4 Days in Key West

You know when you’re feeling low and you decide to book a solo trip? Well that’s what I did in November 2023 and booked a trip to Key West. I flew in on a Friday and flew back on a Tuesday and it was a perfect, restorative trip.

Friday

I arrived Friday around 3pm EST and immediately called a taxi to my hotel. Everything in Key West takes less than 15 minutes to get to, so I got there pretty quickly.

I stayed at The Perry Hotel technically on Stock Island, but rented a golf cart through them and was able to get to Old Town Key West, again, within 15 minutes.

My first stop was The Roost for half price caviar happy hour. It was okay! It obviously wasn’t the best caviar I’ve ever had, but you can’t beat half price.

For dinner, I went to Bagatelle and I do not recommend it. It was so expensive and the food was subpar. I got the caesar salad, key lime martini, and the grouper and it was $110! The grouper was room temp and the martini was not very good. The caesar salad was okay.

Saturday

On Saturday, my first full day in Key West, I got breakfast at Croissant de France on Stock Island. It’s all freshly made, so get there early to get what you want!

After breakfast, I went back to the hotel and changed for my dolphin excursion. I booked this through the hotel, which was so convenient because you get a discount AND you port from the hotel! Johnny, the concierge at The Perry, was amazing to work with.

The bar at The Perry also makes an amazing margarita. I got one and the crab fritters before the snorkel cruise and was set to go.

The dolphin snorkel cruise was 2 hours long and we in fact did see dolphins! We spent the first portion of the cruise looking for dolphins, and the second part snorkeling. I get very nervous in water, so I took a quick dip and then popped back onto the boat. I’m much happier on a boat.

After the dolphin excursion, I got ready to go on a happy hour crawl at the marina. This included:

  • The Boathouse - 4:30 - 6pm 7 days a week.1/2 price apps, beer, wine + margaritas

  • Half Shell - 4:30 - 6:30pm 7 days a week - includes seafood + 1/2 price well liquors, beer, wine.

  • Dantes - 4:30 - 7:30pm Monday-Friday - $5 appetizers, discounted shrimp/oysters, BOGO beer, cocktails, wine.

After the happy hours, I got dinner at Onlywood. I’d go for their happy hour next time instead of outright dinner, but they were very good for some neapolitan pizza and pasta.

This area is very cute, so I continued wandering and ended up at Kermit’s for some key lime pie and sat by the marina with an older man and we chatted while enjoying our key lime pie.

Sunday

Sunday morning I set out to Key West on my golf cart. I got breakfast at Blue Heaven, but I’ll tell you to skip Blue Heaven and go to Moondog Cafe instead. Blue Heaven was insanely busy, very loud, and took a long time. This is just my preference, but I personally did not understand the hype of eating pancakes in a backyard. There also was a very sick looking cat in the giftshop - I asked if there was anyone caring for the cat or if I could donate to its care, and the attendant ignored me repeatedly… So next time, I will go to Moondog instead of Blue Heaven.

A roof chicken at Blue Heaven

Once you’re done with breakfast, you can walk from either of these spots to the Hemingway House. I went solely to see the six-toed cats, which was such a treat. Most let you pet them and were very chill. I actually didn’t even go inside the house, I just wanted to see the cats LOL.

Once I saw enough cats (is there ever such a thing?), I drove over to the Butterfly Conservatory. This was also so amazing! As soon as I walked in, a big blue butterfly landed on me and hung out for about 5 minutes before leaving.

A little side note about this trip… I was feeling extremely heavy with grief. My grandmother had died suddenly in April 2022, and my sweet cat I’ve had for over 20 years passed very suddenly in August 2023. I went to Paris about a month after Paul, my cat, had passed so it was a great distraction, but I came back even more upset and heartbroken.

So I went on this trip alone to help connect with myself and my grief and just sit with it. At Hemingway’s House, I saw a cat that looked just like my sweet Paul. Also, my grandmother LOVED the color blue and butterflies. I took this day as a big big sign that they were together and okay and are looking out for me.

After the Butterfly Conservatory, I had possibly the best meal of my trip… I went to Banana Cafe and had the shrimp and scallop salad with the key lime crepe for dessert… Woweeee it was all so delicious and so fresh! I loved it so much.

Sadly, it was time to leave my golf cart and The Perry behind and check in to my new hotel: The Reach Resort. Overall, I loved The Perry more, but I did LOVE the beachfront access of this hotel.

Once I got settled in, I had dinner at Cafe Marquesa, which was also an incredible meal. I got the she crab soup, the pork belly and scallops, and the dessert trio (which included key lime pie, caramel milkshake, and beignets). I recommend every single one of these items.

Monday

My last full day in Key West! I started the morning on the beach reading my book (Black Friend by Ziwe). There are virtually no waves at all in Key West and very few beaches to access - so it was a nice beach day sitting on a chair!

For lunch, I ventured over to Amigos, which was delicious! I got the shredded chicken tacos, guacamole, and a Mexican coke. It was pretty expensive ($35), but the quality of the food was really good.

I went back to the beach at the hotel for a few hours before getting ready for dinner! I somehow got a reservation at Latitudes, which is on Sunset Key, so you have to take a ferry to the other island.

Overall, I think the experience and the view was better than the food. I got a caesar salad, lobster risotto, and key lime pie. None of it really wowed me… But again, the view was beautiful.

Tuesday

My flight left at 2pm, so I had a few hours to spend this morning. I had breakfast and my coffee on the beach and started a new book (Saturday Night Ghost Club by Craig Davidson). I was all packed up, so I grabbed lunch at The Lobster Shack right when they opened and got the key lime lobster roll. Holy moly! I definitely recommend getting this!

A quick note about the Key West airport… It is tiny. It took me 3 minutes to get through security. I got there an hour and a half before my flight and honestly, could’ve gone like 30 minutes before and still had plenty of time. I wish I had waited to go so I didn’t waste so much time at the airport.

Tips for Key West

  • It is not dressy, don’t bring heels. I wore my linen pants, a blue set, and 2 dresses. I felt extremely overdressed almost everywhere I went.

  • It’s not really beachy, but there are beaches! Don’t listen to the haters - you can beach in Key West.

  • Get a golf cart!!!!!! I had so much fun on my golf cart and was absolutely worth the expense.

  • It’s okay to stay away from old town key west if you have a golf cart. I loved Stock Island! I loved it even more having the golf cart :)

  • There are chickens everywhere. They will scream in the mornings and you will hear them in your hotel room.

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