Key West Recap


There isn’t any place quite like Key West. It is my favorite vacation destination within the United States, and I will pick it every time over the beach and mountains. You may be wondering what is sooo special, which is why I’ve recapped our trip below. Restaurants, bars, and attractions listed below!


We obviously need to talk food first! Key West is known for amazing food, and I’ve rarely been disappointed with a meal here. Here’s a list of all the places you need to visit on your next trip!

Harpoon Harry’s

I’ve had several conversations with Harry himself, and he takes so much pride in his diner. We made it here for breakfast at least three times, and for dinner one evening. If you’re looking for tasty, affordable, and consistent food, this place is for you. Harpoon Harry’s also has old school diner charm and a fully stocked bar. Hello Bloody Mary’s! We start early here in Key West. Cash-only. Get the Corned Beef Hash or the Smoked Salmon, Tomato, and Cream Cheese Omelet.


Date and Thyme

If you’re looking for something healthy or have any sort of dietary restriction, head to Date and Thyme! They have amazing healthy breakfast and lunch options. The prices are not outrageous either. They cater to a paleo, gluten free, vegan crowd, so you can feel good about eating here after a full night of drinking margaritas and eating Cuban food. Highly recommend the Avocado Toast, grab ‘n go options, Cold Brew, and the Rise ‘n Shine bagel. Your food is ready super quick here and the outdoor seating is shaded, comfortable, and cool.

Oasis Mediterranean Cuisine

I never experienced authentic mediterranean food before coming to Oasis. Tucked back off the beaten path, oasis is worth the trip. They have cool, shady outdoor seating, a full bar, and some spots inside (although who would want to be inside in Key West?!). They have a sizeable menu, and they offer some Italian bites as well, they have something for everyone. I highly recommend the Manty (must like Dill), the Gyro Platter, and the New York Style Pizza!


Pepe’s Cafe

So old school they don’t even have a website! Pepe’s has been around since the early days of Key West, and it is one of the most charming places I’ve ever been. If you want good fish done right with amazing seasoning, a vegetable and starch, this place is for you. Order whatever their fresh catch is and say hello to their mascot (a sleeping tom cat). Pepe’s is located at 806 Caroline Street.

Sandy’s Cafe

Sandy’s was in walking distance from where we were staying, so the temptation to go there multiple times a day was strong. Simply the best cuban sandwich on the Island. If you’re not feeling the Cuban, order the pulled pork. Equally delicious.

Cuban Coffee Queen

Getting quality cuban coffee is an essential while I’m in Key West, and I think Cuban Coffee Queen does is best. Any drink you can think to order is absolutely delicious. If you get iced coffee, ask for extra ice. They have coffee ice cubes (so as not to dilute your coffee), and the hot weather can melt them quickly in Key West. If you’re hungry for breakfast order the Key Wester or the Cuban Bread with Guava. Both are seriously out of this world.

El Sibboney

Authentic Cuban dinner. El Sibboney is a locals place, and it is tucked back in a residential area, located in an unassuming family style joint. Roll up on a Saturday at 7pm, and you may find yourself waiting for a seat, though. I ordered the Garlic Shrimp last time, and I can honestly say it was the best meal of my trip. Melinda ordered the pulled pork, and she was raving about how it was cooked to perfection. Every meal comes with buttery cuban bread before the meal, yellow rice, plantains, and black beans. And you should eat every last bit of it.

Chico’s Cantina

Technically, Chico’s is on Stock Island, but it is well worth the five minute drive. This restaurant is my parent’s favorite place to go. They went here three times last trip. Ask to sit out back in the covered patio, order the fish tacos and don’t skip desert. The sopapillas are life-changing.


El Meson de Pepe

I saved perhaps the most important to me for last. I cannot come to Key West without sitting outside and eating dinner on an evening when there is dancing at El Meson de Pepe. El Meson is where I first tasted Cuban food (which is now my favorite type of food.) Not only is the food delicious, but the atmosphere is perfection outside after sunset. The patio is covered, chickens wander up and get shooed away, salsa music is playing, and people are dancing. Everything is good on this menu, but don’t forget tres leches cake if you have room. We had dinner here of course, but one night after eating somewhere else, Melinda and I came here just for the cake and two shots of tequila for her birthday.



