So like I was saying yesterday, I just recently got back from a trip to Key West with my sisters. This was a gift trip from my dad which included:
- First class seats on the flight
- An awesome suite at the Key West Marriott Beachside hotel
- A Mustang convertible to tool around town in
As you can see, there were oh so many things to love about this trip. We came to the decision to go to Key West in the first place because we all wanted some place we hadn’t been before, some place that would be warm in January (but not too far away), and my BFF Lisa has always talked about spending time in the Keys with her fam. According to her, it was an amazing place…and she wasn’t lying.
So we three girls headed out at 4:15 a.m. Friday morning to catch our 6:30 a.m. flight.
Why is it that every single flight I take seems to leave at the crack of dawn.
Anyway, turns out leaving at 6:30 isn’t half bad when you’re flying first class. Free Bloody Mary’s, tons of leg room, a plethora of movies to choose from, warm towels….
The good stuff is just never-ending.
Anyway, after our first flight landed us in Tampa we caught our connecting flight to Key West, which just happened to be a teeny, tiny, 17-seater:
My sisters were less than impressed, to say the least.
I, however, saw it as an adventure 🙂
Anyway, after a quick hop, skip and 1 hour flight, we were finally in the Keys, where we picked up our awesome Mustang convertible!
Then, after only about 15 minutes of tinkering around, we were finally able to figure out how to get the top down:
So that was the first exciting thing to happen.
Our hotel was only about a 10 minute ride from the airport—but when you’re riding in a convertible every trip seems so much cooler.
At the hotel check-in the first day we were confronted with what would be our first clue into the festivities set to take place at the hotel that weekend. Despite his repeated check-ins to make sure that the three of us would have two rooms near each other, when we checked in we were told the hotel was so full, the best they could do was get us a room right above the other room.
Weird, right?
But whatever. We were nonplussed. That’s how you are on vacation, right? Things happen, and you just roll with the punches.
Our first order of business (or Steph’s first order of business, at least), was to check out the beach. Lisa had warned me ahead of time (and I had passed the word on), that the Keys don’t have beaches quite like other beaches. Our hotel just happened to have its own beachfront area, so that was nice, but even so, we ended up spending the majority of our time in the hot tub (where we met a medium, a 15-year-old bull herder, a CIA agent and a retired school teacher, to name a few).
That first night, at the recommendation of our new “medium” friend, we headed to Duval Street for dinner and to hit up Willie T’s, where bar-goers staple signed dollar bills to … well, pretty much anything they can find to staple it on:
After returning to the hotel Friday night we received our second clue as to the festivities of the weekend. Or should I say the festivities themselves made us aware of the festivities. Basically, at around 4 a.m. this incessant blasting of music started, and after about a half hour of listening to it, Steph and I decided to call down to the front desk. Turns out Jen had called as well, and they sent security up to stop it.
The next day we were told a wedding would be taking place at the hotel that night.
Oh, and it was someone local.
Oh, and there were about 500 people invited.
It wouldn’t be until later that day (well technically it was Sunday morning, to be exact), that we would find out it was actually the owner’s daughter who was getting married there.
But more on that to come later.
So after having very little sleep on Friday night, we nonetheless decided to head out to a few other places. First up was the Southernmost point in the U.S. (which is only 90 miles to Cuba), and to get some coconut water (Literally. A man with a drill was drilling holes into actual coconuts and selling them for $3.)
Then it was on to Mallory Square. Unfortunately we weren’t there at sunset, which is supposed to be the most beautiful (and most eclectic) time there. Oh well, that’ll just have to be for another trip.
After Mallory Square we headed over to this local seafood festival we had seen advertised in a park near the hotel. I’m really glad we ended up doing that. It was all local people and local restaurants with tons of booths filled with beer, seafood, artwork and live music. We ended up trying out lobster, conch fritters (Fried conch, basically. Whatever that is!), and shrimp.
After the festival (in which we all bought artwork by a local artist that was framed with used lobster traps! At the time it was cool…and it looks a lot cooler than it sounds, trust me) we went back to the hotel and the hot tub, before heading back out to Duval St. for dinner and—something I had been excited for the entire trip—Key Lime Pie!!
Now, what I forgot to mention before was that earlier in the day we stopped to pick up some provisions in preparation for the upcoming night:
Yup. Those, my dear friends, are ear plugs. But despite that fact that our sister Jen swears by them, Steph and I just could not seem to get used to them. It’s the oddest sensation to have those things in your ears, and try as we might, at around 3 a.m., when it seemed like we were perhaps in the clear and had avoided any ruckus for the evening, I removed the buds.
Bad move.
Turns out the partying wasn’t going to start until 4 a.m. that morning.
From 4 to 7:30 a.m. we sat up listening to the thump, thump, thumping of the base to the terrible music the party-goers were blasting (in, of course, what turned out to be the room right next to where Steph and I were bunked).
Despite my two phone calls, Jen’s two phone calls, and what I’m sure were any number of phone calls from whatever other rooms in that hotel turned out to not be guests of the wedding, there was nothing the poor manager on duty could do. What was she supposed to do, after all? Ask her boss to kindly turn it down?
I don’t think so.
Anyway, lesson learned. Next time you think something might be up…ask. You’re probably right.
It wasn’t a total loss, though. My dad got comped his miles back for the room that night, and on Sunday night Jen and Steph and I were upgraded to an amazing 3-bedroom, 3-bath suite with a kitchen, dining room, porch and roof access.
Not that we actually needed all that, but it just went so nicely with the rest of our indulgent trip, we had to accept 🙂

On Sunday we ended up spending most of the day lounging, but we did head out to breakfast at Blue Heaven where I had shrimp and grits (which brought me right back to my JMU days. Sad!)
And there was live music (as there is most places in Key West), and ping-pong and art work (as there is most places in Key West):
After brekkie it was back to the hotel for more sun and hot tub. We ordered room service (beer and pizza. Dinner of champions!) and spent our last night soaking up our awesome suite and sharing some last-minute sister gossip.
All in all, it was an unforgettable trip. We spent most of Monday traveling, where we had a five-hour layover in Tampa and spent the entire time in the elite travelers lounge (I told you. This was a fancy trip all the way!), drinking free wine and eating cheese, crackers and salsa (oh, and taking over the TV, much to the chagrin of anyone else in the TV room).
A few more notes on The Keys and its awesomeness:
1) There were a group of feral cats at our hotel, which my sisters weren’t quite too fond of, and, as per usual, I was obsessed with:
2) There are also tons of roosters (or hens? Not sure I’d be able to tell the difference) around Key West, which cock-a-doodle-doo at all hours of the day (seriously, not just at dawn):
3) And lastly, if you go to Key West you must ride a bike. Sadly, I do not have a photo of me and my sis’ riding around on a bike, because we didn’t rent any, but it seems that when in Key West, this is the thing to do, so I would recommend it.
And that’s about it friends! My sisters and I were so, so grateful to have had the opportunity to go on this trip together. And I would suggest that if you ever get the opportunity to head over to Key West, I’d jump on it. I haven’t been anywhere else quite like it.
Bis bald, friends!