Enterprise at SFO (780 North McDonnell Rd). Confirmation #2119321327. Compact SUV. Bring Costco membership card.
~1:00 PM
Armstrong Redwoods State Natural Reserve
Stunning old-growth redwood grove just north of Guerneville (~1h 15m from SFO). Easy 1–2 hr walk. Free on foot / $8 to drive in. Great legs-stretcher after the flight.
~3:30 PM
Costco Santa Rosa
~30 min from Armstrong. Stock the cottage with wine, snacks, and supplies for the week. Cold stuff goes straight in the car from here.
~4:30 PM
Drive to St. Helena via Porter Creek Rd → Petrified Forest Rd
Scenic back-road route through the hills (~1 hr). Beautiful at golden hour.
~6:30 PM
Dinner — Gott’s Roadside
Classic Napa burger institution on St. Helena’s main drag. Casual, festive, beloved by locals. Great way to kick off the week without spending big on night one.
~8:00 PM
Check in to Cottages
Get settled, open a bottle, decompress.
Saturday, October 3 — St. Helena / Rutherford / Oakville
Time
Stop
Notes
9:30 AM
V. Sattui — Deli & Picnic Grounds
Pick up artisan cheeses, charcuterie, bread, and pastries for a picnic breakfast on the grounds. Opens 9:30 AM. A perfect, relaxed way to start the day.
11:00 AM
B Cellars
One of the best food-and-wine pairing experiences in all of Napa. Chef prepares small bites on-site in the open-hearth kitchen (Hospitality House experience). ~65–120/person. Book in advance.
1:30 PM
Far Niente
The gorgeous 1885 estate, underground cave, and classic car collection (~$65). Reservations required.
3:30 PM
Silver Oak, Opus One, or Driver’s Pick(optional)
Third stop — pick one based on energy and group preference. Silver Oak for the LEED Platinum building and cult Cab status, Opus One for the iconic modernist landmark, or go with whatever your driver recommends. Walk-in friendly relative to Opus.
6:00 PM
Dinner — PRESS
Michelin-starred, Napa-focused wine list with 2,700+ selections — the largest all-Napa collection in the world. Tasting menu 150–195/person; wine pairing 275–\390 additional. Fri–Sat hours: 5–9 PM. Book well in advance.
💡 Saturday tip: B Cellars is the anchor — don’t skip it. Far Niente at 1:30 is locked. The 3:30 stop is flexible — Silver Oak, Opus One, or driver’s recommendation depending on how the group is feeling.
Sunday, October 4 — Sonoma Road Trip
Time
Stop
Notes
9:00 AM
Drive to Healdsburg/Geyserville
~1 hr from St. Helena via Hwy 29 N to Hwy 101. Healdsburg is your base — LIOCO, Flowers, and Coppola are all within 20 min of the plaza.
11:00 AM
Francis Ford Coppola Winery
Geyserville, 15 min north of Healdsburg. Movie memorabilia, pools, Rustic restaurant. Fun, festive, theatrical. Bar tasting ~25,terrace40. Opens 11 AM (closed Tue–Wed).
1:00 PM
LIOCO Tasting Room
Walk-in friendly tasting room right on Healdsburg’s town square. Casual, music-forward. Restrained Chardonnay and Pinot Noir. ~$75 with food included. Opens noon.
~2:00 PM
Lunch on Healdsburg Plaza
Eat around the square: Journeyman Meat Co (charcuterie & sandwiches), The Parish Cafe (New Orleans comfort food), or graze around the LIOCO tasting. Walk it off.
3:30 PM
Flowers Vineyards & Winery
On Westside Rd, 10 min from the plaza. Stunning redwood-grove tasting room. Sonoma Coast Pinot Noir & Chardonnay only. 55 flight to \150 deep-dive tasting. Gorgeous for late afternoon light.
7:00 PM
Dinner — Valette
Chef-driven, ‘Trust Me’ off-menu tasting, luxurious but not stuffy. Book in advance.
