The planning for this trip actually started way back before Christmas 2015. My flight home for Christmas was overbooked and I courageously volunteered to sit in the airport for 5 hours and watch Netflix for the small payment of $600 in Delta flight vouchers. Once I was awarded for my sacrifice, I immediately called my mom and said I got flight vouchers I’m going to Miami.
I planned my trip very strategically and ended up being able to take an 11 day long vacation from work. Because I am very lucky and have two great friends who live my dream vacation every day, I was able to first visit my college roommate, Summer, in Key West and then visit one of my best friends, Aly, in Miami.
I went to Key West first. I flew into Miami, rented a car, and drove through all the Keys at night (no one warned me how many keys there are). I didn’t know what to expect from Key West I had never been before. My only reference was when I went to the Margaritaville restaurant in Nashville.
I quickly learned they are not known for their beaches. They have, I think, two natural beaches and then the rest are man made. The draw of Key West is definitely the fishing, the water sports, and the drinking.
My first day Summer took me to a bottomless food and drink brunch at Hot Tin Roof on Sunset Pier. And then after hours of eating and drinking everything we could, we decided what better thing to do then dangle ourselves 100s of feet over the ocean strapped to a parachute and we went parasailing. It was my first time parasailing. We went with Sunset Watersports. Our driver, Preston, and first mate, Andrew, were great. They were young locals who knew a lot about the area (always good to find out things to do that are off the beaten path). They were a lot of fun and took great pictures of the whole experience (always the most important part).
One of the biggest draws to Key West is the fishing. They have purposefully sunken large boats around the island to create great places to fish. We (when I say we I mean they) went spear fishing (while I sat on the boat) at the Vandenberg Wreck. They caught fish that made my fear of the ocean 1000x worse. I had never been fishing before especially not for fish that are 40+ pounds. The best part about it was that they were catching dinner.
Never in my life have I been with my dinner from start to finish. When they wrangled this massive grouper on to the boat, I was in shock. Then to watch it be sliced up and put in a plastic bag that we brought with us to the restaurant, was just shocking. This was definitely a new experience for me (definitely brought a whole new meaning to “fresh catch”). We brought the fish to a great local spot, Hogfish. We showed our waitress our plastic bag full of fish and explained we wanted 1/3 grilled, 1/3 fried and 1/3 blackened (it was weird how normal this exchange was). We ordered a ton of appetizers while we waited for our catch to be prepared, including a lobster bisque that I insist the whole world try (literally an entire lobster in huge chunks in it). They prepared our catch better than any fish I’ve ever eaten. I was a little freaked out that I had seen this meal from when it was first caught, but it was so good I was able to forget about it.
After you’ve experienced the water sports and caught your next meal, you need a good drink (because vacation is hard and you should reward yourself for all the work you aren’t doing). Key West has a great downtown area that revolves around its main drag, Duval Street. There’s the usual Sloppy Joe’s, Margaritaville, Fat Tuesday’s and Señor Frogs. But, there’s also a lot of smaller local places hidden in between. My favorite was Rick’s Tree Bar. It is a tiny outdoor bar under a tree (you can’t miss the massive tree, but you might miss the bar hiding under it) that makes amazing drinks from fresh squeezed juices. And there are no open container laws, so you have freedom to take your fresh squeezed alcoholic juices around town.
Key West is definitely a fun island for active drinkers to be out on the water during the day and then drinking like fish at night. It’s a small island with a small tight knit group of locals with a great chill beach town vibe. Definitely one of my favorite adventures I’ve been on and the island will definitely be seeing me again!
*Post about Miami is coming soon!