2-Day Wine Tasting Itinerary in St. Helena

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Courtesy of Beringer

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 eight great wineries in St. Helena.

Day One

Raymond’s Red Room, Courtesy of Raymond Vineyards

Raymond Vineyards

849 Zinfandel Lane, St. Helena, CA 94574, (707) 963-3141
Reservations: Required for groups of 7 or more, and for certain experiences

A visit to Raymond is a true feast for the senses. From the whimsical décor to the “Corridor of Senses,” which invites guests to touch different textures, explore the range of wine color hues, and sniff through a wall of glass vials holding various aromas commonly found in wines, to the blending sessions that turn guests into winemakers for a day, everything at Raymond is designed to give a 360-degree wine experience. Raymond’s Rutherford and St. Helena estate vineyards are also Certified Organic and Biodynamic, and 100% of the winery’s power comes from renewable solar energy.

Insider Tip: For the ultimate VIP experience, book the appointment-only tasting in the Red Room, an intimate, velvet-lined space lit by Baccarat chandeliers.

Martini Park, Courtesy of Louis M. Martini Winery

Louis M. Martini Winery

254 St. Helena Highway, St. Helena, CA 94574, (707) 968-3362
Reservations: Not required, but recommended for certain experiences

This iconic property recently completed a restoration of their historic winery, originally built in 1933 and among the first to open after the repeal of Prohibition. 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 walk-in tastings in a variety of indoor and outdoor settings. Choose from a flight of seasonal wines that change every three months, 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 Jeffrey Russell.

Courtesy of Merryvale Vineyards

Merryvale Vineyards

1000 Main Street, St. Helena, CA 94574, (707) 963-7777
Reservations: Required for some experiences

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 Simon Faury, 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? Book the Artisanal Wine & Cheese Tasting for a semi-private, guided tasting experience that pairs Merryvale wines with locally sourced cheeses.

Courtesy of Beringer


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

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 $30, take the Legacy 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.

Day Two

Courtesy of Fantesca Estate & Winery

Fantesca Estate & Winery

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

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. The winery is now known for small-production, award-winning wines produced by winemaker Heidi Barrett in a stunning setting that includes a 300-foot Spring Mountain cave, sprawling vineyard views, and luxurious wine experiences.

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.

Courtesy of Freemark Abbey

Freemark Abbey

2033 St. Helena Highway North, St. Helena, CA 94573, (800) 963-9698
Reservations: Required for certain experiences and for groups of 6 or more

The inclusion of their 1969 Cabernet Sauvignon and 1972 Chardonnay in the famous “Judgement of Paris” not only cemented Napa Valley — and, in fact, America — as a worthy player on the global wine stage, it also helped put Freemark Abbey on the map as a producer of premium Napa Valley wines. Established in 1898 and one of Napa’s oldest wineries, Freemark Abbey also boasts one of the region’s largest library collections, with vintages dating back to the ’60s. Don’t forget to grab a bite at Roadhouse 29, the winery’s on-site restaurant featuring smoked and grilled artisan meats and no corkage fee so you can sip your Freemark Abbey purchase while you dine.

Insider Tip: Book the winery’s Cabernet Comparative experience and explore the how terroir affects what’s in the glass as you sample and discuss wines from different Napa Valley AVAs like Rutherford, Spring Mountain, and Mount Veeder.

Courtesy of Trinchero Napa Valley

Trinchero Napa Valley

3070 St. Helena Highway, St. Helena, CA 94574, (707) 963-1160
Reservations: Required for parties of 6 or more

Trinchero Winery has been family-owned and operated since 1948. They offer daily tastings in their modern and airy tasting room with bright white furniture and large windows. You can also reserve a spot on the Featured Flight tasting to try four wines that have been hand-selected by Trinchero’s winemaking and tasting room ambassadors. These wines change monthly, so there will always be something new to try each time you visit.

Insider Tip: If you’re interested in learning how soil, climate, elevation, and sun exposure can influence what’s in your glass, sign up for the Taste of Terroir experience, which features a horizontal tasting of four single-vineyard cabernet sauvignon wines from St. Helena, Atlas Peak, and Mt. Veeder appellations.

Courtesy of Rombauer Vineyards

Rombauer Vineyards

3522 Silverado Trail North, St. Helena, CA 94574, (707) 963-5170
Reservations: Required

Founders Koerner and Joan Rombauer developed a passion for wine through Koerner’s great aunt Irma Rombauer, author of the famous “Joy of Cooking” — one of the most published cookbooks in America. Founded in 1980, Rombauer quickly rose to prominence in St. Helena through their iconic chardonnay and have since maintained a reputation for award-winning cabernet sauvignon, merlot, zinfandel, and sauvignon blanc as well. The winery prides itself on balancing traditional with cutting-edge winemaking techniques and sustainably farmed vineyards.

Insider Tip: Grab some provisions and have a picnic in Rombauer’s scenic garden, featuring over 100 varieties of plants and flowers, as well as art collected by Koerner Rombauer.

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Devin Parr

Devin Parr is a San Diego-based freelance writer and consultant specializing in wine, travel and lifestyle. In addition to covering the global wine industry, she is the resident expert in Temecula Valley Southern California Wine Country, serving as the region’s ambassador on behalf of the Temecula Valley Winegrowers Association. She holds a certification in wine expertise from the Apicius International School of Hospitality in Florence, Italy, as well as the Wine and Spirit Education Trust (WSET) Diploma. In 2017, she was named one of Wine Enthusiast Magazine's Top 40 Under 40 Tastemakers. Follow her adventures at @thesocalwinegal and www.devinparr.com.