Florida Keys Trip #4
- BrieannaLenhart
- 53 minutes ago
- 12 min read
Every trip to the Florida Keys means setting sail on a new adventure. Spread across a string of tiny islands, each Key has its own unique character, and every visit leaves you with new stories to tell. The one constant is the unmistakable feeling of escaping to a tropical paradise—one that's as vibrant and full of personality as the islands themselves.
For this Keys adventure, I found myself back in the Middle Keys, but this time we stayed in Islamorada. Often thought of as a single destination, Islamorada is actually made up of several islands, with Upper Matecumbe Key and Lower Matecumbe Key serving as its main hubs.
We stayed in a small neighborhood on Lower Matecumbe Key, where charming, quintessential Keys homes built for laid-back island living and long days on the water sat alongside a handful of modern new builds that felt just a bit out of place.
*My brief soapbox moment* If you want to build a new home in a place with an already established aesthetic, personality, and culture, please respect it. Don't build a house that's meant for a different state or climate. It sticks out like a fishing hook in a thumb.
Anyway—back to the adventure! Where we stayed was a true Florida Keys gem. Not only was the house spectacular, with canal access, a pool, and bikes, but the neighborhood also had its own private beach.
For those who aren’t familiar with the Keys, while Florida is known for its beaches, that's NOT what draws most people here. The Keys are known for their rocky shorelines, and people come here to go boating, fishing, diving, and drinking…..in the history ;)
This local beach is gated, keeping it protected and special for those who belong to the neighborhood. It was very clean, with tables, beach chairs, and the kind of soft, powder-white sand you dream about. There were also plenty of palm trees providing shade, including a hammock strung between two of them where you could rock your cares away.
The water quality near this beach was also quite impressive. While it wasn’t as crystal clear as the waters I experienced in Guam, Tahiti, and Bora Bora, it was clear enough to spot a blue crab and a large hermit crab scurrying across the sandy ocean floor.
After spending the first evening settling into our home for the week, eating and drinking, and watching the sunset behind the canals and fishing houses. I hit the hay early to get up early for my scuba dive the next day.
There are two reasons to wake up early in the Keys: one is to go fishing, the other is to go diving. This time I went diving with Islamorada Dive Center. I made sure to book everything a few weeks before. I already had some basic gear: mask, fin, snorkel, wetsuit, but they have all the gear you need available to rent.
We took the boat out to Victory Reef first and then headed over to what they call “The Fingers” for our second dive.
The guide mentioned how much better the reefs looked after recovering from the previous summer’s intense heat. While the coral wasn’t as colorful as some of the other Florida dive sites I’ve experienced, there were plenty of fish, and we even got to see a huge green moray eel. What a great way to spend our first morning in the Keys—communing with the sea life.
The afternoon was spent chillaxing at our private beach before getting ready for dinner at Square Grouper. I had never received so many recommendations for a restaurant, and with so many people speaking so highly of their dining experience, I’d say this place has become quite the Keys institution. The original location is in Islamorada, but they also have a second location in Cudjoe Key.
Even with a reservation, we still had a bit of a wait, which gives you an idea of just how popular this place is. Luckily, they have a bar, The Sunset Lounge, where you can ride the elevator up to enjoy a well-crafted cocktail overlooking the water. We had only taken a few sips of our drinks when we were called for our table.
The food was excellent—perfectly cooked and seasoned, with nothing overly coated or overwhelmed. Instead, the freshness of the seafood and the crispness of the vegetables really shined through. It was one of the best meals I’ve had, and I can’t wait to go back.
The next day was our paddle adventure. Behind the famous Robbie’s is a mangrove maze where you can paddle your way through the waterways and eventually arrive at “The Nursery,” where you can catch a glimpse of baby sharks and other marine life.
If you’re renting, you can head to Robbie’s to secure your rental watercraft. For those bringing their own gear, there is a drop-in site across from Robbie’s where you can park along the bridge highway and launch. Unfortunately, the spot I had to use was the next site farther down the bridge because the closest one was under construction.
I consider myself a pretty advanced paddler, but this was an especially challenging paddle with my inflatable kayak. The wind would hit you from the side, funneling underneath the bridge and making it difficult to navigate. Luckily, boat traffic wasn’t too bad in the morning, though it does get much busier throughout the day. There are also giant electric pylons you have to be mindful of along the way.
Even while navigating all these factors, I still had an incredible encounter—a spotted eagle ray swam right past me. Unfortunately, I didn’t have a free hand to grab a picture. I guess that moment will just have to remain in my special mental memory box.
While I waited for the rest of my party to pick up their rentals, I got to hang out with Robbie’s famous tarpons, which were all swimming around my board.
For those doing the paddle behind Robbie’s, stick as close to the coastline as possible because the current and wind coming from underneath the bridge can be incredibly strong. Once you’ve curved around the island and enter the mangroves, it becomes a very easy paddle. Keep in mind that you may have to get low and limbo under some mangrove branches along the way.
