Siena visit

Hi Jon, I would begin with one of the smaller villages, maybe head to San Gimignano and then Monteriggioni since it’s directly on the route to Siena. When you reach Siena, you can recalibrate the timing in case you have stragglers in the group, and you will have a better idea of how long it actually took to make an additional stop in each small village. Siena has plenty to see, plus, this should give everyone a chance to have lunch in Siena. Give Siena as much as time as possible with some buffer. If your group has time to stop at one last place on the way back, I would choose one on the main route back. It should also be shared that this last one might need to be dropped due to traffic, etc.

Just a note - San Gimignano, etc. are pretty but also very touristy. Take advantage of asking your driver if there are better options for authentic experiences but less crowds.

We have been to every place you mention visiting, not counting Livorno. I think such a frantic pace would not do justice to any of the places you and the others want to visit. I think your best bet would be to have two groups - one for a trip to Siena and the other for the hill towns.

What ages are members of the group? The pace of twenty somethings is different from that of 60 somethings.

I have seen trips like this from both the inside and outside. We were invited to join friends on a river cruise. I always felt rushed when we'd stop to see the sights. I've encountered day trippers from cruises before. They are overwhelmingly unpleasant to be around. They feel entitled because they've got a tight schedule to keep. I've actually been pushed out of their way.

Seems very unrealistic

A 15 min stop in Monteriggioni isn’t worth the trouble

Be very sure of your drive times and overestimate to be safe

April 25 is a holiday, not sure how that will affect traffic- perhaps Roberto or Dario will weigh in.

I’d do an hour stop in Monteriggioni then head to Siena, getting into the center hopefully before noon.
Spend the day there and be sure to leave with plenty of time to get back to port.

What happens if you miss your boat?

You may have to skip Volterra. It's a long drive on a curvy highway and it takes forever to get there.

Also your times are unrealistic. 1/4 hr for Monteriggioni? It takes that long just to walk from the parking lot outside the wall to inside the wall (then you need time from the freeway to up the hill to the walled town). Same for Siena. Assuming you park at the Stadium, which is the closest parking lot to the city center, you need more than 20 minutes to walk (fast) to Piazza del Campo. Your private car driver is also not allowed to enter Siena's (or Monteriggioni or S.Gimignano's) city center inside the walls. Those areas are totally pedestrianized. Only walking allowed.

Tuesday Apr 25 is a National Holiday, that means you are traveling during a major long weekend with lots of travelers. Traffic may not be bad, but parking lots may be busy with day trippers.

When/where are you planning to eat?

Are you certain you will be able to depart Livorno at 8am, due to how cruise ships time offloading of passengers when in port?