A postcard perfect itinerary through St. Helena. From vibrant public art to historic sips, and stylish stays. Here are ten must-do experiences designed to show off St. Helena one postcard moment at a time.
Art on Every Corner
Soak up the sunshine, color, and creativity all over town. There’s art stops around every corner:
- Snap a selfie at the new St. Helena Bench Project. Artist Simon Bull’s vibrant benches are now installed in #MyStHelena.
- Spot the “Heritage” mural on the Wydown Hotel. A stunning tribute to St. Helena’s deep roots.
- Drop by Nimbus Arts, offering open studios, classes, and public art everywhere you look.
- Make a detour to Raymond Vineyards to see the oversized Eye Sculpture. It’s bold, surreal, and totally photo-worthy tucked among the vines.
Sips as Vibrant as the Scenery
Explore the cutest spot for a colorful pick-me-up at Sam’s General Store!
Here’s what to try (and love):
- Iced Strawberry Matcha with strawberry cold foam which is as pretty as it is refreshing.
- Matcha White Chocolate Cloud Coconut Latte, coconut water + white chocolate + matcha = dreamy!
Wineries that Pour Stories
You have to come experience this next time, total musts for red wine lover:
- Beringer Vineyards is like stepping into a wine fairytale. Sip bold Cabernet inside the Rhine House, surrounded by stained glass and vineyard views.
- Charles Krug Winery is Napa’s oldest, and you can taste the history in every pour. Their Cabernet? Rich, velvety, unforgettable.
Speakeasy Secrets You’ll Love
You have to add this to your night-out plans! It feels like stepping into a hidden world of moody lights, velvet booths, and unforgettable sips.
- Goose & Gander’s is a total gem. Start in their cozy basement bar with a house-aged cocktail (so good).
- The Saint gave full vintage glamour. Tucked inside a restored 1905 bank vault, it has boutique wines, artisan bites, and a live band that made it feel like a private party.
Iconic Bites You Can’t Miss
If you’re eating your way through St. Helena, here are can’t-miss foodie spots to dream about:
- At Farmstead at Long Meadow Ranch, experienced true farm-to-table dining. Wood-grilled meats, fresh veggies, and ingredients straight from their ranch.
- Gott’s Roadside delivered big on flavor with their California Burger and Ahi Poke Tacos.
- A stop at Model Bakery is a must! Grab a world-famous English muffins in the beautifully reimagined space.
A Stay Steeped in Luxury
If you’re dreaming of a wine country escape that feels like a five-star secret, we found the one.
- Stay at Alila Napa Valley, nestled right next to the vines and just steps from downtown St. Helena. The rooms? Think plush bedding, a fireplace on the terrace, and vineyard views that make you forget what day it is.
- Their Spa Alila is a total sanctuary. Calming, quiet, and exactly what you need to unwind.
- Dinner at Violetto is unforgettable: beautifully balanced dishes, incredible service, and a warm, elegant setting.
Culinary Stars in the Making
The Culinary Institute of America at Greystone in St. Helena is a must for food lovers. Future chefs run the show here, and it’s a total treat.
- Dine at CIA Gatehouse Restaurant for a student led fine dining experience.
- Stroll the campus on a sunset tour, equal parts scenic and inspiring.
- Take a Wine & Beverage class to sip and learn like a pro.
Trail Time, Anytime
Get outside on the Napa Valley Vine Trail. Sunshine, views, and fresh air make this stroll a highlight!
- Walk or bike the St. Helena to Calistoga section, an easygoing 8.2 miles of scenic beauty.
- Pack a picnic or stop at a winery. This is wine country, after all!
Luxe Sips & Sparkle
If you’re looking to treat yourself (and you should), this one’s for the sip and savor lovers.
- Stop into the JCB St. Helena lounge for sparkling flights and next level indulgence. Think caviar, curated cheese boards, and chic surroundings.
Main Street Treasures
Wrap up your trip with a stroll through the Historic Shopping District.
- Find one-of-a-kind fashion at Pearl Wonderful Clothing, where local flair meets timeless style.
- Wander into MEUSE Gallery and get lost in Simon Bull’s colorful, expressive artwork.
- Pop into Steve’s Hardware & Housewares a St. Helena staple since 1955 that’s full of nostalgia (and great finds).
Your suitcase might just come home fuller than when you arrived.
