Best Date Night Restaurants in Oakville

Our server, Sebastian, was attentive and knowledgeable, giving us helpful details about our selections.

Proposed to my girlfriend in one of the chalets and it was the most romantic dining we’ve ever had. The food was absolutely incredible and our server Joe was fantastic. He was extremely knowledgeable and fun! The Ameretto Cream Pie was the best dessert we’ve ever had!!! Absolutely recommend this place to anyone and everyone!!!

We had the best time dining with friends at Olive and Oak. Our server was outstanding, along with all of the hosts, bussers, and additional support staff. Our meal was perfectly paced and gave us time to enjoy each course, as well as visit with our friends. The food and drinks were absolutely spectacular, as always. To top things off, we were gifted a bottle of wine before leaving from the manager. Hows that for a wow-factor?!

A fine dining experience worth the time and expense. Large, diverse menu with many daily specials, excellent extensive wine list, great cocktails, excellent food. We eat at Annie Gunns twice per month for date night and the experience is always enjoyable and something we always look forward to.

My husband and I shared the calamari appetizer which was fantastic and very substantial. He ordered the sea bass over asparagus and garlic risotto and I had the special which was lobster and ricotta ravioli with tomato vodka cream sauce. Mine was delicious, though very rich. His sea bass was wonderful and cooked to perfection. The risotto was terrible. It was far from al dente as it was actually crunchy and overpowered by the garlic. Our server (I think his name was Dent) was fantastic. Attentive but not suffocating and made sure our main courses were reserved a reasonable time after we finished the appetizer. I have always enjoyed other Napoli restaurants and I would go to this one again too. Just wouldn’t order the risotto.