Oh Key West, how I love thee. Five years ago, I took my first trip to the Florida Keys. I have always had an aversion to the Sunshine State and my expectations were pretty low. Needless to say, I had an wonderful time; in fact, I fell in love. It is more than tourist bars and crappy souvenir stores. There is so much history, beauty, and fun on this tiny little island.

WARNING: This is a gigantic photo post. You will enjoy looking at it. 

Getting to Key West: you can fly directly into the Key West Airport, which is about the size of my house. Beware of the bumpy landing as they're trying to land a plane on an island that is 4 miles long. And you can to see the freaky Conch Republic family. I wouldn't have it any other way.


Or you can fly into Miami or Fort Lauderdale and take U.S. 1 all the way to the Southernmost Point of the Continental United States. It's about 3ish hours, unless you hit traffic. You will cross over many bridges, including the infamous Seven Mile Bridge. It's a fun trip, but I'll be honest, I don't ever want to do it again. 

Cruisin' around Key West, as close to Cuba as I'll get for now. Key Lime on a Stick! My favorite block in Old Town recently got a rainbow makeover. And I was gifted a reusable tall boy can for a week of walking around with alcohol! 

The Coffee Situation: I am addicted to coffee. I need it to live. When I go on vacation, I have to know what the coffee situation will be. Will my hotel be equipped with a coffee maker and Wolfgang Puck pods? I knew it was going to be a good week; starting every day with a trip to Cuban Coffee Queen. We would order 2 bucci shots (Cuban espresso with cane sugar, in a plastic cup) and 2 iced coffees, no sugar. Their iced coffee comes with coffee ice cubes and it is so damn good. It is tiny counter, that is always poppin'. Later in the week, we discovered the CCQ has a second location down Duval Street, near Old Town. Their second location is way chill; with picnic tables and happy hour. On our last day in town, we indulged in egg & cheese sandwiches(add banana pepper), pressed on Cuban bread. It brought me back to life after a night of karaoke. I'm still dreaming of this sandwich. There is no other place to go for coffee while in Key West! 


Two Friends Restaurant has been a Key West staple since 1967. We love to drop in for happy hour. Great drink specials, huge oysters, and the best lobster bisque I've ever had! I love open air restaurants, especially when pigeons pop in for a crumb or two. They have karaoke a few nights a week, which includes a karaoke cam! I was so thrilled that my dress matched this car.

Two Friends Restaurant has been a Key West staple since 1967. We love to drop in for happy hour. Great drink specials, huge oysters, and the best lobster bisque I've ever had! I love open air restaurants, especially when pigeons pop in for a crumb or two. They have karaoke a few nights a week, which includes a karaoke cam! I was so thrilled that my dress matched this car.

On our second day of vacation, we went on the Ultimate Adventure. A six-hour boat tour that started off with parasailing, jet-sking, kayaking, & floating climbing walls. I've acquired a fear of heights over the years and was a little scared that we were the first people to parasail! Especially when the captain of the boat had to show his assistant how to properly assemble our life-jackets. It was pretty fun, but my hands went numb because I was gripping the bars so hard. I'm glad I can check that adventure off of my list! After a few hours of fun in the sun, we had lunch, and took a trip about seven miles out to the only living coral reef in North America. The past few times that I snorkeled, I wasn't feeling it. I either panic or get stung by a jellyfish. I thoroughly enjoyed this trip, probably because I had a noodle. I loved seeing all of the fish, but promptly exited the water when I heard there was an eel. We had such a great day on the boat; to top it off, we saw dolphins on our way back to land!! 

Key Lime Square, Duval Street. (Second Cuban Coffee Queen is located here!) 

Mallory Square is the only place to watch the World-Famous Key West sunset. You can find tarot readers, wooden christmas ornaments, and James' favorite frozen lemonade. It still blows my mind that people will still watch a guy on a unicycle eat fire. I was so pleased to find this Holy Guacamole stand. I was hangry and this satisfied my craving. There is something so special about watching someone make fresh guac. Then we went to my favorite flamingo shop, where sadly, the flamingo wings didn't fit me. 

The day following our Ultimate Adventure, we planned chillin and exploring on beach cruisers. James was having some digestive issues, so we hit up Juice, a new juice bar in the La Concha Hotel. Is there anything that green juice can't fix?

We had to stop by the Hemingway Home. I don't care that the house hasn't changed since 1937, I just love the vibes there. I'm always so amazed at how incredibly packed it always is. We got a picture in front of the pool, which could be a Christmas card contender. I am thinking about looking into a lifetime membership, since we had our wedding there, but for now I think of my entry fee ($13, cash only)  as a donation to the cats. One day, I'll own a polydactyl. Afterwards, we popped across the street to check out the Key West Lighthouse and Keeper's Quarters Museum. ($10 entry fee) It was so cool to have a 360 view of Key West. There was thank you card from Ernest Hemingway in the museum. I was bummed that they did NOT have a pressed penny machine.

