Before you go 

Two Days in Napa Valley

First thing to do when you land in town:

• Gotts Roadside with locations in both St. Helena and Napa, though the original in St. Helena trumps for its open spaces for kids to run around after a day of travel. Order mini corndogs for the littles, ahi burgers for the grown-ups and milkshakes for all. Don’t sleep on the sweet potato fries with a side of green goddess dressing.

Day 1: Exploring Up Valley

Morning

• Dig into a breakfast sammy: Like your children, the good folks at Model Bakery in St. Helena are early risers; the doors open at 6 a.m. Breakfast sandwiches are made-to-order on the bakery’s legendary ciabatta English muffins (make sure to take some home!) and the bakery now offers gluten-free wraps for breakfast burritos.
• Hit the park with vineyard views: With 12 acres, six public tennis courts and eight bocce courts, as well as a phenomenal kid’s playground with different zones for different age groups, Crane Park is a hub for local families and tourists alike. Got tweens? There’s also a designated skate park area. If you’re visiting between May to October, aim to go on a Friday morning when St. Helena Farmer’s Market sets up next to the playground against a vineyard backdrop. Check out local produce, artisans, food purveyors, and live music. While the local Friday morning bocce league is in season, it’s best to spectate: the competition has at times become so intense, the city had to intervene and take over control of the courts and league. Needless to say, this makes for excellent people watching.

Mid Day

• Be a kid in a candy store: Stop on Main Street and drool at the whimsical handcrafted confections at Woodhouse Chocolates. Choose from a selection of filled chocolates, caramels, bark or seasonal European-influenced molded chocolate figures such as grape bunches, carrots, Easter bunnies, trolls, Santas and dragons exquisitely decorated with edible paints.
• Catch a water-powered mill in action:Continue north on Highway 29 to Bale Grist Mill State Park. Depending on your energy level, you can hike the moderate History Trail (a 2.4-mile round trip) past the historic Pioneer Cemetery and through the chapparal-filled forest. The main attraction is the Bale Grist Mill itself, built in 1846 and one of only a handful of mills of its kind still functioning in the U.S.

Afternoon

• Drink wine (or juice) in a castle: Just south of Bale Grist Mill State Park sits the medieval-style 107-room Castello di Amorosa, a passion project by local winemaker Dario Sattui that was decades in the making and completed in 2007. The Castle, as it’s known, features a moat, drawbridge, armory, a torture chamber (why not?), and yes, a wine cellar. While guided tours are for guests 21 and over, families can take the self-guided tour, which includes a glass of grape juice for the kids and a wine tasting for their parents. Outside of the tasting room, meet the resident peacocks, goats and emus before checking out the suits of armor and weapons in the Armory. (The torture chamber is mercifully off-limits.) Reservations are required and please note, no strollers are allowed inside.
• Roll up to a food truck: If you’re hankering for a snack after storming the castle, check out the Clif Family Bruschetteria Food Truck, which offers an ever-changing seasonal offering of bruschettas—think local mushrooms with fresh chives or farm vegetables with whipped feta— that are best shared.

Evening

• Order pepperoni on the patio: If you grew up in St. Helena, chances are you celebrated birthdays and little league victories at Pizzeria Tra Vigne, one of the most family friendly restaurants in the valley that also happens to sling the best thin-crusted pie in town. The kid’s menu for guests 12 and under features smaller versions of customizable wood-fired sourdough pizzas and pastas their parents are enjoying, while the main menu offers an array of sophisticated pizzas, piadine, seasonal salads and Italian small plates. Inside the vibe is loud and lively, while the outdoor patio is particularly gorgeous when the wisteria is in bloom and you can try your hand at bocce if you were denied at the public courts earlier in the day. Inevitably, nobody leaves without gelato.
• Catch a flick in a historic theater: The 140-seat art deco gem known as The Cameo is one of California’s oldest continuously operated theaters. During the summer months, programming often includes family friendly screenings with scrumptious snacks—and wine for the grown ups. The loveseats in the back of the theater are perfect for snuggling with your little ones and a bowl of popcorn.

