I would really advise that trying to squeeze above legal maximum people into a reservation in Italy is really a bad idea. As others have reported sometimes hotel staff will be able to find a way around things, but it’s not exactly being fair to them. Other times you risk having your family being turned away or being asked to fork up hundreds or thousands of Euros for different accommodation or extra fees.

It just sounds like a terrible idea. You wouldn’t turn up to a 6 seater private jet reservation with 10 people.

If you can afford it, this hotel is absolutely worth it. If not, then the Westin is an excellent alternative. If you need a pool, the Four Seasons is a worthy alternative, but we much preferred this St Regis over the FS and would stay here again without a second thought. We had a vastly superior experience here at the St Regis compared even with the spectacularly beautiful Belmond Villa San Michele in the Fiesole Hills above Florence.

Welcome to FT, even though I see you joined 3 yrs ago. Always a good idea to search if there is an existing thread on the topic to save the mods some work into moving your post.

https://www.flyertalk.com/forum/marr...er-thread.html

Anyhow, something strange about your post. All hotels at Marriott allow you to make award reservations (assuming they have availability). It’s not clear but almost sounds like you tried to send Amex pts directly to hotel which is not possible. Once your Amex pts are transferred to your Marriott account, just make a reservation at the St Regis on the Marriott website and check the “Use Points” box when doing your search. Good luck.

Way back in 2012, we arranged for a private driver through the hotel. We did this before arriving so the driver could customize our tours. Our driver spoke fluent English and Italian. We used him for two days. We had a wonderful experience. I don’t remember how much we paid but it was worth every penny.

Through the St Regis, we paid 1000 euros for car & driver and guide for our Lucca/Pisa day trip, 1000 euros for car & driver (and got extra wine guide by good fortune) for our Chianti wine tasting day trip, and 1000 euros for car & driver (and got extra wine guide by good fortune again) for our Chianti-Siena wine tasting day trip ending at La Bandita Townhouse in Pienza.

Private cars and drivers are very expensive in Italy. For us, it was totally worth it. Especially because we could drink up at lunch and not worry about the driving at all. And also because we used points for our stay!

Also, the wine guide for us turned out to be the wine tour company owner—he knew we had paid extra for some special tastings and that we were getting special attention because I’d done the UC Davis winemaking certificate program. I think he wanted to see what we were offered! But he also was a wonderful wealth of information and interesting stories about the wines and estates in the area.

Of course, the private car & driver we had arranged via La Bandita Townhouse for our Montalcino and Montepulciano day trips was half that at 500 euros each day.

You may want to check more carefully in advance about the visits at Sassicaia and the other famous super Tuscans. Many of those wouldn’t allow visits, even with my UC Davis winemaking certification. It may have been the time of year near harvest (late Sept/Oct 2018), but it sounded like they were not particularly interested in visitors. Your assumption that visits to those are easily arranged on your own may be a bit optimistic. But keep us posted!