Top Healdsburg Holidays

Maximize time in Sonoma with a private, customized wine tour. Visit boutique wineries for guided tastings for a group of up to six people. Personalize the experience according to your interest in certain varietals, appellations, or experiences. Skip the hassle of a rental car and leave the driving up to your guide as you explore scenic Sonoma and Healdsburg.

Embark on a guided electric bike wine tour through Sonoma County with an experienced tour guide. Cruise through vineyards along scenic routes on zippy e-bikes, stopping at two top local wineries to taste the exceptional rosés, whites, and reds this famed region is known for. Your knowledgeable tour leader will provide insights into Sonoma's winemaking history, ensure everyone is safe and comfortable, and share the best of what Sonoma County has to offer. Enjoy a memorable and informative journey through Sonoma's wine country.

Master the art of pairing wine with food and enjoy a delicious meal and four different wines while you're at it with this experience at Williamson Wines. A host will guide you through some of the winery's offerings and bring flavorful wines and dishes to your table that have been carefully selected to pair perfectly.

Learn about the art of wine-and-food pairing as you embark on a walking tour through Healdsburg. Join a small group of food lovers and sample Sonoma’s best bottles and bites as you explore local venues. From local cheeses, jams, and unique dishes, each pairing makes you rethink the way you experience food and wine. Learn about the area's thriving culinary scene and hear the stories behind Sonoma’s family vineyards.

This Healdsburg-focused wine tour promises a day filled with exceptional wines, picturesque vineyards, and delectable culinary experiences, all within the delightful timeframe of 6 hours. This is a black SUV, holds up to 4 passengers, your party only will participate in the tour. It's your day: Tour is fully flexible to stop at wineries or locations you choose. You may stay as long as you like at any stop which will determine how many stops on your tour. If you are not sure where you would like to stop or see, driver can suggest. Wine tasting fees are not included and reservations are generally requested in advance. Special Note: This tour offers options for Concierge Reservations or to extend your tour by 2 hours, see options in checkout. PLEASE PRINT THIS PAGE SO YOU WILL HAVE WINERY LOCATIONS FOR MAKING TASTING RESERVATIONS..

Bike through Dry Creek Valley in Sonoma County on a small-group wine tour from Healdsburg. Taste wines (own expense) and stop for a picnic lunch at a winery. You'll pedal through California's back roads at a leisurely pace on a tour that covers around 15 miles (24 kilometers) with regular stops for wine tastings. Your guide shares commentary about California wine country along the way. Includes lunch, bottled water, guide, and use of bike equipment.

Sample the best of wine country on this food and wine tour of Healdsburg. Led by a local guide, stroll the charming town and progressively dine your way through several local establishments, including a highly acclaimed tapas bar, a farm-to-fork jewel, and a wine boutique. Learn about the sustainable methods of the chefs and winemakers, and treat your taste buds along the way.

Craft your perfect day in Wine Country. Tailored tours, hidden gems, and genuine hospitality. Let me be your guide. Unlike most wine tours, I fully customize the experience for each guest, ensuring they have the best day possible in Wine Country. After booking, I send my guests a questionnaire that I reference to plan their day based on their wine preferences, budget, and overall experience. Backed by years of hospitality experience at world-class wineries, I possess unique industry connections to unlock doors even the general public can't reach. Having personally visited over 300 wineries myself, I have a wealth of knowledge to connect you with your new favorite hidden gems. Easygoing and passionate about hosting, I love sharing my love for Wine Country and showing you a truly unforgettable time.

Your guide leads a relaxed electric trike ride that begins at Bacchus Landing, a vibrant Healdsburg gathering place with seven boutique wineries. Drive eco-friendly electric trikes and follow the professional tour guides who will share the breathtaking beauty and immersive history of the area. Each tour includes a complimentary charcuterie board, featuring local cheeses, meats and seasonal accompaniments. Your visit concludes with a guided tasting at Bacchus Landing (prices vary).

Embark on a guided electric bike wine tour through Sonoma County with an experienced tour guide. Cruise through vineyards along scenic routes on zippy e-bikes, stopping at two top local wineries to taste the exceptional rosés, whites, and reds this famed region is known for. Your knowledgeable tour leader will provide insights into Sonoma's winemaking history, ensure everyone is safe and comfortable, and share the best of what Sonoma County has to offer. Enjoy a memorable and informative journey through Sonoma's wine country.

Northern California is famous for its wine country but it can be difficult to navigate on your own. Book a Sprinter van and driver to transport your group to several wineries over the course of a day. Start your day off with a glass of sparkling wine and then head to the vineyards of your choice, or let your driver select a few for a well-rounded experience of Napa and Sonoma.

With years of hospitality experience at world-class wineries and strong industry relationships, I’m able to unlock access to hidden-gem producers and sought-after cult labels that typically require connections and advance planning. Having personally visited 300+ wineries, I know where the truly special experiences are—and how to create a collector-focused day that’s worth your time and cellar space. Most importantly, you’ll have a professional, discreet host focused on delivering a seamless, high-touch experience from pickup to drop-off—so you can taste at a higher level and experience Wine Country like an insider.

Whether you’re just arriving in California or your trip is ending, this private transfer service gets you where you need to go. Meet your driver at your accommodation in Napa Valley or Sonoma County and enjoy a swift transfer to any of the Northern California airports, for a timely departure. This transfer service can also be done in the reverse.

This Healdsburg-focused wine tour promises a day filled with exceptional wines, picturesque vineyards, and delectable culinary experiences, all within the delightful timeframe of 6 hours. This is a black SUV, holds up to 4 passengers, your party only will participate in the tour. It's your day: Tour is fully flexible to stop at wineries or locations you choose. You may stay as long as you like at any stop which will determine how many stops on your tour. If you are not sure where you would like to stop or see, driver can suggest. Wine tasting fees are not included and reservations are generally requested in advance. Special Note: Concierge Winery Reservation Service is available for this tour, please add in checkout if desired. PLEASE PRINT THIS PAGE SO YOU WILL HAVE WINERY LOCATIONS FOR MAKING TASTING RESERVATIONS.

Gather your coworkers and colleagues together for a trip around Napa Valley's best wineries aboard this corporate charter vehicle. Meet your driver and enjoy a bottle of sparkling wine to start off your adventure. Then visit several wineries, chosen by you or suggested by your driver, and purchase wine tastings, if you'd like. This is a great way to break the ice or start off a corporate event.