Key West, Florida

Key West! The home of several historically significant places including Hemingway House, the Harry S Truman Little White House, and the Southernmost Point of the Continental US…but most importantly Key Lime Pie! — I’m being very serious about the pie. I actually did this trip as a ROAD TRIP with my friend Laura, whom I met in Australia, and her family, who traveled over from the UK and graciously let me crash their family vacay!

The best way to get your bearings in Key West is to take one of the tours at the very beginning of your first day. They have a trolley but we opted for the Conch Train. It’s a little bit cheaper and I think has a bit more personality. We rode the train around downtown once, approximately 1.5 hours, and then walked the first portion of the route as it was the most colorful and the most interesting to us.

We started out from Mallory Square and walked over to Mile Marker 0 of Route 1 for a quick photo opp. US Route 1 was the original easternmost highway, hence Route 1. It connects most major cities along the east coast, running from Key West, Florida up to Fort Kent, Maine and is the longest north-south running highway in the US. One day I would love to road trip Route 1 but for today, we just took our photo with the Mile Marker 0 sign.

We then walked over to The Harry S Truman Little White House. Admittedly we did not do the tour as time and money are always limited, but, being from St. Louis, Missouri, I feel obligated to check out anything related to Missouri including President Truman who hails from Missouri! We did a quick stop and while it was difficult to get a good photo of the house, I can vouch that it is on a very pretty street and worth the small detour from the main road.

After The Little White House we continued on to the Hemingway House, arguably the more famous of the two. We did purchase tickets for the tour in conjunction with our Conch Train tour for a discounted rate. The house itself if beautiful and immaculately maintained. My favorite two things though were the fact that it is the site of the first in-ground pool in Key West, born of a fight between him and one of his wives which resulted in her removing his boxing room and replacing it with a pool.

My second favorite thing about the house was that it is flooded with the most adorable cats ever! Many of these cats are polydactyl, meaning they have 6 toes! You know when Great Dane puppies have those monster paws that are way too big for their bodies and they trip on them but it’s ridiculously cute? The cats looked like that!

Finally, while it was also cool to see Hemingway’s writing studio, if I was hard pressed to pick a third favorite thing, I would have to say the nanny’s bathroom – it had really lovely art deco tiles!

After this we made our way to the “Southernmost Point of Continental US” – just 90 miles north of Cuba. I think it’s closer to Cuba than it is to Miami, which explains all the amazing Cuban food! Try “ropa vieja” if you get the opportunity. It’s so tasty and makes a great leftover too!

We continued over to South Beach. This was, admittedly, not a very good beach. Key West, as it turns out doesn’t really have good beaches, but in my desperate sun-deprived-winter-in-NYC state, I of course put on my bikini and traipsed out into the water and then laid out to pretend like I was tanning. I say pretend because it was a bit cloudy and only 70 degrees, not exactly ideal, but I’ll take what I can get.

We also sat on the pier there for a little while which juts out into the water where the water is beautifully blue and clear beyond the seaweed cluttering the tiny beach.

We wrapped up our first day with the Mallory Square Evening Festival. Every night approaching sunset people gather in Mallory Square where stalls from local artists are set up and local performers put on busking shows. One man juggled fire on top of a unicycle and another trained cats to jump through a ring of fire! (Although the man was a little scary, the cats clearly loved him!) We then caught a movie!

We also happened to be in Key West on the last day of Hannukah. I haven’t mentioned before now, but I was traveling with my friend Laura and her parents from the the UK. They had never seen a Hannukah celebration and weren’t familiar with the story of Hannukah. It was really exciting to get to share that experience with them as they learned the meaning of Hannukah and the importance of being and spreading light to the world. (Not my best photo but I took this one for my Israeli bf halfway through a sufganiyah.)

For our second day in Key West we decided to spend the morning enjoying the shops and the ice cream! We purchased shirts with roosters on them to commemorate all the sleep lost on account of the wild roosters waking us at 3:30AM every morning! Apparently cock fights were once legal in Key West and when they were banned everyone just set their roosters free — they’re the Key West equivalent of squirrels, but much louder!

We then picked up some ice cream and headed over to Sunset Pier. The water was just impeccably blue and the chairs were all sorts of fun colors! It was the perfect place for a treat and super close to our afternoon adventure taking off from the Historic Seaport.

We spent the afternoon with Fury Water Sports, snorkeling, kayaking, and paddle boarding. Although it was freezing by Key West standards and I admit I was very hesitant to get into the water, I’m so happy I did! We were able to watch a sting ray gliding!

After about 15 minutes though I gave up. I was too cold, so I hopped out and enjoyed the open bar and hot fried chicken! After everyone was wined and dined, we hopped into some canoes and paddled over to the protective mangrove keys to learn about the wildlife and environment and do a little singing. The singing was not on the itinerary but I can’t get into a kayak without singing some water-themed Disney songs – cue Moana, Pocahontas, and The Little Mermaid.

Lastly we spent some time on the paddle boards at sunset! I’m really grateful that I didn’t lose my balance in the wind and fall back into the water. I’m sure if I had been freezing in daylight I would have been positively blue by sunset!

A little more fried chicken and champagne to cap off the night before returning to the marina. Laura and I insisted on getting some photos with the crew who had really been a blast! They had also been very helpful when Laura and I were too foolish to pack proper “cold weather” gear, and with a little persuading, generously loaned us their wind breaker jackets! One piece of fried chicken was lost in the making of these photos, but that’s a small price to pay 🙂

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