Vacation Inspiration: My Key West Travel Guide

It seemed only fitting that on the last day of 2015, I would share part 2 of one of my favorite trips of the year! You may remember from my Miami Travel Guide, that we took a trip with our friends Ashley and Jared from Sugar & Cloth. The first half of the trip was Miami and for the second leg, we drove down to the Keys for a few days and stayed in Key West.

Jeff and I had been to Key West before, but this trip was so much different than our last. We had such a good time, thanks to the folks at The Florida Keys and The Gates Hotel, and wanted to share some must-visit places, and plenty of photos, in case you’re planning a trip…

Things to Do

Jet Skiing with Barefoot Billy’s // Definitely recommend doing an island jet ski tour. Last time Jeff and I went to The Keys, we went on this exact same tour. This time around, it was even better…which I think had something to do with the fact that I drove my own jet ski this time, instead of riding on the back with Jeff.

Sunset Cruise on The Appledore // I loved this little excursion. It was so chill and relaxing! They served appetizers and champagne (yum) and everyone was super friendly. *Tip: Make sure you get there early to secure your spot, even if you’ve already made a reservation, because there will most likely be some paperwork that has to filled out.

Scooters from Island Style Ride // We rented scooters the last full day we were there, as something fun to do. Turns out scooters are a little more intense to drive / ride when you’ve never done it before. Feeling like you could fall from a moving vehicle (that is going 30+ mph) at anytime takes a little getting used to. Who knew? But it was really fun and we were able to explore some of the colorful neighborhoods and get some obligatory scooter photos. Haha.

Where to Stay

We stayed at The Gates Hotel Key West, which I would definitely recommend. It’s super laid back, in a pretty central location, and all of the staff are EXTREMELY nice. All the rooms have a cute, beachy meets modern vibe and there’s an onsite food truck (The Blind Pig) and bar (Rum Row) with live music. So you won’t have to go very far for good food, drinks, and entertainment. That was especially helpful on the days when we just felt like sitting around.

Food recommendations at The Gates // The guacamole and fried pita chips are my fave. SO good! And the breakfast tacos are delicious too. And speaking of food…

Places to Eat

BO’s Fish Wagon // If you’re looking for a place with unique ‘hole in the wall’ type ambience, this is it. There were chickens just hanging out and it felt like a locals spot (not sure if it was, but it seemed that way). Try the fried shrimp sandwich. *This was recommended to us by several people, so it’s definitely worth checking out.

Tropical Juices & Drinks // Yep, that’s the name of the place. Which sounds pretty generic, but trust me, it’s worth finding. It’s a teeny tiny place with really good drinks, served in fresh pineapples. YUM! I think Ash and I both ended up getting pina coladas from here, but they have lots of other drink options too.

Garbo’s Grill // I don’t have any photos of this spot because we went at night. But it was REALLY delicious. Garbo’s is actually a food truck, but it has a permanent home. So you won’t have any trouble finding it… It’s right next to / in the back of a place called Grunts Bar.

Southernmost Beach Cafe // A cute casual place to eat that’s right on the beach. I don’t remember what I ate here because I was too busy day drinking. Otherwise, I’d recommend something specific. 

Blue Heaven // This outdoor restaurant was recommended to us by a few people and I think it’s worth a visit.

BlackFin // If you’re looking for a date night type of place in the Keys, this would be a good option. The food was really good (try the goat cheese croquettes and sautéed calamari) and the ambience is a bit fancier than the typical Key West restaurant.

Kermit’s (dessert) // If you’re searching for key lime pie, try Kermit’s. They have a couple of locations in Key West. Pretty good, as far as key lime pie goes.

Better Than Sex (dessert) // I don’t know how we found this place. But it was interesting, that’s for sure. They only serve dessert, it’s super dark and moody inside, and all of the menu items have sexual names. We were all laughing the whole time. If for no other reason, I’d go just to say you went.

Photography by Jared Smith and a few taken with my iPhone 

Have you ever been to Key West before? Honestly, looking back through all of these photos is making me want to go another (sun filled) trip. Have any warm, sunny, tropical recommendations for me? Would love to hear ’em.