Our Napa Valley Wine Tasting Itinerary: Wineries, the Silverado Trail, and What Napa Did to Us
After years of traveling internationally, it felt like the right time to head west. For my 43rd birthday, we put together a 9-day trip to Napa Valley and San Francisco, and the Napa portion ended up being one of the most memorable wine experiences of our lives. This Napa Valley wine tasting itinerary covers the wineries, the food, the drives, and a few lessons we definitely did not see coming.
Naturally, the whole thing started with In-N-Out Burger. We had never been. The hype was real. Real enough that after three tastings on our last night, we ended up back there for dinner. Two tastings in a day is the sweet spot. Three is ambitious. But ending Napa the same way we started somehow made perfect sense.
Staying in Downtown Napa
We based ourselves in downtown Napa, which kept everything easy, walkable, and well-positioned between tasting days. My birthday dinner at Scala Osteria was the kind of meal you keep talking about for months. Every single dish landed. It set the tone for the rest of the trip: thoughtful, relaxed, and better than we expected.
The Wineries
Each tasting stop gave us something completely different, which is exactly what makes building a Napa Valley wine tasting itinerary worth doing carefully.
Hendry Wines was one of the most educational stops on the trip. Set on a family property in Napa, it felt grounded and personal in a way that made us pay close attention to how much the vineyard itself shapes what ends up in the glass. It was less about showmanship and more about craft.
Handwritten Wines in Yountville brought a polished, intimate experience. Their wines felt intentional and beautifully presented. The 2011 they poured was genuinely incredible. One of those pours that makes you stop mid-conversation because you realize you are drinking something special.
Baldacci Family Vineyards stood out for the cave tour. Walking through the cave where the wine is aged added a layer to the experience that a standard seated tasting just cannot replicate. Seeing the process up close made everything that followed taste even better.
Nickel and Nickel was the tasting that really deepened our understanding of Napa Cabernet. Their focus on single-vineyard wines makes clear just how dramatically the same grape can change based on where it grows. Refined, educational, and exactly the kind of stop that makes Napa feel like a wine education rather than just a wine trip.
Krupp Brothers rounded out the itinerary with a strong finish. We visited their tasting room in downtown Napa rather than the winery itself, which actually made it a great way to end the day without another full drive out to the valley. The wines held their own against everything we had tasted all week and added even more range to the trip.
Driving the Silverado Trail
Driving the Silverado Trail between stops was one of the simplest highlights of the trip. Vineyard views, winding roads, and a pace that felt nothing like our usual travel days. Napa has a way of slowing everything down, even when your schedule is full.
We bought and shipped a lot of wine home. The credit card had feelings about it.
What Napa Did to Our Wine Glasses
The biggest surprise of the trip had nothing to do with the wineries themselves. After tasting big Napa reds the right way, we came home and realized our glasses were not doing our bottles any justice.
We ended up ordering a set of RIEDEL Extreme Cabernet glasses, and we have zero regrets. That diamond-shaped bowl is not just for looks. It gives bold reds more room to breathe, opens up the aromas, and smooths out the tannins on big Cabernet wines. At 28 ounces, there is plenty of room to swirl without overfilling.
Napa ruined us. Completely.
Next stop: San Francisco.
If you have the travel bug and are ready to go further, check out our Türkiye recap covering Istanbul, Izmir, and Ephesus. Fair warning: it is a lot more walking and a lot less wine.
