Perfect Napa Valley Itinerary for First-Time Visitors

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  • on SEPTEMBER 18, 2023
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Perfect Napa Valley Itinerary for First-Time Visitors

By Jillian Dara September 18, 2023

At 30 miles long, Napa Valley is relatively small but mighty. The Northern California region that’s about 50 miles from San Francisco is, of course, synonymous with wine. Most renowned for its bold Cabernet Sauvignon, it’s also home to beautiful examples of Merlot, Cabernet Franc, Sauvignon Blanc, and Chardonnay. In fact, there are 16 designated appellations (or AVAs), over 45,000 acres of vines, and some 400 wineries to choose from, making it a must-visit wine region in California.

Perfectly aligned with quality wine is gourmet cuisine, which Napa’s restaurant scene excels at. There’s Michelin-star venues, fine Italian dining, and casual eateries to ensure you’re never hungry here. There’s also an impeccable wellness scene that dates back 500 years ago, when natural volcanic hot springs were discovered at the base of Mount St. Helena and recognized for their healing powers. Today, many spas throughout Napa Valley, particularly in Calistoga, incorporate the natural minerals and healing waters into their spa treatments.

Want to visit Napa Valley for a few days of epicurean immersion—wine tastings, restaurant hopping, and a cooking class—culminating in a healing soak before heading home? Here’s the perfect Napa Valley itinerary for your first visit to this world-class wine region.

Napa Valley Itinerary for First-Time Visitors

Day 1

St. Helena & Rutherford

There’s no better way to begin your first trip to Napa Wine Country than by raising a glass or two at some of the hundreds of tasting rooms throughout the Valley. Since Napa is divided into five main towns—Calistoga, St. Helena, Yountville, Rutherford, and Napa—it’s best to cluster your tastings by location. St. Helena is an ideal spot to start as it has a mix of Napa’s key players and newcomers, as well as plenty of mouthwatering eats nearby.

Start at HALL Wines for a wine tasting among art in their gallery style tasting room. Next up, Faust presents an entirely different tasting experience at their Victorian farmhouse—opt for their picnic option if your visit falls around lunch time. Or save your appetite for a quintessential St. Helena experience; a stacked-high burger from Gott’s Roadside. A downtown institution since 1999, there will surely be a line, but the reward is worth the wait.

If you’d rather enjoy a wine tasting with your meal, try Clif Family Winery, known for their thoughtful culinary pairings. We especially like their Ultimate Street Food Pairing Experience. Or, head across the street to The Charter Oak. Their burger is quite famed too, wood-fired and scrumptiously paired with their fermented vegetable dip.

After refueling, it’s time to check out Merryvale Vineyards and, further down the Silverado Trail, Conn Creek Winery. At the latter, we love their AVA Experience Tasting, which presents guests with a series of Conn Creek’s limited AVA Cabernet Sauvignon to showcase how Napa Valley’s different sub-appellations express themselves through each vintage. This places you en route to your next Napa town, Rutherford, where you can venture to the longstanding PEJU Winery, which recently celebrated its 40th anniversary, or to Grgich Hills Estate, one of the early pioneers in the region.

If looking for a different kind of sampling experience, the Olive Oil Tasting at Round Pond’s Olive Mill educates guests on the olive cultivation, harvest, and production required to create premium olive oil, followed by a guided tasting of the estate’s fresh oils and red wine vinegar blends.

Finish up your inaugural day in Napa by reminiscing on the memories made thus far at one of Up Valley’s dining hotspots. In St. Helena, Acacia House offers a sustainable and seasonal menu of new-American fare, while in Rutherford, The Restaurant at Auberge du Soleil presents a French fine dining experience with a fabulous view. For something a little more casual, try Cook for elevated Italian classics.


Both the Alila Napa Valley and Meadowood Napa Valley offer stunning accommodations in St. Helena to ensure your drive times remain limited. With 68 rooms that feature fire pit-outfitted balconies overlooking Beringer Vineyards, the adults-only Alila Napa Valley is an oasis for couples. Meadowood’s 36 suites and rooms are also romantic, and its luxury cottages make it appealing to friends traveling together.

Meadowood Napa Valley

Day 2

Yountville and Napa

Rise and shine with a breakfast sandwich from Model Bakery, famous for their fluffy English muffins, or get room service delivered to your hotel room before venturing off for another great day.

After spending your first day in St. Helena, now it’s time to focus on the wineries closer to Napa, at the southern end of the Valley. A few must-visits include Hess Persson Estates, Etude, and Burgess Cellars, for their great wine and intimate experiences. Or, consider putting the pedal to the medal with Getaway Adventures to see the Valley and its wineries from a new perspective, while working up a sweat.

