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    Checkerboard Vineyards

    5.0 (6 reviews)
    Ultra High-EndWineries
    Closed 9:00 am - 5:00 pm

    By appointment only

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    Cherboard Wines

    I was curious about Checkerboard Vineyards so my wife and I made an appointment to visit and tour the winery. Long story short, it was the highlight of our visit to the Napa Valley. Gary, our guide, walked us through the cave and gave us an overview of the property. He also provided a truly fantastic tasting experience with knowledgeable insights and great descriptions of the wines from each of the vineyards on the property. We really appreciated the singular attention during our visit along with great conversation. I highly recommend this winery tour and their wines!

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    2 years ago

    Excellent service and sommelier! Ask for Gary he is fantastic, knows his wines and super fantastic service!

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    Castello di Amorosa - Castello di Amorosa in the Diamond Mountain District of the Napa Valley.

    Castello di Amorosa

    4.1(5.1k reviews)
    0.7 mi
    $$

    Very cool winery up on a hill. Castle construction is a cool concept…read more We did the wine tasting and the juice tasting. I thought it was slightly expensive but not terrible. It was very busy. They clearly work on a volume basis compared to other wineries. Since I only like very sweet wines, I was able to find something for me.

    Eli, our tour guide, was amazing! He was incredibly engaging, knowledgeable, and made the whole…read moreexperience really fun. You could tell he genuinely enjoys what he does, and he kept the tour interesting the entire time. The castle itself is stunning and the whole experience felt really unique. The wine tastings were all delicious and added a lot to the visit. The only downside was unfortunately someone in our tour group. One woman made sure everyone knew she was a member and kept mentioning how she had already seen the castle too many times and was bored of it, saying she only came to bring her family for a birthday. It kind of disrupted the experience for the rest of us. When we got to the torture chamber she also started making some really inappropriate remarks, which was a bit uncomfortable for the group. Aside from that situation, we still had a great time and really enjoyed the tour and tastings. Overall it was a memorable experience and definitely worth visiting if you're in Napa. 5 stars for Eli!!

    Photos
    Castello di Amorosa - Castello di Amorosa wines

    Castello di Amorosa wines

    Castello di Amorosa - Morning sun on the Castello. It's always a great day to visit.

    Morning sun on the Castello. It's always a great day to visit.

    Castello di Amorosa - Chocolate pairing's

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    Chocolate pairing's

    Romeo Vineyards & Cellars - Romeo Vineyards off Silverado Trail in Calistoga.

    Romeo Vineyards & Cellars

    4.7(133 reviews)
    1.7 mi
    $$

    To kick off day two of my birthday weekend in Calistoga, my wife and I decided to visit Romeo…read moreVineyards and Cellars. Romeo holds a special place in our hearts because we visited them a little over seven years ago. During that experience (which you can read about in my previous review - if interested), my wife and I had a grand experience with former Business Manager Emma, who administered the delicious tastings. Fast forward to the present, we looked forward to enjoying a glass of their finest red before finding lunch. Upon entering the walkway, we were enthusiastically greeted by an employee named John who quickly ushered us to a vacant table for two. My wife had a slight reaction to the beautiful flowers that were in full bloom. Out of the kindness of his heart, John provided my wife with a bottle of Pure Leaf tea that calmed her allergies. We told John that we were interested in enjoying a glass of red, in which he quickly ran off and returned with a bottle of 2009 Eugenia Cabernet Sauvignon. Upon doing the swirl and sniff test (sounds dirty doesn't it?), I knew that we were in for a treat. Since we were both in dire need of a meal, we sadly could not continue the party. However, we will make a return visit in the near future to enjoy a full tasting experience!

    My girlfriends and I go on an annual trip to Calistoga for some r&r. This time, we stopped into…read moreRomeo to wine taste on their beautiful patio among the tall trees. John let us in and treated us to a wonderful experience. It was so much fun, informative on the wines, and every wine we sampled was delicious. I highly recommend stopping in to see John and enjoy some delicious wine.

    Photos
    Romeo Vineyards & Cellars - Brick-oven pizzas ( seasonal )

    Brick-oven pizzas ( seasonal )

    Romeo Vineyards & Cellars - Indoor tastings available. Artwork by Carlo Marchiori.

    Indoor tastings available. Artwork by Carlo Marchiori.

    Romeo Vineyards & Cellars - Charming indoor tasting space. Artwork by Carlo Marchiori.

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    Charming indoor tasting space. Artwork by Carlo Marchiori.

