Wine Not? Sonoma’s Gayest, Grapiest Weekend Is Back

A wise woman once said, “If anyone tells you it’s too early for wine… unfriend them. You don’t need that kind of negativity in your life!” We couldn’t agree more, and thankfully, at Gay Wine Weekend from July 17-19, it’s never too early for a glass of the fine stuff.

To celebrate their 15th anniversary, they’re heading back to where it all started, Sonoma Valley in the heart of Sonoma Wine Country. Reserve your space for what’s all set to be a fun-filled, wine-fueled weekend of epicurean delights for the LGBTQ+ community. You’ll sip your way through world-class tastings and tours at Sonoma’s most celebrated wineries, feast on fabulous farm-to-table dinners, and raise your paddle (and your glass) at a drag brunch meets wine auction. Then get tipsy at the signature event of the week, the twilight T-party before finishing with one last splash at the sun-drenched closing pool party soirée. Those staying through Sunday night will also see talented singer/spoken word artist Mary Lambert post-pool party.

Gay Wine Weekend is a three-day love letter to the good stuff, so grab yourself a glass—or a bottle—and book your place now.

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.

What you consider moving to Costa Rica?

Take our poll and help us customize your travel content & experience.

Login or Subscribe to participate

ADVERTISEMENT

Your Tropical Gaycation Starts Here! Royal Grand Resorts officially opened April 1st, bringing sun-drenched days, flirty nights, and the freedom to be exactly who you are. This isn’t just a vacation—it’s a vibe. Come experience Costa Rica our way. Get Into Trouble with Promo Code TBT025 for an exclusive 5% TwoBadTourists discount. USE CODE

Just the Tip: P-Town Goes All in for Pride Season

Summer in Provincetown isn’t just a season — it’s a continuous LGBTQ+ celebration, with themed weeks, parades, and signature events unfolding from May through September. Days drift between sun-washed shores and the Cape’s wild dunes; nights thrum with drag shows, costume parties, and waterfront revelry under warm Atlantic skies. 

It kicks off with Memday in May, gathering women and nonbinary travelers for beach meetups, live music, and sunset socials. June’s FROLIC Weekend centers queer men of color with a mammoth six-day fête. July brings Bear Week — one of the world’s biggest hirsute happenings — when bears, cubs, and admirers pack beaches, pool parties, and late-night dance floors. Family Week follows, welcoming LGBTQ+ parents and kids to inclusive town-wide fun. August’s Carnival crowns the season: costumes, performances, and a dazzling Commercial Street parade that turns Provincetown into an open-air queer fantasia. Come October, TransWeek closes the arc for a fun-filled celebration of the trans community. 

Two Bad Tourists have been — and can vouch: during festival season, the whole town becomes one joyous seaside party you simply have to experience yourself one day.

ADVERTISEMENT

Cruise the Rhine with Friends. A great gay group trip should feel like exploring with friends—and that's exactly what Detours delivers. Join their all inclusive Rhine River Cruise from October 1-7, 2026, sailing past castles and vineyards to Heidelberg, Strasbourg, and Alsace villages, blending culture, wine, and convivial fun. CRUISE IN EUROPE

Moroccan Marvels & Mediterranean Magic: Announcing Our New 2026 Cruise!

Cruise, cruise, another cruise—no sleep! Two Bad Tourists are serving up five Virgin Voyages cruises in 2026, and we’re thrilled to unveil our brand-new Moroccan Marvels & Mediterranean Wonders cruise—just as fabulous as it sounds.

This 10-night adventure, July 26 - August 5, 2026, takes us from Barcelona, Spain, all the way to Portsmouth, UK. First stop: Tangier, a vibrant port city on the northern tip of Africa where cultures mix and converge. Next, we head to one of our favorite European capitals—Lisbon, Portugal, bursting with color and charm. From there, we’ll swing back to Spain and dock in La Coruña on the lush, green northern coast (you’ll swear you’re not in Spain!). Then it’s on to the port nearest Bilbao, home to world-class Basque cuisine and the iconic Guggenheim Museum. Our final call is Bordeaux, France—the wine capital of the world, because everything’s better with a bottle… or three.

As always, you’ll enjoy our group perks: shared dinners, onshore excursions, cocktail parties, and—best of all—instant friends.

LAST CHANCE! Bookings close April 30. Secure your spot now to guarantee participation.