There is one major crossing you need to be mindful of because it is a boat channel. It isn’t too wide, and once you cross it, you’re only a few strokes away from arriving at The Nursery. The Nursery feels like a giant pool surrounded by mangroves, and I was lucky enough to see two baby nurse sharks!
After paddling back, we parked our boards and enjoyed a much-deserved meal and cocktail at Robbie’s. Even with it being as busy as a pirate bar during Gasparilla, the service was quick, and the food hit the spot. Robbie’s is one of those major tourist attractions, but it’s one that is definitely worth the visit and completely lives up to the hype.
A Keys trip is not complete without a visit to Key West. If you’ve been several times and want to skip it in favor of exploring the many other Keys, that’s totally fine. But since it was my parents’ first time in the Keys, a drive down to the Key of so many fabled stories, rich history, and legendary mischief was a must.
It was only about an hour and a half drive from where we were staying in Islamorada.
Note: If you’re parking for the day and not staying at one of the hotels on the island, parking can be a bit tricky. We found a paid parking lot behind Hogs Breath Saloon, which is conveniently located near Mallory Square and the docks. This is a very happening area, where you can easily walk to your destination or hop on the trolley or conch train.
If you’re heading down for the day—or staying longer—a great way to get around town and take in the sites is with the Old Town Trolley. The trolley makes its way around the island with 13 stops, making it easy to explore all that Key West has to offer.
While the southern part of the island, where the docks, Mallory Square, and the famed Duval Street are located, is easy to stroll, your feet will thank you for giving them a break. Plus, riding the trolley gives you the chance to learn about the history behind the different buildings, streets, and landmarks you pass along the way. It’s a great way to discover places you may want to circle back to for more exploring.
Note: If you have the Florida HIA card, Members receive a FREE ride and 50% off for up to 3 additional people. All you have to do is show your card when checking in.
Because it was summertime and I was with my parents, choosing this method as a way to traverse this little island was the best idea.
Before hopping on, our first stop was just around the corner. You can’t go to Key West without visiting the famed Cuban Coffee Queen. Located near the docks and just around the corner from the trolley depot, it was the perfect first stop to kick off our Key West day. We started things off properly with an iced Cuban coffee and a guava and cream cheese sandwich.
Our next stop was the Ernest Hemingway Home and Museum. This was one of my favorite places we visited on my first trip down to the Keys. I’ve read many of his books, as I’m a big fan of writers from the 1920s, and Hemingway is such a staple of Key West history.
The house is kept in excellent condition and offers a glimpse into Hemingway’s life, along with stories of those who once roamed the streets of Key West. The beautiful gardens are a highlight, and from the second-floor wrap-around balcony, you can catch a great view of the Key West Lighthouse.
And yes, the house is crawling with lazy, lounging six-toed cats, escaping the tropical heat with cat naps on the antique furnishings.
Next was another iconic stop—Blue Heaven. An absolute Key West must! In my opinion, this restaurant has the best key lime pie ever! With its mile-high meringue fluff, creamy and tart filling, and crumbly graham cracker crust, it’s worth the journey down to this island alone.
We also enjoyed refreshing cocktails in their courtyard while watching one of the wild, roaming hens fluff and dust herself in the dirt of the tiny pet graveyard. It doesn’t get much more Key West than that.
We decided to walk off our pie and drinks by wandering through the many, many shops of Duval Street. Duval Street is the main drag in the heart of Key West, lined with tourist-trap shops but also glittering treasures like Mel Fisher’s Treasures. Bars with open windows ready to pour drinks, and live music pours out onto the streets. It’s the perfect street to wander down and maybe get a little lost in the moment, because no worries, somehow you’ll always end up back by the water.
It’s the kind of street where you can wander, get a little lost in the moment, and not worry too much about where you end up—because somehow, you’ll always find your way back to the water.
We ended our day in Key West with oysters by the water. I’ve always been a big fan of oysters, and my parents were feeling adventurous, deciding that the perfect place to try raw oysters for the first time was in the Keys. For this momentous dining experience, I took them to the legendary Half Shell Raw Bar.
Long famous for its oysters, the restaurant has recently gained even more attention thanks to its cameo on the show Bad Monkey. If you’re an oyster person, this place is a must on your Keys bucket list. I also highly recommend taking advantage of their daily happy hour from 4:30 p.m. to 6:30 p.m. They offer incredible discounts on some of their top seafood offerings, including oysters, along with 50% off well liquors, house wine, and all beer.
It was a very successful day in my book because after just spending 8 hours in Key West, my parents, who were very skeptical about going in the first place, were giggling and reminiscing about our time there and how they couldn’t wait to go back. Driving back, watching the sunset on the Seven Mile Bridge, another perfect day in the Keys concluded.
The following day, we headed back south, but not quite as far, making our way to Big Pine Key in search of some Key deer sightings. Funny enough, we had already spotted a Key deer running along the main highway in Big Pine Key while driving back from Key West the evening before, so we felt pretty confident we’d have some luck finding more today.
About an hour drive from Islamorada, we first stopped at the National Key Deer Refuge Visitor Center, grabbed a map, learned some facts about the refuge, and then set off on our search.
