Workation With Dad Part 3: Our Road Trip to Key West – Post Cruise

If you’re reading this, you probably know that I invited my father on a little workation to Florida and a cruise through the Caribbean. This post is actually part 3 of the entire vacation. So, if you want to catch up on previous adventures, you can do that here. This post, however, will be about the few days we spent in the Florida Keys after the cruise, so lets jump right in.

Docking down and getting in gear…

The cruise docked in Miami and disembarked the boat bright and early at 7 am. We had a big day ahead and were eager to start our second leg of my Florida workstation with Dad. This time, we would be exploring the South Florida Keys. My dad had visited the Florida keys over 30 years before, and he was looking forward to seeing how things may have changed in that time. We even had plans to hunt down his signature in some local bar. Needless to say, it was shaping up to be a proper men’s weekend.

When we disembarked the boat, everything went pretty smoothly. Luckily, I rented from Sixt, and they have a pick-up station right inside our terminal, so went straight to get the car. I booked my favorite car, a Camaro Convertible – I know, the most prominent and most used choice in Florida would be a Ford Mustang – which, don’t get me wrong, is a beautiful car – but I have driven it a couple of times and this time I wanted a Camaro… and Sixt game me my very own Camaro 😀

Cruising down the Florida Keys with my Dad and favorite convertible 🙂

So, the next leg of our adventure began by opening up the rooftop and setting off on our road trip down to Key West.

Key West is a city and an island of the same name in the Florida Keys. Fun fact: It is considered the southernmost city in the continental United States.

Gator scouting in the Everglades

On the way to the Keys, I wanted to treat my dad to another typical Florida experience: a crocodile and alligator tour of the everglades.

So we drove on the highway to our first stop, the Everglades Alligator Farm in the town of Homestead. There is an overwhelming selection of airboat tours of the everglades, so I chose one that was well rated and pretty much on our way to Key West.

Just before we had to exit the highway, it began to pour. We couldn’t stop to put the hood up, so we got a little wet until we were able to exit and pull the top up, which by the way didn’t really matter because as soon as we put it up, it stopped raining.

By the time we got to the farm, the weather was already much better. So this farm has a little zoo where you can see many different animals from the ecosystems nearby. It is mostly alligators but had other small animals from the region, such as snakes, birds, otters, and other amphibians and reptiles. The main attraction, however, was the crocodiles by far.

Before the airboat tour, there was an alligator show and a bird of prey show, which was quite lovely to see. In my opinion, the best part of the excursion was the airboat ride through the everglades.

Dad and I wearing protection for our ears. Airboats are extremely loud.

During the ride, we ventured pretty fast down the swamps, we even got a little bit wet, but it was ok. We got to see some alligators and birds in the wild, which was pretty cool – all in all – a typical experience of the Everglades, which my dad really enjoyed.

Little gator at the Everglades National Park

Choosing the road less traveled

After the Everglades, we continued to make our way down to Key West. From Homestead you can either take the US-1 and drive on the highway all the way down, or, you take a slight detour, and before hitting Key Largo, you can take a bridge that takes you to the northernmost point of the Keys, and from there you can drive all the way down along the coast. I had never been to this area, so we opted for the more scenic route.

So we took the minor road from Homestead towards North Key Largo over the separate bridge. We could see the other big bridge with the US-1 from a distance, which made for an excellent photo opportunity. On the way down, there are some beautiful beaches and other attractions; we didn’t really make too many stops since we wanted to get to Key West early to see some of the towns.

We did stop at a gorgeous beach to enjoy the scenery and for a few other photo apps. We also stopped at a nice restaurant on the water for some food. We enjoyed some burgers and a rack of ribs for lunch before hitting the road again.

Of course, we had reopened the roof and enjoyed our really wonderful road trip in a convertible with beautiful weather. I loved it, and my dad did, as well. The only thing, I really underestimated the time it takes to drive from Miami to Key West, and we arrived just in time to see the sunset.

Final destination: Key West

When we got to Key West, we checked into our very lovely Airbnb, it wasn’t exactly cheap, but it was worth it for the experience I wanted to give my father.

We could also park our car pretty much in the center of Key West, which was really convenient for my dad getting around. It made for much shorter and manageable walks. He was still having some pain since he had been walking a lot during this whole vacation. So we had to be mindful about his feet and his pain, while also being really excited to see the town.

We walked a bit and got to see the sunset from a famous spot at the harbor. We enjoyed a fantastic mojito at Sloppy Joe’s, the bar that gets all the hype when it comes to Hemingway. It is known as his favorite bar during his years in Key West. Apparently, this is where the writer would drink many a night away. In fact, Hemingway became good friends with the owner, Joe Russell – so much so that Hemingway is credited for the name.

On the hunt for the signed coaster, my dad left here 37 years ago – when he was my age.

