If your idea of Napa Valley perfection includes small-production wines, passionate winemakers, and a day that’s more about authentic experiences than tourist crowds, you’re in the right place. This full-day itinerary features four boutique wineries and a relaxed, iconic lunch stop—all curated to delight your palate and soul. Starting and ending at The Cottages of Napa Valley, this journey loops through Highway 29 and the Silverado Trail to give you a scenic, flavorful Napa experience.

Waking up in your private cottage, sipping French press coffee, and enjoying a basket of fresh Bouchon Bakery pastries will give you the boost you need to start this iconic day right!

But before we dig in – A Bit of Napa History: The First Boutique Winery

While you’re enjoying the boutique wineries listed below, raise a glass to Stony Hill Vineyard, widely recognized as Napa Valley’s first boutique winery. Founded in 1943 by Fred and Eleanor McCrea on Spring Mountain, Stony Hill emerged during a pivotal time—when the valley was still recovering from the devastating effects of Prohibition (1920–1933), which had shuttered most wineries and nearly wiped out California’s wine industry.

Rather than following the trend toward mass production, the McCreas took a different path: focusing on small-lot, estate-grown wines crafted with intention. Their commitment to quality and authenticity helped define what “boutique” would come to mean in Napa.

Long before Chardonnay was fashionable, Stony Hill’s crisp, mineral-driven whites set a quiet but powerful standard. Even more pioneering? They sold their wines direct-to-consumer by mail order—a bold move that laid the groundwork for Napa’s now-thriving wine club and tasting room culture.

Stop 1: Trefethen Family Vineyards

Address: 1160 Oak Knoll Ave, Napa, CA 94558
Hours: Daily, 10:00 AM – 4:30 PM
Phone: (707) 255-7700
Reservations: Book via CellarPass

Start your tasting experience at this historic, family-owned estate known for its beautiful 19th-century winery building and organically farmed estate vineyards. Trefethen has remained family-run since the 1960s, a rarity in Napa today.

Their tastings take place in a restored barn or on a peaceful terrace with vineyard views. You’ll taste estate-grown classics like Cabernet Sauvignon, Chardonnay, and their standout Dry Riesling. The staff is knowledgeable and welcoming, offering a guided exploration of both wine and heritage.

If you’re a fan of subtlety, balance, and wines with age-worthy potential, Trefethen is a must.

Stop 2: Elyse Winery

Address: 2100 Hoffman Ln, Napa, CA 94558
Hours: Daily, 10:00 AM – 5:00 PM
Phone: (707) 944-2900
Reservations: Book via Tock

Just a short hop from Trefethen, Elyse Winery delivers one of Napa’s best kept secrets: small-batch, bold reds served in a cozy, home-like setting. With a philosophy rooted in honesty and expression, their wines highlight unique vineyards and distinctive terroirs.

You might find yourself chatting with the winemaker or lounging on the patio with a view of the vines. Standout varietals include Zinfandel, Cabernet Sauvignon, and Petite Sirah. There’s a rustic charm here that makes the experience feel like visiting an old friend who just happens to be a master vintner.

Insider tip: their wine club gives you access to micro-lot wines that often sell out fast.

Lunch Stop: Gott’s Roadside, St. Helena

Address: 933 Main St, St Helena, CA 94574
Hours: Daily, 10:30 AM – 9:00 PM
Phone: (707) 963-3486
Website: gotts.com

No need for white linens and hushed tones—at Gott’s Roadside, lunch is casual, delicious, and unmistakably Napa. This local institution is perfect for a midday recharge. Grab an outdoor picnic table and enjoy their famous ahi burgers, sweet potato fries, and milkshakes.

They also offer local wines by the glass and Napa-brewed beer if you feel like keeping the tasting going through lunch. It’s unfussy, fast, and unbelievably satisfying.

Stop 3: Tres Sabores Winery

Address: 1620 S Whitehall Ln, St Helena, CA 94574
Hours: By appointment, starting at 10:00 AM
Phone: (707) 967-8027
Reservations: Book via contact form

Tucked into the western hills of Rutherford, Tres Sabores (“three flavors”) is a woman-owned, certified organic winery that will charm your senses as much as your palate. The experience here is intimate and often includes visits from the winery dogs and even goats!

Tastings may include homemade treats like olives and jams, as well as their estate-grown Zinfandel, Cabernet Sauvignon, and Petite Sirah. This is a true working ranch, and visitors are welcomed like family.

It’s the kind of place that makes you slow down, breathe, and fall in love with Napa all over again.

Stop 4: Vincent Arroyo Family Winery

Address: 2361 Greenwood Ave, Calistoga, CA 94515
Hours: Daily, 10:00 AM – 4:00 PM
Phone: (707) 942-6995
Reservations: Call to schedule

Wrap up your day with a tasting at Vincent Arroyo, where the vibe is as bold and generous as their wines. Specializing in Petite Sirah, Cabernet Sauvignon, and red blends, this family-owned spot is delightfully down-to-earth.

Tastings are private, by appointment only, and often include barrel samples or an informal tour of the production area. The Arroyo family’s hospitality is legendary, and if you’re lucky, you might be greeted by one of their friendly vineyard dogs.

This is the kind of winery that makes you want to linger. And buy a case.

Return to The Cottages of Napa Valley

After a day of sipping and savoring, head back to your cozy cottage. You can even grab some artisanal cheeses, a baguette, and curated meats from Oakville Grocery or Ranch Market in Yountville on your way back to your cottage. Open one of the bottles you brought back, light a fire, sit under the twinkling lights, and relive the magic of your day.

Memory Tip: Take a 10-15 second video of yourself and loved ones at each stop, and then create a reel and post it to your social media, making sure to tag the wineries (and us!) to commemorate the day.

Final Sip

This curated day through Napa Valley is a celebration of boutique winemaking and local charm. You’ll taste wines that rarely make it to store shelves, hear stories that connect you to the land, and return home with a deeper appreciation for the heart behind every bottle.