Day 01
Saturday
August 15
Arrive, settle in
12:14–12:30
Both groups arrive at SFO Confirmed
Within about 15 minutes of each other
Jeff & Michelle via IAD (UA1773, seats 9D/9E). Abby, Libby, Jack & Holly via IAH (UA2358).
After bags
Pick up National XL SUV Confirmed
Afternoon
Drive north, grocery stop Planned
Then check into the Dry Creek Road Airbnb
Over the Golden Gate and up 101 — the city falls away and the vineyards begin in about ninety minutes.
~5:00 PM
Pre-dinner drink Optional
ROOF 106 or Hotel Healdsburg Garden Bar
~5:30 PM
Casual dinner Optional
Healdsburg Bar & Grill, Bravas, Willi’s Seafood, or pizza backup
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
Saturday rule: Do not over-plan the arrival day. If everyone is tired, skip downtown entirely — there is no must-do reservation Saturday night. Grocery goal: breakfasts, coffee, water, pool snacks, easy BBQ food and a few low-effort dinner backups.
Downtown Healdsburg4K walking tour
Day 02
Sunday
August 16
First pours of the week
Morning
Breakfast at Airbnb & Healdsburg Plaza Planned
Wander the square, pick a coffee shop on the fly
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 Confirmed
Estate Flight & Picnic — lunch included
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 Winery & Farm Confirmed
Creek-side tasting, about two hours
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 Planned
Pool · hot tub · games · relax
Dry Creek VineyardThe winery’s own film
Day 03
Monday
August 17
The big day — nobody drives
Breakfast
Light breakfast at the Airbnb Planned
Keep it light — Jordan includes food
9:00 AM
Private Wine Drivers Confirmed
Mercedes Sprinter — Executive
Nobody counts pours, nobody watches the clock, nobody touches a steering wheel. That’s the whole point of today. Cooler with still and sparkling water provided.
Private Wine Drivers
Executive Sprinter ideal for 4–6 people. Vendor currently notes a 20% host gratuity is additional; verify whether already handled in booking.
9:45 AM
Jordan Vineyard & Winery Confirmed
Estate Tour — continental breakfast, property tour, olive oil, food pairings & Vista Point lunch
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 Estate House Confirmed
Signature Experience for six
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.
MacRostie Estate House
4605 Westside Road, Healdsburg, CA 95448
Russian River Valley setting focused on Chardonnay and Pinot Noir.
3:45 PM
Auteur Russian River Estate Confirmed
Relaxed by-the-glass / bottle service
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.
Auteur Russian River Estate
10520 Wohler Road, Healdsburg, CA 95448
Final stop is intentionally relaxed: by-the-glass / bottle service rather than another formal tasting.
Evening
No dinner reservation Planned
Charcuterie, pizza, leftovers — whatever sounds good
Pool · hot tub · games · relax
Monday evening rule: No restaurant reservation. This is the day most likely to leave everyone happily tired. If the group wants dinner, decide after returning to the Airbnb — not before.
Jordan Estate Tour & TastingJordan’s own film
Day 04
Tuesday
August 18
Under the giants
Morning
Armstrong Redwoods Planned
Choose a hike that suits the group
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. Hike options: Pioneer Nature Trail, Discovery Trail, Armstrong Nature Loop, Pool Ridge Trail, East Ridge Trail.
Armstrong Redwoods State Natural Reserve
17000 Armstrong Woods Road, Guerneville, CA 95446
Parking/vehicle day-use fees apply. About three miles north of Guerneville.
Late morning
Explore downtown Guerneville Planned
Browse shops, casual lunch
Born a logging town literally nicknamed “Stumptown,” adopted by the hippies in the ’70s — now the Russian River’s quirkiest lunch stop.
Early PM
Return to Airbnb & freshen up Planned
~3:00 PM
Ferrari-Carano Optional
Walk the gardens and taste if everyone wants another stop
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.
Ferrari-Carano Vineyards & Winery
8761 Dry Creek Road, Healdsburg, CA 95448
Reservations encouraged, not required. Open daily 10 AM–5 PM.
Early eve
ROOF 106 Planned
Rooftop drinks before dinner — fire pits, open-air seating, wood-fired food
ROOF 106
106 Matheson Street, Healdsburg, CA 95448
Same building as The Matheson. Limited reservations / walk-ins.
8:15 PM
The Matheson Confirmed
Dinner reservation — cancel up to 48 hrs before
Matheson note: About two weeks before the trip, check for an earlier dinner opening and for ROOF 106 reservation availability.
Armstrong RedwoodsPioneer Trail hike
Ferrari-CaranoVilla Fiore gardens
Day 05
Wednesday
August 19
No alarms allowed
Morning
Sleep in, coffee, pool — or kayak Optional
If kayaking: use a morning shuttle so the afternoon stays open
The Russian River runs warm and slow in August — a lazy paddle with a swimming beach around every bend.
River’s Edge Kayak & Canoe
Preferred option. The Rio Trip is an easy, self-guided Class I paddle; 2–3 hours with morning shuttle times.
Russian River Adventures
Alternate outfitter if River’s Edge timing or inventory does not work.
