What’s that? No national park in the title of this blog post? But we were supposed to do three national parks on this trip! Yeah, well. I’m getting ahead of myself. Let’s talk about Key West.
Back in 2011, my mom and I took a Disney Cruise that stopped in Key West for the day and I immediately fell in love. We were only docked there for a couple of hours, but this is the first place I can ever remember visiting and knowing immediately that I wanted to return.

It’s such a fun, walkable town with delicious food and amazing weather. What’s not to love? So I always knew I would come back as an adult and spend more time there. And what better excuse than a national park just 68 miles offshore? So it was a pretty easy decision to include Key West into our Florida vacation. And the island did not disappoint!

Even though I already knew from the moment we hit the start of the Overseas Highway that we probably weren’t going to get to enjoy that national park.

I started planning this trip (our first honeymoon) more than six months ahead of time. I booked our flights and hotels and started looking into national park excursions. But for some reason, I didn’t book our Dry Tortugas ferry at that time. I don’t know what I was thinking. There are only two ways to get to this particular National Park, by ferry or by chartered plane. A chartered plane was obviously out of our price range, but still, for some reason, I didn’t book our ferry tickets right away. And then when I went back to do so several months later, they were all sold out. Of course they were. It was the week between Christmas and New Years, one of the busiest travel weeks of the year.
I was…upset. To stay the least. I had a meltdown of epic proportions and was crying to James that I had ruined our entire honeymoon. It was bad. We do our best to strategically work in as many of these parks as possible whenever we’re in an area. It’s the only way we’re able to afford, both financially and time off-wise, to pull off all these trips. So it was a huge bummer that we were not only going to miss out on a part of the trip I was genuinely very excited for, but also were going to miss out on a national park and then have to pay hundreds of dollars to come back at some future point if we wanted to check them all off.
James and I looked into our options, realized that we definitely could not afford a chartered plane, and decided we would show up that morning at the docks and try to get on standby. We read plenty of success stories of people doing this so we felt reasonably confident. We woke up at 5:00am and walked over to the ferry terminal where they said a standby sheet would be put out at 6:30am. But by the time we got there at 6am, we were already 14th in line. In the end it didn’t matter, because every single person showed up for the cruise that day, so we wouldn’t have gotten on regardless. But it did mean that the other people in front of us got first dibs on the openings for the rest of the week that we could’ve made work. Our Dry Tortugas dreams were officially dead. We’d have to come back another time.
But if you’re going to be sad somewhere at 7 o’clock in the morning, there are much worse places you can be than Key West.

We strolled along the water and through historic neighborhoods, soaking up the morning golden hour. And we stopped at Blue Heaven for some breakfast.

Their “Very Good Pancakes” are incorrectly named on the menu, because these were, in fact, the best pancakes I’ve ever had in my life. I ended up eating half of James’ order. They were to die for. You have to go if you ever find yourself in town. The patio is adorable and the service was great. Highly recommend overall.
Over breakfast we started looking up other boat tours and snorkeling options on the island so that we could still get our tropical fix in. We landed on Barefoot Billy’s Dolphin Watch & Snorkel Tour and definitely did not regret it.

The tour was almost four hours long and we got pretty lucky coming across a pod of dolphins on our way out that we were able to follow for quite some time.

And then it was time for us to get in the water. If you know me at all, you know that I was of course the first person to jump in, but even I was surprised to see that James stayed in the water the longest. He LOVED it!

There were hundreds of different kinds of fish all around us, not to mention the cool coral and drop offs along the ocean floor. It was fascinating. I could’ve floated and watched everything happen beneath me for hours (though it was a bit chilly, even for me). It was like we were inside Finding Nemo. There was a group of frat bros on the boat with us who had just gotten back from Cabo and said this was MUCH better snorkeling than they’d had there. So do with that information what you will.
Eventually I got out of the water to warm up, and the good news was once you were done snorkeling, you could start drinking. This $99 tour came with unlimited drinks (which for obvious reasons you can only start enjoying after you’re done snorkeling). And they kept the drinks coming!

Overall, we had a blast! And it definitely helped ease the sting of not getting to go to Dry Tortugas.
We spent the rest of the evening wandering around Mallory Square to watch the sunset.

