some point. Fast forward ten years, I had not one but two road trips in the Keys, one in 2014 and the second in 2019. And both Aneta and me agreed that we were not done with the Keys yet, we will most probably be back again.

South Florida with Miami and the Florida Keys stretching into the Atlantic ocean (courtesy of Google Earth)
South Florida with Miami and the Florida Keys (courtesy of Google Earth)

Here is a list of the sights and places we like in the Keys, sorted from Northeast (from Key Largo) to southwest (to Key West). Some of them are public spaces, while others are private businesses, but all of the descriptions are based on our personal experience, meaning that none of the listed places have asked or paid for being mentioned. Furthermore, this is not an extensive list as there are many many more gens to discover in the Keys. But the places on the list will keep you busy during at least a three day road trip.

Everglades national park

Ok, this is not really a part of the Keys, but chances are you will be approaching to the Keys from Miami and then the Everglades will be on your way anyway and they should definitely not be missed. The park is huge, but if you want to experience it on a time budget, then I suggest the Anhinga trail. There you can see the swampy landscape, the rich bird life and of course the alligators, all within a nice and child friendly walk of just one kilometer. Just be careful as the alligators sometimes venture out very close to the path. I still remember how I jumped once I realized that there was an alligator just two meters away from us!

Atlantic bay resort

We spent our last night of the trip in this wonderful place. It is a relaxing and cute mini-resort with plenty to do for two to three days.  You can swim both in the sea (the Gulf of Mexico) and in the pool, you can barbecue, ride bikes and even borrow kayaks and stand up paddles. All the decorations and the general atmosphere of the place are quintessentially Florida Keysey (I don’t think “Keysey” is a real word, but you get what I mean). It was a shame that we only stayed for one night.

Lazy days restaurant in Islamorada

I would dare to claim that this restaurant offers the classic Keys dining experience (it is of course not the only restaurant that does this) – a relaxing setting with a beautiful view of the Atlantic ocean, offering large portions of local seafood. It is not fine dining in any sense, but it is fried and greasy and honest and tasty.

Helicopter sightseeing

For the most part, the Keys are magical from wherever you look at them, but they should definitely be seen from the air. There is a company called Old city helicopters at Marathon airport that does helicopter sightseeing and they offer several options depending on what you want to see and for how long. It might be a good idea to book in advance, but drop-ins also work fine (we dropped in during both of our trips and we did not have to wait long on any of the occasions). Helicopter sightseeing is pricey, so make sure not to pay the listed full price by taking them up on their special birthday/anniversary deals (check their Web page). On the negative side, this time our pilot was not as engaged as the first time and he was quite pushy when it comes to tips, which I really dislike (read more here about my general view of tipping).

Sombrero beach

Sombrero is one of our favorite beaches in the Keys. It is very close to Marathon, making it a convenient choice as Marathon is smack in the middle between Key Largo and Key West. As the beach is sandy and the water is shallow even relatively far away from the coast, it is very family friendly. It has a nice and relaxed vibe. Another plus is that just as we were getting ready to leave, we got to see dolphins! On the minus side, the available parking seems to get full fast. Also be aware that you cannot buy food or drinks at the beach.

Sombrero beach
Sombrero beach

Castaway waterfront restaurant & sushi bar in Marathon

Sushi was a big surprise in the States – both the quality and the portion size. We liked Castaway so much that we ate there twice. The food they serve extends beyond sushi to typical Keys sea food, which makes a strange but interesting combination. They are well stocked on beers from local microbreweries. And last but not least, the restaurant had a great, laid back, summer vacation vibe. Just for balance, I have to mention one negative aspect – as its name states, the restaurant is on the waterfront, but the view is only of a canal and some trailer homes.

Bahia Honda state park

Bahia Honda has another great beach with spectacularly turquoise waters. In addition to swimming, we also walked the old Bahia Honda rail bridge which offers nice views of the park and the surrounding waters.  Being a state park, there is quite a lot on offer, for example kayaking, cycling and hiking. One can learn a lot about the nature from the park rangers. There is even a snack bar available. All in all, plenty of activities for a half or full day, and well worth the entrance fee (which was nine dollars in our case). A part of the park is closed for repairs after hurricane Irma devastated the Keys back in 2017.

Key deer

Key deer is a species endemic to the Florida Keys. They are smaller in size than other deer species and they are used to sharing the land (which is scarce in the Keys) with humans, so they usually don’t run away when they encounter us. You have the best chance of spotting them at Big Pine Key. We were lucky enough to get to see quite many of them. When you are on Big Pine Key, make sure to also visit the Blue hole, a former quarry, now a freshwater lake and home to rich wildlife.

Key deer
Aneta and Emili admiring a key deer

Santiago’s bodega restaurant in Key West

Santiago’s bodega is a restaurant we discovered during our first trip to the Keys back in 2014 and we were equally impressed even after our second visit. The restaurant offers tapas of very high quality. And this being the States, also of huge size. Neither sushi or tapas are typical American food, but judging from our experiences, both are done amazingly in the Keys.

Key West

Key West is the biggest town in the Keys and is as far southwest as the US highway 1 will take you (after driving across more than 40 bridges from the mainland). It is at the same time a party mecca and a laid back town. I love its lush green streets full of chickens, roosters and hens that roam free. I love its American South architecture. I love Duval street which, thanks to its bars and restaurants, is fascinating both during day and nighttime. And of course, I love the sunset at Mallory square.

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