If you're headed to Naples, may I suggest stopping in at Inspire Moore Winery. My wife and I have been wine club members there for the past 4-5 years or so. It's a very friendly place with a relaxed atmosphere and very good wines. We enjoy going there so much, that we've opted to pick up our quarterly wine club package as opposed to having it delivered and we live in the Buffalo area. We prefer dry whites and reds, but they have something for most palates. You can do a tasting and/or enjoy a glass of on the adjacent porch/deck with a view overlooking the vineyard. You can also head down to an area directly behind the tasting area and get a great view of the vineyard from ground level.
The Roots Café on the same property, but with different owners, has really nice food if you're looking for some place to eat.