I’m a huge sucker for Christmas lights on palm trees. I find it just delightful.

And this city goes all out with its Christmas decorations!

From there, we wandered down the strip until we stumbled upon a spot with live outdoor music, grabbed a couple of drinks, and had ourselves an evening. Island life is pretty nice.

We finished our time in Key West by hitting the rest of the highlights: the end (or start) of Route 1.

And, of course, eating some Key Lime Pie. When in Rome.

A little history lesson about Key West before we finish our trip back to the mainland. Back in 1982, the US Border Patrol set up a roadblock in Florida City at the end of the Overseas Highway to search vehicles for illegal drugs and immigrants. The people of Key West (and all of the Florida Keys) strongly opposed this because it became a deterrent for tourists to visit the islands. So on April 23, 1982, the mayor of Key West, Dennis Wardlow, ceremoniously seceded from the United States and formed the Conch Republic. His argument was that if the US government was going to treat them like a foreign nation, then they might as well become one. And the stunt worked! It garnered enough public attention that the roadblocks and inspections were eliminated shortly thereafter. Key West still celebrates their “independence” on April 23rd to this day with week long celebrations throughout the island.
Secure in the knowledge that we would not have to wait in crazy traffic and time-consuming roadblocks, James and I began our trip back to Miami, stopping along the Keys as we went. The weather didn’t exactly cooperate, though, and it was pretty rainy, windy, and cold. But we still tried to make the most of it!

Our first stop was at No Name Pub, the self-proclaimed oldest bar on the Florida Keys. It gets its name from its close proximity to No Name Key. This is a great place to stop and get some pizza and drinks. Everything was delicious.
But then it was time to continue our journey down the highway.

The Florida Keys were only accessible by water until the Overseas Railway was built in the 1910s. This railway faced serious setbacks throughout its construction due to hurricane damage and was officially wiped out by the Labor Day hurricane of 1935 (the strongest hurricane on record to hit the US until 1988!) At the time, they were just beginning construction on an automobile bridge alongside the railway and an evacuation train failed to reach the workers before the hurricane hit. Nearly 200 WWI veteran workers died, stranded on the Upper Keys during the storm. Thank god for the present-day weather forecasts and accurate hurricane models that save thousands of lives with evacuation orders. I can’t imagine being stranded like that back then without technology and just having no idea what’s coming for you.
With the entire railway system wiped out by the hurricane, it was decided that the remaining structures would be rebuilt as a roadway, not a railway. And thus the Overseas Highway was born.

Seven Mile Bridge is perhaps the most impressive part of this 113 mile highway. This is also where you can see a 2 mile stretch of the original bridge from the 1900s running alongside Route 1. It’s been closed to vehicle traffic since 2008, but you can still walk and bike along it, and this is now the only way to access Pigeon Key by “land”.

We walked for a bit around this old railway, but it was super cold and windy so we didn’t quite make it all the way to the key.

But even on a cloudy day, I just couldn’t get over how beautiful and teal the water was! Maybe it’s a good thing we have to come back to do Dry Tortugas National Park one day, because there is definitely more along this 113 mile stretch that I would like to explore and just spend more time in.

Of course no road trip would be complete without checking out the local brewery! And we were not disappointed by Florida Keys Brewing.

Eventually, we made it back to the mainland in time for a hockey game. Surprise surprise, I know. We got to check off a new NHL arena AND my favorite hockey player from BU (Evan Rodrigues) scored a goal just for me. It was the perfect end to a whirlwind, roller coaster of a trip!

I know there are a lot of lessons to be learned about going with the flow and not letting little weather cancellations or sold out ferries ruin your vacation. And I will, of course, learn nothing from these lessons and be just as distraught the next time something goes even slightly wrong, but they’re lessons worth learning nevertheless.
Again, I highly highly highly recommend adding Key West to your bucket list! It’s an amazing town! And one you can see almost entirely by foot once you get there. Though, I obviously recommend doing the full drive from Miami and experiencing the Overseas Highway in all its glory. Give yourself several days to make stops along the way, discover a new key or two, and play Kokomo on repeat as loud as your rental car will allow. (Just remember to book those ferry tickets well in advance!)
Cheers!