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  • Newsletter 277: Gay Sailing Across the World, LGBTQ+ Italy Tours + Winter Party in Miami & More

Newsletter 277: Gay Sailing Across the World, LGBTQ+ Italy Tours + Winter Party in Miami & More

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Seas the Gay in Greece, Croatia, France, Caribbean, Thailand or Tahiti with GaySail

Our wonderful world is full of breathtaking coastlines, best experienced from the deck of a luxury catamaran, surrounded by like-minded—and possibly naked—men. GaySail offers just that. As the leading worldwide specialist in gay and gay-nude sailing holidays, their GaySail Exclusive clothing-optional and GayNudeSail Exclusive nude l trips welcome gay men of all backgrounds.

Simply choose your dream voyage from a variety of 2025 destinations and dates, then you’re good to go. Prefer Greece’s heavenly islands and ancient ruins? Or Croatia’s medieval towns and secluded bays? Maybe the French Riviera’s playground of the rich and famous is more your scene? How about the exotic, arcadian paradise of Tahiti in French Polynesia? Wherever you go, a fully gay crew will ensure a fully immersive getaway—where luxury, culture, adventure, and relaxation come together for the full package!. And who doesn’t love a full package?

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.

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Putting the Gay in Gay Paree. Queer love is in the air in Paris. In fact, it always has been! Join Oscar Wilde Tours to uncover all the LGBTQ+ secrets of Paris on a grand tour, spanning everywhere from the Louvre to the Loire castles—and all the hidden spots in between. DISCOVER PARIS

Passion, Pride & Pasta: Explore Italy the Quiiky Way 

Italy is pure spice—from the inclusive, fashion-forward Milan to the romantic canals of Venice to the seductive heat of Sicily. LGBTQ+ friendly travel company Quiiky has an unrivaled passion for every last inch of it, offering an exciting range of tours designed to showcase Italy’s rich queer history and culture. Discover Sicily, an island steeped in Italian culture, with postcard-perfect beaches and even more stunning men, on Quiiky’s Beach, Boat, Food & Wine Tour from August 4-13, 2025. Or explore all seven of Southern Italy’s breathtaking volcanic Aeolian Islands on Quiiky’s Aeolian Gay Sail Adventure, available on select dates in July, August, or September 2025.

For a more in-depth experience that still captures Italy’s magic, take an Untold History Tour, where you’ll uncover the LGBTQ+ stories of three of Italy’s most iconic cities. Learn about the hidden lives of Italy’s most fascinating historical figures—from Caesar to Da Vinci. Italy is all about passion, and you won’t find tours infused with more passion than Quiiky’s.

SPONSORED BY QUIIKY

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Remote, Proud, and Free. Unlock the secrets to becoming an LGBTQ+ digital nomad. Ready to join thousands of LGBTQ+ digital nomads living life on their own terms? Get your hands on our step-by-step blueprint...and discover how to turn your wanderlust into reality.  FREE GUIDE: "The Queer Global Escape Plan" + weekly strategies for breaking free...with insights, inspiration, and community. START YOUR JOURNEY

Make Tax Season into Relax Season with MyExpatTaxes

As American expats, the world is our oyster, but the stress of taxes can really leave a salty taste in the mouth! Luckily, we have MyExpatTaxes to help us through the process—they specialize in making complex tax systems feel surmountable. As the most trusted U.S. expat tax service, they provide professional advice to US citizens working abroad, digital nomads and US retirees. With MyExpatTaxes, users can file through a Base plan (DIY, solo) or opt for a Reviewed plan, where a tax pro double-checks everything. There's also a Premium plan, which includes the option to add a video call  to guide you through the process step by step  for a slight upcharge.

We've been using MyExpatTaxes ourselves for our tax returns over the past two years, and filing early even guarantees you a refund if you're eligible. Let MyExpatTaxes do the hard work, so you can focus on the important things in life—like enjoying a good oyster!

SPONSORED BY MY EXPAT TAXES

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Stay in an Italian Castle. Live out your Italian royalty fantasies with leading gay travel operator Detours. Join thirty guests as they depart from Rome for an epic eight-day adventure exploring Siena, Florence, and Pisa—while staying in an 800-year-old luxury castle in Tuscany. VISIT ITALY

Join Winter Party Festival in Miami…2026 Dates Announced!

Winter Party Festival is a week-long bonanza of huge events, cutting-edge music, and no-holds-barred fun spread across Miami and Miami Beach, which donates a healthy portion of their proceeds to LGBTQ+ causes across Florida. The festival features a world-class DJ roster that includes international talents like Chus, Karsten Sollors, and Tom Stephan, as well as newer up-and-coming LGBTQ+ talent, the festival is now in its 32nd year and welcomes over 10,000 attendees from around the globe annually. This year’s event just wrapped up but you can join in 2026 from February 25–March 3, 2026.

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Art, Architecture, Alcohol and Waffles. Northern Europe has its fair share of beauty, culture, fine cuisine, and even finer wine. From September 5-12, 2025, we’re setting sail with Virgin Voyages from Portsmouth, England, to Amsterdam, Bruges, and Bordeaux. Join us! SPECIAL OFFER! Book a Ltd View Sea Terrace Cabin by March 31 for as low as $2,813. ALL ABOARD

Gay Travel Guide to Ibiza

Ibiza has quite the reputation for being the big party island of Spain. The deceptively small Balearic island has lovingly nurtured its party reputation since as far back as the swinging 1960s, when the island attracted a volatile mix of hippies, artists, and free spirits drawn to its relaxed atmosphere and stunning beaches. The 1970s saw the rise of iconic clubs like Pacha, which blended disco culture with the island’s bohemian vibe, and by the 1980s, Ibiza had become a hub for electronic music, with world-renowned DJs flocking to play at its legendary open-air venues. The gays have always been part of that, of course—aren't we always—and to this day, the small island remains a firm favorite of the gay community looking for some fun in the sun.