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Napa & Sonoma Luxury & Special Occasions

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Napa & Sonoma Tours

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Flying Dress Photoshoot Experience in Napa or Sonoma
5.0 (1)

Flying Dress Photoshoot Experience in Napa or Sonoma

Step into a world of empowerment and beauty with the Flying Dress Experience, designed exclusively for women who want to celebrate themselves. This unique photography...

2 hours • Hotel pickup offered • Free Cancellation
5.0 (1)
from
$500
Napa Valley Wine Tour: Self-Guided GPS Audio Driving Guide
5.0 (1)

Napa Valley Wine Tour: Self-Guided GPS Audio Driving Guide

Drive Napa Valley yourself, with a GPS audio guide that plays automatically as you go. Your booking unlocks the whole region in the free Wine...

2 to 12 hours • Free Cancellation
5.0 (1)
from
$40
Sonoma Valley Open Air Wine Trolley Tour
4.7 (852)

Sonoma Valley Open Air Wine Trolley Tour

Experience the Sonoma wine region in a unique way – on a San Francisco-style trolley, for an open-air ride through rustic, sun-kissed Sonoma Valley. Stop...

6 hours 30 minutes • Free Cancellation
4.7 (852)
from
$145
Napa Valley Wine Trolley Classic Tour
4.6 (762)

Napa Valley Wine Trolley Classic Tour

Come join the “original” cable car wine tasting tour through beautiful Napa Valley. Hop aboard one of our hand-built replicas of a San Francisco Cable...

6 hours 30 minutes • Free Cancellation
4.6 (762)
from
$145
Napa Valley Daily Join In Group Wineries Tour Including Lunch
4.6 (446)

Napa Valley Daily Join In Group Wineries Tour Including Lunch

We offer join-in daily group wine tours from Napa. You will feel you’ve experienced the wine country's beauty and enjoyed great wine. These join-in wine...

6 to 7 hours • Hotel pickup offered • Free Cancellation
4.6 (446)
from
$135
Napa Valley Wine Train with Gourmet Lunch
4.5 (411)

Napa Valley Wine Train with Gourmet Lunch

Step back in time aboard the Gourmet Express, where elegant details like gleaming silverware, crystal-clear glassware, etched glass partitions, rich mahogany paneling, and warm natural...

3 hours
4.5 (411)
from
$278
Napa Valley Wine Trolley Castle Tour
4.4 (289)

Napa Valley Wine Trolley Castle Tour

Experience the Napa wine region in a unique way – on the Napa Valley Wine Trolley. Hop aboard the Original San Francisco Cable Car Wine...

6 hours 30 minutes • Free Cancellation
4.4 (289)
from
$145
Safari West Sonoma Adventure Tour
Likely to Sell Out
Likely to Sell Out
4.7 (124)

Safari West Sonoma Adventure Tour

Meet Giraffes in Sonoma County Step into the heart of Sonoma County’s African Serengeti wildlife preserve. Climb aboard an open-air safari vehicle for an unforgettable...

3 hours • Free Cancellation
4.7 (124)
from
$110
Napa Valley Wine Train Vista Dome Lunch Car
4.4 (50)

Napa Valley Wine Train Vista Dome Lunch Car

Embark on an immersive three-hour journey featuring panoramic 360-degree Napa Valley views, plush dining booths, and unforgettable photo opportunities with your travel companions. The Vista...

3 hours
4.4 (50)
from
$410
Napa Valley & Sonoma Self-Guided Audio Driving Tour
4.5 (43)

Napa Valley & Sonoma Self-Guided Audio Driving Tour

Cruise through California wine country with this scenic self-guided driving tour of Sonoma and Napa Valley. As you drive, you’ll get tips about the wineries...

2 to 4 hours • Free Cancellation
4.5 (43)
from
$25
Healdsburg Cycling Wine Tour
4.7 (17)

Healdsburg Cycling Wine Tour

Bike with this group tour as you ride along the beautiful rolling hills of vineyards through the Russian River Valley Region! You will get some...

4 hours 30 minutes • Free Cancellation
4.7 (17)
from
$199
Private Chauffeured Winery Tour
4.3 (6)

Private Chauffeured Winery Tour

Experience the magic of Napa Valley with your wine country chauffeured private car service, in a Chrysler Town & Country luxury minivan, leather interior, premium...

