A weekend in St. Helena with @sommvivant
If you want a personalized St. Helena experience, travel through the deep roots of Napa Valley with one of wine country’s best! In just 48 hours, explore St. Helena like a local wine expert would. Sip through St. Helena with Amanda McCrossin! Amanda is a certified sommelier, wine personality, podcast host, and Instagram/YouTube/TikTok creator known as “sommvivant.”
With over 220K followers on Instagram and 213K followers on TikTok, Amanda is a leading source of all things wine on the internet. Amanda’s roots run deep in Napa Valley, specifically the iconic wine town of St. Helena, where she spent half a decade as the Sommelier and later Wine Director for PRESS Restaurant, a Michelin-rated restaurant known for having the largest collection of Napa Valley Wines in the world! Here’s your perfect itinerary to plan your next St. Helena trip.
DAY 1
CHECK-IN TO ALILA NAPA VALLEY
Yearning for an unforgettable adult-only getaway in Napa Valley? Look no further than Alila Napa Valley, St. Helena’s acclaimed luxury retreat. Recognized by Forbes with a 4-star rating and lauded by Condé Nast Traveler as one of Northern California’s top three resorts, Alila promises an unmatched escape.
Imagine cozying up by your private firepit, mesmerized by panoramic vineyard views that stretch as far as the eye can see. Whether you choose a Vineyard View Suite or a room overlooking the iconic Rhine House at Beringer Vineyards, your haven provides every comfort imaginable for a deeply relaxing stay.
Carve out precious moments for yourself at the award-winning Spa Alila. Immerse in transformative wellness experiences, from rejuvenating spa treatments to inspiring vineyard view painting classes. Just like Napa Valley itself, Spa Alila offers pure indulgence and rejuvenation for the soul. Insider tip: get special rates here.
Recommended Time: After 4:00 pm
DINNER OR LATE-NIGHT MENU AT CHARLIE’S NAPA VALLEY
Foodies, rejoice! St. Helena boasts a mouthwatering newcomer stealing the spotlight: Charlie’s Napa Valley. Since its 2023 debut, this restaurant has become a local favorite and ignited the interest of discerning palates nationwide. Reservations remain coveted, a testament to the culinary magic within.
Helmed by Elliot Bell, ex-French Laundry sous chef, Charlie’s is more than just a restaurant; it’s a vibrant community fueled by the legacy of his son, Charlie. The menu sings with the bounty of Napa Valley, weaving in globally-inspired flavors to create an unforgettable experience.
Whether you crave the decadence of truffles and oysters or the comforting indulgence of fried chicken and champagne, Charlie’s caters to every craving. A single visit won’t suffice.
Immerse yourself in the lively, fun, and lighthearted ambiance, where even late-night cravings get a gourmet twist. Insider tip: Indulge in the “NYC Happy Meal,” or Regiis Ova Caviar and elevated potato skins–a must-try for adventurous palates.
Recommended Time: 8:00 pm for a late dinner and stay for the late-night menu
DAY 2
DITCH THE DESIGNATED DRIVER DRAMA & HAVE AN EPIC ADVENTURE WITH WILD VINE WINE TOURS
Imagine exploring Napa Valley’s rolling hills and iconic vineyards without worrying about who drives! With Wild Vine Tours, led by two St. Helena locals with nearly 30 years of wine expertise, you can immerse yourself in adventure and exquisite wines–no designated driver required.
Whether you’re an adrenaline junkie seeking an invigorating morning mountain bike ride before savoring Napa’s finest Cabernet Sauvignons or prefer a leisurely pace soaking in stunning views, Wild Vine curates the perfect experience for you and your group. They craft custom itineraries catering to every desire, offering both adventure and wine-focused tours.
Here’s why Wild Vine Tours elevates your Napa Valley experience:
- Local Expertise: Benefit from the in-depth knowledge of seasoned St. Helena locals who unlock hidden gems and exclusive winery access. Also, the owner is a local firefighter–so you’ll be sure to be safe!
- Bespoke Itineraries: No cookie-cutter tours here! Each adventure is tailored to your preferences, ensuring a personalized and unforgettable experience.
- Adventure + Wine: Embark on exhilarating hikes or bike rides through breathtaking landscapes followed by expertly curated wine tastings featuring renowned producers and cult favorites.
- Flexibility: Opt for an active morning or relax and indulge – the choice is yours!
