Ultimate St. Helena Napa Itinerary

A trip to Napa Valley is a quintessential California experience that everyone should have at some time, especially if you love wine! Planning your first trip to Napa Valley can be challenging because there are so many great towns and wineries to choose from. I recently spent a few days exploring St. Helena Napa Valley and want to share the ultimate itinerary for visiting St. Helena wineries. 

Napa Valley Towns

Napa Valley is California’s wine country. There are five major towns that comprise the Napa Valley wine region, and several other smaller towns. When planning your Napa Valley vacation, you’ll choose from Calistoga, St. Helena, Yountville, Napa, and American Canyon. Each town has its pros and cons, and it’s worth returning many times to experience the different regions. 

St. Helena Napa Valley

St. Helena is often called Napa Valley’s Main Street, thanks to its historic charm and relaxed vibe. In addition to the wineries surrounding St. Helena, the downtown Main Street is lined with boutiques, galleries, and amazing restaurants. The small-town charm reminds me of downtown Saratoga Springs, New York, where I’m from. I loved shopping at the well-curated boutiques and had some amazing meals in St. Helena. 

St. Helena Wineries

My first stop in St. Helena is at AXR Napa Valley, an appointment-only tasting room offering some of the best California wines. Set amongst the redwoods, the tasting room is beautiful and I enjoyed several wine samples here, including their Ganzin Red, a Bordeaux-style blend of cabernet, malbec, and merlot. My personal favorites were the 2018 Flagship and the 2018 Sleeping Lady. 

Another excellent St. Helena winery is Hall Wines. This family-owned vineyard is a favorite for serious wine collectors and Cabernet Sauvignon fans. The Hall estate encompasses more than 500 acres of Bordeaux varietals, including Sauvignon Blanc, Cabernet, and Merlot. The tasting room is a great place to sip wine while enjoying the lush scenery and interesting art collection. Private wine experiences can also be arranged. 

St. Helena Dining

I had some fantastic meals in St. Helena, and the amazing collection of restaurants is reason enough to return. I expected great wine in St. Helena, but I was blown away by the food scene. 

Brasswood Napa Valley is a hidden gem located outside of the main area. Backed by Brasswood Cellars, Brasswood crafts dishes that pair perfectly with their elegant wines. Every dish has complex flavors and is carefully crafted to be savored slowly.

I started with hand-pulled fresh mozzarella on crostini; it’s not on the menu, but ask your server for this amazing starter. The herb-infused pappardelle with short rib was one of the best dishes I’ve tried in a long time. Finishing the evening with a butterscotch pannacotta was the ultimate indulgence. 

PRESS is one of the top restaurants in Napa Valley and is on par with many of the Michelin restaurants I’ve tried during my travels. The chef hails from notable places like Per Se, French Laundry, and Le Bernardin.

Some of the menu highlights include caviar, snapper, spring pea soup, beef fat potato, and the Wagyu Ribeye. In addition, the extraordinary wine cellar offers the perfect pairings for your delectable meal. 

Model Bakery is an artisanal bakery famous for the Model Bakery English Muffin. The biscuits are so good, Oprah has had them flown in from Napa. 

For a sweet treat, head to Erosion on Main Street. This wine tasting room has been converted into an ice cream parlor. Along with flights of ice cream, they have dozens of wine and beer on tap, as well as coffee drinks. No matter your tastes, you’ll find something you love at Erosion. 

Other notable St. Helena restaurants that came highly recommended to me include Goose & Gander and Pizzeria Tra Vigne. I can’t wait to return and try these food spots. 

St. Helena Shopping

Much of the charm of St. Helena’s Main Street lies in the eclectic boutiques that are interspersed amongst the tasting rooms. Charming historic buildings hold all kinds of fun shopping experiences. Make sure you set aside time for shopping on your Napa Valley itinerary. 

Olivier Napa Valley is a boutique on Main Street offering home goods and kitchen accessories. This is a great spot to shop for gift baskets. 

elysewalker has been setting the style scene of St. Helena for decades. Their team of stylists curates looks from over 150 designers. Pop in to browse, or schedule an appointment with one of their personal stylists to refresh your look. 

Carter & Co is a ceramic dinnerware company that combines great food, fine ceramics, and functional beauty. The bespoke collection is fun to browse, especially if you’re looking to update your kitchen!

New West Knifeworks crafts premium chef knives that are built to last. These elegant knives are hand-finished in Idaho and available in four retail stores in the Mountain West. If you’re looking for a fun activity, they also offer axe-throwing on site. 

St. Helena Luxury Accommodation
In a region known for weekend getaways, there is no shortage of luxurious accommodations in Napa Valley. You’ll have your choice of boutique hotels, b&bs, and private home rentals. 

Meadowood Napa Valley

For my recent trip to St. Helena, I stayed at Meadowood Napa Valley. This world-class resort is set on a private 250-acre estate and is known for gracious hospitality, classic architecture, and luxurious accommodations. Between the private lodge, first-class service, and indulgent spa, Meadowood is such a relaxing place to stay! You could enjoy a full weekend at the lodge without ever leaving because there are so many things to do on property. If you do need to leave the property, the house car is available to take you to downtown St. Helena. 

My room at Meadowood was so cozy, that it was hard to leave. I had a private porch, plus a living with a fireplace, and one of the biggest bathtubs I’ve ever seen. The private deck was the perfect spot to enjoy my room service breakfast each morning.

The breakfast menu features classic comfort foods highlighting fresh ingredients from the on-site gardens. Of course, I can’t start my day without a Nespresso machine; thankfully, my room came fully equipped with Nespresso pods and a full minibar in which everything was complimentary except the alcohol. 

The Meadowood Spa is a tranquil place to relax and unwind during your stay. I treated myself to the Essential Journey Massage, which included a pretreatment aromatherapy steam shower. The whole experience was unique and incredibly relaxing. For more downtime in the California sun, enjoy one of three swimming pools on property. Meadowood has a fitness pool with lap lanes, a family activity pool, and an adults-only cabana pool. 

The Wine Center is a great place to learn about Napa Valley wines. This educational experience is exclusive to Meadowood guests, and your session can cater to anything from learning how to hold a wine glass to learning about the terroir of the wines. 

If you enjoy tennis, that’s another reason to come to St. Helena and stay at Meadowood. The resort has best-in-class tennis pros, and I was treated to a private lesson with tennis pro Stephanie Wallace. Meadowood is worth visiting for the tennis alone!

Of course, the dining at Meadowood is also top-notch. Besides in-room dining, there’s also the Terrace Cafe serving delectable bites sourced from Meadowood’s gardens. It’s a great place to enjoy a relaxing lunch amongst the towering trees. 

The beauty of Napa Valley is that you can return many times and you’ll never have the same experience. Whether you’re a first-time visitor or a Napa Valley veteran, you’ll enjoy some of the best wineries in St. Helena.