6 hours • Free Cancellation
4.3 (6)
from
$500
Napa River Small-Group History Tour by Tandem Kayak
4.7 (6)

Napa River Small-Group History Tour by Tandem Kayak

See a side of Napa Valley that most visitors miss on a small-group paddle along the Napa River. Share a two-person tandem kayak as a...

2 hours • Free Cancellation
4.7 (6)
from
$69
Sonoma Trike and Hike - 3 hour guided tour
4.6 (5)

Sonoma Trike and Hike - 3 hour guided tour

A twist on our regular tours, for anybody who wants to skip the wine tasting and see some more nature! Join us for your guided...

3 hours • Free Cancellation
4.6 (5)
from
$175
8 Hour Private Tour in Napa Valley Winery
4.6 (5)

8 Hour Private Tour in Napa Valley Winery

World class wines, breathtaking views and a professional chauffeur in a private luxury vehicle will make Napa Valley wine tasting tour experience unforgettable....

8 hours • Hotel pickup offered
4.6 (5)
from
$849
Wine Tour Pros - Corporate Charters and Events
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
Custom 8-Hour Napa Valley Wine Tour in a Luxury Vehicle
4.7 (3)

Custom 8-Hour Napa Valley Wine Tour in a Luxury Vehicle

Experience Napa Valley your way with a private, fully customizable wine tour and professional chauffeur. Travel in the comfort of your luxury vehicle while taking...

8 hours • Hotel pickup offered
4.7 (3)
from
$815
Napa Valley Wine Train with Gourmet Dinner
3.9 (57)

Napa Valley Wine Train with Gourmet Dinner

Spend your evening aboard the Gourmet Express, where time slows down and classic rail travel meets elevated dining. This relaxed evening excursion invites guests to...

2 hours 30 minutes
3.9 (57)
from
$278
Self Guided Full Day E-bike Rental With Picnic Lunch
4.0 (7)

Self Guided Full Day E-bike Rental With Picnic Lunch

FREE $300 of complimentary wine tastings with your rental. Our ebikes make your self guided tour of the napa valley an unforgettable experience. Cruise past...

3 to 8 hours • Free Cancellation
4.0 (7)
from
$159
8 Hour Private Napa Wine Tasting Tour with a Sample Stops
4.0 (4)

8 Hour Private Napa Wine Tasting Tour with a Sample Stops

Begin your Napa Valley experience with private pickup in a luxury vehicle at the location and time of your choice. Spend the day visiting 3–4...

