The Perfect Day In Key West

9 A.M. - Wake up with an iced coffee from Cuban Coffee Queen. The ice cubes are actually made from frozen chunks of coffee, so prepare for a caffeine surge that will get you through a busy day in Key West. Enjoy alongside a Cuban Bagel (cream cheese, Cuban bread, honey, sesame seeds) and a morning stroll on the promenade surrounding the Key West Bight.

10 A.M. - Key West is home to various military sites, and Fort Zachary Taylor--a Florida State Park and National Historical Landmark--is one of the most popular to visit. Wander through the Civil War-era structure, admiring the cannons and well-preserved brick fortress. As you head to the beach just a few steps away, you might catch a glimpse of military boys training on the still-active base.

11:30 A.M. - Check out the Little White House for a healthy dose of politics. Built in 1890, the building was the winter White House for President Truman who spent 175 days in Key West during his term. Immaculately preserved, explore the various rooms as well as the surrounding grounds, which have been kept to look just like they did in the 1940s. Once you've gotten your fill of American history, take a more leisurely tour of the Key West Butterfly and Nature Conservatory. 50-60 different butterfly species are housed in the open green house, as well as stunning plant life, quails, birds, and two flamingos, among other species.

2:00 P.M. - Snack time! Stop at the Casa Marina for seasonal eats and delicious cocktails as you overlook the water. Opt for the house special conch balls, a lightly breaded and fried bite filled with local conch that's served with traditional tartar sauce and a spicy chipotle mayo. Sip on a dark rum pina colada--the best we've had!--before taking a minute to digest on the hotel-restaurant's oceanfront hammocks.

3:30 P.M - Now onto the last cultural attraction of the day. Literary legend Ernest Hemingway called Key West home, living and writing on the island for over 10 years. Make sure you take a group tour of his vacation casa; the enthusiastic guide will keep the information session under 40 minutes and you'll learn just enough to truly appreciate the space. Then meander through the various rooms, outside pool, and writer's studio on your own. Hemingway was obsessed with cats long before internet GIFs, so definitely play with one of the six-toed felines who lounge all over the grounds.

5:00 P.M. - Happy hour at the Island House--a favorite clothing-optional gay resort--is unbeatable (drinks are even free for guests!). Grab an app or two and lounge pool-side with your cocktail. The hotel is a central location for visitors and locals, and everyone who attends happy hour usually wants to strike up conversation.

7:00 P.M. - Once you've warmed your palette with a couple drinks, walk to Azur, a modern restaurant that serves up innovative Mediterranean-inspired fare. Everything Chef Michael Mosi cooks will set your tastebuds off on a culinary rager. We particularly fell in love with the Bacalao Croquettas (a light mix of potato and fish that's crisply fried) and the Walnut Filled Eggplant with Pomegranate Reduction (sweet, earthy, perfect sauce to soak up with a piece of fresh bread). Between sips of refreshing white wine recommended by our server, we enjoyed the Yellow Tail Snapper, whose potatoes, petite shrimp, and lemon caper butter left us satisfyingly full, but of course, still wanting more.

9:00 P.M. - La te Da's historic building has been a staple of Duval Street for many years, and for good reason. The hotel-bar still hosts the coolest tea dance and the best cabaret shows in town. We caught an epic performance by Randy Roberts--who graced the stage as both Bette Midler and Cher--that left us in stitches. Sit back, relax, and try your best to chug though the two-drink minimum between laughs.

11:00 P.M. - Now it's time to hit Duval Street properly. Have a more relaxed drink at Aqua before heading to 801 Bourbon Bar for a drag show upstairs. Once midnight hits, it's off to Bourbon Street Pub where the fun will continue until early morning. Make sure you check out the outside area--you can jump in the pool or recline in the back sitting patio (just mind the nondescript mancave behind you). If you're craving late night eats or even a sauna, find your way back to Island House where the food is 24/7 and the pools never stop running.