The Perfect Napa Valley Itinerary for First-Time Visitors

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  • on APRIL 25, 2024
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The Perfect Napa Valley Itinerary for First-Time Visitors

By Jess Lander April 25, 2024

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 dining scene 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’s also no bad time 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 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.

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

Visit a Historic Winery

Louis M. Martini Winery
Photo 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. From Napa, head north on scenic Highway 128 toward St. Helena, first stopping at Rutherford’s Beaulieu Vineyard, one of the longest continually operating wineries in Napa Valley, before making your way to Louis M. Martini Winery to admire the renovated space while you sip.

Stag’s Leap Wine Cellars
Photo courtesy of Stag’s Leap Wine Cellars
Charles Krug
Photo Courtesy of Charles Krug

Other historically-significant winery stops worth considering include Burgess Cellars, Beringer, Charles Krug (Napa Valley’s oldest winery), Markham and Stag’s Leap Wine Cellars, where you’ll be able to taste iconic wines while discovering more about Napa’s winemaking heritage at each stop.

Explore Downtown Napa

Fieldwork Brewing
Thirsty? Grab a pint! Photo Courtesy of Fieldwork Brewing Company

After a day of wine tasting, make your way back to Napa, where you’ll be able to explore on foot. 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. 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 housemade sourdough bagels from Loveski Deli. Thirsty? Grab a pint at Fieldwork Brewing Company.

Arch & Tower | Robert Mondavi
River Views at Arch & Tower, Photo courtesy of Robert Mondavi

Next, it’s time for more wine. Stop into one of the many wine tasting rooms, wine bars, or restaurants for happy hour, such as Arch & Tower for incredible river views and wine tasting, or Cadet, Carpe Diem, or Compline wine bars. Make a reservation for dinner on the Napa Riverfront at the famous Morimoto or the romantic French bistro Angele, or head to The Grove at CIA to dine on Mediterranean-inspired cuisine under olive trees in the garden.


Andaz Hotel
Book a suite at this urban chic hotel in Downtown Napa. Photo Courtesy of Andaz Napa

Reserve a hotel room in Napa so that you can be within walking distance (or just a short drive) to downtown’s many restaurants, bars, and tasting rooms. The urban chic Andaz Napa is at the heart of downtown Napa activity, where loft-style rooms are both stylish and inviting, while Milliken Creek’s peaceful riverfront location offers guests a quieter escape just a few minutes from the downtown scene.

Milliken Creek Inn in Napa, CA
Photo Courtesy of Milliken Creek Inn

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

pain au chocolat pastry at Bouchon Bakery
Sink your teeth into a pain au chocolat aka "chocolate croissant". Photo Courtesy of Facebook, 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 straight to her front door. For a more elegant brunch option, head to RH Yountville, where dishes like avocado toast on charred sourdough and black forest bacon are perfectly paired with their signature RH mimosa.

Visit a Boutique Winery

Cliff Lede
Photo Courtesy of Cliff Lede Vineyards

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/or boutique wineries to visit UpValley are Goosecross Cellars, Jessup Cellars, and Cliff Lede Vineyards in Yountville, Clif Family Winery and Trinchero in St. Helena, and Staglin Family Vineyard in Rutherford.

outdoor lounge at Sequoia Grove Winery
Outdoor tasting lounge at Sequoia Grove Winery located in Rutherford, CA. Photographer Dakota Moffitt

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 if you need a snack to tide you over until lunch.

Lunch in St. Helena

Clif Family Winery
Photo Courtesy of Clif Family Winery

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, but the burgers and shakes are a can’t-miss. But, if you simply can’t wait, Clif Family Winery’s Bruschetteria food truck is equally enjoyable, offering a variety of seasonally-driven lunch items that will tide you over until dinner. They’re both 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.

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Relax and Recharge in Calistoga

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 luxe resorts like Indian Springs and Solage to hip boutique gems like Dr. Wilkinson’s Backyard Resort & Mineral Springs to more intimate and classically restorative escapes at Golden Haven Hot Springs.

If you have some time after, take a stroll down Calistoga’s main drag Lincoln Avenue and pop into CAMi Art + Wine for a tasting while admiring the contemporary art, or grab a pint at the Calistoga Inn Restaurant & Brewery.

Dine at a World-Renowned Restaurant

Acacia House
Photo 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. St. Helena is home to Chris Cosentino’s Acacia House, Christopher Kostow’s The Charter Oak, and Colin Rupp’s Harvest Table. In Yountville, choose from the late Michael Chiarello’s Bottega, or Thomas Keller’s The French Laundry (if you can get in and money is no issue) or Ad Hoc. Wherever you end up, you won’t leave hungry or disappointed.


Wine Country Inn & Cottages
Photo courtesy of Wine Country Inn & Cottages

Book a hotel in St. Helena 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 & Cottage or the luxurious (adults-only) Alila Napa Valley. 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

hot air balloons
Photo Courtesy of Bob McClenahan Photography

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 Napa Valley Aloft to schedule your flight, which often includes a post-flight sparkling wine toast. However, if soaring above the valley isn’t your thing and you’d prefer to fit in another winery visit, don’t miss exploring the caves and distinct wines of Pine Ridge Vineyards, situated in the heart of the Stags Leap District.


Although three days in Napa Valley only scratches the surface of what this incredible corner of Wine Country has to offer, you’ll make a great head start with this first-timer’s itinerary. From floating above the vineyards in a hot air balloon to sipping Cabernet at wineries both boutique and world-renowned, you’ll truly run the gamut of everything there is to experience in Napa. We won’t blame you if you start planning your next trip before your first is even over.