A Long Weekend in Key West, Florida

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What do you do when one of your BFF’s invites you to celebrate the big 5-0 in Key West, Florida? Well, you say YES, no matter what it takes to get there. Key West is very similar to New Orleans, Louisiana in that it’s a party town but also has some sophistication hidden in nooks and crannies.

Duval Street is the main drag here, full of over-priced t-shirt shops, bars, restaurants, art galleries and liquor stores. It’s super fun to walk up and down, but after a while your soul needs more. Thought I’d share the things we loved to help narrow down what feels like a million options. I skipped the bar suggestions as they start to feel the same, but they are A LOT of fun.

Restaurants: There are a TON of great restaurants in town that don’t include a smelly sports bar.

Blue Heaven for breakfast – the banana pancakes were delish and the place was super cute, situated in a garden setting. The pancakes rival what my friend and I once had on a trip to Bali. In Key West fashion, there is live music to set the tone. If you can’t find live music in this town, I have no words.

Cuban Coffee Queen for breakfast burritos of the Cuban kind – they’re filled with three fried eggs, American cheese, choice of ham, bacon, sausage, chorizo, turkey or pork roll, rice and black beans in a plain or wheat tortilla. Pair it with a Dr Pepper and you have perfection. lol.

Moon Dog Cafe for lunch – They’ve got a great patio out front – we had an excellent burger here. There is also a good looking bakery when u walk in – trying to cut down on the carbs, but it was enticing!

El Meson De Pepe for authentic Cuban food – the pork was to die for. The wait will be long so take advantage of the outside bar for cocktails and live music. If you can get a table outside – do your best. The inside has no ambience, what-so-ever.

date and thyme for yummy juices (I’m on a juicing kick) – also an option for an organic lunch and they have a small market if you need some healthy snacks. They have a great patio if you want to pop a squat there.

Half Shell Raw bar for the freshest Shrimp on the planet. They also have a great happy hour. We tried the fried Conch, but, honestly it was ick. The texture of that particular seafood just grosses me out. (Sorry Conch lovers). We had the table right under the sign – it was great.

Onlywood Pizzeria for some fabulous ambiance and pizza. We found out about this place via some great peeps we met on our sunset cruise. They do have a black cat who’s part of the deal, so if you have a strange issue with black cats, or cats in general, you may want to pass on this one. We had the most fun night here.

Key West Cakes for the best key lime pie EVER. Not too sweet, not too tart. We bought one as my friends b-day cake stand in. We ALMOST bought another one. My mouth is watering as I write this. I missed out on a picture of it – dammit! You’ll just have to trust me.

We ran out of time to experience the eateries below, but should be on your list. Truly, we walked by each of these and said, “Aww, how cute is this place?”.

  • Nine One Five – Had my friend and I been by ourselves we would have at least tried the wine bar – not so fun for the beer drinkers we had in tow.
  • The Little Pearl – They are currently offering a set 4 course meal – this can be tricky for picky eaters.
  • Louies Backyard – It’s oceanfront with an amazing menu. Not quite sure why we didn’t make the rooftop bar, but hey, you can’t do it all.
  • The Thirsty Mermaid – I like the name, the logo, everything.

Shopping: I have to admit, there weren’t a lot of options in this department, but I did manage to find a few great spots

La Rubia for sustainably made Panama hats. They are sooooo cute and there is a good selection. They’re made in Ecuador and are of excellent quality. I actually found a hat that looks half way decent. They also had some cute handbags I couldn’t live without.

Besame Mucho for nicely curated products – lots of drool worthy fragrances and home goods. The jewelry was really nice also. They are closed on Sundays, so keep that in mind. Once you get there, be prepared for a long shopping experience.

Tuckers Provisions for cute clothes and other gifts. They have things for men and women. This was the one place on Duval I REALLY liked for shopping.

Salt Island Provisions for local arts and crafts. I’m a total sucker for handmade things and this shop had some really cute stuff. The woman working there was hip and cool also. It’s right across the street from date and thyme, so you can make an afternoon out of it.

