





Day 01
Saturday
August 15
Touch down, settle in
Midday
Fly into SFO, drive north
Grocery stop on the way up
Over the Golden Gate and up 101 — the city falls away and the vineyards begin in about ninety minutes.
Check-in
Airbnb on Dry Creek Rd Booked
Unpack, breathe, pour something
Dry Creek Valley is only sixteen miles long and two miles wide — and some of the oldest Zinfandel vines in America grow within minutes of the front door.
Evening
Walk downtown Healdsburg
Dinner in town — TBD, follow our noses
A town of eleven thousand with roughly thirty tasting rooms around one square — and a three-Michelin-star restaurant two blocks off the plaza.
Pool · hot tub · games · relax

Downtown Healdsburg4K walking tour
Day 02
Sunday
August 16
First pours of the week
Morning
Coffee & Healdsburg Plaza
Slow start, explore the square
Harmon Heald laid out this plaza in 1857 and sold the lots around it for $15 apiece. It’s one of the last surviving examples of early-California plaza-town planning.
11:15 AM
Dry Creek Vineyard Reserved
Estate Flight & Picnic
The first new winery built in this valley after Prohibition (1972), founded by an MIT engineer who put a J-Class racing yacht on the label and coined “Old Vine” Zinfandel.
2:30 PM
Aesthete Reserved
Creek-side tasting
Winemaker Jesse Katz’s once members-only label — for nearly a decade you couldn’t taste it without knowing someone. Adirondack chairs on the banks of Dry Creek, rescue goats on the farm.
Evening
BBQ at the Airbnb
Pool · hot tub · games · relax

Dry Creek VineyardThe winery's own film
Day 03
Monday
August 17
The big day — nobody drives
9:00 AM
Private Wine Drivers Booked
Mercedes Executive Sprinter for the day
Nobody counts pours, nobody watches the clock, nobody touches a steering wheel. That’s the whole point of today.
9:45 AM
Jordan Estate Tour Reserved
Breakfast & lunch included
Tom and Sally Jordan raised this French château in eighteen months, finishing one week before their first harvest in 1976 — then left most of the 1,200-acre estate deliberately wild.
1:45 PM
MacRostie Signature Experience Reserved
Steve MacRostie was planting Pinot Noir in 1992, years before anyone chased it. The Estate House looks over Thale’s Vineyard — named for his wife — pouring fruit from thirty-plus Chardonnay sites.
After
Auteur Optional
If everyone's still standing
A husband-and-wife Burgundy obsession: four Chardonnays and four Pinots poured side by side. None of the Chardonnay ever touches malolactic — all nerve, no butter.
Evening
Dinner in Healdsburg or BBQ at the Airbnb
Pool · hot tub · games · relax

Jordan Estate Tour & TastingJordan's own film
Day 04
Tuesday
August 18
Under the giants
Morning
Armstrong Redwoods
Easy & moderate hike options
The Colonel Armstrong Tree has stood here over 1,400 years; Parson Jones is taller than a football field is long. A lumberman saved this grove in the 1870s — the last old growth in Sonoma County.
Lunch
Guerneville
Then back to the Airbnb to freshen up
Born a logging town literally nicknamed “Stumptown,” adopted by the hippies in the ’70s — now the Russian River’s quirkiest lunch stop.
~3:00 PM
Ferrari-Carano
Walk-in — the gardens alone are worth it
Rhonda Carano spent sixteen months planting the five acres of gardens at Villa Fiore — over 2,000 labeled species, with a French underground barrel cellar beneath it all.
After
Downtown Healdsburg tasting room Optional
Evening
Dinner in Healdsburg

Armstrong RedwoodsPioneer Trail hike

Ferrari-CaranoVilla Fiore gardens
Day 05
Wednesday
August 19
No alarms allowed
Whenever
Sleep in — or kayak
The river's right there
The Russian River runs warm and slow in August — a lazy paddle with a swimming beach around every bend.
Afternoon
Shopping & tasting rooms in Healdsburg
A dozen tasting rooms within two blocks of the plaza — no car, no reservations, no plan required.
Evening
Dinner in town
Pool · hot tub · games · relax
Day 06
Thursday
August 20
Where the vines meet the Pacific
Morning
Bodega Bay & coastal views
Hitchcock shot “The Birds” here in 1963 after watching crows gather outside a waterfront restaurant. The bay itself sits right on the San Andreas Fault.
Lunch
Seafood on the coast
The Tides Wharf got into “The Birds” because its owner demanded three things: the town be called Bodega Bay onscreen, the lead be named Mitch — his name — and a speaking part. Hitchcock agreed to all three.
2:30 PM
Flowers Winery Reserved
Sonoma Coast Journey Tasting
Walt and Joan Flowers answered a classified ad in Wine Spectator in 1989 and bought a ridge two miles from the Pacific that everyone said was too cold for grapes. It made the Sonoma Coast famous.
Evening
Final evening at the Airbnb
Make it count
Pool · hot tub · games · relax

Bodega Bay4K coastal drone
Day 07
Friday
August 21
One last city night
Morning
Leisurely morning, pack up
Drive to South San Francisco
Check-in
DoubleTree by Hilton SFO South Booked
The warm chocolate-chip cookie at check-in is non-negotiable — they bake tens of millions a year. Take two.
Evening
Uber into San Francisco
Farewell dinner & evening walk
Forty-nine square miles, one last night. End it somewhere with a view of the bridge.

San Francisco4K aerial — Golden Gate & downtown
Day 08
Saturday
August 22
Until next time
Morning
Shuttle to SFO, fly home
Wine shipments to follow





