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  • Newsletter 280: Taxes for Digital Nomads, Our Madrid Tour + Gay Waterpark Party & More

Newsletter 280: Taxes for Digital Nomads, Our Madrid Tour + Gay Waterpark Party & More

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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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GaySail in Greece and Croatia. The world is full of breathtaking coastlines and secluded bays, best experienced from the deck of a luxury catamaran or sailing yacht,, surrounded by like-minded—and possibly naked—men. GaySail offers just that. Join them this year for an unforgettable island-hopping adventure in either Greece or Croatia. BOOK NOW

Taxes Made Easy for Digital Nomads

Just because you’re abroad doesn’t mean you’re invisible—and Uncle Sam with his taxes is the ultimate buzzkill at a digital nomad’s party. Luckily, MyExpatTaxes is on hand to take the weight off when complex tax systems rear their unwelcome heads. As a highly trusted tax service for U.S. expats, MyExpatTaxes offers expert guidance to American citizens living abroad, digital nomads, and retirees. Users can choose the base plan to file their taxes independently, the Reviewed plan for an extra layer of review by a tax expert, or the Premium plan, which includes a 30-minute phone consultation for step-by-step assistance—though availability fills up fast! Listen to our recent podcast episode where we interviewed their CEO, Nathalie about the challenges faced by expats abroad.

We've personally relied on MyExpatTaxes for the past two years, and filing early can even secure you a refund if you qualify. Show Uncle Sam the door with MyExpatTaxes.

SPONSORED BY MY EXPAT TAXES

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Feel the Heat in Bogota. From the gorgeous colonial-era old town to the best bars and clubs in the local gay scene, discover the hottest locations in Bogotá with an LGBTQ+ friendly local guide from Guides4me.com. VISIT BOGOTA

Our Home is Your Home for Our 2025 Madrid Tour

Madrid is the best city in the world—but we would say that, we live here! Join us for 7 Days in Spain – Madrid, Toledo & Segovia from September 18-24, 2025, and let us show you why. Stay in a gay-friendly hotel in the heart of Madrid, explore the city’s history with David, and see Picasso’s iconic Guernica painting at the Reina Sofia Museum with our local gay guide.

As night falls, we’ll take you for a Spanish Drag Queen show over dinner, then set out into Madrid’s (in)famous gay nightlife on a—guaranteed to be eventful—bar crawl in the gayborhood. We’ll also visit Toledo, a stunning medieval city and former Spanish capital, and Segovia, home to a legendary Roman aqueduct, a fairy-tale castle, and some quirky traditions—you’ll have to see to believe! In Spain, we like to say, “Mi casa es tu casa”, and this October, our home is indeed yours. Read our reviews here.

SPECIAL OFFER!

Book by April 30 and solo travelers pay no single supplement.

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Three Countries, Seven Nights. Our gay group trips are for everyone, and our brand-new Barcelona to Cannes, Rome & Ibiza cruise June 22-29, 2025, is no exception! With us, you’ll enjoy group dinners, shore excursions, cocktail hours, amazing entertainment, and more! OFFER EXTENDED! Book Sea Terrace cabin by March 31 & save $300 + get $800 onboard credit, only $2,440/person. ALL ABOARD

Water Park Parties, Sexy Romans, Top DJs and Pure Magic!

Three pool parties, four massive Pride festival parties, three spicy after-hours parties, and hordes of half-naked men—all in one wet and wild package. That’s One Magical Weekend! Head to Walt Disney World Resort in Orlando from May 30 – June 1, 2025, for our favorite Pride event of the year. One Magical Weekend has a loyal following of thousands—us included—amassed over the last thirty years and it’s easy to see why! This year is all about unleashing your inner LGBTQ+ magic and you can expect iconic events featuring internationally renowned DJs over four exhilarating days. Dance and ride some slides at the legendary RIPTIDE party at Disney’s Typhoon Lagoon Water Park, unsheath your sword for Rome at ROMA, dive into the surreal at the Cadabra Afterparties, make a splash at the Therapy pool parties, and celebrate WorldPride at Born This Way. One Magical Weekend isn’t just a party—it’s a journey. But hurry, prices increase on April 1.

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Portsmouth, Amsterdam, Bruges and Bordeaux! Prepare yourself for a 2025 full of cruising by joining our new European cruise with Virgin Voyages on September 05-12, 2025. Dare you brave the Northern Seas to experience four European cities in four countries in just one week?! SPECIAL OFFER! Book a Sea Terrace Cabin by March 27 for as low as $2,813. ALL ABOARD

Gay Travel Guide to Sitges

Sitges is a small Spanish town with a big personality, located just forty minutes by train south of Barcelona. On one hand, it exudes the quintessential beach-town vibe, with the typically Spanish white-painted buildings, windows framed in bright blue, and an impressive church perched on a rocky outcrop along its seafront. On the other hand, it boasts a gay scene to rival cities twice its size, featuring a variety of gay bars, cruising spots, and shops offering the usual gay paraphernalia like bum-bolstering speedos and sexy jockstraps. Sitges isn't exactly the place for sightseeing, but rather a spot to escape the humdrum of city life, tan among other beach hotties, and dive into its lively nightlife or one of its many annual festivals and street parties.