There’s something undeniably magical about Wine Country—the rolling hills, the winding roads, the way time slows just enough for you to savor each sip and moment. But what if you could take that feeling and stretch it across two iconic regions, exploring some of the most distinct and dynamic wineries along the way?

That’s why we’ve partnered with Foley Family Wines to create the Ultimate Wine Country Road Trip, a multi-day adventure through the best of Foley’s collection of legendary estates across Sonoma and Napa Valley. United under the vision of founder Bill Foley, this diverse portfolio is all about pairing unforgettable wines with equally unforgettable experiences—think culinary experiences in grand European-style villas to elevated tastings that put you high above the valley floor.

The Ultimate Wine Country Road Trip: Six Estates, One Legendary Journey through Sonoma & Napa

Whether you’re a seasoned wine lover or just beginning your journey, this curated itinerary promises a perfect blend of scenic drives, terroir-driven wines, and immersive hospitality. Buckle up, because it’s time to hit the road!

Day 1: Healdsburg to Santa Rosa — Sonoma’s North Side

Stop 1: Ferrari-Carano Vineyards | The Italian Soul of Sonoma

Begin your road trip with a touch of la dolce vita at Ferrari-Carano, a Dry Creek Valley gem where Italian heritage meets elevated Sonoma hospitality. The grand Villa Fiore feels like it was plucked right out of Tuscany, and in spring, the surrounding gardens explode with more than 10,000 tulips and daffodils. Talk about a beautiful sight.

Inside, tasting experiences range from curated flights to farm-to-table pairings. For something extra delightful, book the new Aperitivo Pergola Wine & Food experience, featuring wines paired with seasonal bites beneath olive trees and lush landscapes.

Stop 2: Banshee | Rock the Rules

Next, head 10 miles southwest to Alexander Valley’s Banshee Wines. Banshee breaks the mold with a tasting room that feels more like your favorite record store or art-forward lounge. Set against a stunning Sonoma backdrop, this is where serious wines meet laid-back fun.

Pinot Noir may lead the pack, but the full lineup—from bright Chardonnay to bold Cabernet—brings fearless energy. Grab a flight, kick back, and embrace the no-pretense atmosphere that sets Banshee apart in Wine Country. If you want to do something a little bit different during your visit, book the Vintage Lunch Club experience. We don’t want to ruin the surprise by sharing all the details—just trust us and bring your appetite for something different.

Stop 3: Chalk Hill | Grown from the Earth, Elevated by Design

End your first day with a sense of awe at Chalk Hill Estate, perched high above rolling vineyards with panoramic views and a terroir-driven focus. Known for its volcanic soils, estate-grown varietals, and culinary garden, Chalk Hill is where precision and passion come together.

Don’t miss the Vineyard Overlook Tasting or a guided tour of the property on the Estate & Garden Hummer Tour & Tasting. This is wine elevated—literally and figuratively.

Driving Distance Between Wineries: 21 miles

Day 2: Sonoma Valley — Classic Meets Cool

Stop 1: Chateau St. Jean | Timeless by Design

Kick off the day at Chateau St. Jean, where manicured gardens, heritage oaks, and a stately chateau set the tone for timeless Sonoma elegance. Nestled at the base of Sugarloaf Ridge in the picturesque Sonoma Valley, this storied estate blends classic architecture with laid-back luxury.

Here, tastings unfold on sunny patios or inside the grand chateau, with highlights including the estate-grown Chardonnay and the signature Cinq Cépages red blend. The 90-minute Chateau Experience is a great introduction to the winery’s limited releases, but the private outdoor picnic-style Pique-Nique au Chateau is hard to beat on a nice day.

Stop 2: Sebastiani | Legacy in Stone

Just a few blocks from Sonoma Plaza, Sebastiani Winery brings old-school cool and deep history to the table. Founded in 1904, this enduring estate still showcases its original stonework, redwood tanks, and timeless charm.

The lineup leans bold—think structured Cabernets, expressive Merlots, and rich Zinfandels made to last. Pair that with a relaxed downtown location and you’ve got a tasting that blends legacy and accessibility in one memorable stop.

Driving Distance Between Wineries: 12 miles

Day 3: Napa Valley — Views & Vintage Elegance

Stop 1: Silverado Vineyards | Above the Valley, Beyond the Expected

Wrap up your road trip with a drive to Silverado Vineyards, perched above the Silverado Trail with sweeping Napa Valley views. Since 1981, this iconic estate has produced elegant, estate-grown wines rooted in heritage and hillside terroir.

Cabernet is the star, but don’t sleep on the expressive Merlot or bright Sauvignon Blanc. Opt for the Legacy Cabernet Experience, which features estate Cabernets from Stags Leap and Coombsville, or indulge in the White Wine & Caviar Experience on the terrace. Either way, it’s the perfect high note to end your Wine Country adventure.