Recommended Time: 10 am pick up from your hotel
STROLL ST. HELENA’S HISTORIC SHOPPING DISTRICT
Unveiling the captivating past, St. Helena’s Main Street transports you to the late 1800s with its historic buildings (many proudly listed on the National Register) and vibrant shopping experience. Stroll past California’s oldest single-screen movie theatre, Cameo Cinema, or sip at the Saint, a wine lounge housed within an old bank vault – each step imbued with history.
But no journey through St. Helena is complete without a visit to Woodhouse Chocolates. Boasting over 1,000 intricate chocolate molds and mesmerizing all-chocolate window displays, some claim it’s the finest chocolate shop in America. Indulge your senses – step inside and be whisked away to Parisian elegance under a sparkling chandelier. Sample their handcrafted chocolates, and treat yourself (or impress loved ones back home) with the decadent Dark Chocolate Caramels with Fleur de Sel.
The shopping is undeniable here. Find one-of-a-kind boutiques like Fideaux for your pet or Napa Valley Vintage Home to fill your space. Love Art? Explore Aerena Galleries or high-end luxury stores such as Elysewalker and AF Jewelers at your fingertips.
Recommended Time: 10 am – 5 pm
WINE & FOOD PAIRING AT PRISONER WINE COMPANY
Dive into sensory symphony at Prisoner Wine Company, where they elevate a classic food and wine pairing to an unforgettable culinary adventure. Their “trio of culinary bites” goes beyond mere pairings, intentionally challenging your palate and amplifying the wines for a truly memorable experience.
This philosophy echoes their iconic Prisoner Red Blend, released two decades ago. This bold blend of unusual Californian grapes shattered expectations, forever changing the game for red wines. Renowned as a “cult” brand by fans and critics alike, Prisoner embodies boldness and innovation.
But their story doesn’t end with groundbreaking wine. Step into their tasting room, an architectural and artistic masterpiece that defies traditional winery aesthetics. Immerse yourself in art adorning every corner, from the soaring ceiling to the modern architecture and striking interior design. Prisoner Wine Company isn’t just a winery; it’s an Instagrammable haven for sensory exploration.
Recommended Time: 11:30am
SEE THE VALLEY FROM ABOVE AT CATHIARD VINEYARD
Experience Napa Valley with European flair at Cathiard Vineyard, the Californian sister estate to the renowned Château Smith Haut Lafitte in France. Embark on a captivating journey through their gravity-flow winery and horseshoe cellar carved into the hillside, uncovering the rich biodiversity and fascinating history of this unique property.
Step back in time to the charming 1940s estate home, once the haven of winemaker Louis Martini. Insider tip: For an unforgettable adventure, hop on Cathiard’s open-air electric vehicle and traverse the scenic backroads nestled within their hillside terroir. Savor a glass of wine at the summit, awash in breathtaking panoramic views, before enjoying a curated tasting of the Cathiard lineup at the owner’s favorite on-site location.
Recommended Time: 2:00 pm
HAPPY HOUR AT ALILA NAPA VALLEY’S TERRACE BAR
As the Napa Valley sun paints the mountains in fiery hues, indulge in the ultimate relaxation experience at Alila Napa Valley’s Terrace Bar. Sink into plush cushions on the spacious terrace, breathe in the fresh air, and let the mesmerizing views melt your worries away.
But the magic doesn’t stop there. The Terrace Bar boasts a seasonally-inspired menu featuring delectable small bites crafted to complement the breathtaking scenery.
Craving a taste of sunshine? Don’t miss their signature Mexico City-style Margarita, guaranteed to transport you to a tropical paradise. Whether you’re lounging on a comfy couch or soaking up the ambiance from a bar stool, the Terrace Bar promises an unforgettable sunset ritual.
Recommended Time: 5:30 pm
DINNER AT THE ACACIA HOUSE
Even if Alila Napa Valley isn’t your home base, don’t miss the culinary gem nestled within – Acacia House Restaurant. Imagine arriving at a picturesque 1905 Georgian farmhouse mansion, welcomed by complimentary valet parking. As you ascend the photo-worthy staircase, prepare to be dazzled by an unforgettable dining experience.
Acacia House takes American cuisine to the next level, showcasing the bounty of Napa Valley with an imaginative flair. Indulge in dishes crafted with seasonal produce sourced from their on-site gardens and local farms. Start your meal with the ever-popular duo: house-made waffle chips dipped in creamy whipped labneh and topped with delicate trout roe. Share hearty salads bursting with flavor, or delve into a selection of mouthwatering main courses.
Insider Tip: Weekend reservations are highly recommended – a testament to the popularity of this Napa Valley treasure.
Recommended Time: 7:00 pm
