Q – We are six friends traveling together to Tuscany next summer. Call us luxury travelers for this trip, a celebration of two anniversaries. We’ve decided that we want to use Tuscany as a base, get a few vehicles, perhaps hire a chef or do some upscale dining, and we would like to do some stops in wineries arriving via helicopter. The problem is we really don’t want to rent a villa so we’re trying to find a hotel that feels like a private villa, isolated yet within driving distance of the towns in both Tuscany and Umbria. We trust this site and look forward to any suggestion you might make. If you can come up with a place that will “Wow” us please recommend the best way to book it directly, or otherwise. Thanks and keep up the good work.
A – It strikes us that you might be extremely pleased with the Hotel Castello di Casole, a 4,200-acre estate in Tuscany perfect for bicycle rides in the countryside, wine tastings (the estate produces several signature wines) or cooking classes. You might even spend an evening in the original Amphitheater listening to a string quartet play under the stars. 
As with all better properties worldwide, you always want to book with benefits through an agency that enjoys a proprietary relationship with the property. You will also be VIP’d that way, given the fact that you have two important celebrations. One caution, this oceanfront property is extremely appealing to small corporate groups so make sure none are booked during your planned stay. The helicopter is no problem but you may have to land several roads over from the actual vineyards.
