We’ve been to Key West several times since 2010 (Sharon also went an additional time in 2008). It’s a quick getaway for us, within driving distance or a short flight away. We like going to places we’ve been to before because many of the stresses of traveling are diminished when you know something about where you are. I totally get that some people will be like, “You shouldn’t go back to somewhere you’ve already been. There are so many new places to discover!” I also 100% agree with that and we do our best to get to new places, too. But we also do our best to revisit places where we’ve had a really good time. It’s like watching a movie you’ve seen or re-reading a book you like; it’s a comfort and you know it will be enjoyable.
One of the nice things of going to a location you’ve been before is that you have a pre-made list of favorites made by the best travel consultant you know – YOU!
This is a list of the places we really like to go to in Key West, that fit our travel style. I’ll try and explain why we like each place so you can decide for yourself if you might like them as well. As with everything on this website, Your Mileage May Vary. I’ll work from breakfast to late-night snacks.
Sarabeth’s – 530 Simonton St.
Sarabeth’s is now our go-to place for brunch. So much so that we’ve been known to go there twice on the same trip. It’s located a bit off the tourist strip so the vibe is more laid back and less hectic. There’s seating inside and outside (it can be pleasant for people watching or a bit warm, depending on the season.) They just do so many things right that it’s hard to find a fault with eating here. I mean, look at the size of the coffee cups!
They have a bunch of interesting breakfast champagne cocktails with fresh juices and they serve toast with their own brand of preserves (we bought a jar of the peach-apricot preserves last time we were there. Delicious!). We knew we made a good choice when, after checking in on Facebook, our social media lit up with likes from our friends who visit Key West.
We liked the Key West location so much, we went to check out one of their Manhattan spots. Here’s our review.
Louie’s Backyard – 700 Waddell Ave.
We’ve been going to Louie’s Backyard since our first stay in Key West in 2010. We’ve had brunch and dinner there, along with drinks on the back deck. I’d say that we like going for brunch the most (reservations are recommended). We enjoy that the dog beach is right next to the deck and we spend much of our meal watching the doggies playing in the water. The menu for brunch does change frequently and we’ve not been thrilled with the selections the last couple of times we visited, but that’s always going to be hit or miss. We did come here for drinks to watch the sunset one time but since Louie’s is on the southern side of the island (near the Southernmost Point marker), there’s not a great sunset view. We did eat dinner here once and weren’t thrilled with the experience; it’s a classier vibe and the menu was much more expensive. The food was fine but for us, most of the appeal here is the view and that isn’t much to look at in the evening, once the sun has gone down. But for brunch, we’ve generally really enjoyed our experiences here.
Rick’s Tree Bar – 202 Duval St.
I know I said this was a list of places we liked to eat when we are in Key West. However, this is Key West and sometimes we choose to have a liquid lunch. The Tree Bar is part of the larger Ricks and Durty Harry’s complex, which is quintessential Duval St. Think live music, cheap drinks and lots of drunk people. That’s not our style. Fortunately, the Tree Bar is none of that. All the liquor is premium and the juices are squeezed fresh to order. I also understand they make one of the best Bloody Marys on the island but we’re partial to the Pina Coladas. One of our favorite bartenders in the world used to work here, but she’s long gone and relocated to North Carolina. Regardless, Rick’s Tree Bar still holds on strong for a good drink.
Cafe Marquesa – 600 Fleming St.
We’ve stayed at the Marquesa Hotel on two of our trips to Key West and we’ve eaten at the Cafe Marquesa during each of those stays. The hotel made all the arrangements and it was nice to have a really wonderful dinner and then just go back upstairs to our room. The restaurant only has about 35 seats so it books up fast. Cafe Marquesa gets consistently high ratings from Zagat Guide, Travel + Leisure and TripAdvisor and is priced accordingly, with entrees going for roughly $50-$80. We’re not against paying that for a dinner but we’d rather save that type of money for a trip to Bern’s Steakhouse in Tampa. If money is no object or you’re celebrating something special, you can’t go wrong eating here.
Nine One Five – 915 Duval St.
Besides the Cafe Marquesa, finding somewhere good to eat for dinner in Key West proved incredibly difficult. We’ve gone to the best-rated places on Yelp! and TripAdvisor and were disappointed time and time again. We’ve never seen ourselves as quitters though, so we kept trying and we finally found a winner. Nine One Five is housed in a classic-style home right on Duval. The location on touristy Duval St. would normally turn us off but it’s far enough away from Mallory Square to keep most of the tourists away.
The atmosphere was wonderful and we sat at a table right on the front porch. Service was great and I think Sharon might possibly leave me for the “Absurdly Addictive Asparagus.” (Note from Sharon: Fortunately, the Absurdly Addictive Asparagus can’t reach the top shelf for me, so I promise I won’t leave you LOLOL!)
Our food pictures aren’t going to garner any awards on Instagram but trust me, the food here was amazing. By far some of the best we’ve ever had in Key West. We will definitely be stopping back during our next trip.
Caroline’s Cafe – 310 Duval St.
I can almost imagine Sharon’s jaw dropping to the floor when reading this (Note from Sharon – it did) because I’ve done almost everything I could to avoid eating here again. I find the atmosphere bland and the food uninspiring. But you see, here’s the thing that makes me include Caroline’s on the list. The food is consistent, the location is excellent and they’re open late. I guarantee that if you walk around Key West enough, you’ll eventually walk past Caroline’s at a time when you’re hungry and don’t want to look for somewhere to eat. That’s when you’ll eat here – when you’re borderline hangry and your feet hurt and you just want to sit down. If you’re in a similar situation, don’t be afraid to grab a chair and eat some unidentifiable fried fish/chicken/meat on a plain roll smothered with mayo and a leaf of lettuce.
You’ll leave full, rested and ready to continue your day (or night). Sometimes, that’s all you want to do. I’m sure I will eventually eat here again when the stars align and I don’t want to bother looking for anywhere else. 🙂
So did I leave out any of your favorites? What’s your go-to place in Key West?
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