After sunset, my dad was excited to see we could find the bar he had been to over 30 years ago. He had actually left his name and signature on a coaster on the wall of this bar. He was eager to see if he could find this memorabilia and if they still had it hanging on the wall after all this time.

Key West – One of my favorite places in the U.S.

We didn’t really find what we were looking for, but we still really enjoyed the bar. There were an amazing female singer singing covers, and I basically left my dad there for a few hours while I went to make some consulting calls. When I got back later, he was having a great time requesting old songs from this lovely singer. We stayed there for a while, and it was pretty cool to listen to the music he loved.

After, we went for a nice dinner and some drinks out in Key West. We went to the famous Duval Street, where there are plenty of things to see and do. It is a beautiful little party street filled with great bars and pubs.

After the long day, we just went home to rest. We were both looking forward to the next day, which was a pretty big day, our last day in the Keys before driving back to Miami to catch our respective flights out of The States.

I was particularly excited about the adventure the following day. After all, we were going to do something I have wanted to do for a long time. You see, I had been to Key West before, but back then I was a poor backpacker. I stayed in a hostel and only had enough money to take a small boat tour around Key West and some parasailing.

Times change and dreams come true…

This time, however, I wanted to take my dad to an extraordinary place. This place is part of the Travellers Century Club territories and a high ranking destination among many exclusive travel lists. This is not the only reason I wanted to visit, of course, we ventured there because it is a place known for being equally beautiful and rich with history.

The Dry Tortugas National Park is the site of some pivotal points in U.S. history. Dry Tortugas National Park is a United States National Park that contains a cluster of islands about 70 miles west of Key West, more specifically: Garden Key.

The park preserves Fort Jefferson and the seven Dry Tortugas islands; they are actually the westernmost and most isolated of the Florida Keys. It is not possible to build a bridge to this island, just like a few other ones in the area – islands that are not connected to Key West by a bridge.

The park is accessible only by boat or seaplane, and it takes just under an hour to get there by a fast catamaran. So you can say it’s not really close to the mainland. In fact, it is actually closer to Havana, in the Gulf of Mexico.

Dry Tortugas is noted for its abundant sea life; the archipelago’s coral reefs are the least disturbed of the Florida Keys reefs. Moreover, it’s tropical bird breeding grounds, colorful coral reefs, and legends of shipwrecks and sunken treasures make visiting the park a vibrant and multifaceted experience.

The park’s centerpiece is Fort Jefferson, a massive but unfinished coastal fortress. Fun fact: Fort Jefferson is an enormous brick masonry structure in the Western Hemisphere, and is composed of more than 16 million bricks. This fort was actually very significant during the American Civil War.

Dry Tortugas National Park – Great day in a big Fort on a remote island.

Today, It is also a marine reserve with plenty of corals and nice fish surrounding the islands. And we had a full day there to explore. As you know, I love to geek out about the history, so naturally, we visited the fort and the museum first.

The fort itself is quite big, and you can go inside and access all the floors. It is made of several stories high, and the outdoor top is all lined with grass, and you can walk around the entire fort, about 2 miles on all the floors. Keep in mind that not everything is opened on every level, some parts are very much ruins, on the verge of collapsing.

If you’re a history buff like me, it’s an excellent place to visit; not too much to see but super exciting from a historical standpoint. There are lots of descriptions, old artifacts, weapons and cannons, and the former prison, fascinating stuff.

Some history about the Dry Tortugas…

About five years after Spain sold Florida to the United States for $5 million, in 1825, The U.S. Navy inspected the Dry Tortugas islands as a possible destination for a naval station. Back then, the Dry Tortugas was found unfit for any kind of maritime establishment.

The U.S. government then thought the islands were a good location for a lighthouse to guide ships around the area’s reefs and small islands. A small island called Bush Key, later called Garden Key, was chosen as the site for the lighthouse.
By the 1940s, a new perspective emerged within the U.S. government that the Dry Tortugas was an excellent area for a strategic naval base location. Not only do they consist of 11 small keys where the surrounding reefs and banks serve as a break for the sea. But they make an outer and an inner harbor.

This is of strategic importance because the inner harbor afforded a safe anchorage during all seasons and was large enough to let a large number of ships ride at anchor. Think of a port in Catan, and you’ve colonized all it’s access points.

Because of this, the U.S. realized that if a hostile power occupied the Dry Tortugas, United States shipping in the Gulf would be severely compromised. However, if occupied and fortified by the U.S., the Dry Tortugas would constitute the advance post for a defense of the Gulf Coast. On September 17, 1845, the Dry Tortugas became a national military reservation.

Construction of Fort Jefferson (named after the third U.S. President, Thomas Jefferson) was begun on Garden Key in December 1846.

