Napa Valley is famous for incredible Cabernets, dreamy vineyard views, and tasting rooms that make you feel instantly on vacation. But here’s the delicious secret: Napa is also a chocolate-lover’s playground. When you pair the right wine with the right chocolate, something magical happens—fruit tastes juicier, tannins feel smoother, and suddenly you’re picking up flavors you swear weren’t there a second ago.
If you’re planning a Napa Valley wine and chocolate tasting day (or just want a “sweet stop” between wineries), this updated guide walks you through the best places to book a true chocolate-and-wine pairing, plus the top local chocolatiers where you can stock up for tastings, hotel-room pairings, or the ultimate picnic.
A quick guide to nailing a wine and chocolate tasting
Before we get into the best spots, here are a few tips that make the whole experience taste better:
- Go sweeter than you think. Chocolate is often sweeter than wine, so very dry wines can taste bitter next to it. Pairing works best when the wine is similarly “rich” (think lush reds, dessert wines, or sparkling with a touch of sweetness).
- Start light, end bold. Begin with white chocolate or milk chocolate, then move into dark and extra-dark.
- Small bites win. One small square of chocolate per sip is perfect. Big bites overwhelm your palate.
- Don’t skip water. A little water between pairings keeps each combo tasting fresh.
- Always check outside-food rules. Many Napa wineries don’t allow outside snacks—so buy chocolate for later unless the winery explicitly says it’s okay.
The best Napa Valley wineries for chocolate and wine tastings
Trinitas Cellars (Napa): a dedicated Chocolate & Wine Pairing
If you want a classic, purpose-built Napa wine and chocolate tasting, Trinitas Cellars is one of the easiest “yes” answers. Their Chocolate & Wine Pairing is specifically designed around the concept, and it’s described as seasonal, which is exactly what you want (fresh pairings that make sense with what’s in the glass). They also note the chocolates come from a local maker, making it feel very “Napa.” Trinitas Cellars
Good for: first-timers, couples, anyone who wants a straightforward pairing experience
Tip: book ahead—chocolate pairings are popular and often limited
Artesa Vineyards & Winery (Carneros): add a Premium Chocolate Pairing
Artesa is a gorgeous stop in Carneros with sleek architecture and big views—and it’s also a great place to work chocolate into your tasting. Their current “Taste of Artesa” experience includes optional enhancements, including a Premium Chocolate Pairing. It’s a nice way to keep your tasting elevated without turning it into a super long, formal program. Artesa Estate Vineyards & Winery
Good for: scenic tastings, groups that want customization (some do chocolate, some don’t)
Tip: if you’re doing chocolate here, lean into reds—Cab-forward pairings are often the crowd-pleaser
Rutherford Ranch Winery (Rutherford): a polished tasting stop (ask about chocolate options)
Rutherford Ranch is open daily and offers multiple tasting formats, including reservations through their site. While wine-and-chocolate pairings may not always be promoted as a standing experience, it’s still a strong winery to include on your “sweet sips” day—especially if you’re building your own pairings with chocolates you buy in town afterward. Rutherford Ranch Winery
Good for: classic Napa Cabernet country, easy planning, a reliable tasting experience
Tip: if chocolate is your priority, call or message and ask what pairing add-ons (if any) are currently available
B Cellars Vineyards & Winery (Oakville): food-and-wine pairings that often end in chocolate
If you love the idea of chocolate as part of a full culinary tasting, B Cellars is a standout. They’re known for food-and-wine pairings—and their published pairing menus regularly feature chocolate desserts (think items like chocolate crème brûlée or red-wine chocolate cake, depending on the season). B Cellars Winery
Good for: foodies, celebratory trips, anyone who wants a “course-style” tasting
Tip: this is a fantastic “one-and-done” experience if your group wants fewer stops but higher impact
Hess Persson Estates (Mount Veeder): wine, art, and occasional culinary pairings
Formerly known widely as The Hess Collection, Hess Persson Estates blends wine tasting with a serious contemporary art component—yes, you can tour the art collection when you visit. They’re open for tastings and have clear visitor details and reservation guidance. They also host special events that include wine paired with seasonal bites prepared by their culinary team (not always chocolate-specific, but often “treat-adjacent” around the holidays). Hess Persson Estate
Good for: art lovers, couples, “we want something different than the usual tasting room”
Tip: if chocolate is non-negotiable, look for limited-time events or pair Hess with a chocolatier stop afterward
Clif Family Winery (St. Helena): seasonal chocolate pairings + great food energy
Clif Family has a cozy tasting room on Main Street in St. Helena, plus a beloved food-truck program that keeps things fun and flavorful. They also publish seasonal events—like a Valentine weekend dessert + Cabernet pairing that specifically mentions chocolate. If your trip lines up with February (or holiday weekends), this is a smart place to watch for limited-time wine and chocolate experiences. Clif Family Winery
