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Top Healdsburg Luxury Tours

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Healdsburg Tours

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Sonoma Horseback-Riding Tour

Experience Wine Country's largest and most beautiful park on horseback on this 90-minute, guided, small-group tour. Discover hundreds of acres of vineyards and the crystal …More

Likely to Sell Out
Likely to Sell Out
5.0 (294)

Sonoma Horseback-Riding Tour

Experience Wine Country's largest and most beautiful park on horseback on this 90-minute, guided, small-group tour. Discover hundreds of acres of vineyards and the crystal...

70 to 90 minutes • Free Cancellation
5.0 (294)
from
$129
Guided Healdsburg Wine Country Bike and Wine Tasting Tour with lunch

On this moderate bike tour, we ride approximately 15 miles (24 km) in picturesque Dry Creek Valley, home to the town of Healdsburg. As you …More

5.0 (83)

Guided Healdsburg Wine Country Bike and Wine Tasting Tour with lunch

On this moderate bike tour, we ride approximately 15 miles (24 km) in picturesque Dry Creek Valley, home to the town of Healdsburg. As you...

5 hours 30 minutes • Free Cancellation
5.0 (83)
from
$209
Healdsburg Small-Group Food and Wine Walking Tour

Discover what makes Healdsburg one of Sonoma County's hottest destinations on this 3.5-hour food and wine walking tour of Healdsburg. Your local guide will share …More

5.0 (445)

Healdsburg Small-Group Food and Wine Walking Tour

Discover what makes Healdsburg one of Sonoma County's hottest destinations on this 3.5-hour food and wine walking tour of Healdsburg. Your local guide will share...

4 hours • Free Cancellation
5.0 (445)
from
$133
Full Day Guided Electric Bike Wine Tasting Tour with Lunch

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, …More

5.0 (42)

Full Day Guided Electric Bike Wine Tasting Tour with Lunch

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,...

6 hours • Free Cancellation
5.0 (42)
from
$199
Healdsburg Wine and Food Pairing Guided Walking Tour

This is Healdsburg's “original” Wine & Food Pairing Walking Tour. Our 4-hour guided taste adventure, hits all the gourmet highlights of charming Healdsburg, the hippest …More

4.9 (422)

Healdsburg Wine and Food Pairing Guided Walking Tour

This is Healdsburg's “original” Wine & Food Pairing Walking Tour. Our 4-hour guided taste adventure, hits all the gourmet highlights of charming Healdsburg, the hippest...

4 hours • Free Cancellation
4.9 (422)
from
$139
Half Day Guided Electric Bike Wine Tasting Tour with Lunch

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, …More

5.0 (55)

Half Day Guided Electric Bike Wine Tasting Tour with Lunch

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,...

4 hours • Free Cancellation
5.0 (55)
from
$169
History Walking Tour of Healdsburg

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 …More

5.0 (40)

History Walking Tour of Healdsburg

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...

1 hour 30 minutes • Free Cancellation
5.0 (40)
from
$45
Private Napa or Sonoma Wine Tour—Your Day, Fully Planned

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 …More

Likely to Sell Out
Likely to Sell Out
5.0 (13)

Private Napa or Sonoma Wine Tour—Your Day, Fully Planned

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...

7 hours • Hotel pickup offered • Free Cancellation
5.0 (13)
from
$750
Wine Tour Pros - Sprinter Van Wine Tour: Up To 14 Guests

Privately Driven Wine Tour Experience! We will welcome you in one of our luxury vehicles ready to go on your Napa wine tour adventure! Explore …More

5.0 (44)

Wine Tour Pros - Sprinter Van Wine Tour: Up To 14 Guests

Privately Driven Wine Tour Experience! We will welcome you in one of our luxury vehicles ready to go on your Napa wine tour adventure! Explore...

6 to 8 hours • Hotel pickup offered
5.0 (44)
from
$1,300
Deep Space Night Sky Tours in Sonoma County

Discover the universe in the serene setting of Sonoma County during our Premium Deep Space Night Sky Tours. Located in the picturesque Dry Creek Valley, …More

Likely to Sell Out
Likely to Sell Out
5.0 (1)

Deep Space Night Sky Tours in Sonoma County

Discover the universe in the serene setting of Sonoma County during our Premium Deep Space Night Sky Tours. Located in the picturesque Dry Creek Valley,...