Best sunset experiences: The sunsets down here are truly amazing. Finding a spot without a million people can be tough. We got creative here and were able to witness the sunset in all its glory. There are a ton of spots but these 2 were our favorites.

First, the tip of the island at Fort Zachary Taylor Historic State Park. We found some cheapo Mexican blankets at a drug store, whipped up a charcuterie plate and cracked open a bottle of birthday champagne. It was a great way to spend our last night. Ask the person at the guard shack where the best spot is and he or she will tell ya. One thing to note, they are DEAD serious about the closing time of the park so be prepared to get booted out right after sunset.

Second, the night we had dinner at the Half Shell Raw Bar, we saw the most beautiful catamaran docked in the harbor. THAT was the boat we wanted for a sunset cruise – the SV Argo Navis – a 75ft long, 35ft beam, luxury catamaran. It’s not one of the giant boats with a bunch of drunk, unruly tourists and loud music. This was truly civilized and peaceful. The boat comes with a top-shelf open bar and 5 or 6 appetizers on a stick. Don’t let the stick fool ya, they were all fantastic. We couldn’t have been happier that night. Take a look at Hindu Charters for a great experience!

Other things to do:

Rent bikes to explore the town on wheels. Early morning is the best, when traffic is at its lightest. If you had doubts about Key West upon arrival, the bike exploration will give you new appreciation. The architecture is truly beautiful. I don’t have a recommendation on bike rentals, just take a look at the ones for rent and make sure they aren’t covered in rust. You can rent them for about $10 a day.

Put on some comfortable shoes and just walk around. You are SURE to see something that will spark your interest.

There is a large LGBTQ presence in town so if that is your thing, there’s plenty to do between the drag brunch and bingo, as well as, cabaret shows.

Get your photo taken at the southern most point of the United States (wave to Cuba while you’re there), visit the Hemingway House, take in some sun on one of their tiny beaches (Key West is not known for their beaches, I’ll say that) – there is sooo much more to do than I thought possible on this tiny island of ~25,000 people.

You can be as cheesy (or not) as you’d like.

What can I say, we had a total BLAST. I am forever grateful for our friends and their milestone birthdays!

…i choose this…



  1. Sounds like a wonderful trip! We stayed in Key West way back in the early 1990s and loved it. We went to watch the sunset along with a bunch of locals as well as other visitors and the atmosphere was great. And I loved visiting Hemingway’s House. If we come again that pizzeria sounds perfect for us as we both love cats (any colour!) and while I like pizza my husband is an addict! The sunset cruise sounds wonderful too πŸ™‚

    Liked by 1 person

    1. We did have a great time! I’m glad you did also!!! The pizza place was sooooo cute – I am a cat lover so I thought it was cool :-). The cruise was a pleasant surprise for sure. We were watching the other crammed boats and shaking our heads. lol.

      Liked by 1 person

  2. I love everything about Key West and sorry I haven’t been able to go in a while. I tell people it’s like New Orleans only much cleaner (and I love New Orleans too.) Looks like you hit a lot of great spots!

    Liked by 1 person

    1. You are sooooo right about how clean it is!! Sean said the same thing multiple times. The food in NO cannot be beat, but it sure was nice to be by some pretty water. Have you ever taken the boat out to the Dry Tortugas? I have a friend taking her kids to KW – wondering if this excursion is worth it.


      1. I’ve taken a catamaran out in that direction and kayaked in the mangroves, but never actually been to Dry Tortugas. I can’t imagine it being a bad trip, though. Every water excursion I’ve done out there was great.

        Liked by 1 person

  3. Pam, I love seeing your pictures and reading about your time in Key West!! My husband and I have been there twice and your blog brought back many great memories. You are so right, much to see and do like the Little White House, Hemmingway House and all the locals for starters. And the food and drink – wonderful!! I’m ready to return. πŸ˜€

    Liked by 1 person

    1. Hi Syliva! I’m glad this took you back to a great place! It is sooooo clean on top of everything else. We had such a great time. Nothing like a fun beachy vacation. Hope you can get back there soon. Have a great holiday!


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