Lose your inhibitions in Key West

It’s not hard to find people who will tell you that Key West isn’t what it used to be, that it’s not as gay as it used to be. Things change, it’s true. Destinations evolve. But there’s no denying that Key West is still really gay, and if you’re looking for a vacation where you can get naked, work on your tan, and have some fun with other guys, then Key West still ticks all of those boxes.

There’s a range of gay guesthouses, accommodation options, bars, and businesses on Key West, with most of the action centred around Duval Street.

Regardless of where you’re staying, the rhythm of your stay on Key West will probably revolve around the two poles of Island House and New Orleans House.

Island House is one of the world’s best-known gay resorts. It’s men-only, and clothing optional. As well as hotel rooms and a large outdoor pool, Island House has all the facilities you’d expect from a bathhouse or sex-on-premises sauna.

You don’t have to be staying at Island House in order to immerse yourself in the experience – day passes are available.

They have a happy hour each evening that attracts a busy crowd, and if they’re having a pool party then this is where you want to be.

The atmosphere is relaxed, but undeniably and irresistibly sexual.

New Orleans House is also a clothing-optional accommodation option, but its selling point is that it’s connected to Bourbon Street Pub where you’ll probably be drinking most nights that you’re on the island.

Bourbon Street Pub is the indoor space that faces out onto Duval Street, and is generally featured on TV coverage of New Year’s Eve. New Orleans House is the outdoor garden and pool area where the accommodation is located.

One of the features of Bourbon Street Pub is its roster of enthusiastic go-go boys. There’s not much these guys won’t do for some dollar bills, and they work the bar with their cocks out as they grind to the music.

I caught up with Josh, the General Manager of New Orleans House, to compare notes on my recent visit to Key West.

“Key West is not a cheap place to visit…” confirmed Josh. “We try to keep our rates as affordable as possible so as many people can visit us as possible. The average age range of the guys who stay with us varies, but tends to skew older. However we consistently have young groups of friends and couples in their 20s and 30s who visit as well.”

During my time on Key West, I was impressed by the mix of guys that I encountered.

“Guests come from all over…” agreed Josh. “We have lots of international visitors from across Europe, Asia, Australia, and South America, plus we get lots of visitors from nearby cities like Miami, Fort Lauderdale, and Orlando. You never know who you might meet.”

“Some days there are a lot of naked guys, some days people are more shy…” said Josh, when I asked just how optional the clothing-optional policy was. “We do host no-clothing-allowed parties twice a year, in collaboration with Bone Island naked weekends – they’re in July and December.”

“In the same way, some days are more sexual than others…” added Josh. “Sex happens. Some people prefer to be more discreet, and others like being in full view – either option is acceptable. The third-floor deck is pretty active most nights, and especially active on weekends. We also host lots of parties and events throughout the year and they’re generally more sexually active than just an average day, so it’s always a good idea to check the events calendar.”

I checked in with some of our readers, to compare Key West experiences.

“I loved Island House…” confirmed Mark from Tampa, recalling his recent visit. “All the guys were very accommodating, and friendly as could be. The compound atmosphere – with a pool, grounds, restaurant, and bar – made it perfect for an escape. Plus, it was always hot to watch the go-go boys at Bourbon Street – it adds a visual experience to drinking and socialising.”

“I was single when I went…” said Ruben from Mexico City. “There were lots of cute guys, and I took a few back to my hotel room.”

Personally, I like being in situations where guys are uninhibited enough to just get it on with each other without worrying about who was watching. While working on my tan beside the pool at Island House, there was plenty of pool-side action to keep an eye on – guys making out, jacking each other off, sucking dick, and just generally enjoying the intimacy of being naked together.

Key West has a bit of a reputation as being a destination that’s mainly for older guys. While there is some truth to that, I found there to be an enormous range of guys who were out and about and looking for fun.

Plus, I tend to go for guys who know what they want and have enough experience to have left their hang-ups behind them. The fact that the swimming pool wasn’t awash with twinks wasn’t an issue for me.

Destinations such as Key West also seem to be a good opportunity to spice up a relationship or explore new things together.

One couple that I met at Island House were Brad and Mark from Boston. They’re in their late 30s and have been coming to Key West every year together for eight years. Both blond and gym-fit, they turned heads and caught everyone’s eye as they arrived pool-side.

“I just really love seeing my husband’s hole being stretched by another guy’s cock…” explained Mark, as we chatted over drinks. “I like seeing his hole being stretched by my cock, but I see that all the time. To see some guy who’s a bit thicker than me stretching his hole and pushing his limits, that turns me on so much.”

If you’re travelling by yourself, then it might be a good idea to time your visit with an event such as Bear Week. If big and burly guys are your thing, then signing up for Bear Week means that there’s going to be plenty of parties and events to keep you entertained, and a veritable bear buffet to keep you satisfied.

Bone Island is another option if you’re looking to line your travel dates up with an event. Bone Island is a gay event that’s all about being a naturist and getting naked. The perfect way to hook-up with some guys who are all keen on working on an all-over tan.

Equator Resort is another popular men-only and clothing optional accommodation option. It has outdoor swimming pools and also hosts regular events. In July of 2019, the Victor Cody porn studio will be shooting scenes at Equator Resort.

New Year’s Eve is one of the most popular times to visit Key West. Bourbon Street Bar is the centre of the celebrations at midnight – there’s a giant shoe-drop – but this is a great time of year to spend a few days in the sunshine. The weather is great, everywhere is busy, and the guys are ready for action.

Have you been to Key West? Is it on your travel wish-list? What other gay destinations tick your boxes? Slide into our DMs or pound into our comments section below to share your thoughts, experiences, and fantasies.