  1. For solos: Avoid single supplements and join our roommate matching program to save big!

  2. For couples & friends: join for as low as $2,450 per person.

ADVERTISEMENT

Book David in Medellin, Pansada in Vientiane, Rayan in London, or one of our other Holiday Houseboys in 210 destinations worldwide. A Holiday Houseboy is a gay friendly tour guide who looks after your safety and welfare at all times. Contact Alan on whatsapp +34 676 78 63 51 for further info. CHECK IT OUT

Bringing Wanderlust to the Water: The Nomadic Boys Board Rainbow Cruise 2027

Diversity is the spice of the seas when it comes to LGBTQIA+ cruises, and Rainbow Cruise: The Next Chapter – A Future of Unity is all set to be the colorfully diverse ship to hit the waters in 2027.

What’s more, the charismatic duo—and our good friends—the Nomadic Boys are hopping aboard to share in five nights of fun, frolics, and floating fabulousness. Join them from September 28 - October 3, 2027, for a round trip from Palma de Mallorca with ports in sunny Palermo (Sicily) and Cagliari (Sardinia).

Alongside an eclectic range of shared activities aboard, you can expect A-tier entertainment from a diverse cast of LGBTQIA+ icons, including Eurovision winner Conchita Wurst, Germany’s favorite lesbian pop star Lucy Diakovska, and drag powerhouses Miss Ivanka T, Katy Bähm, and Pam Pengco. What’s a cruise without spicy themed parties? Rainbow Cruise’s are set to be the kind that’ll keep you up way past bedtime—KitKatClub’s infamous Piep Show, to name but one. Where the Nomadic Boys go, fun often follows, so book now and be part of what’s set to be one of the most diverse and fun cruises of 2027.

ADVERTISEMENT

See Madrid, Toledo and Segovia. Madrid is a paradise for LGBTQ+ travelers! Join us from September 17-23, 2026, for our 7 Days in Spain – Madrid, Toledo & Segovia tour, where we’ll show you the best of our home city and the nearby towns of Toledo and Segovia. VISIT US

Flamenco, History, and Heat: Journey Through Southern Spain with Two Bad Tourists

We’ve held tours in Barcelona, Sitges, and Madrid—now it’s time to give Southern Spain a little of the Two Bad Tourists’ love! Join us from November 11-19, 2026, as we head to Andalucía, the birthplace of Flamenco, for our 9 Days in Southern Spain, visiting Seville, Córdoba, and Granada.

We’ll kick things off in our home city of Madrid for two days, including a walking tour with David, a tapas tour with our local Spanish foodie, and a night out in the gayborhood. Then we’ll hop on a high-speed train to Spain’s most “Spanish” city, Seville. We’ll catch a flamenco show, visit the Alcázar and Cathedral, dine in authentically Spanish restaurants, and enjoy a night out in the local LGBTQ+ hub. Córdoba makes for a perfect day trip, filled with architectural highlights like its mosque-cathedral, Jewish Quarter, and iconic Roman Bridge.

Finally, we’ll head to Granada, a fairytale city at the foot of the Sierra Nevada, where we’ll explore its winding streets and end with a tour of the breathtaking Alhambra, the world’s most impressive Moorish palace.

Andalucía is where Spain’s spirit runs deepest. Let us take you into its heart. 

ACT FAST!

Book by April 30 to guarantee your visit to the Alhambra, one of Spain’s most iconic sites. Tickets are likely to sell out.

ADVERTISEMENT

12-Days, 4 Countries, 1 Epic Voyage. From Santorini’s romantic views and Dubrovnik’s historic charm to Bodrum’s vibrant bazaars and Mykonos’ legendary LGBTQ+ parties, our huge 12-day cruise from May 30 - June 10, 2027, is set to be our biggest yet. Get yourself onboard with us—it’s going to be epic! SPECIAL OFFER! Solo travelers can join for just $3,150 for a private inside cabin. Hurry, these cabins will sell out fast. BOOK NOW

Gay Travel Guide to Berlin

The Capital of Kink is, unsurprisingly, one of the most LGBTQ+-friendly capital cities in Europe—and certainly the edgiest. Berlin is counterculture to its core and serves as a haven for artists and independent thinkers. Evidence of this is everywhere, from its distinctive street art and gritty neighborhoods—still bearing remnants of the East German GDR era—to hip and trendy districts like Kreuzberg and Schöneberg. So, whether you're exploring vast museums or raving in warehouse basements, the Berlin experience never fails to leave an impression… or trigger an existential crisis.

ADVERTISEMENT

Pride Tapas in Chueca. Chorizo, cheese and gazpacho—with a side of Pride! Celebrate Madrid Pride Week (June 29–July 2) as you explore the best restaurants in Chueca, Madrid’s gayborhood, in just three hours. Taste Spanish food and wine while discovering the LGBTQ+ history and festive spirit of the neighborhood. BOOK NOW

How much per person do you typically spend on a 1-week trip including flights & transportation?

Take our poll and help us customize your travel content & experience. Currency in US Dollars.

Login or Subscribe to participate

1  

Keep Reading