    Chateau Montelena Winery - Indoor - wine serving area

    Chateau Montelena Winery

    4.0(765 reviews)
    3.6 mi
    $$$

    Wanted a special place to celebrate our 29th wedding anniversary weekend. Couldn't be more pleased…read morewith the experience. Booked a tasting and was hosted by Lin - she was a delight. Super personable & knowledgeable - total class. In our top 3 tastings of all time - very special juice. "crazy yummy" was the phrase of the day. The winery history is remarkable and the various tasting and display rooms are well designed. Stroll through the Japanese gardens - will not disappoint. Bravo to the Chateau Montelena team!

    A perfect 10. Chateau Montelena is The Napa Valley standard for the best winery in the area What…read morean amazing visit to spend for my 50th birthday. I wish I would've gotten something special for my occasion while there. Like a signed bottle or something marking the special occasion. It was just the perfect experience all the way around. interesting that it was also the 50th anniversary of the Chardonnay that made Chateau Montelena & Napa Valley famous. Of course, we checked out and bought 2 bottles of reds at the end of the tasting without even thinking about buying the white. So disappointed that didn't occur to me to this morning. I mean the red cab's are just to amazing on there own. Ok so here is how the visit went. When we showed up early at 9:30am, we actually meant to just walk around the lake and view the birds. We made no reservations as we figured the place was fully booked for months. So we just wanted to at least see the famous vineyard.. we drove up and we immediately noticed the beautiful grounds. I mean stunning in every way. We even watched and photographed a beautiful white swan gracefully move throughout the lake. Afterwards, we walked up the path to the chateau and was presented with a old historic and charming building residence. Absolutely stunning, a complete representation of the movie bottle shock. We continued to walk around the building where we were allowed to enter the wine tasting room. At first, we were unsure of what to expect. I believe her name was Lynn invited us to have a tasting. Everyone was so gracious and nice. Just felt so sophisticated & elegant in every way. Lynn was so nice and inviting that I just wanted to say thanks to her again. You made our tasting feel amazing. We ended up buying 2 bottles of red cab when we were there to avoid paying for the tasting. I mean I'm so happy that I got to experience this winery. The history and quality wine making really is the standard for the area. A complete must visit if your ever in Calistoga. Thank you.

    Photos
    Chateau Montelena Winery - Tasting

    Tasting

    Chateau Montelena Winery - One of the attractive features.

    One of the attractive features.

    Chateau Montelena Winery - Barrels (photo opp)

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    Barrels (photo opp)

    Olabisi Wines - Exterior

    Olabisi Wines

    4.3(45 reviews)
    1.8 mi
    $$

    We were camping at the nearby state park and were looking for a place that was open for wine…read moretasting and picked this one. It was around 5pm on a Thursday and we were the only ones around. The tasting cost $40 for 6 pours, starting with a rose and ending with a Cabernet Sauvignon. I am not very fond of reds but all the ones that were on the tasting menu that day were very good. The rose was my favorite. I was talking to the owner and he mentioned that he prefers to be out making wine instead of pouring and I can see that. Also, the pours were very tiny. There was not much information shared about the wine etc, he left the bottle with the information side turned towards you to read up on your own. The place itself is beautiful and it used to be a hardware store. It's right next to the city hall and across the street from the police station. There is street parking as well as a public parking lot next to the police station. The place is dog friendly and the owner bought out a bowl of water for my baby. I didn't buy anything but I would visit again.

    We happened to drop in to Olabisi in Calistoga on a whim just walking through town, and we're so…read moreglad we did. We were fortunate to meet the owner, Ted, who was very kind and knowledgeable, and the wine was Excellent and a Great value. The tasting room was cute, clean, comfortable, and bright. We left with 6 bottles and wish we bought more; will be ordering more soon. We went to several other bigger/more "famous" wineries in the area, and Olabisi was our favorite. Thanks again Ted!

    Photos
    Olabisi Wines - Stunning interior at Olabisi Winery Tasting Room on Downtown Calistoga

    Stunning interior at Olabisi Winery Tasting Room on Downtown Calistoga

    Olabisi Wines - Olabisi is an african girls name meaning--
  "JOY MULTIPLIED"

    Olabisi is an african girls name meaning-- "JOY MULTIPLIED"

    Olabisi Wines - Winemaker Ted Osborne gesticulating his excitement about sharing wine.

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    Winemaker Ted Osborne gesticulating his excitement about sharing wine.

    Checkerboard Vineyards - wineries - Updated May 2026

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