
Restored Pullman cars rolling the 36-mile round trip from downtown Napa to St. Helena and back, with a multi-course lunch or dinner, wine by the glass, and the whole valley sliding past the window. The one tasting day where nobody has to drive.
About 3 hours (lunch or dinner)$$$$Tickets → 
A full-scale, thirteenth-century-style Tuscan castle in the hills above Calistoga — 107 rooms, a drawbridge, frescoed Great Hall, torture chamber and vaulted barrel cellars — built over fifteen years by winemaker Dario Sattui. Tours and tastings by reservation.
2-3 hours (tour and tasting)$$$Tickets → 
The 1966 Oakville estate that put Napa on the world map, reopened in April 2026 after a three-year rebuild — Cliff May's famous arch and tower restored, new tasting rooms over the To Kalon Vineyard, and the new To Kalon Collective.

The Taittinger-founded sparkling-wine chateau on a hill in Carneros — a French-style terrace over the vines, seated table service, bubbles and small plates, and the gateway to Napa from the south. Adults only, by reservation.

A sunrise flight of about an hour over the vineyards, drifting with the morning breeze above Yountville or Upvalley estates, with an optional sparkling-wine brunch after landing. Year-round, weather permitting; book early in your trip.
3-4 hours (about 1 hour aloft)$$$$Tickets → 
Downtown Napa's food hall on the river — oysters, burgers, bakery buns, cheese, charcuterie, gelato and local beer under one roof, open daily from early morning into the evening. Free to wander, easy on the budget, and the best casual meal in the valley.
Sink into warm volcanic-ash mud, then soak in geothermal mineral pools — the century-old Calistoga ritual at the top of Napa Valley, offered by a cluster of walkable spas from the classic Works package to resort-style treatments.
California's grandest town square — shady lawns, a duck pond and City Hall ringed by tasting rooms, cafes and adobe history, with the last of the California missions and the Bear Flag story at its corner. One small fee covers five historic sites.
The Glen Ellen ranch of the author of The Call of the Wild — the haunting stone ruins of Wolf House, his writing cottage, the House of Happy Walls museum, vineyard and winery ruins, and 26-plus miles of oak and redwood trails up Sonoma Mountain.
FreeNorthern Sonoma's prettiest town square — a shady plaza with a bandstand, ringed by more than two dozen tasting rooms, bakeries, restaurants and boutiques, at the meeting point of the Dry Creek, Russian River and Alexander valleys.
Half a day to a full dayDetails → 
An ancient coast redwood grove above Guerneville — the 310-foot Parson Jones Tree, the 1,400-year-old Colonel Armstrong Tree, flat accessible trails through cathedral-quiet forest, and the Russian River and Sonoma Coast beyond.
The Santa Rosa museum of the creator of Peanuts — original comic strips, a re-creation of his studio, rotating exhibitions and hands-on art for kids, across the street from Snoopy's Home Ice. Tickets sold on arrival; closed Tuesdays.