A few years ago, we attended a fundraiser for Family House, an amazing San Francisco organization providing a home away from home to families whose children are undergoing treatment for life-threatening illnesses at UCSF Medical Center. They serve thousands of families every year, offering comfort and support completely free of charge. Family House relies solely on donations, and we try to do our part by donating meals and gifts, attending events and bidding on auction items. It was at one of their fundraisers that we secured this special weekend escape to St. Helena, California.
Because of the pandemic, it took a few years for our visit to happen. Given that, this weekend away was our first real vacation in a long time and we were excited for new scenery. We packed out bags for a weekend full of wine tasting, farm-to-table meals and a special stay at the Gandona Estate guest house. The owner graciously donated a weekend stay along with a tour and tasting for four, and we were the lucky recipients.
The Perfect St. Helena Itinerary
Before meeting friends for our first wine tasting, we decided to grab lunch in downtown St. Helena. Northern California Wine Country has so much to offer, including many restaurants that offer the most spectacular food in a laid-back setting, which I love. Market Restaurant is no exception. This popular location is located on bustling Main Street in the heart of St. Helena. The street is lined with restaurants, wineries, art studios and boutiques (Allison in Wine Country is a must-visit), offering something for everyone.
The menu at Market Restaurant is broad, from burgers to mussels to salads. We opted for salads since we had a lot of eating and drinking ahead of us, and they were delicious. The Market Dungeness Crab Louie Salad was the favorite, loaded with crab and amazing flavors. The Sesame-Soy Chicken Salad was also very tasty, filling, and paired perfectly with a glass of Salvestrin Sauvignon Blanc.
After lunch, we met our friends at Davis Estates for our first wine tasting. Following, we headed to the beautiful 17-acre Gandona estate on Pritchard Hill with stunning views of Lake Hennessey. Check out our full itinerary below with recommendations for some of the best wineries and restaurants in St. Helena.
Day 1: Lunch, Wine Tasting, Drinks, Dinner
Lunch at Market Restaurant
Great salads, sandwiches, burgers and more in a casual setting in the heart of St. Helena. The popular location has been in business nearly 15 years. Grab a table inside the stone-walled dining room, or sit at the historic bar. Either way you can’t go wrong for lunch or dinner.
Wine Tasting at Davis Estates
Reservations are required, so call ahead. We toured the property (the barn is incredible!) and enjoyed the estate wine and food pairing in a beautiful open-air room that was reminiscent of Maui. Every wine was perfectly paired with a delicious small plate. Mike Davis, who owns the property with his wife, Sandy, even stopped by to chat with us while we tasted, which is common according to our hostess.
Drinks at The Charter Oak
It was my first visit, but definitely won’t be my last. Owned by Christopher Kostow, who came from three-Michelin star The Restaurant at Meadow, The Charter Oak has perfected approachable, local, seasonal food. The cocktails were unique, perfectly balanced, and delicious. There’s a large open dining area and a beautiful outdoor space. A great place for any meal, drinks or a special event.
Dinner at Cook St. Helena
This is a go-to for me and my husband ever since we stumbled upon it years ago. It’s been a highlight among locals and visitors since 2004, offering tasty Northern Italian cuisine in a quaint, unassuming space. There aren’t many tables, so reservations are recommended. Every dish was spot-on: homemade pasts, mussels in tomato broth, fried calamari and a wine bible loaded with a dizzying amount of great options.
Day 2: Breakfast, Lunch, Wine Tasting, Reset, Dinner
Breakfast at The Model Bakery
One of my all time favorite bakeries is Model Bakery. The St. Helena storefront has an amazing amount of pastries, breakfast sandwiches on homemade english muffins, enormous cookies, and plenty of coffee and espresso options. There are other locations throughout Northern California as well.
Lunch & Tasting at Gandona Estate
We stayed on property and were excited to walk over to the main winery to enjoy lunch and taste the French-inspired wines. Manuel Pires, vintner, was our host for what turned out to be a spectacular afternoon. We started with a tour of the property, taking in endless vineyards and lake views, hearing the history of the relatively young winery which opened in 2006. Afterwards, we were treated to an incredible lunch: cheeses, roasted veggies, charcuterie, salmon. Everything was fresh, local and delicious.
The wines were equally amazing. Winemakers Philippe Melka (well-regarded throughout the world) and Adam Casto focus on crafting well-balanced Cabernet Sauvignon from the estate. We were lucky to get to taste some smaller production white wines as well. We sat for hours, eating, drinking and enjoying our delightful host and our chef, Pete.
Reset
After all of that food and wine, we needed a reset (check out my steps to planning a perfect day in Napa). We went back to the guest house and walked around the property, visiting the goats and chickens, picking fresh oranges and wandering through the vineyards. Feeling refreshed, we headed into town to met our friends again for a final dinner.
Dinner at Farmstead
Long Meadow Ranch’s Farmstead offers American farmhouse cuisine. Popular since it opened, the large property includes and indoor and outdoor restaurant, an outdoor cafe and a general store where you can sample their wines and olive oils, and buy artisnal foods to take home with you. They recently expanded outdoor seating options and we enjoyed a lively dinner outside near the bar. Food can be hit-or-miss on busy nights, but it’s worth a visit. My previous meals were delicious and the atmosphere is one of the best in Napa. Reservations highly recommended.
