Jason and I just returned from four glorious days in Key West. We went for our 5th anniversary in 2014 and decided to go back this year for our 9th anniversary. It is, without a doubt, one of our very favorite vacation spots.

It’s relatively easy to get to from Destin (and by easy I mean two flights or drive 14 hours), so it’s high on our list of warm, tropical getaway destinations.

Obviously the most important part of any vacation to us is the FOOD! We start booking our dinner reservations as soon as we book our flights. Jason and I had multiple conversations during this trip about how AMAZING the food was! Every meal was unique from the last and delicious in its own way.

Without further adieu, here’s where we ate (in order of our meals for ease on my brain):

Little Pearl

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I read plenty of reviews of Little Pearl on Trip Advisor prior to our vacation and it sounded great. We didn’t have a reservation, but lucked out and snagged two spots at the very tiny bar. The entire restaurant was really small, cozy, and dark.

Everything on the menu sounded fabulous, but we shared the seared sea scallop appetizer (life-changing!), pork dumplings that were on special, and a giant ribeye for dinner. Each bite was better than the last.

I would HIGHLY recommend Little Pearl for an exceptional meal in a sophisticated, yet inviting setting.

Blue Heaven

Blue Heaven is our absolute favorite spot for brunch! It’s really funky and kind of a mash up of different buildings with a big open courtyard and chickens walking around everywhere. Plan on waiting at least an hour, but brunch is totally worth it!

I love the BLT- bacon, lobster, and tomato Benedict (I add avocado) and Jason loves the banana pancakes. You really can’t go wrong with anything. Grab a mimosa and enjoy the scenery and people watching at this Key West institution!

Santiago’s Bodega

This is one of the most highly regarded restaurants in all of Key West. Its Trip Advisor reviews are through the roof and every local we asked confirmed the fanfare. It’s a Spanish-style tapas restaurant which is our very favorite way to eat!

We literally wanted every tapas on the menu, but finally narrowed it down to the beef carpaccio (which was THE BEST THING EVER, but sadly, doesn’t photograph well), avocado and pear salad, saganaki (which is this ridiculous torched saloumi cheese with pita bread), and seared beef tenderloin with blue cheese butter.

We will absolutely make a trip back to Santiago’s Bodega on our next visit and try all different tapas! The pitcher of sangria was fabulous, too.

Cuban Coffee Queen

One of the most fun things about Old Town Key West is that everything is bike-able. We rented bikes the first day and rode them every morning to breakfast. Cuban Coffee Queen was such a fun spot!

Cuban coffee is very popular in Key West. There is lots of Cuban influence around the island since Cuba is only 90 miles away!

Anyway, Cuban Coffee Queen might be a bit touristy for the locals, but we loved our coffee and breakfast sandwiches. I failed to snap any pics, but Jason had basically a Cuban Egg McMuffin (sausage, egg, and cheese on crusty Cuban bread) and I had a killer breakfast burrito full of sausage, egg, cheese, beans, tomatoes, and jalapenos. Neither of us could finish our breakfast.

Louie’s Backyard

I have been wanting to try Louie’s Backyard the last couple visits to Key West, but it never worked out until this trip. It’s kind of like three spots in one. Louie’s Backyard is an upscale restaurant, but it also has a sprawling back deck overlooking the Atlantic (but no food out here). Afternoons out there are amazing.

Upstairs is a separate concept- Louie’s Upper Deck– and it’s a completely different menu than downstairs. It’s small plates- our favorite! We started with the best bottle of rose I’ve EVER had. And I’ve tried a lot.

Let me just tell you, if you go to Louie’s and don’t get the Truffle Fries with Fontina Fonduta, you are missing out big time. These were LIFE=CHANGING and I still have garlic breath from them (Sorry the picture sucks. It was very dim and I suck at food photography).

We also tried and loved the grilled baby wedge, lobster risotto, Vietnamese shaking beef (best of all!) and creme brulee for dessert. It was all fab! One of my favorite meals.

Duece’s Off the Hook Grill

Ok, so this is a pretty cheesy name for a restaurant, but don’t be fooled. The food was great and quite a few locals recommended it to us!

We started with two-for-one mimosas and shared half a pound of stone crab claws. They were in season and we couldn’t resist. Doesn’t everyone have crab claws for breakfast?

Jason had the biscuits and gravy and I devoured the huevos rancheros. It was awesome! The crispy breakfast potatoes were delicious, especially dipped in the ancho sour cream.

Latitudes

For our final meal of the trip, we chose to go back to Latitudes on Sunset Key (we originally dined here in 2014 and LOVED it). The setting is just stunning. You have to take a ferry from near Mallory Square in Key West, but it’s a quick 10-minute boat ride and you feel like you’re on the edge of the earth.

We shared the beef carpaccio (can you tell it’s Jason’s very favorite?) and the lobster bisque to start.

Jason had the scallops and I had the Wagyu beef steak for our entrees. I will say, we were a bit underwhelmed by this second visit to Latitudes. I would still recommend it for first-timers. It’s very romantic and the service is top-notch. We just weren’t as blown away as we remembered being. Especially considering how pricey it is.

Obviously we at like kings (and Cuban Coffee Queens ) on our most recent visit to Key West. Thankfully Jason loves food as much as I do. We certainly live to eat, not the other way around. Here’s to more tasty adventures soon!

PS- where are your favorite places to eat in Key West?