The Estate
This is where you'll be staying. Free of charge. Try not to break anything.
Inside the Rooms
Every couple gets their own bedroom and bathroom. No sharing. No drama.
You are cordially invited to
Estate of Mind
Healdsburg, California
Hint: say it with confidence.
You are cordially invited to
Estate of Mind
Healdsburg, California
September 9–13, 2026
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You are cordially invited to abandon responsibility and join us in Healdsburg for a highly sophisticated, definitely mature getaway.
Because we'll be staying at a private residence, we're treating this as a true off-the-grid retreat. Post your pics, live your best life — but please don't share this website, the property address, or any details about the homeowners. Consider this your official invitation to the Inner Circle. Good vibes, great wine, and total discretion.
If you've seen White Lotus, you know what happens to guests who don't respect the property. We'd hate for anyone to end up floating in the pool.
This is where you'll be staying. Free of charge. Try not to break anything.
Every couple gets their own bedroom and bathroom. No sharing. No drama.
Sonoma and Napa Valley are aggressively beautiful and almost offensively well-stocked with things to do. Here's what's within striking distance of the estate. A true day-by-day agenda is coming soon — for now, just know the options are unreasonable.
The estate has a pool, a hot tub, and a water slide. You will rotate between all three like a lazy river of poor decisions. The hot tub will become the unofficial headquarters for every late-night conversation that didn't need to happen but absolutely had to. Bring a float, a drink, and zero plans.
aggressive loungingThe town square is dangerously charming. Tasting rooms, boutiques, restaurants, and the kind of bookstore where you buy a $40 cookbook you'll never open. Peak wandering energy.
main character walkPrivate court on the property with a ball machine, so you don't even need to find a willing opponent. Pickleball gear is also on hand for those who've made it their entire personality. Work out your competitive demons or just look good in a headband. No skill level required, only confidence.
unearned athleticismFarm-to-table is not a marketing term here, it's just how restaurants work. We'll hit some incredible spots in town, but we'll also be cooking at the estate — grocery runs for charcuterie boards, fancy sandwich spreads, and whatever else the group decides it can't live without. The kitchen is built for this. Expect competitive cheese plate assembly.
reservations + grocery runsYou're in the middle of Dry Creek Valley, Alexander Valley, and Russian River Valley. World-class wineries are a short stumble away. Zinfandel, Pinot Noir, Chardonnay — find your grape personality and defend it loudly.
mouthfeel territoryRunning since 1978 and one of California's original certified farmers' markets. Saturday mornings, 8:30 to noon — local produce, artisan cheeses, honey, flowers, prepared foods, live music, and cooking demos. The kind of place where you buy a $12 peach and don't regret it.
saturday morning ritualHealdsburg has no shortage of ways to be professionally relaxed. We're looking into bringing a massage therapist directly to the estate — because why leave the property when the property is this good? Failing that, you can visit the Montage Healdsburg for an excellent spa. Either way, the full "I deserve this" experience is happening.
aggressive self-careStart the day like someone who has their life together. Yoga on the estate grounds with vineyard views, because nothing says "wellness retreat" like stretching in wine country before drinking wine.
optional enlightenmentJoin Josh for an unsolicited but allegedly life-changing talk on how to use AI tools to automate the parts of parenting no one tells you about. Can a large language model pack a school lunch? Probably not well. Will Josh claim it can? Absolutely. Topics include prompt-engineering your toddler's bedtime routine, using computer vision to find the other shoe, and why your Google Calendar is a cry for help. Attendance is mandatory. Heckling is encouraged.
September in Healdsburg is what happens when California decides to show off. Expect hot, dry days with wall-to-wall sunshine and cool evenings that actually feel like evenings. It's the tail end of summer and the start of harvest season — the best weather window of the year, and it's not even close.
A rough guide to the financial damage. Wine country isn't cheap, but it's cheaper than therapy and arguably more effective.
The best things on this trip are free: the pool, the company, the sunset arguments about nothing, and the group photo no one will ever post.
Healdsburg is in northern Sonoma County. It's close enough to San Francisco to feel accessible and far enough to feel like you've escaped your life.
No need to rent a car — we're handling the pickup. The plan is to arrange a van or shuttle that gets everyone from the airport to the estate in one glorious, chaotic trip. Between Josh and Alyssa's cars and whatever oversized vehicle we can get our hands on, you'll have a ride. Just land, text us, and look for the people who are way too excited to see you.
Try to arrive by midday — the time change works in your favor, and it's about a 1–2 hour drive up to Healdsburg
September in wine country means warm days, cool evenings, and at least one outfit you packed "just in case" that you absolutely will not wear. Here's what you actually need.
Healdsburg, California — September 9–13, 2026