The Perfect Napa Valley Itinerary for First-Time Visitors

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One hour north of San Francisco, all of life’s greatest indulgences — wine, food, relaxation, and adventure — can be experienced all at once in Napa Valley, one of the top Wine Country destinations in the world.

Thirty miles long and five miles wide, this small slice of heaven is home to more than 500 wineries throughout a collection of six quaint towns: Napa, Yountville, Oakville, Rutherford, St. Helena, and Calistoga. Each has its own personality and places to discover; from Napa’s urban wine trail to Yountville’s renowned fine dining to Calistoga’s detoxifying hot springs, there’s something for every kind of traveler, whether you’re a oenophile, foodie, adventurist, or self-care aficionado.

There is also not a bad time to visit to visit Napa Valley. While September and October are the busiest and warmest months, offering the chance to experience the annual grape harvest in action, the winter months have their own appeal. It’s quiet, uncrowded, and not too chilly with temperatures mostly hanging out in the 50s and 60s. Plus, many hotels offer hard-to-beat off-season rates. Your best chance of rain is in the spring, but the blooming fields of bright, yellow mustard also make it one of the most Instagram-worthy seasons to plan a trip.

For whenever you do decide to pack your bags and pay Napa Valley a visit, we’ve put together the perfect itinerary for the first time visitor, covering all of the “must do’s” over a long weekend trip.

Day 1

Wine and Dine On Board a Train

Courtesy of Louis M. Martini Winery / Kristen Cropper

You can’t visit Napa Valley without a trip to some of the area’s most historic and famous wineries where this great wine region began to make its mark on the world. The best way to do this is to board the Napa Valley Wine Train for their Quattro Vino Legacy Tour. This six-hour journey down Napa’s Highway 29 is one of the best tours around; it takes you all the way back to pre-prohibition and the 1800s for a crash course in Napa Valley history. The trip features scenic views from a refurbished, antique railcar, a four-course gourmet meal, and stops for wine tastings at Robert Mondavi, Charles Krug (Napa Valley’s oldest winery), and V. Sattui wineries.

If you decide to take the self-guided route by driving yourself or hiring a driver, some other historically-significant winery stops to consider are Merryvale Vineyards, Inglenook, and Stag’s Leap Wine Cellars. And make a point to stop by the historic Louis M. Martini Winery to admire the newly renovated space while you sip.

Explore Downtown Napa

The Perfect Napa Valley Itinerary for First-Time Visitors
Courtesy of Fieldwork Brewing

The train will drop you off in Napa, within walking distance to downtown. Stroll over to the Oxbow Public Market, where you can shop from a myriad of local vendors for souvenirs and gifts, like locally-made olive oils or spirits from Napa Valley Distillery. You can also grab a pre-dinner snack — think, oysters from Hog Island Oyster Co., a mini Sweet S’mores or Chocolate Velvet cupcake from Kara’s Cupcakes, or organic ice cream from Three Twins, in flavors like Mocha Difference and Land of Milk and Honey. Thirsty? Grab a pint at Fieldwork Brewing Company.

Next, cross over the First St. Bridge to the main part of Downtown Napa. Here you can stop in at one of the many wine tasting rooms, wine bars, or restaurants for Happy Hour. We love Cadet, Carpe Diem, and Compline wine bars for pre-dinner drinks. Make a reservation for dinner on the Napa Riverfront at the famous Morimoto or the romantic French bistro Angele. If you fancy a nightcap, Silo’s, also on the Napa Riverfront, has live music almost nightly.


The Perfect Napa Valley Itinerary for First-Time Visitors
Courtesy of Facebook: The Westin Verasa Napa

Reserve a hotel room in downtown Napa so that you can abandon your car for the day. The Westin Verasa Napa is conveniently across the street from the Wine Train station, while the Andaz Napa is at the heart of downtown Napa activity.

Day 2

Spend your second day exploring the towns that put the “Valley” in “Napa Valley.” The small towns of Yountville, Oakville, Rutherford, St. Helena, and Calistoga are referred to by locals as the “UpValley,” so use that term if you want to blend in.

Breakfast in Yountville

The Perfect Napa Valley Itinerary for First-Time Visitors
Courtesy of Bouchon Bakery

For breakfast, head to chef Thomas Keller’s famous Bouchon Bakery in Yountville for pastries and espresso. Most likely there will be a line out the door, but it moves quickly. If you want to double down, you can head to Mini Model across the street. This is a smaller location of the locally-acclaimed Model Bakery. Get the English muffin. It’s so good that Oprah Winfrey actually has them flown in to her.