1 hour 15 minutes • Free Cancellation
5.0 (1)
from
$96
Healdsburg 6 Hour Wine Tour with Luxury SUV - Seats up to 4

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. …More

5.0 (3)

Healdsburg 6 Hour Wine Tour with Luxury SUV - Seats up to 4

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....

6 hours • Hotel pickup offered • Free Cancellation
5.0 (3)
from
$599
Healdsburg Wine & Food Holiday Walking Tour

Offered for just five weeks each year, the Holidays in Healdsburg tours began in 2011 and have become a cherished seasonal tradition. Experience the magic …More

5.0 (36)

Healdsburg Wine & Food Holiday Walking Tour

Offered for just five weeks each year, the Holidays in Healdsburg tours began in 2011 and have become a cherished seasonal tradition. Experience the magic...

4 hours • Free Cancellation
5.0 (36)
from
$149
Wine Tour Pros - Napa Wine Tour: SUV Up To 6 Guests

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 …More

5.0 (4)

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

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...

6 hours • Hotel pickup offered
5.0 (4)
from
$950
Wine Tour Pros - Corporate Charters and Events

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 …More

4.5 (4)

Wine Tour Pros - Corporate Charters and Events

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...

4 to 6 hours • Hotel pickup offered
4.5 (4)
from
$1,300
Wine Tour Pros - Napa Hike with Wine
What’s included
  • Bottled water
  • Hotel pickup and drop-off (if option selected)
  • Glass of Champagne
  • Driver/guide

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 …More

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...

6 hours • Hotel pickup offered
from
$1,201
Wine Tour Pros
What’s included
  • Bottled water
  • Hotel pickup and drop-off (if option selected)
  • Glass of Champagne
  • fuel charge

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 …More

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...

6 hours • Hotel pickup offered
from
$1,450
Bodega Bay Sunset Tour

Privately Driven Tour Experience! We will welcome you in one of our luxury vehicles with a bottle of bubbles ready to go on your tour …More

Bodega Bay Sunset Tour

Privately Driven Tour Experience! We will welcome you in one of our luxury vehicles with a bottle of bubbles ready to go on your tour...

6 hours • Hotel pickup offered • Free Cancellation
from
$1,100

Frequently Asked Questions

These answers are based on answers previously given to Cool Destinations customers' questions.

