Experiencing a Weekend in Napa with Three Generations

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It’s safe to say that multigenerational travel can be a bit stressful at times, but when it’s done right, beautiful memories are made. Guest contributor, Whitney Rider, is taking us along with her family as they take three generations to spend a fun weekend in Napa Valley.

Michelin-starred food, grape-covered hillsides, and afternoon wine tastings—it’s no secret why more than three million visitors make the trip to California’s Napa Valley. But try to plan a three-generation weekend trip, including a toddler, and tippling through wine country might not make the top of your list.

Don’t write it off too quickly though. With the right planning, a multigenerational weekend in Napa Valley can make everyone happy.

Weekend in Napa itinerary

Grandpa and toddler looking out over a Napa vineyard
Taking in the valley views.

Of course, for most adults, the star attraction is the wine, so let’s start there. It’s true that most wineries do not appreciate, or do not allow, persons under 21 in their tasting rooms.

A reminder—you are in beautiful Napa. Who wants to stand around in a crowded tasting room?

Many wineries offer full tastings in their outdoor spaces and several are particularly suited to children. One of our favorites was Frog’s Leap. Not only are the wines terrific, but a garden or patio tasting allows everyone to enjoy the organic gardens. And our toddler loved exploring the grounds, visiting the barn, and playing with the winery dog.

Toddler in a green coat smelling pink tulips on a multigenerational weekend in Napa Valley
Someone knows how important it is to stop and smell the tulips …

Your multi-generational group might also like Sterling Winery, which features a unique gondola ride up to its scenic grounds. Castello di Amorosa, not only looks like a real castle, but has a moat, free-roaming animals, and a guided tour for children 5-20 years. If you have the energy, you can also conduct your touring by rented bicycle.

While you are enjoying your tastings, you’ll need to balance your wine with some of Napa’s renowned food. Ironically, many wineries are prevented by regulation from serving real food, but a few have meal-worthy nibbles.

Long Meadow Ranch, which offers 4×4 tours of its grounds, also hosts a substantial farmers market, a popular burger, and live music when weather permits. V. Sattui’s grounds are a great place to take advantage of their extensive deli options plus BBQ or pizza offered on the weekends.

Where to eat on a multigenerational weekend in Napa Valley

Many wineries are happy to allow visitors to bring their own picnics and relax on the grounds with a bottle of wine from the winery. Stop at Oakville Grocery to pick up photo-worthy sandwiches, salads, and cookies for your own brown bag lunch.

Several of Napa’s other iconic stops are also kid-friendly, including Boon Fly Café, known for its donuts, and Gott’s Roadside (formerly Taylor’s Refresher), a classic drive-up grill. It’s always packed, but the fenced picnic area is good for kids to wait. The Oxbow Public Market next door has a dozen dining and shopping options.

The rustic building of Bistro Jeanty in Napa
The charming front entrance of Bistro Jeanty.

When it comes to splurge meals, the options are endless. Our clan had a delicious, if button-popping, lunch on the relaxed outdoor patio at Bistro Jeanty, Napa’s only French-owned and operated restaurant. R+D Kitchen, the Hillstone family restaurant at the other end of town, also features casual outdoor dining, with charming Adirondack chairs clustered around fire pits. Conveniently, both venues are just blocks from a public park so you can wear out any rambunctious youngsters before sitting to lunch.

Weekend in Napa Valley
Finding fun along the scenic walk to Villagio’s Marketplace.

To stay awake (and still fit in your pants) you’ll have to space out your gluttony, but we managed to sneak in one more memorable meal at Brasswood Bar + Kitchen. Brasswood is not ideal for young children, so we sought out some babysitting assistance to enjoy some adult-only time for our final dinner. If you don’t have a local referral, there are several services in the area.

Where to stay on a family weekend in Napa

open air walkway in Napa Valley
Villagio’s open air walkway.

Continuing our kid-friendly outdoor theme (noticing a pattern here?), the Villagio Inn and Spa provides rooms and suites with patios and balconies, all connecting to a landscaped open air walkway with fountains, aqueducts, and statues.  The walkway extends to V Marketplace, a high-end market with several restaurants opening out on manicured lawns where our toddler member delighted in running around while we enjoyed wine and chocolate.

toddler playing in a fountain
Playing in the fountains.

If you still have any room left, you can always partake of the Napa Valley Wine Train. We didn’t have the time, so I guess we’ll have to come back! After we take some time to digest…

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