Napa Valley 3 Day Itinerary: How I’d Plan Your Trip

I get this call all the time. Someone has a few days, they finally want to see Napa, and they have no idea where to start. So they ask me to build the itinerary.

I'm Leah, and my family has been planning trips in this valley for almost twenty-five years. Gloria has been building itineraries here even longer, more than thirty. This is the place I've been lucky enough to call home my whole life, and after thousands of trips I have a strong opinion about how to spend a few days in it. There is no single perfect Napa Valley itinerary. The best one is the trip built around you.

So if you called me today and said, "Leah, how would you plan our few days in Napa?" this is exactly what I would tell you. Give me four nights. That gets you three full days, room for two wine tour days without rushing, and a real vacation instead of a scramble. Here is how those days come together.

Your Three Days, Mapped

Here is the whole itinerary on one map. Gold pins are the wineries, dark pins are where you stay, terracotta pins are dinner, and the taupe pin is where we grab lunch to go. Tap any pin for a note from me and a link for directions.

First, the Part That Makes Everything Easy: Your Driver

You do not need to drive here, and honestly I would rather you didn't. We have you picked up at the airport, and here is the part people love most. The same driver who picks you up is the same driver for every wine tour and the ride back at the end. He is with you the whole trip. You get to know each other, and by the last day you are basically family. Some of our drivers have been with our transportation company for fifteen years and more, and clients who come back a few times a year request the same one by name.

The car is a black-car service, a Mercedes or a Cadillac, SUV or sedan, whatever you like. On a tour day he texts you when he is out front, you walk out of the resort, and you are gone. No parking, no white-knuckling the hill roads, and nobody at the table has to be the one who skips the pour to drive everyone home.

The Shape of Three Days

Before the detail, here is the rhythm I aim for. Not a schedule, a shape.

Day One: Landing, Settling In, and an Easy First Night

How your first day goes depends a little on when you land. If you get in early, I will often set a welcome lunch at a winery so the trip starts the minute you arrive. Progeny up on Mt. Veeder is one of my favorites for that, a quiet table looking out over the hills.

From there we check you into your hotel. Two of my favorite resorts in the valley are Hotel Yountville and Bardessono, both an easy walk from dinner, and you will find a welcome note from us waiting with a nice bottle of wine. Then the afternoon is yours. Lie by the pool. Do nothing on purpose. You earned it on the flight.

For the first night I keep it easy, because you will be tired from traveling. We build dinner around the food you told us you love on your onboarding form. If Italian is your thing and you are staying in Yountville, that might be Bottega, right off Washington Street. You walk up, you eat well, you stroll home. No getting back in a car after a travel day. That is the whole point of the first night.

Day Two: A Wine Tour Day Up in the Hills

This is the day most people picture when they imagine Napa. Two to three wineries with lunch in between. And because I tend to send our clients to the small boutique wineries up in the hills, we plan the day so it actually flows instead of zigzagging the valley floor.

One trick I use all the time. Order lunch ahead at Oakville Grocery and carry it up the hill with you. Good sandwiches, eaten at a winery with a view, beats driving back down the mountain in the middle of the day.

So what does a day up there look like? Often something like this.

Nothing about the day is rushed. When you are done you head back to the resort, sit by the pool, and let it all settle. On a wine day I always plan a dinner you can walk to, so in Yountville that is Ad Hoc or Bouchon. And that is day two.

Day Three: A Second Wine Day, or a Day Off the Wine Trail

With three full days, the third one is yours to shape. Here are the two versions I plan most.

If You Want More Wine

Up on Diamond Mountain

Point the car toward Calistoga. Start at The Vineyardist, where Kristi sets out a beautiful cheese and charcuterie spread. Then Theorem, to walk the vineyards with Sasha, plus John and their team. The two sit right next to each other, so it is an easy two minute hop, and the wine at both is incredible.

From there, head up to Diamond Mountain Vineyard to see Wendy and those views. Let the wineries put out cheese and charcuterie so lunch stays light. It leaves room for a real dinner that night.

If You Want a Break From Tasting

Things to Do in Napa Besides Wine

Some of my favorite days here are not tastings at all:

• —A hot air balloon ride, picked up right from your Yountville resort at sunrise.
• —A bike tour out of Yountville, at your own pace.
• —Horseback riding through the vineyards.
• —A private cooking class.

Or make it a town day. Wander Yountville, head up to St. Helena for the shops and lunch at Farmstead, then down to Napa for Scala in the evening, my favorite Italian restaurant in the valley.

Where I Send People to Dinner

A few of the tables I keep coming back to, so you can picture the evenings.

• —Bottega, Yountville. Italian and walkable.
• —Ad Hoc and Bouchon, Yountville. Both an easy stroll after a wine day.
• —The Restaurant at RH Yountville. Pretty and right in town.
• —Scala, downtown Napa. When you want to end the trip with great Italian.
• —Farmstead, St. Helena. For a relaxed lunch or dinner.

A Few Things I Always Tell My Clients

• —On a wine day, stay somewhere you can walk to dinner. After a day of tastings, the last thing you want is another drive.
• —Keep lunches light. Let the wineries do cheese and charcuterie so you have room for a proper dinner.
• —Do not do two wine tour days in a row unless you are up for it. Put an activity or a town day in between.
• —Four nights is the number. Three full days lets you do two wine days and still breathe.
• —If you love your driver, ask for him next time. Most of our repeat clients do.

Napa Valley Itinerary Questions I Hear Most