Help Selecting Destination for 40 Birthday Group Trip
 

Hello! I am starting to plan a trip for my 40th birthday in late October and need some help selecting the perfect destination. I would like to rent a house/villa for a group of friends -- combination of single people/couples all between 35-45. Ideally, the location would have the following criteria:

1. Warm weather -- I would like to get a house with a pool where it's warm enough for swimming, sunning, etc.
2. Close proximity to a town or village for restaurants etc.
3. Good food/wine
4. Not overly touristy
5. Relatively easy to get to from New York

I'm picturing something like Tuscany or Sonoma, but I worry those places won't be warm enough for the pool in late October. Also, I can't do anything with Zika concerns, so that rules out a lot.

Thanks in advance for your help. All suggestions are welcome!