The new fort was built so that the existing Garden Key lighthouse and the lighthouse keeper’s cottage were contained within the walls of the fort. The lighthouse continued to serve a vital function in guiding ships through the waters of the Dry Tortugas Islands until the current metal light tower was installed atop an adjacent wall of the fort in 1876. The original brick lighthouse tower was taken down in 1877.

During the Civil War (between 1861 up until 1889), the fort served as a prison for war criminals and civilians.
In 1889, the Army turned the fort over to the Marine Hospital Service to be operated as a quarantine station. The U.S. Navy used the Key as a coaling station.

Neglected, stripped by vandals, swept by repeated tropical storms that crushed brick and concrete and bent girders, Fort Jefferson deteriorated rapidly.

It remained unoccupied until the war with Spain broke out in 1898. The American fleet was stationed there.
In 1902, the property was transferred to the Navy Department, and coal rigs and water distilling plants were built. When these were destroyed by hurricanes in 1906, the fort was again abandoned.

Two years later, the entire group of islands was set aside as a federal bird reservation. Until 1934 Garden Key and the crumbling ruins were merely a rendezvous for fishers and tourists.

During WWI, the lighthouse was decommissioned, but a wireless station and naval seaplane facility were operational.
On January 4, 1935, President Franklin D. Roosevelt designated the area as Fort Jefferson National Monument. It was then listed on the National Register of Historic Places in 1970, and finally, in 1992, the Dry Tortugas, including Fort Jefferson, was established as a National Park.

Beautiful scenery out at the Dry Tortugas

I love this place because, as you can see, Dry Tortugas is unique in its combination of a mostly undisturbed tropical ecosystem with wildly significant historical artifacts and landmarks.

A perfect example of this balance is that after the fort, I went off to explore life underwater while my father rested by the beach. We both really enjoyed our time there.

There are lots of things you can do while at the park. For instance, snorkeling (which I highly recommend), picnicking, birdwatching, camping, scuba diving, saltwater fishing, and kayaking. A full day of fun, no doubt!

For the remainder of the day, we walked along the beach and through other parts of the island, which is pretty small.


We also visited the seawall, which rumor has it was built to make it harder for prisoners to escape the fort. It’s a wall built in the middle, between the sea and the fortress. Apparently, there used to be lots of sharks swimming there ready to catch any prisoner that wished to escape. Today, there are no sharks there, well, at least not officially. 😉

This used to be a prison at one point. They kept sharks in the moat to make it more difficult to escape 😉

I actually went snorkeling around this wall, and it was pretty nice, there are a lot of Carolinas hanging along the walls with lots of fish leaving nearby. It was actually the best snorkeling site on the whole island. We also saw some turtles as we were walking along the wall, so yeah, definitely lots of exciting marine life right are your fingertips.

Later that afternoon, we took the catamaran back to Key West, and the water was actually quite rough. A few people (including me) got a bit seasick; thankfully, I didn’t have to vomit.

It was a really enjoyable day with my father as I crossed off another territory from my world travel list.

It was cool to spend the day basically halfway to Cuba, well not really halfway because the island is more west and Cuba is straight south, but you understand what I mean.

Actually, I want to do another tour of Cuba with my dad and his best friend, who’s never been. My dad has only been to Varadero and some other tourist sites like Trinidad, so I want to show him the real Cuba. We already wanted to do this two years ago after he went for the first time, but his health situation has kept us from making it happen. We had hoped for this year, but COVID happened. Either way, I’m confident next year I can travel with him to Cuba and finally show him the real Cuba.

For our last evening in Key West, we did pretty much the same thing we did the night before: delicious dinner, walk about the town, and have a nightcap on Duval St. before calling it a night. I was happy that my dad really enjoyed being back in Key West.

The next day we drove straight back to Miami, without any pit stops. My father had a flight in the afternoon, and I had mine in the evening. Actually, we did make a stop before heading to the airport; I had one last piece of business to carry out in Miami, it was a workation after all. I had to go to Miramar, to open a bank account for my newly formed LLC, and that’s exactly what we did.

I went to PNC bank and was able to open the account swiftly and efficiently. Unfortunately, shortly after the account was closed without reason. Well, it was actually probably my fault that it was closed. A few weeks after opening the account, I was traveling through Africa and Somalia, and I missed a few calls from bank representatives and the president of the bank. Due to my limited network coverage, I didn’t call back, and they closed the account. It’s all good anyway, because, at the time, it was the perfect mix of business and pleasure vacationing through Florida and the Caribbean with my dad.

We arrived at the airport in time for my dad’s flight, which was quite a bit before mine. Thanks to my AMEX, I was able to go into one of the nicest lounges at MIA, The Centurion Lounge. It is much nicer to wait for a flight when you can enjoy nice surroundings, good wifi, and a nice (free) drink. 😉

Miami Airport is a big mess, but at least they have a nice AMEX lounge 🙂 Make sure to check out the Centurion Lounge next time you’re at MIA.