Napa and Sonoma Wine Country Tour: Free 2-Day Trip Itinerary (Expert)

Going to Napa and Sonoma is a pilgrimage even the most casual oenophiles adore. These world famous wine regions are stunning, and visitors have seemingly endless options in terms of viticultural areas, wineries, and tasting rooms to add to their itineraries. However, most wine enthusiasts don’t know about the best treasures California’s wine country has to offer, seeing only the most popular, well-known, and oft-recommended destinations.


Even if you are a veteran visitor to the Sonoma and Napa Valleys, you may not know about some of the best gems, hiding in plain site. Even if you know where to find these darlings of wine country, gaining access to these exclusive opportunities without a bit of insider assistance from your own wine country expert could be nearly impossible. To help you unearth these (unintentionally) best-kept secrets, we’ve created an itinerary with valuable tips for two glorious days off the beaten path in Napa and Sonoma. Cheers!


Day 1: Napa Valley

Trying to see it all in Napa is tiring…and impossible, even if you are sticking to the treasures of wine country. Your first-day itinerary is designed to show you some of the gems of the valley, but be sure to make an appointment well in advance if you don’t have a tour guide to get you VIP access. The jewels of Napa aren’t too keen on walk-ins.

10:00 AM – VIADER Vineyards & Winery

Founded by Argentine native Delia Viader in 1986, the picturesque VIADER Vineyards & Winery is a fantastic first stop. Sample wine and take in the breathtaking views of Napa Valley from their terrace on Howell Mountain.

The Portfolio Wine Tasting features a flight of three to four selections, but if you have four or more in your party, consider the Reserve Library Wine Tasting to experience their more highly coveted selections. With whatever tasting you choose, just be sure to get in for that 10:00 AM tasting—complementary winery and cave tours are included.

12:00 PM – Reverie Winery

Getting to Reverie is like going on an uncharted adventure—maps may not work, and your GPS may fail you. Reverie offers directions on their website, but a local expert should be able to get you there in a snap without needing to wait weeks to get in.

Reverie accepts reservations for up to four people for an outdoor wine tour they describe as amazing. The tour doesn’t take you over their entire 40-acre winery, but it does last an hour, which leaves you time for a quick outdoor lunch at their winery.

Food isn’t available at Reverie, but a local guide can set up a true VIP experience complete with a catered lunch from Upper Crust, a new local favorite.

2:00 PM – Saint Helena Winery

Saint Helena Winery is truly one of Napa’s prized places. The winery specializes in small lots, and is run by a small team of Napa locals under the purview of respected winemakers Aaron Pott and Elizabeth Tangey.

You may not know Saint Helena now, but you definitely won’t forget this winery after paying a visit! But be sure to book in advance if you don’t have an “in” if you want to experience their relaxing, quiet estate house surrounded by vineyards and flanked by mountains on the east and west. This is a special opportunity, not generally available to the public, with only a limited number of visits are available.

4:00 PM – Caldwell Vineyard

John Caldwell and his vineyard have quite the history, and you can experience it first hand with a unique private tasting experience. Tastings are hosted in Caldwell’s 20,000 square foot cave, and usually feature six wine selections paired with locally sourced cheese, charcuterie, and tall tales.

One of the most exclusive experiences Napa has to offer, it’s an exciting way to end the day before heading off to dinner. If you don’t have a guide, be sure to book very well in advance—at the time of writing, almost all available tastings were booked up within the next five to six months.


Photo Credit: Taste of Adventure

Day 2: Sonoma Valley

Treasure hunting in Sonoma makes for a relaxing second day exploring wine country. This schedule is designed to let you discover Sonoma at a casual, comfortable pace.

10:00 AM – Robert Hunter

Robert Hunter Winery is the state’s smallest champagne house, found a hop, skip, and a jump off the beaten path. Make a reservation to tour the grounds overlooking the vineyard, including the garden featuring a hardscape designed by renowned landscape architect, the late Thomas Church.

The superlative views and fine and rare plants are lovely, but you should be sure to have some wine while you are there. In addition to the bubbly Brut de Noirs, Robert Hunter offers Chardonnay, Pinot Noir, and Cabernet Sauvignon.

After your tour, don’t leave! Robert Hunter is one of the Sonoma wineries with space available for picnicking. After the hectic pace of Napa, have a relaxing lunch before sampling some more fantastic finds Sonoma has to offer.

1:00 – Kamen Tasting Room at Sonoma Plaza

The Kamen Estate Wines Vineyard is definitely a treasure, but you can’t do it all in a day. However, you can spend some time at their tasting room at the Sonoma Plaza to get a taste of what this winery has to offer. Choose from two flights at affordable prices (waived with a minimum purchase).

2:30 – B Wise Vineyards Estate Winery Cave

Brion Wise has some good friends in the wine industry, including John Caldwell, whom you should remember from day one, but that isn’t what makes B Wise such a shining star. It’s the passion Brion and his team has for wine, and their continuous mission to produce inspiring, memorable wine that is both authentic and graceful.

The Estate Winery Cave, located on the private estate, is also a gem in itself. A unique environment, the cave’s décor is distinguished, and tasting there is an exclusive experience. Appointments are required, and we’d recommend you attempt to get on the books at least three weeks in advance if you are planning your visit yourself.

You can either use our itinerary to make appointments on your own, or you can book a driver through Simply Driven and let us arrange your visit. Then you can sit back and enjoy a safe, relaxing two-day exploration of some true Napa and Sonoma treasures.

Download Travel Itinerary Here