We recently went to Key West and almost didn’t come back. Seriously. It is now one of my favorite places for so many reasons. I feel like the general vibe running throughout Key West is come as you are and do whatever the hell you want, whenever you want- and what’s not to love about that? Absolutely nothing, especially when on vacation.
Oh you want to go sit at a bar at 9 am and start drinking? Go for it. Oh you wanna wear neon leopard print leggings and a bikini top out to dinner? You do you girl! Oh you wanna ride a bicycle barefoot while wearing a banana hammock with your pet ferret riding shot gun in the basket? Go right ahead. Oh you wanna be served brunch by drag queens? Key West has just the spot for you. You get the point- there are tons of different kinds of people, all harmoniously waving their freak flags together and I absolutely love that. In addition to the people and the general island vibes, the views and THE FOOD we’re also fantastic.
We flew Southwest from BWI to Fort Lauderdale, then drove down the Keys. This was an amazing experience and one you must do at least your first trip down there. There is also an option to fly direct to Key West from Fort Lauderdale which you could also do since you really don’t need a car once you are in Key West.
Where to Stay:
We used Air Bnb. This was a great option for us and our place came with a little kitchen and a living room. We didn’t use those areas much but it was great to feel at home once we got back at night. There are tons of little bed & breakfast spots in Key West as well as a few larger more fancy hotel options as well. Whatever level of accommodation you are looking for, you can find it here! You can even stay on a boat if that’s your thing!
This is a rare view of Duval Street with no one on it. Generally it’s pretty packed as it is the main drag in Key West. We arrived early in the morning after a short flight and a beautiful (though dark) car ride down The Keys. Arriving early in the morning meant we got to take a stroll down Duval Street before everyone else in Key West was awake. We grabbed Cuban coffees at Ana’s Cuban Cafe for our walk. This was a neat little spot with a simple wooden window where you place your order. The place felt really authentic and that combined with my ordering anxiety lead me to make the rookie mistake of ordering a regular coffee instead of a cafe con leche. Key West lesson numero uno, you must get the cafe con leche! Mike let me take sips from his until it was all gone as we walked down Duval. What a coffee angel that man is.
Along Duval there is a bar or restaurant everywhere you turn and there is something for everyone. And I mean EVERYONE. There are tiki bars, country bars, open air island vibe type bars, bars where topless women will serve you drinks, bars where drag queens will serve you drinks, sports bars, upscale bars and my favorite, dive bars. There is even a bar with a tree growing through the center of it.
You will find a great spot no matter where you go, but here are a few of my favorite spots to hit on Duval:
Willie T’s: A great spot for a drink and live music! Kenny Chesney was telling the truth when he sang about this place “a little tin roof bar down a path you have to follow… it’s like nowhere else you’ve ever been and we’ll write your name on a dollar bill, put it on a wall it’ll still be there next time we come back girl, to the bar at the end of the world.” And we did just that! We wrote our names on a dollar bill, saw some great music and had many drinks. Get a mojito if you go here- it’s there thing and they make a bunch of different types.
Captain Tony’s Saloon: This bar houses a bunch of Key West history and has a tree growing right through the center of the building. Interesting facts about this place: It’s the bar that Jimmy Buffet got his start at and when the building was first constructed in 1852, it was an ice house that doubled as the city morgue. Don’t miss the hand written Jimmy Buffet lyrics on the men’s bathroom wall, written by Jimmy Buffet himself!
Irish Kevin’s Bar: Where their motto is “I came, I drank, I don’t remember!” Enough said. Go.
Fat Tuesday’s: A New Orleans inspired spot serving loads of frozen drinks with the option to get a floater of your choice. If you’re looking for a hang over (also known as the Key West flu) this is the place to go. I may or may not be speaking from experience.
Hog Fish Bar & Grill: If you eat nothing else while in Key West, you must go to Hog Fish Bar & Grill for the hog fish sandwich. It’s a little bit off the beaten path but SO worth the trip. It’s one of the top ten things I’ve eaten this year, maybeeee even in the top five.
Caroline’s: Arguably the best fish sandwich in Key West, they are an open air restaurant with the most perfect bar that faces out to the street for people watching. Get a rum runner or two to go along with your fish sandwich. You won’t regret it (or maybe you will, but that’s all a part of the fun of visiting Key West.)
Kermit’s Key West Key Lime Shoppe: The best Key Lime Pie!
The Waterfront Brewery: Great beer and fantastic bar food.
Garbo’s: An old air-stream parked in the back of a bar serving up tacos, burritos, burgers and gourmet dogs!
Drinks and people watching at Caroline’s!
See & Do:
One of the most special and free experiences Key West has to offer are the sunsets. The first night we were there we went to the Sunset Celebration at Mallory Square. Most evenings, two hours before sunset, until the sun slips down into the ocean, there’s a sunset celebration with street performers, food vendors and live music. We walked along the waterfront and people watched until the sun was gone. If you get there early enough you can grab a spot at Sunset Pier for food & drinks. We opted to go the opposite route and went for a late night dinner and drink after the sunset crowd had cleared out. Either option is great and you can sit right along the water.
A point of interest you have to see on your first trip to Key West is Southern Most Point. It’s a basic marker that marks the spot of the southern most point in the United States. Also a great opportunity for cute & super touristy photos. I’m not above it. #90milestocuba
We were lucky enough to accidentally book our trip during the Key West Songwriter’s Festival. We saw Old Dominion, Cam and Maren Morris, all for FREE. Best happy accident to date. The festival started in the afternoon and went well into the night. If you’ve got the chance, I would definitely try to book your trip for this week! Protip: Buy beers at a local deli and make your boyfriend hold them in his cargo short pockets so that you don’t have to keep leaving the festival to refresh your beers.
And finally one of the last and best things we did was a sunset sail. For only 35 bucks you can go on a sailboat sunset cruise that includes unlimited booze and amazing views. Lots of company’s do this but we went with Sebago and were not disappointed!
Other great spots to check out:
- Smather’s Beach
- Truman’s House (The Little White House): A good rainy day activity that I didn’t get a chance to do, but plan to check out next time!
- Key West Aquarium
And the best part was getting to see this babe’s favorite place:
Until next time KW.