Splurge & Explore Over-The-Top St. Helena

Are you looking for an over the top experience that will WOW your vacation dreams? In the midst of vineyards and small boutique wineries, St. Helena offers exceptional over the top experiences to make your vacation one you won’t forget!  

A quick drive from San Francisco, in between two mountain ridges, St. Helena is more to it than tasting wine in vineyards. These wineries and restaurants will give you an unforgettable experience that will WOW your expectations of Wine Country.

The Red Room at Raymond Vineyards

Before checking into your hotel, you will first visit Raymond Vineyards. Raymond Vineyards is a dynamic destination dedicated to inspiring their guest’s passion for wine in an environment of exploration, creativity, and elegant whimsicality. Taste current release wines in the Red Room, that is designed specifically in all red velvet! Did someone say selfie? This property offers great photo opportunities around each corner. 

Las Alcobas

Head north and check into the luxurious Las Alcobas Napa Valley. This adult only resort will have your senses on overload, every detail does not go unnoticed. From the fine custom craftsman ship of each room, floor to ceiling glass door that opens to the sweeping views of Beringer Winery, and a gorgeous soaking tub surrounded by marble and stoneware you may never want to leave your room!

On property, Acacia House is a Georgian inspired designed restaurant where locally infused ingredients are influenced by rich cultures such as Spain, Italy, and France will have your taste buds enthused for its next bite. If weather allows, sitting out on the porch is always a wonderful way to unwind after a day of travels.

Your first full day of wine county indulgence begins. First, enjoy room service out on the beautiful terrace overlooking the vineyards. The fog rolls over the mountains in St. Helena that makes for chilly mornings, so we recommend turning the fire pit on for a relaxing and cozy start to your day.

Castello di Amorosa

Head to your first experience at Castello di Amorosa, a medieval Italian inspired castle located in the heart of Napa Valley. Immerse yourself in the beautiful designed architecture. You’ll taste current release wines while exploring the castles hidden treasures, including the torture chamber! You may see peacocks on the property, don’t worry they are very friendly!

Caves at Del Dotto

Your next experience will have you exploring caves! Not mountain caves, wine caves. These are a wonderful feature to wineries as they keep the wine at the perfect temperature for aging. At Del Dotto Vineyards you will tour their Venetian inspired cave while tasting wines thieved right out of the barrel. Afterwards, enjoy house-made sourdough pizza featuring cultured yeast from their own grapevines. Overlooking the vineyards, you’ll be sure to feel like royalty.   


Inglenook, a winery that began its winemaking legacy in the late 1800s. Here you will learn the rich history of the property and explore the old-world style grounds estate. On the tour, you will visit the Chateau, a walk through the vineyards, and ending with a seated tasting of wine and artisan cheeses in the private infinity cave.

Head back to your hotel and take a dip in the pool for relaxation and rejuvenation before dinner.

The Charter Oak

At The Charter Oak, their cooking style is minimal, showcasing little to no garnishes, and highlights one or two ingredients at a time. They offer an al la carte menu, but if you are looking for an over-the-top dining experience ask for the family dinner. No need to decide on the many delicious offerings, the team will curate a personalized dinner just for the table. Don’t skip out on dessert!

Food at The Charter Oak

Your extravagant vacation doesn’t have to end when you check out of the hotel. Cakebread Cellars Food & Wine pairing offers you the experience to enjoy four original recipes from the winery chefs while tasting alongside a selection of Cakebread wines. This is a grand way to say cheers to your memorable wine country getaway vacation.