Visit a Boutique Winery

The Perfect Napa Valley Itinerary for First-Time Visitors
Courtesy of Sequoia Grove Winery / Dakota Moffitt

Because you visited some of the oldest, largest, and most popular wineries on Day 1, make an appointment at a boutique or family-owned winery next and compare experiences. A boutique winery can mean several things: a more personalized experience (sometimes with the winemaker or owner), less of a crowd, and super primo wines (especially cabernet sauvignon, which Napa Valley is best known for). Some of our favorite family-owned and boutique wineries to visit UpValley are Goosecross Cellars, Stewart Cellars, and Cliff Lede Vineyards in Yountville, Turnbull Wine Cellars in St. Helena, and Staglin Family Vineyard in Rutherford. Also in Rutherford is the family-owned Sequoia Grove Winery, where a variety of tasting experiences await. Add a seasonal cheese and charcuterie plate to your tasting on the patio during the warmer months and you’re set.

Lunch at Gott’s Roadside

The Perfect Napa Valley Itinerary for First-Time Visitors
Courtesy of Gott’s Roadside

For lunch, continue to head north and pull over at the original Gott’s Roadside location in St. Helena. Formerly Taylor’s Automatic Refresher, when Gott’s took over, they kept the old, 50s-style roadside building, now a Napa Valley landmark. There may be a line here too, but the burgers and shakes are a can’t-miss. Gott’s is located at the gateway of St. Helena’s charming Main Street, so you can walk your meal off afterwards with some window shopping at the local boutiques.

Relax and Recharge in Calistoga

The Perfect Napa Valley Itinerary for First-Time Visitors
Courtesy of Calistoga Motor Lodge Moonacre Spa

For the better part of the afternoon, drive the eight miles from St. Helena to Calistoga for some spa time. This quirky, little town is best known for its healing mineral waters from natural hot springs, plus mud baths that’ll make your skin as smooth as a newborn. Make an appointment for a spa treatment ahead of time; there are so many local spas to choose from, from super luxe resorts like Indian Springs and Solage to more intimate and classically restorative escapes at The Moonacre Spa and Golden Haven Hot Springs.

If you have some time after, take a stroll down Calistoga’s main drag Lincoln Avenue and grab a Happy Hour cocktail at Sam’s Social Club or a pint at the Calistoga Inn Restaurant & Brewery.

Dine at a World-Renowned Restaurant

The Perfect Napa Valley Itinerary for First-Time Visitors
Courtesy of Acacia House

For your last supper of the trip, go big and make a reservation at one of Napa Valley’s finest dining establishments from an acclaimed chef. In Yountville, choose from Michael Chiarello’s Bottega, or Thomas Keller’s The French Laundry (if you can get in and money is no issue) or Ad Hoc. St. Helena has Christopher Kostow’s The Restaurant at Meadowood and The Charter Oak, Chris Cosentino’s Acacia House, and Charlie Palmer’s Harvest Table. Wherever you end up, you won’t leave hungry or disappointed.


The Perfect Napa Valley Itinerary for First-Time Visitors
Courtesy of Facebook: The Wine Country Inn & Cottages

Book a hotel UpValley for the second night of your trip. For a true Wine Country getaway among the vines, snag a room at the intimate Wine Country Inn; for something more contemporary and convenient, check out the Wydown Hotel on St. Helena’s Main Street.

Day 3

Take Flight in a Hot Air Balloon

The Perfect Napa Valley Itinerary for First-Time Visitors
Courtesy of Facebook: Napa Valley Balloons

Schedule your travel plans home later in the day so that you have time for one last hurrah. One of Napa Valley’s most sought-after adventures is a sunrise hot air balloon ride over the vines. We promise that the 6 AM wake up call is worth it. Don’t forget your camera!

Check out Balloons Above the Valley, Napa Valley Aloft, and Napa Valley Balloons, Inc. to schedule your flight, which often includes a post-flight breakfast with sparkling wine.

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Jess Lander

Jess Lander is a freelance wine, food and travel writer based in Napa Valley and exploring all things California wine country. Follow her on Instagram at @willwrite4wine to get Napa and Sonoma #travelinspo.


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