Hog’s Breath

Melinda and I are regulars here when we come into town, and we’re on a first name basis with three bartenders here. We miss you Nathan!! While I love to dance and get wild, I’m a dive bar kinda girl at heart, and this place has it all. It’s always our first stop of the evening. We grab our drinks and sit at the bar until the band gets rolling, dance a little bit, and close out.

Sloppy Joe’s

We typically roll here right afterwards. Sloppy Joe’s is popping every night of the week, and there is always a live band here too. The dance floor is large, so be prepared to cut a rug, and not hear the person next to you when they talk.


This place is WYLD. Spelled like that. It has several bars within one joint, so you can club to today’s hits on the top floor, hear a band play some 90s tunes on the bottom floor, sing karaoke in one area, and have a quiet drink in another part. This is usually our last stop of the evening, and they don’t close until 4am most nights.

Things to Do

Sunset Cruise

This was my favorite part of the entire trip. At $40 a person you get an intimate evening trip out to sea at sunset. The cruise is about an hour and half, and never fails to remind me of the grandeur of this planet. Drinks are provided by the way. Don’t forget to tip your crew!

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Key West Garden Club

I almost didn’t want to put the garden on here, because I feel like it’s a well kept family secret, but I don’t think there’s a more beautiful place on the island. You can look at the ocean from behind the walls of the fort in the most lush garden. Sounds like a fairytale because it looks like one. Bring your radio or ukulele and a cold drink and sit on a bench in here and enjoy those island vibes. Don’t miss out on the butterfly garden either. Admission is free, donations appreciated.

Higgs Beach

Despite being an island, key west has a real lack of beaches. I love the beach, but personally, I don’t miss it in Key West. This can be controversial among Key Westers, but I think Higgs Beach is WAY better than Fort Zachary Taylor. It’s much less rocky, there are usually less people, and there’s a bar/restuarant ten feet away. They also recently redid the pier which means you walk out past any rocks and jump in crystal clear blue waters. Fort Zachary Taylor requires admission, and umbrella fees are expensive (no thnx, thnx so much). Plus Higgs has volleyball courts and a children’s playground if you have little ones!


*Two places I didn’t visit this trip, but have in the past, below!

Bahia Honda

If you rented a car, I highly recommend making the drive out to Bahia Honda. It is a beach about an hour’s drive, and it is absolute paradise. Get there early on a weekday to have it almost entirely to yourself. Absolutely clear blue water and white sand.

Dry Tortugas

This is truly the most beautiful place I’ve ever visited in my life. You can take a boat or sea plane out there. Be sure to get snorkeling equipment. I’ve seen so much wildlife just on the beach here, and it is stunning. There are so many areas to have all to yourself and take in the views of this historical fort. Book this before your vacation and financially plan for it. It’s a splurge, but a once in a lifetime trip.

1. You need to drink to have fun. That couldn’t be farther from the truth. The vibe of Key West is fun and carefree, and you don’t need to be intoixcated to participate in that attitude or fun. I’ve came here at age 20 and had a blast. My friend has lost her ID and she couldn’t drink, but still had fun. My father has been coming to Key West consistently for years, but not once has he been out to a Key West bar.


2. It’s too wild. I go out every night in Key West, and not once have I seen a fist fight. I’ve seen drunk people, sure, but not once have I been seriously worried about someone. I’m not saying it’s a utopia, but something about the island vibe keeps people happy.

3. There are a lot of tourist traps. This is one thing that I thought would be the case when I first came to Key West, but I was proven wrong. Yes, there are an abundance of overpriced t-shirt shops, but restaurants are generally very good. If people don’t like a restaurant, it generally won’t survive. Key West has a TON of locals. Who wouldn’t want to live here??

1. If it’s in the budget, fly directly into Key West. I’m sorry that drive may be pretty and all from Miami, but I think it’s long, boring, and a pain in the you know what. Plus, the Key West airport is AH-mazing. The runway is tiny so the landing is so exciting (seriously everyone applauds upon landing), you get to walk outside across the tarmac, and security literally takes two seconds.

2. Rent a golf cart or scooters. Do not ride or drive intoxicated. That should go without saying, but IMMA SAY IT. I think this is the best way to get around the island. Personally, I think there’s too much traffic to get everywhere on a bicycle, and the island is just a little too large to walk if you are anywhere off Duval Street, which is the main road in town.

3. Again if it’s in the budget, rent some place that has a pool. The best hangover cure is getting in the pool. Swear to goodness.

Brady CollinsComment