The Clothes Don’t Make the Man at Island House Key West!

Not only is Island House one of the first gay resorts in the world, but it’s also the best! A bold claim, we know—but having had the good fortune to stay there ourselves, we can vouch for it! Island House Key West is a clothing-optional gay resort that delivers every time in terms of quality, comfort, inclusivity, and no-nonsense fun. Island House is a space where you’re free to be yourself—however naked that self may be, of course. Their facilities include multiple Jacuzzis, a sundeck, tropical gardens, a gym, and a large pool with a 24-hour poolside café/bar, which hosts weekly pool parties designed to bring you closer to your fellow guests. Whether you’re a solo traveler, with your partner, or part of a group, all are welcomed by friendly staff ready to help you make the most of your stay in Key West. Island House Key West has it all—it’s just missing you!

SPONSORED BY ISLAND HOUSE

This newsletter was written in collaboration with one or more travel brands or businesses. We may receive compensation when you click the links and make a purchase. Read our full advertising policy here.

Tackle Your Credit Card Debt With 0% Interest Until Nearly 2027

Did you know some credit cards can actually help you get out of debt faster? Yes, it sounds crazy. But it’s true. The secret: Find a card with a “0% intro APR" period for balance transfers. Then, transfer your debt balance and pay it down as much as possible during the intro period. No interest means you could pay off the debt faster. Check out these cards today so you can focus on planning your next trip.

SPONSORED BY FINANCE BUZZ

Spanish Kings, Drag Queens & Endless Tapas in Madrid

Madrid is not “tolerant” or even “accepting” of LGBTQ+ people, it’s positively welcoming! Honestly, walking through its streets it often seems like there’s more gay men than straight. And we’re lucky enough to call the city home. From September 18-24, 2025, we humbly invite you to see for yourself on our 7 Days in Spain – Madrid, Toledo & Segovia for a week-long bonanza of culture, history, nightlife and tapas! 

Prepare yourself for tours of the city seeing all the key sights. We’ll visit the spectacular Reina Sofia gallery, dine in authentic Spanish restaurants, attend a Spanish drag show, bravely venture forth into Madrid’s vibrant nightlife on a pub crawl in Chueca - Madrid’s spicy gay zone - and much much more. We’ll even venture out to the historically rich towns of Toledo and Segovia - each with their own distinctive personalities, cathedrals, castles and ancient histories to uncover. We love Madrid and, after visiting us, we’re sure you will too. Read our reviews here.

HURRY, BOOKINGS CLOSE JULY 18!

Bitch Better Have My Honey - The 12 Best Bear Weeks in the World

Bear weeks offer a welcoming space where bears, otters, chubs, and their admirers can socialize, party, and celebrate one of the biggest gay subcultures there is. Originating in the 1980s in San Francisco, the bear movement emerged as a counterpoint to the more mainstream, often stereotypical image of gay men and their bodies. In the bear community, this stereotype is subverted with bigger and hairier bodies celebrated within inclusive and welcoming spaces. Nowadays, the scene has grown so much that they are perhaps the most visible of all the gay subcultures—anywhere you can find gay bars, you can probably find bear bars too. Bear weeks bring bears and their admirers from all over the world together, like one big metaphorical bear hug.

Cruise with Class and Sass through the Netherlands, Belgium & France

Looking for a shore thing to add to your calendar in late 2025? Hoping to sea more of Europe next year? Sailing puns aside, why not sign up for our 7 Days in Amsterdam, Bruges & Bordeaux cruise with Virgin Voyages from September 5-12, 2025? We’ll hop aboard at Portsmouth in England and glide across to Amsterdam, a beautiful canal-filled oasis to let loose in. After an overnight stay in the city, we’ll cruise down to Bruges, an enchanting medieval Belgian city known for its cobblestone streets, historic buildings, and chocolate shops. Finally, we’ll visit Bordeaux for a taste of Northern France—and no doubt, wine from their legendary vineyards…lots of wine! Just as on all our gay group trips, you’ll always be part of the group through an eclectic range of activities from group dinners to cocktail hours. Come if you’re traveling solo, come with your partner(s), or come with a group of friends. Just be sure to come!

SPECIAL OFFERS!

1 – For Friends & Couples: Book a Sea Terrace cabin by July 30 and pay just $1,300 per person. Based on double occupancy.

2 – For Solos: Reduced Single Supplements. Book Sea Terrace cabin by July 30 and pay just $1,988. Hurry, this offer is based on availability and can end at any minute, so ask fast!

Hurry, bookings close on July 30.