Sipped, Swirled, and Sashayed: Gay Wine Weekend in Healdsburg
Packing our best wine-tasting outfits and tea dance poses and moves, we hopped over to the west coast for Gay Wine Weekend in gorgeous Healdsburg, California. We heard it was a grand celebration that served glamour, grapes, and good times, so we had to find out for ourselves. From July 18th to the 20th, liver be damned as wine country transformed into a fabulous showcase of LGBTQ+ joy, friendship, and flavor. Whether you were there for the vino, the music, or the men, it was the summer escape we all had been craving.
The weekend’s stylish home base? There were actually two locations most of the gays stayed at, one was The Lodge at Healdsburg, the main host hotel, and the other was the charming Best Western Dry Creek Inn, perfectly situated next door to The Lodge, both were easy access to all the festivities — plus both have a pool for cooling off between events. We chose to stay at the Inn as we needed two separate beds in one room and the Inn was a better fit for that option.
The weekend was jam packed, but with a flight from Florida to San Francisco, a 2 hour drive up the state, we had traveled to be dazzled, entertained, and wined and dined. Here’s how the weekend went.
Friday: Sipped, Dined, and Danced
The weekend kicked off with the VIP Opening Reception at The Lodge at Healdsburg Event Center, where the pours were generous and the crowd was festive. Vendors were present and wineries, too. Tasting wines surrounded by new friends, yeah, the weekend was starting off great. I will say each event had its own energy and purpose whch made the weekend so layered, full, and energizing.Â
After the reception / social hours, some of us did the first of many costume changes and headed to La Crema Winery for an unforgettable Winemaker Dinner — complete with divine wine pairings, California cuisine, and laughter echoing through the magnificent post and beam barn. We all looked at each other as the food was served family style. The greens, the broccoli, the chicken, the couscous, and of course the wines were all show stoppers. We did look at each other and said many times, if the weekend ended here, it would be a success. It may have been the many tastings we’ve had all day, but doubtful.
Hello you four single men from Denver, it was a pleasure sharing a table with you and Lisa Valtenbergs. And that was an enjoyable part of the Winemaker Dinners as we learned from the winemakers themselves. In 2024, Lisa’s two decades of vineyard, winemaking, and blending skills were instrumental to La Crema’s addition of a Sonoma County Cabernet Sauvignon to their line of superlative Burgundian-varieties and category-leading Sauvignon Blanc. And I think it was stated that we had one of the first pours of this new addition to the La Crema family, the Official Wine Partner of the WNBA. La Crema is women-owned and women-led and so many homosexual men working for them, you gotta support them. But also, such a great product!
And because the night was still young, the party continued upstairs at Little Saint for a pop-up gay bar afterparty. Don’t think little as the venue was a surprise as we came up the stairs into this grand open venue. Dancing and drag were plentiful, and of course the adult beverages, too. Some left early, some stayed all night.Â

Saturday: Wine Country’s Big Gay Dance Day
The morning began with a guided Russian River Valley Wine Tour, exploring boutique vineyards and sampling some of the region’s best vintages. We were shuttled to three different ones, Hartford Family Winery, Russian River Vineyards, and Kobler Estate Winery, each with their own feel, taste, environment, and experience.
Hartford Family Winery – A beautiful main building, wonderful wines, we saw some of the equipment and barrel rooms, and tasted in the barrel room, in the production area, and on the front patio. That moving around and education kept that visit vibrant and enjoyable.
Russian River Vineyards – Embracing the wilderness and redwoods, we sat outside and sipped some great offerings and had lunch in their picnic table area. And it was another chance to make new friends over wine.
Kobler Estate Winery – Intimate, cute, amazing views, family owned and operated, wonderful gay representation, we loved the wonderful cheeses, bites, and especially the wines. It takes a great product to make you say wow after having 12 other tasting pours earlier that day. We were also able to walk through the vines and see the growth that was happening, saw where Mike married his husband. Mike Kobler is the co-founder and chief operating officer of Kobler Estate Winery, returned back to his family in Sonoma County during COVID. He and his father launched Kobler Estate Winery, a family-owned boutique winery in Healdsburg, and he’s been pouring ever since.
There were many other tours as the Gay Wine Weekend had many attend. I believe we were the 6th shuttle to leave the hotel and we all went in opposite directions. So if you attend GWW again, make sure to pick a different tour package.Â
By evening, all roads led to the legendary T-Dance at La Crema’s Richard’s Grove — a twilight reception, dancing under the stars, and endless Instagram-worthy moments.
When the music faded, the afterparty at Arandas at 27 North kept the energy going into the night.
Sunday: Queens, Auctions, and Poolside Perfection
Gays and Sunday? What better thing to do than to celebrate in wine country with a Drag Queen Brunch & Wine Auction at Rodney Strong Vineyards . The weather all weekend was crisp in the morning with the daytimes nice and sunny. We were out on the lawn and Gaga bless those drag queens doing what they did in the daylight, the heat, and heels across an acre of lawn.
The auction was wonderfully exciting watching party-goers bid on rare vintages and fabulous prizes while enjoying performances that had everyone cheering. One of the auction items was ONE BIG SONOMA STARTER WINE CELLAR and A 5-STAR SCENIC RIVER CRUISE ADVENTURE.
The weekend wrapped with the Closing Pool Soirée at a private Healdsburg estate.

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Bonus Thursday: Lights, Camera, Queerness
If you’re going or not, make sure you get on the email list. We’ve been on the email list for some years and our schedule finally worked out to experience Gay Wine Weekend. Our plans had us arriving on the 18th, but received news that there was a little pregaming pre-weekend activity happening. Early birds this year enjoyed a cinematic treat with a special screening of the cult classic Trick at True West Film Center.
Director Jim Fall was in the house for a post-film Q&A, spilling tea on his next project – Out in the Vineyard – now in pre-production. It was a great re-viewing of Trick and we had forgotten some of the bits and pieces of this classic. And it was great to meet other wine weekend attendees, Jim, and to learn about his upcoming creation.
More to See, Do, and Drink
If the weekend does not align for you, check out the other events Gary Saperstein offers at other times of the year.

Final Thoughts
Whether attendees were sommeliers-in-training or simply there for the party, Gay Wine Weekend proved that the best pairings are wine and community. Gary Saperstein is the ultimate host as zero worries, hundreds of men, thousands of sips, and millions of laughs were had was the perfect home base for a weekend no one would soon forget.
We cannot wait to go again. And that will happen. Yes, the vent is in California on the west coast and I live on the east coast but making this whole trip about a nothern California experience had me loving every single aspect of the journey. We were so relazed that when we came back, people could see a difference. You deserve it.
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