Livorno - Pisa - Montepulciano? Reasonable?

[SLOTheta]

I am organizing a group of friends who are on a HAL cruise for a good friend's wedding.

 

We have a group of 15 who would like to (in no particular order) have:

1) Transportation from Livorno Port to Pisa (stop for an hour)

2) Meal at: http://www.acquacheta.eu

3) Stop at 2 wineries in Montepulciano (or friends really love this area, but it seems really far to me). If there's a better and closer alternative, please let me know. I'm a wine list creator at restaurants in the US, but I am unfamiliar with Italian wines.

 

On a map, if shows 2.5 hours to Montepulciano. My friends are dead set on going to eat at Acquacheta in Montepulciano.

 

 

We are in the Livorno port 7-7pm. Is it nuts to drive 5 hours round trip just to eat and go to wineries?

 

Any suggestions for wineries in Montepulciano?

 

Suggestions for a company that provides transportation? We don't need a tour guide, just a driver

 

 

 

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