Top Healdsburg Tours, Sightseeing & Cruises

Sample Sonoma’s best bottles and bites on this wine-and-food pairing walking tour through Healdsburg’s charming downtown. Join a small group of food lovers as you follow your foodie guide to bakeries, wine shops, and cafés, and taste local fare along with wines from distinctive cellars. Try creative dishes, artisan cheese, and charcuterie, learn about wine country's thriving culinary scene and hear the stories behind Sonoma’s family vineyards.

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. This small-group tour is limited to eight people for a more intimate experience.

Bike through Dry Creek Valley in Sonoma County on a full-day wine tour from Healdsburg. Taste wines and stop for a lunch of fresh local goods at a winery. You'll pedal through California's back roads at a leisurely pace on a tour that covers about 20 miles (32km) with regular stops for wine tastings. Your guide shares commentary about the history of northern California and the region's wine industry along the way. Includes lunch, bottled water, guide, and use of bike equipment.

Experience an intimate wine-tasting at Williamson Wines in Healdsburg. During your tasting experience, you'll learn about wine pairings and meet the winemakers. Taste 5 wines, such as cabernet sauvignon, sauvignon blanc, chardonnay and pinot noir. While you try some of California's best varietals, learn about how to best pair them with food at home. Munch on snacks like stuffed mushrooms, blue cheese, dark chocolate brownies and honey-drizzled local pears. Tour scheduling and duration varies and is flexible according to your needs.

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.

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.

Plan a safe and luxurious day of wine tasting in the world-famous Napa Valley with a private chauffeured tour. A professional driver picks you up in San Francisco, Napa, or Sonoma in a luxury SUV with a welcome glass of bubbly. Choosing among hundreds of wineries can be daunting, but your driver and guide will help you select a handful of Napa's best estates based on your personal tastes.

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.

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.

Discover the best that Napa Valley has to offer on a private tour to the wineries of your choice. This customizable trip makes visiting several vineyards in a day easy. Tell your driver which estates you’d like to visit and enjoy a relaxing journey, with complimentary bubbles, to each one. Spend a day imbibing, exploring, and learning about wine all without the worry of driving.

Privately Driven Wine Tour Experience! We will welcome you in one of our luxury vehicles with a bottle of bubbles or rosé ready to go on your tahoe ski adventure! Yes, you can drink in our vehicles! Carefree ride up to ski. Drink or nap on the way home. What a perfect day!  **Tour details: You are purchasing a 6 hour tour. Driver gratuity is not included and will be collected at the end of the tour. Subject to weather conditions. About your host. Jeremy is labeled “The King of All Wine Tours”. He and his team have their own intimate and unique knowledge of the Napa Valley and surrounding area. Every tour is an adventure to celebrate their community in the Napa Valley. With friendships made organically over the years with vineyard owners, wine makers, chefs and vineyard host educators we can provide the very best experience available. Group photo available! Just ask your driver to take a memorable photo of your group.

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.

Privately Driven Wine Tour Experience! We will welcome you in one of our luxury vehicles with a bottle of bubbles ready to go on your Napa wine tour adventure! Yes, you can drink in our vehicles! Explore the best wineries in Napa Valley while finding out some of its secrets.  **Tour details: You are purchasing a 6 hour tour. 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. Jeremy is labeled “The King of All Wine Tours”. He and his team have their own intimate and unique knowledge of the Napa Valley and surrounding area. Every tour is an adventure to celebrate their community in the Napa Valley. With friendships made organically over the years with vineyard owners, wine makers, chefs and vineyard host educators we can provide the very best experience available. A group photo from your trip will also be provided so you can commemorate your amazing time spent in Napa!  

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!

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.

Privately Driven Wine Tour Experience! We will welcome you in one of our luxury vehicles with a bottle of bubbles or rosé ready to go on your hike and wine tour adventure! Yes, you can drink in our vehicles! A short hike and wine tasting! **Tour details: You are purchasing a 6 hour tour. 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. Jeremy is labeled “The King of All Wine Tours”. He and his team have their own intimate and unique knowledge of the Napa Valley and surrounding area. Every tour is an adventure to celebrate their community in the Napa Valley. With friendships made organically over the years with vineyard owners, winemakers, chefs and vineyard host educators we can provide the very best experience available. A group photo from your trip will also be provided so you can commemorate your amazing time spent in Napa!  

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 6 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. If you know specific wineries, points of interest or lunch spots you wish to see or visit, please contact us in advance. While admission to wineries is free, reservations for wine tastings are required at most wineries. Let us know in advance of any stops you would like to make.

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. 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.

Cycling enthusiasts this is an amazing opportunity to discover and experience car-free paved trails, quiet country roads, challenging climbs, exhilarating descents and unforgettable vistas. Unlike other Napa Valley bike tour companies, cycling is the focus and winery and food experiences are the icing on the cake. Our tours range in length from 25-60 miles and depend on whether you choose a half-day, full-day and what wineries to visit. Our guides are avid local cyclists who provide friendly hospitality and personalized route customization based on your fitness level, skills and interests. They also have deep knowledge of our wineries, terroir and best lunch/picnic spots. Private tours are available for when you pay for a group of at least 4 people (i.e. you pay for at least 4 people, but you could be one person). Please let us know you want your tour to be private after booking.