Day 2: Southern Napa Charm

Morning

• Get a sweet start: Before you think about coffee, first place an order for a baker’s dozen of warm donuts at the Boon Fly Café, nestled in a charming red barn in the Carneros region at the south end of Napa Valley. The friendly staff will make you feel instantly at home while you dip the donuts in chocolate sauce and contemplate whether you have room for chicken and waffles or the green eggs and ham.
• Hop the tracks: Head into downtown Napa where kids can run along the riverfront and explore large-scale art murals along Downtown Napa’s Rail Art District (RAD Napa). Parking is available at the Napa Valley Wine Train and you can follow the path parallel to the tracks past towering murals toward the Napa River and Oxbow Pubic Market.
• Get lost in a book: Napa Bookmine is a stall inside Oxbow Public Market, which features an array of children’s books and games before investigating the many specialty food shops and confectioners. If you happen to be there on a Tuesday or Saturday, head across the street to the Napa Farmers’ Market with close to 100 vendors. There’s usually a story time at the Saturday market.

Mid Day

• Take a bite of history: Napa’s oldest adobe building, circa 1840, is now home to relative newcomer La Cheve Bakery and Brews. Known to locals as the Old Adobe, the woman-owned Mexican hotspot serves excellent comfort food and awesome baked goods. Of course that’s a winning combination for long wait times, so your best bet is to come on the early side.
• Refuel at a fancy filling station: Stop for a latte and soft serve at Honor Market in Yountville (and, for later, grab a half bottle of Schramsburg—which is the first winery you’ll visit when you return to Napa without kids). Then, you’ll head across the street to the Yountville Park, where adults can relax at a picnic table while kids climb the jungle gym.

Afternoon

• Find sanctuary for yourself, and the animals: Oasis by Hoopes is refuge in the heart of wine country where you can settle into a Mexican string chair and enjoy vineyard views and a fabled glass of Hoopes Cabernet Sauvignon, while kids visit with chickens, goats and pigs on the property’s animal sanctuary. For a fee, kids can enjoy a snack and an activity box. Advance reservations required.
• Cool down with a cone: You can smell the homemade chocolate from a block away as you approach Anette’s Chocolates. Perhaps best known for their artisan truffles, chocolate wine sauces and beer brittles, we’re hooked on their small-batch ice creams.

Evening

• Enjoy the nightlife al fresco: At this point, you’ve eaten all the eats, enjoyed sips of exquisite Napa Valley wines, so tonight you’re keeping it casual outdoors at Napa Yard Beer Garden where you may order a pulled pork slider or two, split the onion rings with housemade ranch, and let the kids pick familiar favorites from the children’s menu. Or maybe you can’t get that platter of Tamales Bay oysters on ice out of your head that you saw earlier this morning at Hog Island Oyster Co. at Oxbow Public Market, knowing there’s a Cowgirl Creamery grilled cheese or bowl of chowder to satisfy younger appetites. Either way, if you remembered to put the Schramsberg on ice, tonight the kids are going to bed early after dinner or reading the books they picked up at Bookmine, while you uncork some blanc de blancs and toast your success on a family road trip that your unimaginative friends assured you wasn’t possible without leaving the kids at home.

If you have three days

All of the above, but add…

• Explore weekend cooking and art classes at Connolly Ranch and learn about farm life, the role of animals and ecology through nature-based crafts, hikes and activities.
• One of the most storied and historic wineries in the region, Beringer Vineyards offers a “Sip and Stroll” outdoor experience for families. Upon arrival, select your favorite glass from the tasting menu and explore the expansive grounds and gardens at your leisure.
• If you can’t leave the area without a Michelin-approved experience, book a family dinner at Ciccio in Yountville. Housed inside a former Italian market, Ciccio serves up casual plates of pasta, fresh ricotta made daily, and a meatball-stuffed chard that is worth the visit alone. Try one of their excellent takes on the Negroni and order Italian cream sodas for the kids.

If you have four days, plus

All of the above, but add...

• You’ll be the only tourist in line at La Luna Market & Taqueria, tucked inside a Mexican market on the Rutherford Crossroad. The made-to-order Mission-style burritos are massive; ditto the quesadillas. Get your order to go and have a picnic at nearby Tres Sabores Winery, where they’ll set your table with linens, palm plates and silverware (advance reservation required) while you enjoy your burritos with an intimate and relaxed wine tasting amid century-old vines.
• Kids will thrill at the novelty of riding an aerial tram to reach the hilltop winery at Sterling Vineyards, where all can choose a self-guided tour enjoyed at your own pace—a lifesaver with fidgety kids—before relaxing on the patio with a cheeseboard, wine tasting and panoramic views.
• There are only three designated “old faithful” geysers in the world—so called because they regularly erupt—and one of them is in Calistoga. while you’re waiting for the geyser to erupt, which happens every 30-45 minutes, you can visit the Tennessee Fainting goats, as well as sheep and llamas, in the petting zoo. There’s also a geology exhibit, corn hole, and two bocce courts for the region’s unofficial pastime.