Checkmate Artisanal Winery

Absolutely brilliant winery. We are so glad we ended our stay in Osoyoos with a visit to Checkmate. Jackson was our person, and he treated us extremely well. We had great chats with him and he really helped us with our decisions on the wine. In the end we purchased six bottles of wine, including a great collection of chardonnays and merlots. The presentation of the six bottles in the gift box were exemplary, and well worth the cost. Thank you to Checkmate, and most of all Jackson, for a wonderful afternoon!

The Grandmasters Tasting Experience: Jackson did an outstanding job of presenting Checkmate wines in a personable and engaging fashion. He also toured us through the property and winery before seating us at the best patio in the Okanagan. The wines, charcuterie and views were amazing. We also appreciated the time taken by membership manager James to make us feel welcome and set up the rest of our VIP day touring two other premium wineries in Oliver. It was a five-star experience. We'll be back for more.

We had an exceptional tasting experience at CheckMate a few days ago. Colin was absolutely fantastic—warm, knowledgeable, and a true pleasure to spend time with. The wines were outstanding, and the panoramic view from the balcony is simply breathtaking. We’re so glad we made the trip south—it was well worth it and truly memorable. Highly recommend!

We had such a wonderful experience at Checkmate Winery thanks to our server, Amanda. She was incredibly knowledgeable about the wines, offering thoughtful recommendations that made our tasting feel personalized and special. Amanda struck the perfect balance of professionalism and warmth and she made us feel welcome and taken care of without ever rushing us. Her passion for the wines and genuine hospitality really elevated our visit.

Had an amazing experience at Checkmate during the summer. Our server Amanda had so much knowledge and passion for wine and winemaking and was so great to chat to. The scenery was incredible, wine delicious, and charcuterie to die for! Thanks Amanda and Checkmate, we will be back.

We had an amazing time at checkmate with John Schmidt. Beautiful tour, with amazing wine, loved the Chardonnays lot’s to talk about. Loved to see how the different millésimes evolved through the years!

Exceptional experience and wines! From the moment we walked in we felt extremely welcome, Amy and the entire team took extra special care of us and made our engagement weekend one to remember! Thank you everyone, we will definitely be back!

Checkmate is my favourite winery in the Okanagan. Allison and James always provide a luxurious experience with some of the most amazing wines I’ve ever had. You have to give this winery a try, not only for the wine but for the amazing views and architecture.

One of the most beautiful wineries we've visited. All of their wines were amazing but the initial white wine provided to us when we walked in was spectacular. Wonderful service as well.

The Grand Master's Table tasting at Checkmate was exceptional! The setting is beautiful. Jack's extensive knowledge and enthusiasm is contagious. He customized the tasting to us. The wine and wine tasting experience was outstanding! We have done wine tasting and vineyard tours across the world and this would rank among the best.

An amazing winery that has unreal Chardonnay and Merlot. We highly recommend checking this winery out, it was such a pleasant visit and the views from the winery are spectacular. Adi was so kind and taught us so much about what Checkmate was about! We can't wait to come back again in the future.

This place is top. Top quality. Top dollar. Top of the hill. We had heard about the views and the wines at Checkmate from another winery, so really wanted to check them out. For some reason we thought we needed to call ahead, which we did, though it turns out it wasn't necessary since it wasn't off season. We were wowed from the start--the views from their tasting room are stunning as you stand in a small container box structure with glass window walls on three sides. A set of tasting glasses, bottled water, and rosemary bread sticks were set out waiting for us. There were 5 different Chardonnays to taste and 2 Merlots. While this may sound odd to only have two types of wine, it was awesome to taste the variation in their product based on their different treatment of the grapes. Hand's down the best wines we tasted at any of the 26 wineries we went to over the long weekend. I'm not even a huge fan of Chardonnay, but was a convert after tasting the Fool's Mate. We also loved the Silent Bishop Merlot, which had me at the first sip. I don't know if they show everyone the wine production area, but we had the chance to do so, which was really neat. (There were no other customers while we were there.) Some folks were picking through the grapes and we got to hear about their production process. Despite the price tag, we cannot say enough good things about Checkmate. The wines + the experience were awesome. Sometimes you have to treat yourself to the good things in life; and a visit to Checkmate is definitely one of those times.

We had one of the best tasting experiences at CheckMate in Oliver BC Their wines are exceptional and the service was amazing Nastacia was our sommelier and she is incredibly knowledgeable about vineyards in the area and especially, of course, Check Mate's vineyards She knows each of the wines inside and out and has impressive knowledge of the history of particular vines in the area We are from California and frequent the Napa area. Our experience at CheckMate was superior to any vineyard we have visited there, all due to Nastacia Go see her NOW!

When ChechMate first opened I heard they had only Merlot and Chardonnay wines. These wines are my least favorite as I am Cab Sav predominant. I went for a tasting and to my surprise the wines of CheckMate were the best I had ever tired in Merlot and Chardonnay. The Merlot was so amazing it reminded me of a Napa Cab. These are the only Merlots that I have in my wine cellar and not a couple bottles, but many bottles. I rate the Merlots 100 points. Visit immediately. Edward Geric

What a pleasure learning about the development and craftsmanship that underpins the products of CheckMate Winery. The enthusiasm and passion for the process was evident as Jack led us through an experience of tastings surrounding the stunning wines of CheckMate.

If you want to taste the very best wine you possibly could, you must sign up for a wine tasting with Checkmate. It's an experience, and well worth the wine tasting fee ($35 - and if you buy a bottle, this gets applied to the purchase). The staff are extremely knowledgeable and friendly, and their passion shines through as they describe each wine. Even though they could have an attitude ... they don't. Christian was our host and he truly wanted to share his love of wine with us. He was delightful. Every single wine was astounding, and it was hard to pick a favorite. Yes, the wines are expensive, but worth every penny. Treat yourself to the wine tasting and I guarantee that you'll be leaving with a smile and some great bottles of wine.

The latest venture from the owner of the popular and ostentatious Mission Hill winery, Checkmate is the polar opposite. Tastings are by appointment only, and there is no sign at the entrance. The tasting room has a rustic wood table, a separate Riedel glass for each wine, and the offerings consist of 5 Chardonnays. The wines names are chess themed (Capture, Attack, etc.), and there is a considerable variety in bouquet and flavour profile between them based on the vineyard they come from and the fermentation process used. The mantra here is to explore the full range of expression of the Chardonnay grape with small batch carefully crafted wines of the best possible grapes. I had the Attack at a blind tasting and it handily beat the big name French competition for me. Refined but not stodgy is the most succinct was to put it. The single vineyard Capture I purchased is a mix of both wild-fermented and select yeast, and this is their first release of all five wines (2013s released in 2016). All of Checkmate's wines are serious, expensive ($80-120) and can be cellared for several years. If you are looking for a special Chardonnay, this place is in a class of its own in Canada.

When a customers spends $500 on wine purchases it is just WRONG to add the cost of the tasting on top of the purchase. I wrote to them and phoned in my complaint and no one ever bothered to return my call or email. We have lived and worked in Kelowna for 40 years and you are the only winery that has ever done this. We will not return nor will we recommend you to others. With so many wineries to choose from you are going to to elite yourself right out of the running.