We rode our bikes to Fort Zach Taylor State Park aka the only real beach in Key West. Beware, it's rocky, so I highly suggest wearing water shoes. There is also a small fee ($1.50 per biker) to enter, but it is very worth it. The water is so blue and beautiful and you can definitely check out lots of fish. This is great place for a family picnic. James and I set up our double-wide hammock and napped. It was a nice way to relax in the middle of the day.

On our way back into town, we stopped by the Key West Cemetery. It has been around since 1847 and there are atleast 100,000 people buried there. I normally don't do cemeteries but felt safe in numbers. I made sure to not ride my bike on the grass, as we admired gravestones. I was rather impressed with the gigantic conch shell sculpture. 

The next morning after exploring, I woke up feeling miserable. The combination of prolonged sun exposure and happy hour wine finally caught up to me. I was toast before dinner. So remember to stay hydrated on vacation, Judys!!! On our fourth day of vacay, we planned to do stand-up paddle board yoga with Lazy Dog. Minutes before we left, I was barfing Pepto and eating watermelon; I was in bad shape. The only thing that helped me survive were chia seeds. I truly believe in the powers of chia. 

It is a life goal of mine to headstand on a paddle board , but I knew that wasn't happening this day. My only short-term goal was to not barf in the water. It was so cool to see tarpons swimming by as we posed. It wasn't until we got into warrior 2 that I felt unstable and finally fell in. I swear, the first dip really helped my hangy. I know you're not supposed to think during shavasana but I was on the board, looking out in the distance and I spotted my guiltiest pleasure: McDonald's. In that moment, I hoped for a family trip through the drive-thru. On our way back to the marina, our instructor took us through the mangroves, which actually turned out bad for me. Not only was I hangry, but I got stuck in between a mangrove, where I thought a crab was a tarantula. I had a mini-temper tantrum so bad that I opted out of post-paddleboard pictures!! Who am I?? Despite all of my self-inflicted personal drama, it was a really fun day. The only way to beat a hangover is to sweat it out.

For lunch, we went to Conch Republic, one of my favorite restaurants in Key West. It was the very first bar we went to on my very first trip. It is on the dock of the marina and the island vibes are in full effect. PLUS, they have a functioning pressed penny machine. Some fishermen had just returned from a catching loads of mahi. They were nice enough to give my nieces some leftover bait fish to feed the tarpons. The fisherman showed us a blown-up pufferfish in the belly of the fish he was cleaning. 

Our evening activity consisted of a champagne sunset cruise. The boat left around 6:30pm and we rode around til the Sun went down a little after 8. Nothing makes me feel more boujie than wearing resort wear while drinking champagne on a boat.  After the boat cruise, the siblings went out for a night on the town. We were all sleepy and exhausted but we found our second wind!! We walked thru Old Town and had some beers at the Southernmost Point. It's so busy during the day, but v chill at night. We made our way back up Duval for a mini bar crawl. We planted at Irish Kevin's, where there was a 90s cover band! I made friends with a sailor themed bachelorette party and we played ring toss. We bopped across the street for karaoke at Rick's, where the DJ only had 2 Madonna songs. What a disgrace! I had to sing Mariah Carey and our second songs got skipped, so juggalos could sing Pink Floyd. I'm a little high maintenance when it comes to karaoke, can you tell? We shut properly shut down Duval Street and I can't remember the last time I saw 4am. 

Friday was our last full day in Key Key (as I like to call it). We took a leisurely walk down Whitehead Street aka we were walking to the Post Office. We passed the original office of Pan-Am and oh, how I wish I could have taken that airline. 

I love walking out of the front door to see a gigantic cruise ship. We spent Friday AM playing pool bingo, where we did not win a thing! We purchased the rest of our souvenirs and packed the our bags, so we could enjoy the rest of the day. 

We decided that for our last night, we would hit the best drag bar in town, Aqua. I went to Aqua for my bachelorette party and it was incredible. These drag queens are ON POINT. Never in my life have I see a queen do a number with aerial silks. How do you even follow that? Oh, I know, wear a pot leaf dress and sing 'Marijuanaville". Hands down, the best drag show I have been to. It was the most perfect Key West finale. 

Our flight home left at 8am, so we were up with the Sun. I loved these last few moments in Key West. 'Til next time! 

Check out my Key West Flickr Album here 

Luscious JudyComment