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Sonoma County itinerary in 4 days


Glen Ellen:

Olea Hotel


Beautiful, charming hotel in the town of Glen Ellen which is in the heart of Sonoma Valley. Very nice rooms. Excellent home-cooked breakfast. They serve afternoon wine and hors d'oeuvres which was very nice to have while sitting on their relaxing patio. Highly recommended.

This was my first trip to Northern California - which included Sonoma County, Northern California's wine region. This area is a great spot for rest and relaxation while enjoying good wines, eating delicious local food, enjoying hikes, cycling and seeing beautiful art.  

We combined this trip with my San Francisco itinerary and the spectacular Pacific Coast Highway itinerary, driving south to Los Angeles. 

Day 1



Arrived in San Francisco and picked up our rental car. We headed to Sonoma Valley stopping along the way at a small winery, called the Imagery Winery, for our first wine tasting and to kickstart the trip!


We arrived at the Olea Hotel, in the town of Glen Ellen. This beautiful, charming hotel is in the heart of Sonoma Valley. Aside from their delicious home-cooked breakfast, they serve afternoon wine and hors d'oeuvres which was very nice to have while sitting on their relaxing patio. 


We drove into the town of Sonoma, walked around the main square/park and went for dinner. We had dinner at the Harvest Moon Cafe Restaurant which is right in the town. We sat in the back patio, which was lovely and had a delicious dinner prepared with fresh local ingredients and a bottle of Sonoma wine.

Day 2


Morning and Afternoon

We hired a private guide/driver, Dan Dolen from Reserve Wine Tours, to take us on a full-day tour of Sonoma and Napa Valleys. I highly recommend hiring a driver as he/she can give you some history of the wineries and the region. An added bonus is that it will allow you to do as many wine tastings as you like without the worry of drinking and driving. It was a beautiful sunny day, driving through gorgeous scenery of rolling mountains and vineyards.  

Our first stop was at the Vella Cheese Factory in the town of Sonoma where the proprietors make their own cheese. We went into the back to watch them at work and then had some tastings of their delicious cheeses.

We wanted to combine our love of art with our love of wine, and had read about several wineries that have art collections. Some of the wineries we visited and tasted included: 

  • Cliff Lede Vineyards which has Keith Haring sculptures in their beautiful garden

  • The Hess Collection Winery which has an impressive, private contemporary art gallery

  • The Schramsberg Winery which produces sparkling wine in old caves that were hand carved in the 1800s by Chinese labourers. We did a very interesting tour of the winery and caves which I highly recommend.


Around mid-day we stopped at Round Pond, an olive oil factory and winery, We did a tour of the olive groves, and learnt about the production of olive oil at their estate mill, as well as the proper way to taste olive oils which was a lot of fun. This tour included a nice lunch.



We decided to walk out for dinner in the town of Glen Ellen. We ate at Glen Ellen Star, which is small with a lovely atmosphere. After dinner we walked around the town which is very quaint and quiet - really just one short main street. There isn't much there except for a few restaurants. 


Day 3


This morning we decided to do a hike near the town of Sonoma along the Sonoma Overlook Trail. It was very beautiful and peaceful. The highlight of the hike was seeing a family of deer a few feet away from us. There are some uphill climbs but overall it was a relatively easy trail.


We had lunch in the park at the Farmers Market in the centre of Sonoma.

After lunch we went on a lovely afternoon bike tour with a guide, which we booked through Sonoma Valley Bike Tours. We rode through lush vineyards and stopped for tastings at two wineries:

  • Buena Vista Winery which is one of the oldest wineries in the Napa/Sonoma Valleys. Its original building, built in 1857, houses the winery, tasting rooms and Visitors Centre and is a California Historical Landmark. 

  • Ravenswood Winery which is the home of one of our favourite zinfandel wines. 


We drove to the town of Napa for dinner at Angele restaurant. We sat in the patio and went for a walk along the river in Napa after dinner.



Day 4



We packed up and checked out of the hotel.

On our way out of Sonoma we stopped at Cornerstone Gardens which has a series of around twenty gardens individually designed by twenty landscape architects and designers. We loved this - the gardens ranged from traditional to contemporary and abstract. It was so unique and interesting - I highly recommend it. They also have a beautiful shop.


We continued our trip by driving to San Francisco, which takes just a little over an hour.


See my San Francisco itinerary in 4 days for ideas of fun things to do. 

Guides and Tours


  • Dan Dolan - Reserve Wine Tours. Good driver and guide with excellent knowledge of the Sonoma and Napa wineries. 
    Phone: 707-953-1763

  • Sonoma Valley Bike Tours - Good place to rent bikes and book a tour with a guide.
    Phone: +1 707-996-2453

Noteworthy Restaurants


  • Harvest Moon Cafe and Restaurant.
    Nice restaurant in the town of Sonoma. Lovely back patio and delicious food.

  • Glen Ellen Star. This is a nice, intimate restaurant in the town of Glen Ellen. 

  • Angele Restaurant. This a very nice restaurant in the town of Napa. The food is excellent and it has a lovely patio on the river.

Sonoma Itinerary
Itinerary Add-ons

This itinerary can be combined with:

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