Where: Key West, Florida
When: March 9, 2004; March 10, 2005; March 20, 2008
With: College friends, but mostly Chris, Steve, and Mikey (also Suzannah and Doug!)
The Florida Keys are an archipelago of islands that extend out in a crescent from the southern tip of Florida. Of the 800 islands, most are rural, some are fancy, and some are just plain fun. What they all have in common is palm trees, turquoise waters, and beautiful weather. Each island in this chain is considered a Key.
I have only been to one Key in the chain, and that would be the last one, furthest west, appropriately named Key West. However, while I may have only visited one, I have been three times, and each time, I love it more and more.
The reason I have been there so frequently is that it is a popular stop on cruise ships. Cruises were the bread and butter of my spring breaks while in college in Florida. They were inexpensive, left from Miami (so no plane tickets required), and pleased the large group we usually traveled with. We ended up in Key West on both my junior and senior year spring breaks, as well as a trip my college friends all took a couple years after graduating. We called it "adult spring break" in which we may have been out of school and working, but our maturity levels when handed fruity drinks on a boat had not changed.
Each visit back to Key West was unique in its own way and I got to explore a different piece of the town in the short time I'd spend on land. This is the only complaint about a cruise ship: our time at port is limited by the cruise schedule, so rarely we spent more than a few hours here.
Junior year spring break was my most memorable. It was the first full day of our trip, and my first ever cruise (or proper spring break for that matter). We docked at 6am. I couldn't believe how turquoise the water was around our ship.
When: March 9, 2004; March 10, 2005; March 20, 2008
With: College friends, but mostly Chris, Steve, and Mikey (also Suzannah and Doug!)
The Florida Keys are an archipelago of islands that extend out in a crescent from the southern tip of Florida. Of the 800 islands, most are rural, some are fancy, and some are just plain fun. What they all have in common is palm trees, turquoise waters, and beautiful weather. Each island in this chain is considered a Key.
I have only been to one Key in the chain, and that would be the last one, furthest west, appropriately named Key West. However, while I may have only visited one, I have been three times, and each time, I love it more and more.
The reason I have been there so frequently is that it is a popular stop on cruise ships. Cruises were the bread and butter of my spring breaks while in college in Florida. They were inexpensive, left from Miami (so no plane tickets required), and pleased the large group we usually traveled with. We ended up in Key West on both my junior and senior year spring breaks, as well as a trip my college friends all took a couple years after graduating. We called it "adult spring break" in which we may have been out of school and working, but our maturity levels when handed fruity drinks on a boat had not changed.
Each visit back to Key West was unique in its own way and I got to explore a different piece of the town in the short time I'd spend on land. This is the only complaint about a cruise ship: our time at port is limited by the cruise schedule, so rarely we spent more than a few hours here.
Junior year spring break was my most memorable. It was the first full day of our trip, and my first ever cruise (or proper spring break for that matter). We docked at 6am. I couldn't believe how turquoise the water was around our ship.
Transportation from the port to the town was by wooden trolley. Such a cute way to travel.
We were up surprisingly early for college kids, but this was spring break, and there was no time to waste. The boat left at 2pm! So what did we do? We headed straight to a bar! This was Irish Kevin's.
This was actually one of those pivotal life moments for me. You see, I wasn't a huge drinker at that point in my life, and I hadn't really found a taste for beer. But man, something about sitting at a bar at 8:30am and ordering a Bud-Lite with the warm weather outside and nothing to do but enjoy made that the best beer I'd ever had in my life and I've loved beer ever since.
The bar was hopping in a way that you'd never know how early it was. I guess this is Key West culture. There was a guy with a guitar on stage singing cover songs. The place was packed. It was hysterical. My friends even got up on stage to do some karaoke.
One of my favorite scenes of the day was at a place called Flying Monkeys selling every type of tropical alcohol slushie in the world out of pre-mixed machines: daiquiris, margaritas, piña coladas, you name it. As we walked up and debated whether $20 would be worth the drink (that's a LOT for a college kid!), a weathered man wearing sandals and an open Hawaiian shirt sat on a stool sucking one down. The guy spun on his stool, fell over to face us and said, in the most cliché drunken voice "it will be the best f'n $20 you ever spent in your life". Wow!
These bars both sat on Duval Street, which is party central on the island of Key West. It is lined with bars, restaurants and tourist traps, but the scene is a good time. It is like the Bourbon Street of Key West.
Time drifted by pretty quickly and next thing I knew, everyone was at an outdoor patio smoking hand-rolled cigars and paying homage to Key West's most famous resident, Ernest Hemingway. The rest of the day was a slight blur.
Our senior year visit to Key West was slightly different than our first. This time we docked in the afternoon, so when we rocked up to Flying Monkeys for a drink (ballers), it didn't feel as ludicrous to be intoxicated.
This year we were able to squeeze a little bit of sightseeing in with bar hopping. Sat at the southern end of Duval Street is a monument marking the southernmost part of the continental United States. As the large, stone monument indicates, it is only 90 miles to Cuba from here.
Southernmost photo shoot. No one else is more southern than us right now.
Love this photo. It's so beautiful.
As the sun went down, we headed back to the boat and got some stellar views of the surrounding islands at dusk from port. Definitely a beautiful place.
When we returned as "adults" in 2008, it was a trip more similar to our first visit. We got in early and had a nice view of our boat at port in the turquoise water.
We also rode the trolley in to town.
This time, we ended up at Sloppy Joe's for our early morning Bud-Lites.
There was a guy up on stage singing songs and just like last time, my friend's jumped up for games and karaoke.
This time, as we left, I paid attention to another fun fact about Key West. The famous Route 1 highway that runs from Maine down to Florida along the coast actually hits the end here in Key West. And here was mile marker 0. A well-known road trip is to take this drive down from Miami to Key West, a 3-1/2 hour drive in total, but meant to be enjoyed along the several bridges that connect each of the islands together. One day, I'm hoping to make this trip.
And so, while my Florida Keys trips have been limited to the one western key, I feel like I've done my best to take in the vibe on this beachy, party island. Hopefully, with all my trips to Florida to visit parents, I can eventually make a road trip to explore more!






















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