Good for: casual-but-quality tastings, foodie groups, Valentine vibes
Tip: even when a chocolate event isn’t running, it’s a perfect stop before/after a chocolate shop crawl in St. Helena
Notes on two names you might see online
A couple of businesses from older “wine + chocolate” lists have changed how (or whether) they host the public:
- O’Connell Family Wines / “Gabrielle Collection taste+”: the wine brand still exists online, but the “Gabrielle Collection taste+” tasting venue is reported as closed. If you’re set on trying these wines, look for alternative retail or event pours, and confirm any tasting plans directly. Clif Family Winery
- Yao Family Wines: the brand remains active, but tasting-room availability and chocolate-pairing details aren’t consistently posted in an official, bookable way. If this is on your must-do list, verify current hospitality options before you build a day around it. Yao Ming Wines
The best Napa Valley chocolate shops for pairing (or take-home gifts)
Vintage Sweet Shoppe (Downtown Napa): chocolate shop + wine tasting bar
This is one of the easiest “chocolate and wine in one place” stops in downtown Napa. They describe themselves as a handmade chocolate store with a wine tasting bar, and they’ve been around for decades—ideal if you want a low-lift pairing moment without committing to a full winery program. Vintage Sweet Shoppe
Anette’s Chocolates (Napa): two shops + chocolate tastings available
Anette’s is a longtime Napa favorite, and their own site notes two Napa locations and that chocolate tastings are available (with details tied to their gift/tasting offerings). It’s a perfect place to grab truffles, brittles, or wine-friendly bonbons before heading to your next reservation. Anette’s Chocolate Factory
Kollar Chocolates (Yountville): modern bonbons and a “wow” factor
Kollar is the “take your time and stare at everything” kind of chocolate shop—high-design, giftable, and fun. Their site notes the Yountville shop is open seven days a week, making it an easy add-on while you’re strolling V Marketplace. Kollar Chocolates
Woodhouse Chocolate (St. Helena): classic Napa Valley chocolate on Main Street
Woodhouse is a St. Helena staple, and their site clearly lists their Main Street location and hours. This is a great stop if you’re tasting up-valley and want something elegant to bring back to your hotel (or to nibble with that bottle you “accidentally” bought). Woodhouse Chocolate
La Forêt (Napa): small-batch, chef-driven chocolate
La Forêt is frequently highlighted as a Napa Valley artisan chocolate destination, known for small-batch production and a fine-dessert approach. If you love the “craft” side of chocolate—infusions, textures, seasonal creativity—this belongs on your list. Visit Napa Valley
What type of chocolate goes with wine?
Pairing wine and chocolate isn’t one-size-fits-all—different chocolates behave wildly differently. Here’s a practical cheat sheet you can actually use:
- Sparkling wine + white chocolate: bright bubbles + creamy sweetness = easy win
- Pinot Noir + milk chocolate: fruit-forward red + gentle cocoa is surprisingly harmonious
- Zinfandel / Syrah + dark chocolate: bold fruit and spice can stand up to cocoa richness
- Port / sweet dessert wines + very dark chocolate or nutty chocolates: the sweetness keeps everything balanced
The biggest rule: match intensity and (often) match sweetness. Chocolate coats your palate, and wines can taste sharp or bitter if they’re too dry next to it.
A simple (and fabulous) one-day Napa wine and chocolate itinerary
If you want an easy plan that doesn’t feel rushed:
- Late morning: a dedicated pairing at Trinitas or a scenic tasting with chocolate add-on at Artesa
- Lunch: keep it light—salads, seasonal veggies, grilled chicken, or a simple sandwich (save your palate!)
- Mid-afternoon: chocolate shop stop—Kollar (Yountville) or Woodhouse (St. Helena), depending on where you are
- Final tasting: a food-and-wine experience at B Cellars (if you’re going big) or a Main Street stop at Clif Family
- Evening: enjoy your “bonus chocolates” with a bottle back at your lodging (the coziest pairing of all)
FAQs
How can I do a wine and chocolate tasting in Napa Valley?
Book one dedicated pairing (like Trinitas), then add a chocolate shop stop to your day. If a winery doesn’t advertise chocolate pairings, you can still do a “pairing-style” tasting by enjoying chocolate afterward—many wineries don’t allow outside food during tastings, so buying chocolate in town keeps things simple.
Should I eat chocolate before a wine tasting?
If you’re doing a standard (non-chocolate) tasting, wait until after. Chocolate can dominate your palate and flatten delicate aromas—especially in white wines.
Can I bring chocolates to a winery?
Sometimes, but not always. Many Napa tasting rooms have strict policies on outside food. If you want to pair on-site, choose a winery that explicitly offers chocolate pairings or food options.
With years of expertise in curating unforgettable experiences, Vacation Napa brings you the ultimate guide to the best Napa Valley wineries for chocolate and wine tasting, ensuring an extraordinary journey through the region’s rich flavors.