Just north of San Francisco in the heart of Sonoma County lies the delightful city of Healdsburg. Surrounded by three major wine-producing regions, Russian River, Dry Creek, and Alexander Valley, this is truly wine country. This charming city is a treasure for food-lovers and offers stunning views as you bike along the rolling hills of grape vines.

Our newly redesigned California Wine Country 4-Day Weekend trip takes you through these captivating landscapes and lets you unwind in the charming epicenter of Healdsburg. Here you can sip on very good wine at countless wineries and tasting rooms and feast on equally good food at one of the award-winning restaurants. In a city where old-town culture combines with new, award-winning features, Healdsburg will in some way or another win your heart. When you’ve got the time to take in the city on your own, here’s where I would go to get the most out of my visit.

Ride past vineyards on Trek Travel's California Wine Country bike tour

Where To Go to Wander: Downtown Healdsburg
Just steps away from Hotel Healdsburg, take a stroll through the downtown center surrounding the town plaza. Each block is lined with charming shops, tasting rooms, galleries and outstanding restaurants. In true Wisconsinite-fashion, I search out specialty cheese shops to indulge in new bites of local flavors. Stop by the Cheese Shop of Healdsburg for local artisan cheeses and accoutrements and take your snacks and a blanket to the plaza for a relaxing afternoon picnic. Stop for a pick-me-up with the perfect cup of coffee at Flying Goat Coffee, or for a lovely cup of tea, chai, or hot chocolate. If you have Saturday morning available, be sure to visit the Farmers’ Market one block west of the Plaza to enjoy the the local food community.

Where To Go for Baked Goodss: Downtown Bakery & Creamery
Stopping in to this family run bakery is a must while visiting Healdsburg. Owner Kathleen opened this bakery in 1987 with her friends, all former colleagues at the award-winning and renowned Chez Panisse. Today Kathleen and her children run the bakery, serving up the best baked goods in the area. Using the best local and organic ingredients they can find, the quality of their creations is impeccable. Satisfy your post-biking sweet tooth with one (or two) of the famed sticky buns, or peel apart one of their fresh, buttery croissants. Don’t miss out on trying the cinnamon and sugar-dusted donut muffin that is raved about by locals and visitors.

Where To Go to Dine: Bravas Bar de Tapas
Healdsburg is considered the gourmet center of Sonoma County, and there is no shortage for where you can grab a really great bite to eat just a walk away from your hotel. Enjoy Bravas Bar de Tapas, awarded with “One of the top 20 tapas restaurants in the US” by Travel + Leisure and a “Top 100 Bay Area Restaurant” by the San Francisco Chronicle for the past three years. This tapas bar serves up traditional Spanish and modern tapas-style dining. Owners Mark and Terri Stark are James Beard nominees and own a few restaurants in Sonoma County, this one being their newest, and well-recognized already. They have created a relaxing and fun space to share plates and sip on a cocktail from their impressive drink menu. Sit out on the patio under romantic strings of lights and share the paella with a group of friends or try a selection of smaller plates. This restaurant is a top-choice for locals and visitors, so be aware of busy weekend nights. I’d recommend calling ahead to reserve a table, 707-433-7700. Read more culinary favorites by our Trip Design Manager Meagan Coates from her trip to California Wine Country, including Charlie Palmer’s Dry Creek Kitchen and h2’s Spoon Bar.

Visit Healdsburg SHED on Trek Travel's California Wine Country Luxury Cycling Vacation

Where to go for a snack and shopping: SHED
Winner of a 2014 James Beard Award for restaurant design, SHED is a community gathering space designed to bring us closer to the way we grow, prepare, and share our food. Part market, part café, part farm, this culmination is a delightful stop for fresh flavors and local shopping. Earlier this year we had the honor of interviewing owner Cindy Daniel to learn more about her creation of SHED. The offerings start with a large menu selection including beverages made at their fermentation or coffee bar and a café serving up combinations of fresh, local ingredients. While you’re there pick up artisan-made goods in their packed “pantry” that you won’t be able to resist perusing. Try a refreshing kombucha or shrub at their fermentation bar or a sandwich or salad from the café, grab a seat on the terrace and enjoy.

About Guest Choice:
You will often hear us say, “It’s your day, you decide,” because our smaller group size allows the flexibility for you to decide how your day unfolds. In addition to multiple daily ride options and shuttle flexibility, this also means that we offer ‘guest choice’ nights designed for you to indulge at a local restaurant of your choosing, or explore the local sites. Whether you want to order take-out while relaxing by the hotel pool or get dressed up for a fancy dinner in town, guest choice nights let you craft your own perfect evening.