Custom curated wine tours & itineraries in: Healdsburg, Napa Valley, Sonoma and Anderson Valley

Windsor Wine Tours creates amazing experiences for their clients. Timely, gracious and accommodating to your travel desires.

We had the best experience with Ian at Windsor Wine Tours. Before the trip, Ian was super responsive to all our inquiries and requests. He helped us set up two wine tours with him (one in Sonoma and one in Healdsburg) with great winery recommendations in each place. We also got the best sandwiches based on a local place he recommended that we ate in between wineries! He continued to provide us great recommendations of places to check out on the days we weren’t doing a tour! Ian was punctual both days and helped keep us on schedule (without being pushy or making us feel rushed). Overall, we had a fantastic experience and would highly recommend!

Ian is a real gem and you should not hesitate to book with him, if he’s even available. - Great driver - Great selection of wineries for us - Great relationships with the vineyards/wineries - Super clean and comfortable car - On time - Great communication via text, phone or email - Anticipated needs and his goal is to make it an amazing experience Success! I would definitely book with him again when in the area.

8 girls had Ian for 2 full days in Napa. Very patient, professional and actually, the best driver I can ever remembering having!

The best wine tour and driver I’ve ever had in Sonoma and Napa. I would recommend Ian to anyone and I am picky!

We (four women) had Ian drive us for two days for really great wine tastings in both Napa and Sonoma. He was prompt each day in picking us up, gave us some great information about the area and suggestions for dinner. He made our trip fun. We would definitely use his services again.

Ian was very nice and professional, van was super comfortable, would use him again!

While planning our mother/daughter wine country trip to Northern Sonoma County, I was researching options for a wine tour and requested information from several of the local companies I found online. Ian, with Windsor Wine Tours contacted me personally within 15 mins of submitting the online form. He was super friendly and informative and helped us plan the perfect itinerary! He booked all the tastings for us and even gave us a recommendation for a wonderful deli where we ordered lunch (that he picked up for us). The day of our tour he arrived promptly in a beautiful, comfortable Lincoln Navigator. We had the best day touring 3 amazing vineyards! Ian gave us tons of recommendations and information about wine country and then got us back to our hotel safely. We truly couldn’t have asked for a better time! If you are looking to book a wine tour, I cannot imagine anyone being better than Ian with Windsor Wine Tours!

Ian is a very personable, knowledgeable tour guide for wine country. A group of four, he picked us up on time and drove us to our preselected destinations. His vehicle was clean and comfortable. I recommend Ian and Windsor!

Ian was awesome. Very flexible and courteous. Would recommend highly.

Knowledgeable, accommodating and a great guy to be around.

Great experience with Ian. Perfect recommendations and outstanding service. He was flexible, professional, and extremely knowledgeable.

Our group of 8 had the best day with Ian! He picked us up in Sonoma at the crack of dawn and drove us up to our early tasting at Schramsberg. Our 1:00 tasting cancelled on us but Ian saved the day with a tasting room recommendation in Yountville (RH). It was gorgeous and available. After our last tasting at Black Stallion we asked him to drive by Artesa so we could pick up a few bottle for the house. They were able to accommodate us for bottle service so we ended up hanging out there for an hour. Then Ian dropped us for dinner in Sonoma. Loved the cooler filled with sparkling wine and Fiji water!

First trip to Sonoma County and Ian with Windsor Wine Tours was so helpful. I started a conversation with him several days in advance. He had suggestions and even offered to help any way he could. His suggestions were top notch and the experiences couldn't have been any better. We enjoyed his SUV since it was only my wife and I. He has a larger van for groups. You will not be disappointed with Windsor. Very fun and safe relying on him to drive you from tasting to tasting.

We had a great day in Sonoma with Ian. We visited 3 wineries and stopped at a nice market to grab lunch! Ian laid out our day and we just enjoyed! Fun day with friends!

Ian is great! My husband had a couple days of business meetings in Napa, and I had Ian set-up one day of wine tastings for me during this time. Ian set-up some great tastings for me, kept all my purchases cold, and provided a true 5 star experience!

Ian was great. He showed up in a beautiful, black Lincoln , Navigator, that was spotlessly, clean. Picked up our friends at a neighboring hotel and greeted us all with a bottle of bubbly to start off our journey. He helped us make our choices of wineries in the area, and we had the best experience. He was very helpful, professional and knowledgeable. I would highly recommend Ian if you are considering doing a small private tour.

Ian was the absolute best. He pays such attention to detail and was such a joy to be around. Very professional and insightful. Thanks Ian! Until next time.

