They say the 50s are the new 40s. And as the world’s best clothing-optional resort, Island House Key West hits its 50th anniversary, it has never looked better!

Over the years, Island House has garnered a worldwide reputation as not just a place to stay, but a community known for its laid-back vibe and open-arms—well, open-everything-else too—approach to hospitality. Surrounded by like-minded—often naked—men, you’ll enjoy a 24-hour gym, multiple Jacuzzis, a sundeck, tropical gardens, and a large pool with a poolside café/bar, all at your leisure. You can also choose from a range of comfortable rooms styled for the modern gay man.

With a range of events taking place at the resort such as its infamous weekly pool parties, everything is set up for you to make the experience exactly what you want it to be—whether that be a place to just kick back and hang out (so to speak) among kindred souls or to dive right into an adult playground of opportunity. At fifty Island House is hot, it’s experienced and it wants you!

SPONSORED BY ISLAND HOUSE

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Portugal is already one of Europe’s dreamiest destinations, but experiencing it with a welcoming LGBTQ+ group makes it even better. 

Pride Adventures is hosting an 8-day Portugal journey from Lisbon to Porto, with stops including Sintra, Évora, Coimbra, and Porto. Expect historic streets, beautiful architecture, local culture, shared meals, and the kind of built-in community that makes solo travel feel easy. The trip runs November 1-8, 2026, and is designed for travelers who want connection, culture, and adventure without having to plan every detail themselves. 

Use code LISBON250 for $250 off!

SPONSORED BY PRIDE ADVENTURES

Virgin Voyages and Two Bad Tourists are sailing soulmates at this point, having worked together for the last three years to bring our guests the best cruising experiences on the high seas. And we’re at it again from October 4-11, 2026, with our new 7 Days in Greece, Italy & Spain cruise. Join our gay group aboard the Scarlet Lady for a week of fine dining, exciting excursions, and sassy themed parties (including a PJ party, an ’80s night, and the infamous Scarlet Night). Between onboard fun, we’ll port at the gay-favorite island of Mykonos, seductive Sicily, the stunning Amalfi Coast, and even Civitavecchia—better known as the gateway to Rome—before arriving in beautiful Barcelona.

Our trips are for everyone, whatever your background, age, relationship status, or shoe size! So don’t feel intimidated if you’re traveling alone, because our group activities, dinners, and excursions will help you forge friendships with your fellow shipmates that last way after you disembark. 

SPECIAL OFFERS!

Book by June 10, when the special offers expire. Plus, we’ll only be running one Virgin Voyages gay group cruise next year. So if you can’t make our May 2027 trip, this is your last chance before 2028.

Confidence is not something you either have or you don’t. Nor is it a trait reserved for guys lucky enough to have struck gold on the biological lottery. Confidence—just like our bodies—is something that can be worked on. It can—and should—be shaped, challenged, and strengthened over time. Like so much in life, it is learned, not innate.

We explore why that struggle is so real for gay men, what you can do to build your own body confidence, and throw in a few tips for grooming, the gym, and dressing to impress (yourself) while we’re at it.

Spanish food is some of the best in the world—just ask a Spanish person, they’ll soon tell you! But why not decide for yourself during Madrid Pride Week (June 29-July 2) on our Madrid LGBTQ Tapas Tour. Join our local guide and avid foodie on a festive journey through Chueca, the beating heart—and during Pride, the glittering epicenter—of Madrid’s LGBTQ+ community. You’ll visit four restaurants, sampling standout tapas and superb Spanish wines while learning all about both what you’re tasting and the vibrant LGBTQ+ history and Pride traditions of the area. With daily departures during Pride Week, it’s an easy, delicious way to join the celebration. Join us in Madrid for unforgettable flavors, fierce festivities, and fantastic vibes

SPECIAL OFFER! Use promo code PRIDE2026 to get 15% off Madrid Pride week bookings.