Hess Persson Estates
Take an ATV Tour through the vineyards! Photo Courtesy of Hess Persson Estates

You’re never too old to learn a new skill and since we know you’re already a wine enthusiast—you’re in Napa, after all—why not try sabering? The act of opening a bottle, usually of sparkling wine, with a saber dates back to the ages of Napoleon Bonaparte, and V Wine Cellar in Yountville is ready to teach you all about it. Book a session with them or just stop by for one of their daily tastings. Grab lunch nearby at Ad Hoc + Addendum or the soon-to-be-opened The Kitchen at Priest Ranch, or head towards Napa for more tasty food options.

On the banks of the Napa River, in downtown Napa, is the Oxbow Public Market. Nicknamed as “the local gathering place,” there are almost two dozen vendors here, all promising a delicious lunch. Gott’s and Model Bakery also have a presence here, in case you opt for the sit-down options on previous days, or should you already be craving another bite.

Spend the afternoon perusing downtown Napa’s or Yountville’s many boutiques, tasting rooms, and wine bars before settling down for your next meal: dinner. At the heart of downtown Napa, the One Michelin-starred Kenzo beckons with its premier prix fixe sushi and kaiseki menu. Nearby, TORC’s global farm-to-table dishes include copious amounts of truffle. Yountville boasts acclaimed chef Thomas Keller’s The French Laundry; the Three-Michelin-starred restaurant requires over three hours per reservation, which has to be booked many months in advance. If you couldn’t snag a reservation or the prix fixe menu is too costly, chef Keller’s Bouchon is only a couple blocks away. Slide into a bar seat and order an overflowing pot of moules frites.

If you decide on dinner in Yountville, pop over to Regiis Ova Caviar & Champagne Lounge for a sparkling night cap and live jazz. Otherwise, in Napa, try Be Bubbly for a number of talented independent acts.

Bouchon Restaurant
Bouchon Restaurant in Yountville, CA. Photo Courtesy of the Thomas Keller Restaurant Group


While you could easily stay your second night in St. Helena, you may want to be closer to the day two restaurants and wineries on this itinerary. In Carneros, a few minutes from downtown Napa, the Carneros Resort and Spa is a lovely spot to rest your head, where you’ll be surrounded by vineyards from your serene, standalone cottage. If you’d prefer to be closer to the action, Andaz in downtown Napa offers chic rooms and a convenient setting close to tasting rooms and wine bars (such as a few of our favs: Acumen, Compline, and Brendel Wines). In Yountville, you can’t go wrong with Bardessono and Hotel Yountville, each offering spacious dwellings that place you within walking distance to premier tasting rooms, restaurants, and activities.

Day 3

Before getting too down that today is your last day, let Napa Valley Aloft or Napa Valley Balloons fly you high above the vines for a new vantage of the Valley. The balloons take off early in the morning and usually finish with a picnic breakfast inclusive of bubbles.

Afterwards, make time to finally discover Napa Valley’s wellness side. If time isn’t an issue, you can head back Up Valley for a soak or mud bath at Dr. Wilkinson’s Backyard Resort & Mineral Springs, located in Calistoga, or for a massage at Spa Alila back in St. Helena. But if you’d rather not drive that far and want to stay in Napa, try a specialty treatment (like the rose quartz facial) at Spa Terra, the 22,000-square-foot spa cave at Meritage Resort and Spa.

We couldn’t let you leave Napa without one last world-class gastronomic experience. But in this case, you’ll be doing the work. Sign up for one of the hands-on cooking classes at CIA at Copia, The Culinary Institute of America’s downtown Napa location. Their private classes are customizable to whatever you want to learn or create before you depart the Valley. But don’t worry, with so many things to do in Napa, we know you’ll be back soon.

When To Go

Napa Valley has year-round appeal. In the summer, days are warm, the vineyards are lush, and everything’s green, but it’s also high season. Beat the crowds and visit during the shoulder seasons—October through December or February through April—when the daytime temperature is moderate in the 50s or 60s, but there’s still plenty of activity. The winter also has its allure; many hotels are equipped with ensuite fireplaces or outdoor fire pits for cozying around with a glass of Napa Cab.

A Few Tips

  1. Designate a Driver:

    When it comes to going wine tasting, it’s important to think about who’s driving. While Rideshares like Uber and Lyft are available in Napa Valley, it’s often unpredictable and there are limited drivers. You’d be better off booking a private service to zip around safely, like Beau Wine Tours & Limousine Service, or use your own vehicle to start the day and rely on Designated Drivers Napa Sonoma to take the wheel on the way home.

  2. Spit, Often:

    See, swirl, sip, repeat may be the wine tasting standard, but if you’re visiting Wine Country for the first time, it’s best to master the art of tasting and spitting (yes, we want you to actually utilize that spittoon bucket). Oh, and only plan to visit 2-3 wineries a day, so you can enjoy each moment without feeling rushed (or overserved).

  3. Plan Ahead:

    While some Napa Valley wineries accept walk-ins, most now require reservations in advance. Even if it’s a Tuesday and you think you’ll be fine without a reservation, it’s best to plan ahead so you know for sure there’ll be room for your party. That said, some tasting rooms, such as in downtown Napa or Yountville, will gladly take walk-ins, so just do your research in advance.