Our Gay Florida Road Trip: Key West

Where to eat, stay, party and play in Key West!
October 04, 2016

Where to Stay

Island House

1129 Fleming St, Key West, FL 33040; (305) 294-6284)

Nothing will provide gay Key West experience quite like Island House. This clothing-optional gay resort is the perfect collage of hot tubs, steam rooms, beautiful men and an erotic lounge for your daring side. Sure, the nightly price tag may be a lot higher than most other hotels in the area, but if you can afford it, there shouldn’t really be another option. Have drinks and food at the poolside café and bar, workout in the nude if you like and take in all the sun needed for that perfect tan. Oh and if you pay for 4 nights, you will get 3 free! Stay all week!

Equator Resort

822 Fleming St, Key West, FL 33040; (305) 294-7775

Also clothing optional, Equator Resort is another amazing option for your stay in Key West. With two gigantic pools, large patios and a friendly staff, your stay here will be both comfortable and relaxing. Here, you can let it all hang out and embrace your wild side. When you consider all of these perks and add in free drinks nightly from 5:00 – 6:30pm, staying here should be a mighty attractive option.

Where to Eat

Nine One Five

915 Duval Street, Key West FL 33040; (305) 296-0069

Excellent homemade pastas, ceviche to die for and unique snacks and bites will make any food lover happy. You will get all of that and an incomparable ambience at Nine One Five restaurant. This Key West favorite is a stylish Victorian home with a large patio. The building adds a nostalgic feel to the friendly and welcoming environment where any gay can fit in.

El Siboney Restaurant

900 Catherine St, Key West, FL 33040; (305) 296-4184

With sangria made in-house, this is the perfect restaurant where you and your friends can drink and catch up away from the busy strip. Affordable prices, generous portions and a cozy home cooked meal feeling makes this the ideal place to eat on your road trip. If you want to live a little be sure to try the key lime pie or rice pudding!

Where to Party

The Bourbon Street Pub

724 Duval St, Key West, FL 33040; (305) 294-9354

This Key West staple is everything you would expect from a tourist den. This is often a fun and tipsy mix of middle age locals, young men in crews looking to get wasted and girls who party hard and want nothing more than a fun night on the town. Diversity, cheap drinks and top 40 music make this pub the prime party destination for gay Key West visitors.

801 Bourbon Bar

801 Duval St, Key West, FL 33040; (305) 294-4737

If you’re a fan of drag queens, this is certainly the bar for you. 30 years later, this iconic party stop continues to thrive. 801 Bourbon Bar provides an interactive party experience of sorts. The stunning drag queens will get you involved in their performances, karaoke nights will give you a chance to be a star and show your vocal skills or you can even play a game of bingo and get to know the locals if you’re passing through town on a week night.

What to Do

Higgs Beach

Atlantic Blvd. Key West

While some may think that this isn’t the most attractive beach, it’s calm and beauty makes it worthwhile in our opinion. While parking can be difficult at most places in and around Key West, Higgs Beach offers free parking. Additionally, here is where you can find all of the things that tourists and visitors love. Dolphin tours, jet ski rides and parasailing are just some the fun activities that you can partake in. You can even opt to rent a kayak or just have a picnic on one of the benches at the beach.

Mallory Square

400 Wall St, Key West, FL 33040; (305) 809-3700

Mallory Square can be seen as your one-stop destination for great food, drink and entertainment. Known as the place where people gather to watch the stunning sunset, Mallory Square is a must visit on your road trip. Make sure your phone is charged up… there will be plenty here to see and take snapshots