Located in the heart of Napa Valley, the picturesque town of St. Helena is a world-class destination all its own. With its wealth of locally owned boutiques, eclectic mix of restaurants and tasting rooms, and close proximity to the valley’s most historic wineries, St. Helena is ideal for a Napa Valley day trip. 

Below, we’ve curated an insider’s itinerary for the best day ever in St. Helena. And because you aren’t going to want to drive back after a day of wining, dining, and unwinding, it’s a good idea to book a place to stay for the night. For easy walkable access to Main Street boutiques, restaurants, and wineries along 29, check into Hotel St. Helena, Southbridge, or the ultra-cozy Inn St. Helena. If waking up to vineyard views is your thing, look no further than Wine Country Inn & Cottages, The Alila, or The Inn at Salvestrin Winery

You can also find a full listing of places to stay in St. Helena here

Did You Know?

Three blocks of St. Helena’s downtown is listed as a National Historic District on the National Register of Historic Places. 


Main Street at dusk in St. Helena, Napa Valley


Swing by The Station SH for a coffee and grab-and-go breakfast (don’t miss the best cold brew in town, and the bacon breakfast sandwich is also top-notch), and then start your day with a dose of nature. Moore Creek Park includes 1,600 acres of rugged terrain including oak woodlands, douglas fir & madrone forest, grasslands, and chaparral. Wildlife in the park is plentiful, including large mammals such as black bears, mountain lions, bobcat, gray fox, and coyote, and well-marked hiking trails offer stunning views of Lake Hennessey - one of St. Helena’s best-kept secrets. 

Next on the agenda is a bit of retail therapy, and downtown St. Helena is the perfect place to stroll and shop. With more than 30 boutiques and shops lining Main Street — offering up everything from home decor and gift items to world-class art, luxury clothing, jewelry, and accessories — you’re sure to find a taste of St. Helena to take home. Favorites include Trick Pony, Alison in Wine Country, Acres Home & Garden, and Napa Soap Company.  

Insider Tip: Pop into New West Knifeworks to test out your tomahawk-throwing skills! Foodies and inspiring chefs will also love the totally unique selection of hand-made chef knives. 


Shopping in Napa Valley


To maximize your time, enjoy an alfresco food and wine pairing in exchange for lunch. The Clif Family Farm Feast Lunch is a wine and culinary exploration featuring a tasting menu composed of special off-menu and seasonal dishes paired perfectly with Clif’s small production wines. Come hungry, as you’ll enjoy five courses in total, with Chef to personally describe each course. 

St. Helena is home to the roots of Napa Valley winemaking, along with some of the very best views in the surrounding mountains. It wouldn’t be the best day ever without exploring a few of the town’s most off-the-beaten-path wineries and soaking in those vineyard views. Over on the Spring Mountain side, Barnett Vineyards (pictured in the feature image above) sits 2,000 feet above the valley floor and offers sweeping 360 views of Napa Valley from the tasting room patio (and Ziggy the Golden Retriever is one of the friendliest tasting room hosts in Napa Valley). 

Next head to the other (eastern) side of the valley and up into the mountains surrounding Angwin for a visit to Cade Estate. Elevated high above the fog line on the dramatic slopes of Howell Mountain, Cade takes its name from Shakespeare, who used the term to describe wine casks, or cades, shipped from Bordeaux to England during Elizabethan times. The Cade Tour & Tasting experience includes a tour of the LEED-Certified property followed by a tasting of current release sauvignon blanc and cabernet sauvignon set against a backdrop of the most dramatic views of Napa Valley. 


Cade Estate Winery Napa Valley


Now that all that sipping and swirling has worked up an appetite, it’s time for dinner at a local favorite. Brasswood Napa Valley is a veritable celebration of all things food and wine, where you can experience the best in terroir-to-table focused cuisine that puts a spotlight on the natural bounty found here in Napa Valley. Be sure to ask for the fresh pulled mozzarella, and we also love the duck bolognese when it’s on the menu!

Not ready to call it a night? Raise a glass with locals at The Saint Wine Bar. This favorite haunt is open until 9 pm on weekends, and their speakeasy-style bar features cozy tables and one of the best wine lists in town. If you’re visiting during October, mark your calendar for The Saint's HalloQueen Dinner & Drag Show on the 27th! You can also check out Ana’s Cantina for dive-bar-style fun until 2 am.


The Saint Wine Bar Napa Valley


Think one day just isn’t enough time to explore all St. Helena has to offer? (It’s not.) Explore The Ultimate Guide to St. Helena and discover our top picks for three fun-filled days in “Napa Valley’s Main Street.” And if you’re visiting during St. Helena Dreaming month in October, be sure to enter our #StHelenaDreaming photo contest for the chance to win a dream getaway!