On the final day of 2015 I wanted to share part two of one of my favorite trips of the year. After spending time in Miami with friends Ashley and Jared from Sugar & Cloth, we drove down the Florida Keys and spent a few days in Key West. The second leg of the trip felt very different from our previous visit — more relaxed, sunnier, and full of great experiences thanks to the Florida Keys and The Gates Hotel.
Things to Do
Jet Skiing with Barefoot Billy’s – An island jet ski tour is a must-do. We’ve taken this exact tour before, and it was even better this time. I especially enjoyed driving my own jet ski instead of riding as a passenger.
Sunset Cruise on The Appledore – This chilled-out cruise is perfect for watching the sunset. They serve appetizers and champagne, and the crew is friendly and welcoming. Tip: arrive early to secure your spot and complete any required paperwork.
Scooter Rentals from Island Style Ride – Renting scooters is a fun way to explore colorful neighborhoods and capture memorable photos. If you haven’t ridden a scooter before, give yourself a little time to get comfortable — they can feel intense at first when traveling at higher speeds.
Where to Stay
We stayed at The Gates Hotel Key West and highly recommend it. The hotel has a laid-back, centrally located vibe and exceptional staff. Rooms blend a beachy feel with modern touches, and the hotel features an on-site food truck (The Blind Pig) and a bar (Rum Row) with live music. It’s an ideal spot for relaxing at the hotel when you want a low-key day.
Food highlights at The Gates – The guacamole with fried pita chips is a standout, and the breakfast tacos are delicious. If you prefer to stay close to your room, the hotel’s food and drink options make it easy.
Places to Eat
BO’s Fish Wagon – This spot offers a genuine hole-in-the-wall atmosphere with a casual, local feel. You might even see chickens wandering around. The fried shrimp sandwich comes highly recommended and was suggested to us by several locals.
Tropical Juices & Drinks – Don’t let the simple name fool you. This tiny place serves excellent drinks in fresh pineapples. It’s a delightful stop for tropical cocktails like pina coladas and other fruity options.
Garbo’s Grill – A food truck with a permanent location, Garbo’s serves flavorful dishes and is easy to find near Grunts Bar. We visited at night and found the food exceptional.
Southernmost Beach Cafe – A relaxed, beachside restaurant that’s perfect for casual dining. It’s a fun spot for day drinking and enjoying ocean views.
Blue Heaven – An outdoor restaurant recommended by several people. The setting is charming and worth experiencing.
BlackFin – If you’re planning a date night or want a slightly more upscale meal, BlackFin is a strong choice. Try the goat cheese croquettes and sautéed calamari for standout flavors.
Kermit’s (dessert) – For classic Key West key lime pie, Kermit’s is a reliable option with multiple locations on the island.
Better Than Sex (dessert) – A dessert-only restaurant with a moody, provocative theme and playful menu names. It’s an unusual but fun spot to visit just for the experience.
Photography by Jared Smith and a few taken with my iPhone.
Have you visited Key West? Looking back through these photos makes me want another sunny trip. If you have recommendations for warm, tropical destinations, I’d love to hear them.