Top Healdsburg Tours, Sightseeing & Cruises

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.

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.

Go where cars can't and soak up the scenery of California wine country on a horseback ride in Sonoma County. With a guide, you'll have the chance to admire the vineyards of Dry Creek Valley and the waters of Lake Sonoma as you traverse the rolling wilderness on horseback. This experience takes you well beyond the beaten path and doesn't require any prior experience.

A great 90 minute introduction to the fascinating history of Healdsburg. Where else can you learn about history, get recommendations for shopping, art galleries, wine tasting, and restaurants and spend the day outside in the fresh air. You'll walk the streets with an experienced guide who will answer your questions and go at the only suitable pace for this city WALKING! You'll get an overview of the city, her history and the people that have made Healdsburg a destination for travelers since it's founding day. Discover why The Healdsburg Walking Tour is the best in town.

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.

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.

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.

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.

During the winter holidays, go food and wine tasting in northern California on a half-day walking tour in downtown Healdsburg. Sit for private guided wine tastings paired with foods from renowned local eateries in the heart of Sonoma's wine country. You might sample fresh baked goods, gourmet chocolates, and more at three tasting rooms. This tour takes place for just five weeks in November and December when Healdsburg sports colorful holiday decorations and lights, window displays, and a towering Christmas tree in the historic plaza.

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.

Our very unique, immersive adventures are the only ones of their kind. We, unlike other companies, provide your very own remote, interactive, live host to assist and encourage you along through your phone. We are an Austin, TX-based global custom event design company offering scavenger hunts and other events in 300+ cities in North America and beyond. Our specially hand-crafted adventures are equal parts tour, creative challenge, detective hunt, and social experiment! Guests get to discover in an alternate reality our favorite hidden gems off the beaten trail and creatively interpret fun art, history, and culture clues - for points! They get to enjoy fame and glory while appearing on our website’s international leaderboard, no matter what their score. They get to essentially race other teams in other cities, even if they don’t have competitors who have signed up in their city that day. Get ready to discover unusual oddities, laugh out loud, and make the experience your own!

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.

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.

Enjoy the fine dining experience in Style! We will welcome you in one of our luxury vehicles with a bottle of bubbles or rosé to enjoy on the way to dinner. Yes, you can drink in our vehicles! Need restaurant recommendations or information on setting up a private dinner for a special occasion? No problem, we are here to help you plan something special. **Tour details: You are purchasing a 3 hour dinner charter. Driver gratuity is not included and will be collected at the end of the tour. All tasting fees are not included in the price of the tour. ** About your host. Let Wine Tour Pros can help make your dinner transportation amazing.