Lunch
Deli picnic, cafe, or back at the Airbnb Optional
Afternoon
Shopping, tasting rooms, brewery, walk, nap, pool, cards Optional
A dozen tasting rooms within two blocks of the plaza
6:30 PM
Bravas Bar de Tapas Confirmed
Dinner for six — regroup downtown for tapas
Wednesday philosophy: The day stays deliberately open until dinner. Explore, kayak, shop, nap, taste, or split into groups — then regroup for the 6:30 PM Bravas reservation. If plans change, backup inspiration: Lo & Behold, Guiso Latin Fusion, Willi’s Seafood & Raw Bar, PizZando. About two weeks before departure, ask who wants to kayak and reserve only the boats needed.
Day 06
Thursday
August 20
Where the vines meet the Pacific
~8:00 AM
Leave Healdsburg for Bodega Bay Planned
~9:00 AM
Bodega Head Nature Trail Planned
Roughly 1.9 miles, generally easy — allow time for photos
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.
Bodega Head / Sonoma Coast State Park
High bluff views over the Pacific. Treat the coast as a look/walk/photo destination; surf can be powerful and unpredictable.
~10:15 AM
Drive north on Highway 1 to Portuguese Beach Planned
~10:30
Portuguese Beach Planned
Walk the sand, photos, enjoy the Pacific — no swimming plan
Portuguese Beach
Beautiful sandy beach framed by rocky headlands — a different perspective after Bodega Head.
~11:30 AM
Fishetarian Fish Market Planned
Walk-up seafood lunch by the harbor
Chowder, fish & chips, tacos and harbor-side outdoor seating. Opens at 11 AM. Backup: Ginochio’s Kitchen.
~12:45
Leave Bodega Bay, drive inland Planned
2:30 PM
House of Flowers Confirmed
Sonoma Coast Journey for six — 60 minutes
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. Highlights Chardonnay and Pinot Noir from the Sonoma Coast.
Evening
Final wine-country night Planned
Completely open — BBQ, spontaneous dinner, or just the Airbnb
Pool · hot tub · games · relax
Bodega Bay4K coastal drone
Day 07
Friday
August 21
One last city night
10:00 AM
Check out of Airbnb Planned
No rushed departure
~11:00 AM
Arrive downtown Petaluma Planned
Park once, explore, shop — split into smaller groups if desired
Della Fattoria (artisan bakery, 143 Petaluma Blvd N), Sax’s Joint (1950s diner, 317 Petaluma Blvd S), Wild Goat Bistro (6 Petaluma Blvd N #A5), Petaluma Pie Company (125 Petaluma Blvd N, Suite B) — or just wander the riverfront blocks.
~11–1:30
Brunch / lunch wherever looks good Optional
~2:15 PM
Battery Spencer / Golden Gate overlook Optional
Skip if fog, parking, or luggage security makes it a poor idea
Classic elevated Golden Gate Bridge view from the Marin Headlands. Parking along Conzelman Road is limited and often full.
Battery Spencer Overlook
Luggage note: The rental SUV will still contain luggage before hotel check-in. Keep all bags fully concealed. Do not open the cargo area at the scenic stop. If luggage cannot be concealed, skip Battery Spencer.
After
Drive across the Golden Gate into San Francisco Planned
~3:00 PM
DoubleTree check-in Confirmed
275 South Airport Blvd — leave SUV at hotel, regroup
The warm chocolate-chip cookie at check-in is non-negotiable — they bake tens of millions a year. Take two.
DoubleTree by Hilton San Francisco South Airport Blvd
275 South Airport Blvd, South San Francisco, CA 94080
~4:15 PM
Rideshare to Ferry Building Planned
Begin waterfront sightseeing
Ferry Building Marketplace
1 Ferry Building, San Francisco, CA 94111
Start here around 4:30 PM. The historic F-line streetcars stop directly in front.
Late PM
Ferry Building → F-line streetcar → Pier 39 → North Beach Planned
Sea lions, Alcatraz views, walk into North Beach
The goal is a great evening, not a checklist. Do not add Coit Tower, Chinatown, Lombard Street, or a cable-car detour unless the group has unusually high energy.
7:30 PM
Firenze By Night Confirmed
Farewell dinner — North Beach Italian since 1987
After
Gelato on Columbus Avenue Optional
Walk by and decide — rideshare back to hotel
Lush Gelato
520 Columbus Avenue, San Francisco, CA 94133
Small-batch gelato; no commitment — just an option after dinner.
Alimento
507 Columbus Avenue, San Francisco, CA 94133
Across Columbus from Lush; another easy gelato choice.
San Francisco note: Leave the rental SUV at the hotel and use rideshare for the evening. The Ferry Building / Embarcadero / Pier 39 / North Beach route is the intended corridor. There is no reason for this itinerary to wander into the Tenderloin. Use normal city awareness and keep phones/wallets secure in crowded areas.
San Francisco4K aerial — Golden Gate & downtown
Day 08
Saturday
August 22
Until next time
Morning
Leave hotel Planned
Allow time for fuel, rental return, bags & security
8:30 AM
Return National XL SUV at SFO Confirmed
10:05 AM
Four-person itinerary departs SFO Confirmed
10:46 AM
Jeff & Michelle depart SFO Confirmed
The hotel is only a few miles from SFO. Plan the departure and rental-car return around the earlier 10:05 AM flight. Wine shipments to follow.