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- Newsletter 321A: Gay Sailing Across the World, Our New Italy and France Tour + Madrid Tapas Tour & More
Newsletter 321A: Gay Sailing Across the World, Our New Italy and France Tour + Madrid Tapas Tour & More

It’s Sailing Men! Hallelujah!
As the leading worldwide specialist in gay and gay-nude sailing holidays, GaySail is sending out the call for all types of gay and bi men to shed their clothes in 2026 and hop aboard luxury yachts bound for an eclectic range of destinations worldwide. Maybe you fancy setting sail from the beautiful, dual-cultured island of Saint Martin into Caribbean waters. Or perhaps the understated sophistication of the Côte d’Azur in France is more your style, or the idyllic beaches and rich culture of Thailand. Maybe your dreams of a naked sailing trip point you toward the diversely beautiful islands of Greece or Croatia’s medieval towns and secluded bays. GaySail is setting its sights on them all in 2026 and they want you to join them.
So whether you’re tall, blonde, dark, or lean… rough, tough, strong, or mean… come get yourself soaking wet on the gay sailing trip of your dreams with GaySail.
SPONSORED BY GAYSAIL
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.
Book before it’s too late! WorldPride 2028 will bring tens of thousands to Cape Town, and Sikeleli Travel’s insider access is already in high demand. Secure one of their 4 curated Pride packages now before they’re gone - and don’t forget to add-on an unmissable Safari adventure! BOOK BEFORE IT’S TOO LATE! |

What if payday got here early, every time?
Getting paid is good. Getting paid early is even better. When you deposit paychecks into Cash App, you can make that a regular thing. As soon as we get your paycheck, it’s ready for you—up to 2 days earlier than many banks. You’re in control of what happens next—choose a percentage of your paycheck to save, invest, or even buy bitcoin.* And with no monthly fees, your money stays yours. Plus, you can relax knowing your money is protected by 24/7 fraud prevention and real-time activity alerts.
SPONSORED BY CASHAPP
Cash App is a financial platform, not a bank. Banking services provided by Cash App’s bank partner(s). Direct deposit and savings provided by Cash App, a Block, Inc. brand. Prepaid debit cards issued by Sutton Bank, Member FDIC. See Terms and Conditions. *To earn the highest interest rate on your Cash App savings balance, you need to be 18 or older, have a Cash App Card, and direct deposit at least $300 monthly into Cash App. Cash App will pass through a portion of the interest paid on your savings balance held in an account for the benefit of Cash App customers at Wells Fargo Bank, N.A., Member FDIC. Savings yield rate is subject to change. **No fee overdraft coverage of up to $200 for Cash App Card transactions is available when you direct deposit at least $300 monthly into Cash App. Eligibility requirements apply, see terms for details.
Revel in the intimate playground of Descanso. Hollywood Moderne style creates the ultimate gay men’s retreat; newly refurbished, completely reimagined. Enjoy gourmet breakfasts, weekend wine hours, spa, firepit evenings, and mountain views. Spacious king rooms and attentive service await. BOOK FOR 2026 |

Pasta, Piazzas & Parties: See Italy’s Coast with Us
Italy is every bit as beautiful as the men who live there. So we thought it deserving of some special attention on our Sicily, Naples, Cannes & More Cruise, setting sail from Rome (Civitavecchia) on August 22-31, 2026. Join our gay group aboard a Virgin Voyages vessel for ten days at six ports around the coast of Italy with eclectic entertainment, group dinners, parties, and plenty of surprises aboard too.
The first stop is Catania, the jewel of Sicily and star of White Lotus, where dramatic landscapes meet irresistible charm. Next, we head north to Naples, a lively city filled with UNESCO-listed historic streets, bustling piazzas, and rich Baroque treasures. From there, it’s on to Ajaccio in Corsica, the French-speaking island that blends Mediterranean beauty with Napoleonic heritage. Then we’ll soak up the glamour of Cannes, France’s sophisticated playground of the rich and famous. Finally, we return to Italy at Livorno, the gateway to two Tuscan gems: Pisa and Florence, before looping back to Rome.
Get on board with us as we give Italy the spicy loving it deserves!
SPECIAL OFFER!
For solos: join for just $2,250 and get a private cabin.
For couples & friends: Book a Sea Terrace cabin by February 23 and save 10%. That’s just $2,203 per person. Terms apply, based on double occupancy.
Seven Days in Spain. Spain is one of our biggest passions. Let us share it with you for four nights in Barcelona and two in the gay-friendly coastal town of Sitges from May 13-19, 2026. Viva España! SPECIAL OFFER! Book by Oct 31 & solo travelers pay no single supplement. VISIT SPAIN |

Gay Travel Guide to Palm Springs
Palm Springs has been an LGBTQ+ getaway for decades, dating back to the glamorous days of Hollywood in the early 1930s. Actors working in Hollywood would escape to the oasis, just a two-hour drive away, to let loose and mingle with other closeted members of the entertainment industry. Today, Palm Springs may have a reputation as a destination primarily for middle-aged or retired visitors, but don’t be fooled, it remains a playground for all generations.
Cruise, Culture, Cocktails, and Connection. Embark with us on our longest adventure yet! Join Two Bad Tourists’ Moroccan Marvels & Mediterranean Wonders cruise with Virgin Voyages, July 26-August 5, 2026. From Barcelona to Portsmouth, enjoy culture, connection, parties, wine tastings, and unforgettable fun across Tangier, Lisbon, Bilbao, and Bordeaux. SPECIAL OFFER! Solo travelers can join for just $2,250 & get a private cabin. BOOK NOW |

Eat Like A Madrileño on Our LGBTQ Tapas Tour
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 on our Madrid LGBTQ Tapas Tour. Join our local guide and avid foodie on a tour of Chueca, the beating heart - or should that be grumbling stomach - of Madrid’s LGBTQ+ community. You’ll visit four restaurants, sampling the best tapas and drinking the best wine - while learning all about both what you're putting in your mouth and the eventful LGBTQ+ history of Chueca. Join us in Madrid for some good food and good vibes.
Mykonos Moons and Italian Indulgences. We love Europe, and Greece, Italy, and Spain are firm favorites of ours. See all three on our October 4-11, 2026 cruise. Join our gay group aboard the Scarlet Lady for a week of fine dining, onshore excursions, and sassy themed parties. SPECIAL OFFER! Solo travelers pay just $2,240 for a private cabin. BOOK NOW |