Recent tour reviews
Our guide, Linda Cook,...
New York City
History Walking Tour of Healdsburg
Colette_P, Sep 2026
Our guide, Linda Cook,...
Our guide, Linda Cook, was extremely knowledgeable and friendly. Its obvious that she holds much pride for her beautiful city.
Read more
Fun Bike tour
New York City
Half Day Guided Electric Bike Wine Tasting Tour with Lunch
mayab142, Sep 2026
Fun Bike tour
Great trip through many vineyards. Will, was awesome. Vineyards were fun with great views!
Read more
Must do tour! Five star experience!
New York City
Healdsburg Small-Group Food and Wine Walking Tour
April_B, Sep 2026
Must do tour! Five star experience!
Must do your! Tammy is a wonderful resource of knowledge about the town. Amazing food and drink locations. Second time we have toured with Tammy and absolutely love her!
Read more
Happy Palate, Empty Glasses
New York City
Healdsburg Wine and Food Pairing Guided Walking Tour
N8534ZKamandas, Sep 2026
Happy Palate, Empty Glasses
What a lovely way to spend several hours of a weekend in Sonoma. Carol was a kind, attentive, and knowledgeable tour guide. All of our stops were so welcoming and educational without being too intense about it. The group size was perfect and my group of 3 got to mingle with 2 other pairs which made for nice conversation. The food completely changed the wine experience and I highly recommend if you have anyone that is iffy on wine or wants to just enjoy it more than they already do!
Read more
Emma was the best
New York City
Sonoma Horseback-Riding Tour
Jennifer C, Sep 2026
Emma was the best
We had an amazing trail ride on the backs of El Negro and Tucker led by Emma… she was so relaxed and put us on just the right horses for our experience level! If we ever get to the area again, we will for sure go for another ride!!
Read more
Do this trip!
New York City
Half Day Guided Electric Bike Wine Tasting Tour with Lunch
521lorib, Sep 2026
Do this trip!
Great day! Gorgeous bike ride through wine country, easy on the e-bike not challenging at all. Passed many vineyards, made stops at 2 which were amazing! Highly recommend this excursion.
Read more
A great way to visit wineries and get some exercise!
New York City
Guided Healdsburg Wine Country Bike and Wine Tasting Tour with lunch
pmk1025, Sep 2026
A great way to visit wineries and get some exercise!
We had a great time on the cycle trip ! Megan our host was fantastic! She said it was her first day touring alone, but you would have never known! The E Bikes were brand new and so easy to use! The choice of wineries were perfect… Family owned, which we really liked! Lunch was served in the winery which was also so enjoyable !! Highly recommend Getaway… would do it again!!!
Read more
Awesome!
New York City
Guided Healdsburg Wine Country Bike and Wine Tasting Tour with lunch
Q8246PWlisaw, Sep 2026
Awesome!
Can’t say enough about our experience. The E bikes are recommended. Megan our guide was amazing. The lunch provided was great and unlimited water. Loved the family owned wineries.
Read more
Super Fun Bike Tour
New York City
Full Day Guided Electric Bike Wine Tasting Tour with Lunch
mcb315, Sep 2026
Super Fun Bike Tour
Fabulous full day tour. Our guide Bill was very friendly, safety minded and informative. The bikes were great, the scenery was fantastic, the 2 wine tastings super fun and the lunch yummy. Great time had by all.
Read more
Great Tour!
New York City
Healdsburg Wine and Food Pairing Guided Walking Tour
843christief, Sep 2026
Great Tour!
Harold was a great guide - he knows the area well and offered several places for dinner - pairings were great and we learned quite a bit
Read more
We are so glad we booked...
New York City
Sonoma Horseback-Riding Tour
Miguel_L, Sep 2026
We are so glad we booked...
We are so glad we booked this experience for our family. The trail horse back ride was a really fun experience and very different than riding on the beach which we have done before. This Ranch sits on top of the lake and the overlooks are really cool and riding along the trail edges is exciting. The second part of the ride brought us into a pocket or Redwood trees which totally changes the landscape of the ride and feels like riding in Forrest. Thank you for a memorable experience in Sonoma and hope more people can experience your ranch and the Horses were all really well behaved :). Please give Amigo and Tucker a nice treat for us!
Read more
Great way to enjoy seeing the area around Healdsburg
New York City
Full Day Guided Electric Bike Wine Tasting Tour with Lunch
GoGoConnie, Aug 2026
Great way to enjoy seeing the area around Healdsburg
We had an outstanding day biking around Sonoma / Healdsburg area with Shannon. My friend and I booked the full day tour in late August, and it was hot, but the ebikes made it easy. Shannon tailored our day to fit what we enjoyed, and we rode about 25 miles with 2 lovely winery stops / tastings (Mount and Kokomo), a stop at a Dry Goods store, and at a local garden. Most of the riding was on roads shared with cars, but we felt comfortable since they were mostly backroads with light traffic. The ebikes were comfortable and easy to use. Shannon gave us a lot of information about the area history, the wineries and the plants we were seeing - having the miked helmets was great! Definitely would recommend this tour!
Read more
Amazing Gazing
New York City
Deep Space Night Sky Tours in Sonoma County
parthp780, Aug 2026
Amazing Gazing
Dan is great, walks you through everything in the sky and answers all questions. Worth trying!
Read more
Incredible service and experience!
New York City
Healdsburg 6 Hour Wine Tour with Luxury SUV – Seats up to 4
Susan_R, Aug 2026
Incredible service and experience!
Our experience was incredible. Wonderful driving service. I would recommend highly!!! Definitely will be a return customer.
Read more
Peaceful history walk
New York City
History Walking Tour of Healdsburg
277jaymeh, Aug 2026
Peaceful history walk
Linda was fantastic. She was very knowledgeable about the history of Healdsburg and very pleasant. The walk was fun and informative, and the stop at one of the local coffeehouses was a bonus. Highly recommended.
Read more
Wine Tour pros nailed it!
New York City
Wine Tour Pros – Sprinter Van Wine Tour: Up To 14 Guests
694tamin, Aug 2026
Wine Tour pros nailed it!
We did two days with Wine Tour Pros. Each day was filled with fabulous boutique wineries. These are the “hidden gems” that make Napa so much fun. Jeremy took the time to listen to our needs and planned our route perfectly. Our driver, Kristo was prompt and attentive. He took great care of us both days. The Mercedes Sprinter was nice classy and clean for our large group. Overall, I would book with them again and look forward to the next adventure with Wine Tour Pros!
Read more
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