The Perfect Napa Valley Itinerary for First-Time Visitors

  • Guides
  • by JESS LANDER
  • on OCTOBER 23, 2023
  • 496863
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Guides

The Perfect Napa Valley Itinerary for First-Time Visitors

By Jess Lander October 23, 2023

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 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

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.

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.

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 for pre-dinner drinks. 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.

Stay

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.

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 in to her. For a more leisurely breakfast, try Lucy Restaurant at the LEED Certified Bardessono, where breakfast options highlight what’s local and seasonal.

Visit a Boutique Winery

outdoor lounge at Sequoia Grove Winery
Outdoor tasting lounge at Sequoia Grove Winery located in Rutherford, CA. Photographer 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, Jessup Cellars, and Cliff Lede Vineyards in Yountville, William Cole 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 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 here too, 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.

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 super 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 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 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. 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 is home to PRESS—one of our favorites for exceptional food and wine—as well as Christopher Kostow’s 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.

Stay

Wine Country Inn and Cottages in St. Helena, CA
Courtesy of Facebook: 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 & Cottage; 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

Napa Valley Balloons
Soar above the clouds. Photo Courtesy of 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 Napa Valley Aloft to schedule your flight, which often includes a post-flight sparkling wine toast.