Known as “Napa Valley’s Main Street,” many consider St. Helena to be the heart of the region. It has a rich history of California winemaking dating back to the 1800s and boasts Napa Valley’s first commercial winery, Charles Krug, not to mention dozens of charming shops, restaurants, and hotels.

Most importantly, St. Helena is home to many iconic and boutique wineries that will make any trip to Napa Valley complete. To help you navigate all that this region has to offer, we have created a two-day wine tasting itinerary that will take you through six great wineries in St. Helena.

Day One

Louis M. Martini Winery

Originally built in 1933 and among the first to open after the repeal of Prohibition, this iconic property underwent a restoration of their historic winery a few years ago. Famous for their Cabernet Sauvignon, Louis M. Martini Winery no doubt played a significant role in putting Napa Cabernet on the map. The winery offers tastings in a variety of indoor and outdoor settings. Choose from a flight of seasonal wines that change regularly, in-depth library tastings, or selections of Louis M. Martini’s most popular wines, paired with local delicacies.

Insider Tip: For true indulgence, reserve a spot at the Underground Cellar Experience, which—as you might have guessed—takes place in the winery’s historic underground cellar and features small-lot wine releases served with curated pairings from Chef Aaron Meneghelli.  

Visit: 254 St. Helena Highway, St. Helena, CA 94574
Contact: (707) 968-3362
Reservations: Required

Merryvale Vineyards

Family-owned and operated, Merryvale Vineyards’ historic building was the first winery built in Napa Valley following the repeal of Prohibition. This rich history shows in the winery’s stunning gardens, barrel rooms, and vineyards. Its proprietors, the Schlatter family, and winemaker Jeff Crawford, focus on Bordeaux varieties, employing thoughtful farming and winery practices to ensure the wines are world-class and reflective of Napa Valley terroir. To that end, Merryvale Vineyards is Napa Green Land and Napa Green Winery certified.

Insider Tip: Want a little cheese with that wine? The Terroir and Grand Cru experiences include a selection of cheeses alongside the wines, but you can also add food to any experience, including small bites and multi-course meals. 

Visit: 1000 Main Street, St. Helena, CA 94574
Contact: (877) 887-7763
Reservations: Required for some experiences

JCB St. Helena

Owner Jean-Charles Boisset lives, eats, and breathes wine—and this dedication to viticulture comes through in the quirky wine tastings available at JCB St. Helena. Located in the heart of downtown St. Helena, JCB is dedicated to producing biodynamic wines, which you can sip in their whimsical wine lounge that feels like you’ve stepped inside a French art gallery. Choose between options like the Burgundian Flight, an ode to Jean-Charles’ roots, or the Napa Valley Reds Flight for something a little closer to home. As if these experiences didn’t already feel lavish, tastings are served in JCB’s very own Baccarat crystal glasses.

Insider Tip: JCB offers a constantly rotating list of fun events, including weekly Bubbles & Brunch. Pair sparkling wines with delicate bites, like smoked salmon bagels and caviar service. No reservation required.

Visit: 1320 Main Street, St. Helena, CA 94574
Contact: (707) 963-3454
Reservations: Recommended

Day Two

Fantesca Estate & Winery

This property was originally the dowry of Caroline Bale for her marriage to Charles Krug in the mid-1800s. Current owners Susan and Duane Hoff wanted to recognize this rich heritage when they purchased it, naming it after a clever and strong-willed lead female character from the Italian Commedia dell’Arte, which was the inspiration for Cirque du Soleil. Fantesca Estate is now known for small-production, award-winning wines produced in a stunning setting that includes a 300-foot Spring Mountain cave, sprawling vineyard views, and luxurious wine experiences. Trust us, it’s beautiful.

Insider Tip: Got a favorite quote (yours or someone else’s)? Submit it to be considered as a “Fortune Corkie” and printed on one of Fantesca’s wine corks.  

Visit: 2920 Spring Mountain Road, St. Helena, CA 94574
Contact: (707) 968-9229
Reservations: Required

Beringer

Jacob Beringer and his brother Frederick came to Napa from Mainz, Germany, ultimately purchasing 215 acres in 1875, which would become home to what is now California’s oldest continuously operated winery. Beringer would build on this tradition of industry “firsts,” becoming the first to give public tours in 1934, and the first and only winery to have both a red and a white wine named #1 Wine of the Year by Wine Spectator. Be sure to visit the iconic Rhine House mansion for its stunning stained-glass windows and architecture while sipping reserve and single-vineyard wines. 

Insider Tip: For $35, take the Legacy Cave Tour, where you will sip a selection of wines as your guide leads you through the Old Winery and historic tunnels while sharing details of Beringer’s rich history and commitment to quality. 

Visit: 2000 Main Street, St. Helena, CA 94574
Contact: (707) 257-5771
Reservations: Not required but recommended for most experiences

Markham Vineyards

This longstanding winery got its start with the dawn of winemaking in Napa Valley. The original builder of Markham Vineyards’ iconic Stone Cellar came to Napa from Bordeaux, initially arriving with other Gold Rush pioneers. Instead of gold, the winemaker discovered Napa’s rich soil, perfect for growing wine grapes, and utilized his skills in viticulture to become one of the largest producers prior to Prohibition. Markham’s tasting room is a beautiful space to sample the winery’s renowned Merlots. We particularly love the Exploration of Markham Tasting, which includes coveted new release and library selections, culminating in a behind-the-scenes barrel tasting.

Insider Tip: If you happen to be in town for one of Markham Vineyards’ events, be sure to snag tickets! All of these experiences take place in the historic Stone Cellar, featuring floor-to-ceiling wine barrels and a beautiful stone interior. Events include everything from dinners with renowned chefs to craft classes like wreath making.

Visit: 2812 St. Helena Highway N, St. Helena, CA 94574
Contact: (707) 963-5292
Reservations: Recommended