We went last month and really enjoyed.
Winter Park is a charming little town with shops and restaurants.
The Wine Room was delightful.
We went during the day and it was not crowded. The employees were helpful and extremely knowlegeable. It is located in an old bank-they even have a vault with wine downstairs. You pay for a card and load $ onto it. Than taste and drink to your hearts content. They do have a menu for snacks and food.
It is about 30 minutes (most likely more depending on I-4 traffic which is always busy ) north of Disney.
The Farmer's Market she showed off is also very cool if you can make it on a Saturday morning. You'll find plenty of good places for lunch, and then stick around for some wine in the afternoon!