8 hours • Hotel pickup offered
4.0 (4)
from
$849

Frequently Asked Questions

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

Recent tour reviews
Worth it for the drive alone
New York City
Napa Valley Wine Tour: Self-Guided GPS Audio Driving Guide
Michael_W, Sep 2026
Worth it for the drive alone
Used this for a day in Napa with my wife and a friend. Entered the Cool Sonoma code in the app, picked three wineries, it mapped the drive. Audio started on its own as we got near each place and gave some background on the property, a couple of minutes each. Also talked on the road between stops, which we didn't expect. Download it before you leave town, signal is patchy up valley. Otherwise no complaints. Cheaper than a guide and we went at our own pace.
Read more
Great activity
New York City
Napa Valley Wine Trolley Classic Tour
Jessica_W, Sep 2026
Great activity
Had to much fun. Richard our guide was great and learned lots about the Napa Valley area and the wine tasting at the different Vineyards were great.
Read more
Paul was the absolute...
New York City
Napa Valley Wine Trolley Classic Tour
Jen_D, Sep 2026
Paul was the absolute...
Paul was the absolute best guide, and really made the whole experience so fun and amazing. Each vineyard we went to had a different vibe, fantastic wine, a delicious lunch, and we met beautiful people from all over the country that we even hung out with after the tour. It was one of the highlights of our Napa girls trip and I highly recommend!
Read more
Napa Train Ride For Lunch
New York City
Napa Valley Wine Train Vista Dome Lunch Car
819alexandriac, Sep 2026
Napa Train Ride For Lunch
It was a really nice and relaxing experience in the Vista Dome with beautiful scenery and views. Staff was professional and friendly, and food was top notch. Only thing I would say is the bathrooms and speaker system need to be upgraded, and they need to have better climate control because it was cold and the AC was really loud. Other than that, I enjoyed the experience.
Read more
Hemingfield’s/Reid’s
New York City
Napa Valley Wine Train with Gourmet Lunch
O6369WNjaner, Sep 2026
Hemingfield’s/Reid’s
Excellent experience all around - food was first class and whole journey was helped by having Jamie as our waitress
Read more
Napa Valley Wine Train
New York City
Napa Valley Wine Train with Gourmet Lunch
richardeL4807LO, Aug 2026
Napa Valley Wine Train
Great experience. Mark was wonderful. Highly recommend taking the Napa Valley Wine Train. Lunch was very good.
Read more
Superb
New York City
Napa Valley Wine Train Vista Dome Lunch Car
EG2007, Aug 2026
Superb
We took this train trip for my husband’s birthday. The train itself is beautiful inside and out. The dome car is very plush and offers excellent views. From the moment we sat down until the time we disembarked our waiter Max was very attentive. The food was superb and the wines were wonderful. Maxx provided many interesting facts about the areas we traveled through and when we asked for a recommendation on wine he did not disappoint! Overall it was a wonderful trip and well worth the money.
Read more
Highly recommend the trolley tour!
New York City
Sonoma Valley Open Air Wine Trolley Tour
Tracy_W, Aug 2026
Highly recommend the trolley tour!
Our driver, Paul, was knowledgeable and fun! We went to 4 different wineries and enjoyed all of them. One of the highlights for us was getting to know the other people on the tour. It was a fabulous group!
Read more
Best driver in the Napa area!!
New York City
Private Chauffeured Winery Tour
Voyager11347365622, Aug 2026
Best driver in the Napa area!!
Paula made everything so very easy! We told her our likes answered a few questions and she booked us the most fabulous day!! She shopped for our lunch and it was amazing. Had cool waters ready for us and it truly was door to door service!! Infact, we loved her so much we had her create another day for us! We booked another day!! And it was just as amazing. She really knew the best places to take us based on questions we had answered!! Best trip ever! We can’t wait to come back!!
Read more
Worth it!
New York City
Napa Valley Daily Join In Group Wineries Tour Including Lunch
Ariel_B, Aug 2026
Worth it!
It was a wonderful day! The wineries we went to and the food was great! Our driver was knowledgeable and even took us into an art gallery.
Read more
Sonoma Winery Trolly tour
New York City
Sonoma Valley Open Air Wine Trolley Tour
Y1044PGconniet, Aug 2026
Sonoma Winery Trolly tour
Paul was Super! Lunch was excellent! Would recommend
Read more
Drive and learn
New York City
Napa Valley & Sonoma Self-Guided Audio Driving Tour
AmazinginAK, Jul 2026
Drive and learn
Excellent narration. The voice of the narrator is pleasant and easy to understand. It is able to pick up where it left off, even if it’s days later, because you did something else. Loved to learn all the tid-bits and history. Great drive and learn, definitely recommend it, if you need a guide and want to drive Sonoma- Napa on your own pace.
Read more
Hosts were nice and...
New York City
Napa Valley Wine Trolley Castle Tour
Jean_H, Jul 2026
Hosts were nice and...
Hosts were nice and helpful. The castle was the highlight id the 3 stops!! You can opt out of the tastings if you wish. The lunch spit was delish! The second two wineries were less impressive. Would be nice to add a stop that includes a tour of the vineyard!
Read more
Tour places from your car
New York City
Napa Valley & Sonoma Self-Guided Audio Driving Tour
Veena_R, Jul 2026
Tour places from your car
The Audio Tour is amazing if one wants to drive around a place and hear interesting and fun stories about each stop on the tour. We learnt a lot about wines and their owners and all the other places along the route. It's easy to download onto your phone and then connect it to your car so you can listen while driving.
Read more
Vacation Wine Train event
New York City
Napa Valley Wine Trolley Castle Tour
Tommy_P, Jul 2026
Vacation Wine Train event
The wine Train had great personal services all the way from the check-in service , to train boarding and staff on board the train.
Read more
Photos to last a lifetime!
New York City
Flying Dress Photoshoot Experience in Napa or Sonoma
bondilynj, Jun 2026
Photos to last a lifetime!
My husband and I had a wonderful experience shooting flying dress photos with Suzanne of She, Shoots. Shots. She makes you feel so comfortable throughout the entire experience, and helps stage you in sexy and attractive poses. We shot three different dresses in three different locations, and ended up with a bunch of gorgeous photos. I’m so happy to have done this, b/c we now have photos capturing a special moment in our lives that we’ll cherish forever! Highly recommend!
Read more
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