⚠️ Sunday action item: Kent & Andrea to confirm driver can stay late for dinner, or move dinner earlier so the driver doesn’t need to extend.
Monday, October 5 — Napa
Time
Stop
Notes
8:30 AM
Breakfast
Model Bakery in St. Helena (famous English muffins, pastries — a Napa institution); Gillwoods Cafe (beloved locals’ diner in St. Helena); or grab coffee near the Wine Train station in downtown Napa.
10:30 AM
Wine Train — Grape Stomp at Grgich Hills
Check-in 10:30 AM · Board 10:50 AM · Departs Downtown Napa 11:30 AM. 3-course gourmet lunch on the train → arrive Grgich Hills (Rutherford) at 12:30 PM → 1 hour grape stomp + Reserve wine tasting → board back 1:30 PM → dessert & coffee → back by 2:30 PM. 2025 experience includes a special Judgment of Paris 50th anniversary commemorative flight. ~400–495/person.
3:30 PM
Palmaz Vineyards
2-hour private guided tour (~150–195/person). An 18-story underground cave carved into Mount George — genuinely unlike anything else in Napa. Book well in advance (appointment only). ~15 min drive from the train station.
If Palmaz unavailable
Shopping in St. Helena
Main Street boutiques, Napa Style, local galleries. Good fallback for the 3–6 PM window.
7:00 PM
Dinner — French Laundry OR Cottage Night
French Laundry (Yountville): Reservations open 60 days out on Tock. September dates open August 1 — Justin & Kenzie to check early August and most likely call as a group on Aug 1 to reserve. Allow 3–4 hours; it’s an event, not just dinner. Cottage Night: Pop bottles collected across the trip, do a blind tasting, vote on favorites. Equally memorable in a different way.
⚠️ French Laundry reminder: Reservations open on Tock — September dates open August 1. Justin & Kenzie to check early August and most likely call as a group on Aug 1 to reserve for Oct 5.
Tuesday, October 6 — Calistoga
Time
Stop
Notes
10:00 AM
Castello di Amorosa
Opens 9:30 AM. Authentically built 14th-century Tuscan castle — 107 rooms, drawbridge, dungeon, Great Hall, chapel. No reservation needed for groups under 15. Cheese + wine pairing ~$40/person. Allow 1.5–2 hours. The most theatrical winery visit of the whole trip.
12:30 PM
Schramsberg Vineyards
~5 min south of Calistoga. 1800s cave tour + sparkling wine tasting. White House wine supplier since Nixon. One of the most atmospheric winery visits in Napa. 70–\100/person. Book in advance. Allow 90 min.
2:30 PM
Calistoga Spa(recommended)
Indian Springs or Calistoga Spa Hot Springs for volcanic ash mud bath + geothermal mineral pools. The quintessential Calistoga experience — very restorative after 4 days of wine. Book treatments in advance.
Alternative
Aadland-Moody Vineyards
Note: they’re only open Fri–Sun, so Tuesday is likely a no-go — call ahead to confirm. If available, this is the rebuilt Spring Mountain winery with a new cave (2020 Glass Fire survivor story).
7:00 PM
Dinner — French Laundry OR Cottage Night
Whichever evening you didn’t use on Monday. If neither, consider Brasswood Bar + Bakery in St. Helena (upscale, wood-fired, great for a last night) or a relaxed dinner in Calistoga at Evangeline (New Orleans-inspired, fun, lively).
Wednesday, October 7 — Travel Home
Time
Stop
Notes
8:00 AM
Last coffee + Vine Trail walk(optional)
The St. Helena–Calistoga section of the Napa Valley Vine Trail (opened 2024) runs right through vineyard land. A quick 20–30 min walk before loading the car is a lovely send-off.
9:30 AM
Drop off rental car at SFO**
Enterprise at 780 North McDonnell Rd. Confirmation #2119321327.
9:30 AM
Drive to SFO terminals
~1h 30m from St. Helena. Budget extra if flying before noon.