Note: This facility has excellent restrooms, so whether you are out exploring the refuge or need a little emergency stop-off on your trek down through the Keys, I suggest having this stop pinned.
We drove down to Key Deer Blvd to Watson Trail. There is a small parking lot off the side of the road, and not far from the lot is Blue Hole where you can see resident crocodiles and alligators. Florida is a unique place, especially the Keys, where you can see these two modern dinosaurs coexisting.
We thought that by following Watson Trail through Florida scrub away from the road we would be sure to see Key deer hiding and peeking through the foliage, but we saw diddly squat.
Starting to feel hungry and disappointed, we decided to call off the search and drive to No Name Pub. A friend of mine who lived in the Keys for many years told me about this treasure of a dive bar, and the idea of drink, food, and getting out of that hot sun seemed like the best move to raise our spirits.
On our drive, we wound our way through some neighborhoods and, lo and behold, KEY DEER everywhere! They were just strolling down the road and prancing through the yards. One even came right up to our car!
Now feeling victorious in our hunt for some deer sightings, we continued on the No Name to celebrate.
No Name Pub is the ultimate Keys dive bar. Easily missed unless you know about it, this small yellow building tucked among the pines has you descending into a dark wooden bar covered with dollar bills, where locals sit and waste away the hot afternoon hours with some A/C and a cold drink.
Around since the 1930s and the oldest bar in Big Pine Key—probably the only one for a long time—this place has a colorful past, serving as a general store, a brothel, and a bait and tackle shop. But perhaps even more notable than its history is its delicious, famous pizza, which is an absolute must.
This isn’t a place of Instagram-worthy murals or meticulously plated dishes. No Name Pub represents the true Keys lifestyle—a cool, dark dive bar built for fishermen, sailors, and pirates looking for a place to hide away and while away the afternoon hours.
Finishing up our meal, we decided to finish our drive down the road to where the island ends and the ocean begins.
Making a few pit stops on our way back up to Islamorada, we stopped at Bahia Honda State Park. I had visited here on my second trip to the Keys, but that time we arrived in the evening, just around sunset. This time, with the sun high in the sky and a perfectly clear day, the water was a sparkling blue that could rival any Mediterranean destination.
Bahia Honda is worth the visit for two main reasons. Number one, it’s home to one of the few true beaches in the Keys, complete with opportunities for swimming and snorkeling. Number two, it offers the chance to hike up the remnants of the Florida Keys Overseas Highway.
Henry Flagler, a major tycoon and especially influential in the railroad industry, had a dream of creating a rail line that would connect Miami to Key West. Unfortunately, a hurricane swept through on Labor Day in 1935, causing devastating damage to the railroad tracks and bridges. Today, a remaining slice of history allows visitors to travel back in time for a brief moment, standing on the bridge and taking in the same views that passengers aboard Flagler’s train would have experienced in the early 1900s.
A cute little $8.00 per vehicle fee, this place is a must, whether you spend the whole day soaking up the sun, water, and history, or just an hour or two.
You can’t have a trip to the Keys without enjoying some fresh seafood. And if you can find a place to stay with a kitchen where you can cook up that fresh catch, well, that’s the meringue topping on the Key lime pie.
One of my personal favorite places to pick up fresh seafood is Key’s Fisheries in Marathon. If you’ve read my other Keys blog post, you already know I’m a fan of their lobster Reuben. But they’re also pulling in fresh catches daily. We grabbed some huge shrimp (or prawns, depending on what you like to call them) and some grouper. I know people say it all the time, but fresh seafood really does taste better—it’s like it literally jumped out of the sea and landed right on your plate.
Closing out our final full day on this Keys adventure, we chose to jet ski through the mangrove islands and open ocean. Our guy Carlos, who helped my parents out with their kayak rental from Robbie’s, was super cool and mentioned that he leads jet ski tours. My dad had never been on one, so I thought, what better way to close out our trip than a father-daughter jet ski adventure!
Before I wrap up this adventure, I also wanted to mention a photographer. People travel for all kinds of reasons, whether it’s a vacation, a quick getaway, or simply an adventure. Whatever brings you there, there’s always a moment you’ll want to capture and reminisce about later.
We wanted some current family photos, so I went searching for a photographer who wasn’t heavily wedding-focused and reasonably priced. That’s when I found Lisa & Greg Poland Photography. He chose a beautiful location in Islamorada, and the timing couldn’t have been better—we had that perfect magic-hour sunset lighting.
Greg brought a great sense of ease to the shoot. He knew exactly where to position us for the best backgrounds and light, and the whole process felt super relaxed and chill. There was no pressure to pose perfectly or make everything feel overly staged, which made it easy for us to just have fun and be ourselves.
Below is one of my favorite photos he took. It was toward the end of the shoot, when we were just goofing around—and sometimes those are the photos that end up meaning the most.
And just like that, the sun sets on another adventure in the Keys. I can’t wait to see what adventures await the next time I find myself among the islands of Hemingway, Buffett, and fellow salty dogs.
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