No trip is complete without a little food adventure, and Key West definitely delivered. Over the course of our long weekend, we managed to squeeze in a ton of great meals, snacks, and frozen drinks (so many frozen drinks). So here’s a quick look at everything we ate, with some short reviews of each spot — the hits, the misses, and the things we’ll be dreaming about until our next trip.
Southernmost Bar & Food Truck
Since we were staying at the Southernmost Point Guest House, having the Southernmost Bar and Sandy’s Cafe Food Truck right there was super convenient. The vibe was fun — live music during the day, casual patio seating, and a steady crowd. Drinks were just okay, but hey, you can’t beat a free drink per guest per day with your hotel stay. (You do have to pick them up daily, but still, free is free.)
The food truck (menu here) had tacos plus your classic beachy fare — hot dogs, fries, and conch fritters. The hot dogs and fries were great for a quick snack. The conch fritters were just okay — not the best we’ve had, but it’s hard to complain when you’re sitting under an umbrella with a drink in hand.
Definitely a good spot to stop for a drink when you make the trek down to the Southernmost Point buoy for that obligatory Key West photo.
Island Dogs Bar
We stumbled into Island Dogs Bar near the cruise port because the kiddo was suddenly starving (as kids tend to be with no warning). It was casual and easy, with no wait at all.
And my Café con Leche Martini was surprisingly delicious. The pizza was decent, good enough for a snack, and the service was quick and friendly. Maybe it’s not gourmet food. But it’s a perfect little stop when you need a fast, easy bite.
The Frozen Drink Stand at Duval and South Street
We could see this frozen drink stand right from our balcony, and my kid made it his personal mission to visit it as often as possible over the weekend. I still don’t know if this place has a name, as it’s not even listed on Google Maps. But you can find it in front of the Mansion on the Sea hotel.
The drinks are mostly alcoholic but the Blue Raspberry is alcohol free – and luckily that is my kid’s favorite flavor. So we grabbed the souvenir cup – I believe it was $10 and a few bucks cheaper for refills for the rest of the trip.
Great deal, and my son thought it was so cool to walk across the street and grab his own drink while we watched from the balcony like helicopter parents…but cool ones. If you have kids – stop by here.
Ram’s Head Southernmost
Ram’s Head Southernmost was a fun dinner stop for us, mostly thanks to the courtyard filled with lawn games like ping pong and corn hole, which kept my son entertained. The food was solid but not mind-blowing. The highlights:
- Stuffed Avocado was amazing — definitely order this.
- Mahi sandwich was very fresh but a little dry.
- Tuna entree was pretty tasty.
- Kids meals were a hit — but bigger eaters may need two (my son polished off both a burger and a grilled cheese).
Bonus points for having fly fans and “chicken repellant” bottles on the tables — classic Key West touches.
We actually went back for lunch later in the trip, but there was a long wait for a regular table. Luckily, the bartender over by the lawn games hooked us up with drinks and a kids’ meal at the high tops. Kudos to her for saving the day (or at least lunch hour)!
Clemente’s Wood-Fired Trolley Pizzeria
One of our favorite meals of the trip! Clemente’s is a tiny little place known for their wood-fired pizza, and it did not disappoint. We had the Mediterranean Pizza (delicious) and my son went classic with cheese pizza — both were amazing.
Friendly, laid-back service, good wine list, and cozy atmosphere. It’s small inside, so there might be a wait — but it’s absolutely worth it. If you call ahead, they will put your name down to help shorten the wait time a bit.
You may notice that I’m lacking a picture here. And that’s because I was starving and the pizza looked so dang good that I forgot to snap a pic before diving in. ;)
La Grignote
We needed a good coffee spot for the mornings, and La Grignote delivered. My husband loved their Cuban coffee, and I was all about the iced lattes. It’s a small bakery and café vibe, with a few outdoor tables. Perfect for a quick morning pick-me-up before a day of adventures. Check out their menu here.
Santiago’s Bodega
If you’re looking for a great dinner spot in Key West, Santiago’s Bodega is a must. It’s a small plates/tapas menu, and almost everything we tried was amazing. Favorites included:
- Saganaki (flaming cheese, because yes please)
- Brussels sprouts
- Smoked salmon carpaccio
There’s no formal kids menu, but they had a quesadilla and meatballs that my son liked. The only miss was the sangria — it just wasn’t good. Stick with wine.. Make a reservation, because this place fills up fast — and for good reason.
Mattheessen’s
Mattheessen’s is your classic, old-school ice cream and dessert shop. They had all the crowd-pleasers — good ice cream, plus giant cookies and cheesecake slices that looked ridiculously good. We stuck with ice cream and weren’t disappointed. I mean, how can you go wrong with ice cream?
Original Rainbow Cone
We made a stop at the Original Rainbow Cone location near the cruise port. They’re famous for their stacked rainbow cone — layers of chocolate, strawberry, Palmer House, pistachio, and orange sherbet all in one.
My son skipped the famous cone and went for Superman ice cream instead, which is always a big hit. It’s very casual, grab-and-go style — perfect for a quick sweet treat while wandering around downtown.
Final Thoughts!
Overall, we ate really well during our Key West weekend! The best meals of the trip were easily Santiago’s Bodega for dinner and Clemente’s for pizza. Biggest surprise hit? The frozen drink stand (according to my kid, at least). Already planning what we’ll try on our next trip!
More Key West Trip Planning Tips
If you’re planning a trip to Key West, be sure to check out these other helpful articles: