Healdsburg Holidays
Top Healdsburg landmarks

Top Healdsburg Holidays

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17 results

Healdsburg Wine & Food Holiday Walking Tour
4.9
(34)

Healdsburg Wine & Food Holiday Walking Tour

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.
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  • 4 hours
  • Free Cancellation
from
$129
Sonoma & Healdsburg Wine Tours
5.0
(15)

Sonoma & Healdsburg Wine Tours

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.
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  • 6 hours
  • Free Cancellation
from
$675
per group
Healdsburg Small-Group Food and Wine Walking Tour
5.0
(370)

Healdsburg Small-Group Food and Wine Walking Tour

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 six people for a more intimate experience.
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  • 4 hours
  • Free Cancellation
from
$133
Icon Wine & Food Pairing at Williamson Wines in Healdsburg
4.9
(64)

Icon Wine & Food Pairing at Williamson Wines in Healdsburg

Experience an intimate winetasting at Williamson Wines in Healdsburg. During your tasting experience, you'll learn about wine pairings and meet the winemakers. Taste four 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.
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  • 1 hour 30 minutes
  • Free Cancellation
from
$50
Guided Electric Bike Wine Tour Through Sonoma County
5.0
(7)

Guided Electric Bike Wine Tour Through Sonoma County

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.
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  • 6 hours
  • Free Cancellation
from
$199
Healdsburg Wine and Food Pairing Guided Walking Tour
4.9
(363)

Healdsburg Wine and Food Pairing Guided Walking Tour

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.
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  • 4 hours
  • Free Cancellation
from
$132
Guided Healdsburg Wine Country Bike and Wine Tasting Tour with lunch
4.9
(74)

Guided Healdsburg Wine Country Bike and Wine Tasting Tour with lunch

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.
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  • 5 hours 30 minutes
  • Free Cancellation
from
$270
7 Hour Private Wine Tasting in Napa or Sonoma Valley
5.0
(8)

7 Hour Private Wine Tasting in Napa or Sonoma Valley

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.
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  • 7 hours
  • Free Cancellation
from
$650
per group
Wine Tour Pros - Corporate Charters and Events
3.8
(5)

Wine Tour Pros - Corporate Charters and Events

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.
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  • 4 to 6 hours
from
$1,300
per group
6 Hours Healdsburg Wine Tour with Luxury SUV
5.0
(1)

6 Hours Healdsburg Wine Tour with Luxury SUV

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. Tour is 6 hours so if you finish early at these wineries we can always add another stop.
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  • 6 hours
  • Free Cancellation
from
$699
per group
Wine Tour Pros - Napa Wine Tour: SUV Up To 6 Guests
5.0
(4)

Wine Tour Pros - Napa Wine Tour: SUV Up To 6 Guests

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.
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  • 6 hours
from
$950
per group
Vintner's Private Wine Tasting Experience

Vintner's Private Wine Tasting Experience

Don't just taste with a sales associate or wine guide. Get the story right from the owner/wine maker's mouth. Take the wine from the source, sample products that are in various stages of production, and make yourself feel like part of the family.
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  • 1 hour 30 minutes
  • Free Cancellation
from
$20
Wine Tour Pros - Dinner Transportation: SUV for Up To 6 Guests

Wine Tour Pros - Dinner Transportation: SUV for Up To 6 Guests

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.
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  • 3 hours
from
$444
per group
Wine Tour Pros - Airport Pickup to Napa or Sonoma

Wine Tour Pros - Airport Pickup to Napa or 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.
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  • 2 hours
from
$525
per group
Wine Tour Pros - Napa Hike with Wine

Wine Tour Pros - Napa Hike with Wine

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!  
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  • 6 hours
from
$1,201
per group
Wine Tour Pros

Wine Tour Pros

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!  
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  • 6 hours
from
$1,450
per group
6 Hours Private Wine Tour in Healdsburg Featuring Coppola Winery

6 Hours Private Wine Tour in Healdsburg Featuring Coppola Winery

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.
... More
  • 6 hours
  • Free Cancellation
from
$699
per group
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