Windsor wine tours in Healdsburg, ca was great. Ian gave us a list of wineries and we chose; he gave us a personal trip to three tastings. he arranged for lunch and was patient with our pace. We use him again when we return to Sonoma.

We had a wonderful experience with Windsor Wine Tours! Our group of six were ambitious in taking on Napa's wineries all day and Ian was so helpful in coordinating all the reservations and offering tips and tricks along the way. We kicked things off with a sparkling toast and great conversation. As we enjoyed the wineries we were able to sneak in an extra stop in Yountville for lunch in a small, beautiful park and to pick up some AMAZING macarons per Ian's recommendations. The ride was comfortable and Ian was a total champ towards the end when we subjected him to some impromptu karaoke to some 90s hits. We would definitely recommend Windsor Wine Tours for your next adventure in Napa (or surrounding areas)! Cheers!

This was the perfect way to visit different wineries in the area. From the first contact with Ian’s business until he dropped us off back at our hotel after the tastings, the whole experience was pleasant and stress-free. He recommended wineries to choose from (three was the perfect number to visit in one day). He helped us with lunch options, had a very comfortable vehicle and was a personable host. I highly recommend Windsor Wine Tours.

For my 40th birthday, we hired Windsor Wine Tours to plan the perfect trip for 12 women. We had interviewed several different companies that made their tours complicated, overwhelming and confusing. However, Ian from Windsor Wine Tours took a different approach. He personally reached out to us with a phone call, inquiring about our preferences and genuinely caring about how we wanted to spend our time. As a group of wine-loving women, our main goal was to have a fun and intimate experience by visiting smaller vineyards off the beaten path. We gave Ian the green light to plan the entire trip for us, and it turned out to be the best decision. Ian was highly communicative leading up to our events and even assisted us in deciding which vineyards to visit after our transportation from SFO to Santa Rosa. On the day of the tour with WWT, we couldn't have been happier with the 5-star experience provided by Ian and Zach. They arrived on time, dressed professionally, and presented us with beautiful, clean nice vehicles. To kick off the day, they even surprised us with a champagne toast for my birthday, which was a special touch. The vineyards included in our itinerary were truly amazing. Among them, Croix was our favorite. Ian made sure we had a private table, patio, or tasting room at each location. To our surprise, every vineyard added a special birthday touch, showcasing Ian's commitment to going the extra mile. He even helped us organize a memorable lunch experience including a farmers market and shopping! Ian and Zach truly exceeded our expectations, making my 40th celebration extra special. They even assisted us in arranging transportation back to the airport. Overall, this was a luxury 5-star experience that I wholeheartedly recommend. Ian's expertise and dedication made it a once-in-a-lifetime experience that surpassed all our expectations. If you're hesitant, I assure you that you won't be disappointed. Book a tour with Ian and prepare yourself for an unforgettable journey.

Wife and I decided last minute to do some wine tours and tastings. Ian was fantastic in arranging some great tastings and food pairings at several Vineyards. Very personable and attentive and the ride was great. Wife is already planning another trip and Windsor will be our go to company.

Ian & Zack were a very professional, Personable, very responsive and reasonably priced. Zack’s car was immaculate and provided us water, snacks and cooler! We had lots of laughs and Zack even serenaded us with Neon Moon. I highly recommend Windsor Wine Tours!!

Ian did an excellent job of helping us plan our tour. He is exceptionally friendly, professional and knowledgeable of the area. I highly recommend his services.

Couldn’t have been happier. So helpful with the planning and his recommendations were perfect our group. He was knowledgeable about area and wines, so personable and fun to be with, we loved our experience and couldn’t recommend Windsor Tours more highly.

My wife and her friends had the best time and couldn’t be happier with the entire experience. Thanks Again !

Just had the best girls weekend and we owe it all to Ian. I booked a wine tour through another company originally and it didn’t workout because where we were staying. I was very nervous about trying to find another company on such a short notice but everything worked out better than I could’ve imagined. Ian helped me out and booked all our tastings. We started at Frank Family which was incredible and the Arroyo, and lastly Temper Bey. Each place was different but delicious. I will never forget this day! Thank you Ian!!

I have used Windsor Wine tours for business and for personal travel. Amazing service, professional, family owned and great recommendations. If you are looking for a reliable and friendly service this is the way to go!

We have been referring Windsor Wine Tours to our guests in Napa Valley but this time my family and I got to experience Ian’s services first hand. We used his car service to experience multiple wineries and we truly appreciated the company’s professionalism, punctuality, and super comfy SUVs! Looking forward to using Ian’s car services for our next family trip to Napa!

Ian picked us up from San Francisco for the day and took us to 3 wineries and for lunch in Sonoma over the course of a day, returning us safely in the evening.He picked the wineries by giving us many options within our preferences and time limitations. We had a wonderful experience with him and would highly recommend Windsor Wine Tours!!

Ian was so wonderful! We had ZERO luck with Ubers and he saved the day. We relied on him for the remainder of the trip. It was a top notch service and professionalism! We will definitely be using his services the next time we visit wine country!

We cannot thank Ian and Windsor Wine Tours enough for our fabulous day in the Russian River area. From his sense of urgency with setting up our day, to detailed recommendations, to his warmness it was by far one of our favorite days here visiting the west coast. The wineries were amazing they all know him which made our time at the wineries even feel more special. Oh, he also has elite food suggestions, they were all on point too!! Thanks so much Ian for our amazing day!

Ian did an outstanding job during the planning and in the day of. Wineries were great, his knowledge of the area- suggestions on things to do were top notch. Will definitely use him again when we return. Thank you Ian for making our trip memorable!

Ian was absolutely amazing!!!! He picked up our lunch order and had in the car for us. Also provides waters in the cooler. He was very easy going and up for anything. He was very knowledgeable about the area and gave wonderful winery suggestions. If you are looking for an amazing driver that is alot of fun Ian is your man. Highly recommended Windsor Wine Tours!!!!

Ian Gustavson provided my long-time (49 years) college friend and I with a wonderful and very memorable experience! He provided imput on places we could like (per our request), made appropriate suggestions on details of our trip, was prompt, and a very pleasant driver! We thoroughly enjoyed his recommendations and his company. Being novices with all this, we didn't know what we'd experience. It was one of the best days of our vacation! We're planning on returning in a few years and contacting Ian's business again. One can use his services with confidence.

Ian was amazing - helped us plan the whole day as we were not locals, even booking the tastings for us. He was punctual, polite, thoughtful, and professional. I would recommend Windsor to anyone in the area.

Ian and Windsor Wine Tours we’re fantastic. They gave great recommendations on wineries to visit and was very pleasant during our day around the Napa valley. He was prompt, courteous and a great host. He had a very nice Lincoln Navigator and made our day wonderful. Thanks Ian!

Ian was very helpful and responsive, I received a call shortly after requesting info through the website. We talked through a few winery visits I had put together and he helped sanity check the timing and fill out our day. The vehicle was very clean and comfortable. Definitely recommend.

What an amazing experience with Ian and Windsor Wine Tours. Ian planned some outstanding wine tastings for us on super short notice and it was such a pleasure having him taking us around. He was incredibly professional and had so much insider knowledge on both Napa and Sonoma. I couldn’t have asked for more and would highly recommend him.

The car is very clean, comfortable, and spacious. Ian was an excellent and accommodating driver with a thorough knowledge of Napa Valley and all of his restaurant recommendations were excellent. I highly recommend Windsor Wine Tours and will definitely hire them again the next time I come to Napa.

Ian was excellent and we would be happy to hire him for any of our driving needs in the future. The suv was very comfortable and even had enough room in the back for the 2 guys who are 6 feet tall to fit without feeling crushed. The suv fit 6 guests plus the driver. He had also brought snacks and waters which were very much needed during our tour of 5 wineries. He has a lot of knowledge of the area and was always promptly waiting for us as we wrapped up. Ian is very amicable and definitely enjoys what he does, he didn’t mind us asking to take detours and make short stops to take pictures or run to the restrooms. If I could offer up more than 5 stars I would do it in a heart beat.

They show up on time, appropriately dressed, in a clean and comfortable car. He knew the places to go, how to get there, and was easy to work with. We had a great trip and he was an intricate part of making that happen. Five star all the way Ian!!

Ian was great! Prompt, friendly, courteous, Made great recommendations for additional stops. Would highly recommend! Ian made the trip fun!

Ian is great. Highly recommended.

Had a great experience with Ian driving us for the day wine tasting around Healdsburg. He was very communicative, friendly and helpful from the moment I inquired about booking. The car was clean and comfortable and he brought us water and snacks and offered to pick up sandwiches and bring a picnic blanket for us. Would definitely book again and recommend to anyone. Thanks so much for a great day Ian!

We had a fantastic and comfortable day touring Sonoma wineries with Ian. He is kind and extremely knowledgeable of the region. He had terrific recommendations of eateries along with must-see spots. We look forward to future trips with Windsor Wine Tours.

Ian was so great! He worked with me on scheduling a group pickup at the end of a Wedding near Mendocino even though he was coming from over an hour away. I really appreciated the effort he put in to make sure my group and I had an easy, friendly experience. He was great at communicating leading up to the day and on the day of. Would definitely book again in the future. Thanks, Ian!

Amazing service, great price, and very reliable.