Please help with our retirement trip to Tuscany

Personally I would stay in Rome for a night and take the train in the morning to Civit.... There is absolutely nothing in Civit...... And Pisa is not worth two nights. Again, not much there. Maybe a night there and move on.

Borgo alle Vigne is in Terricciola, not far from Pisa. However for flights check Florence (FLR) as well. Pisa has mostly flights with low cost European air carriers. FLR has more options with major airlines.
Assuming you fly to PSA, I don't see a reason to stay in Pisa two nights. You could go straight to your final destination (Borgo Alle Vigne Hilton in Terricciola) and visit everything from your base. Besides you can visit everything there is to see in Pisa in less than 2 hours. I presume you have a car in Terricciola. If you don't I recommend you rent one at the Pisa airport. Borgo alle Vigne in Terricciola is in the middle of nowhere and you need your own wheels. Return the car in La Spezia before going to the Cinque Terre.
For TUSCANY ideas see here:
www.borghiditoscana.net

Nanci:
Pisa is a popular airport, however many don't think of the city as a destination.

Lucca is very close, and it's a great, quiet place to recharge your batteries.

You can easily take a train from Lucca to LaSpezia where you catch a short local train up to the C/T.
On the return trip, you can catch a train back to Bologna, 10 miles east of Borgo alle Vigne.

If you're renting a car, Bologna is a tough one hour drive south to Florence. And it's really not the best place to do day trips to Siena and San Gimignano. (We love Volterra.) But it would be a great place to stay if you wanted to take the Ferrari Experience and see the Lamborghini factory. And the incredibly beautiful Lake Garda is also close by.
If you want to tour the Tuscan hilltowns, you'd do better to stay at an agriturismo outside of Siena or San Gimignano.

Sounds as if you're going to have a great trip.

Oh my! Thanks for the suggestions. I think now we will only stay one night in Pisa. Luca sounds great too. We were hoping to not rent a car at all. I need to contacted the Hilton to see if they have some shuttles that we could jump on to do the day trips around there.

I'm not sure which Borgo alle Vigne David is referring to. Bologna in nowhere near that. The Borgo alle Vigne Hilton is in the Val d'Era (Era Valley).

Agree with Roberto, you need to rent a car. from the Pisa airport you are around 30 minutes

from the Hotel complex. Without a car you are at the mercy of frustrating bus and tour

schedules. Look @ Kemwel car rentals.

A taxi would be around 30 minutes and cost $50-60. by train/bus combo it would take 2+hrs.

The alternative would be to head to Lucca which is a 30 minute train ride.

Edit
From Lucca head to the CT, then rent a car in La Spezia and drive to the Hilton.

Tour Tuscany. Other towns in the area Castellina in Chianti, Volterra if you drop the car in Orvieto,

Montepulcino is on the way.

Drop the car in either Pisa or Orvieto train into Rome.

Lucca and Pisa are next door to each other. You can see both in the same day trip. Same for Siena, one day trip. A lot of walking. Pisa and Lucca are flat. Siena is hilly, a lot of climbing.

Thanks for all the advice. I going to re-map the trip a bit. Will 2 days & 1 night be enough for CT. We are thinking of staying in Vernazza. How many nights do we need in Rome?

Going thru your schedule, Nanci, it seems to me that time to breath besides your several displacements will be really poor, may be you need to squeeze something in order to have a right idea of where you'll be staying.
Anyway -where will you be taking off from? : the flight to Pisa -is non stop from JFK , but from other important US cities and lowest fares, it might be wise to fly to London, or Paris, or Frankfurt, or Amsterdam or Zurich, and then to Pisa.
Two more things: San Gimignano is always crowded, except in January and February, so be prepared beeing September in the highest season of the year; ok 'Cinque Terre' by train, the only reasonnable way to reach them.
Have a nice trip, and cruise -Ephesus is just magnificent (and the greek islands too of course).
cf, Firenze

We are flying out of JFK

Thanks for all your suggestions. This is how our trip stands now.
Flying from JFK to Pisa & staying one night there...
San Gimignano, one night (this one I'm second guessing) ...
Hilton Tuscany for 3 nights...
CT 2 nights...
Civitavecchia for one night & board our ship for 10 days to Greece/Turkey/Naples...
After the cruise we are spending 3 nights in Rome then flying home.

I would rent a car upon arrival and book your Hilton two nights earlier. You can visit all those places from the comfort of that location by car. From Terricciola Hilton to San Gimignano is a short drive, why change hotels so often?

If you don't rent a car, I'm not sure how you are going to cope. the Hilton is really isolated in the middle of nowhere.

We were very lucky to get 3 nights being HGVC members because it's booked solid for the month of September. So we have no choice on that. I wanted to stay close by to make sure we see as much of Tuscany as we can. We were hoping to see it without a car...maybe take buses or trains into all the towns. We are older & didn't want to drive the roads on our own. Would Sienna be better to stay in instead of San G?

This is where that new Hilton is:

https://www.google.com/maps/place/Hilton+Grand+Vacations+Club+at+Borgo+alle+Vigne/@43.5494071,10.6828379,2328m/data=!3m1!1e3!4m2!3m1!1s0x132a0b98e2fd9d6b:0xad6494b637d942d8

There will be no trains and almost certainly no buses because it's not in a town, it's in the middle of the countryside. Maybe there is a bus from Pontedera that goes through Selvatelle, but it's going to be infrequent and it's still a long walk to the hotel (and very dark at night since you are in the middle of fields). You can take a taxi from Pisa, but it's not going to be cheap because it's almost one hour drive. Probably a bit cheaper from Pontedera. Then when you are at the Hilton, you will be stuck there without transportation. The hotel can arrange private cars (limo) to take you around but it's going to cost you hundreds of $$ each day to visit things. If you can drive at home, you can probably drive there.

In terms of your San Gimignano choice, that is also not that easy to reach from Pisa.
You need to take a train to Empoli. Change trains then take one to Siena but stop along the way in Poggibonsi, where you will take a bus which takes you from Poggibonsi to just outside San Gimignano ancient walls. Buses aren't that frequent, so you need to check the schedule carefully if you take trips outside of San Gimignano.

For the type of hotel arrangements you have and the type of trip you envisioned ( visitingTuscany's small towns) a rental car would be very valuable unless you are willing to spend a fortune in car service with driver (like a limo service).

I would call the Hilton there and find out about transportation arrangements if you absolutely don't want to rent a car.

Okay... you talked us into renting a car. I agree that is the best way to go. Thanks Roberto for all your advice. Should we return the car in Pisa before we go to CT or park it there then drive to our port for the cruise?

Pick up your car at the Pisa airport. Rental car offices in Pisa are only there.
Your Delta flight arrives at Pisa in the late morning and with a car you don't need to spend the night in Pisa. Pisa is a one trick town. Once you have seen the cathedral and leaning tower, you are done. I would leave the luggage at the airport and visit the tower for a couple of hours, then take a taxi back to the airport to pick up a rental car. You could also drive to the tower from the airport on your own, but it requires some driving in town which might get you lost along the way.
With the car you would head to a location that is convenient for day trips. You will now have two nights available before you return to the Hilton. I would choose a hotel in the countryside in the Colle Val D'Elsa area. That would be very convenient for visiting places like San Gimignano and also for returning to the Hilton (via Volterra).
People in this forum can give recommendations.
After the Hilton stay, you will go to the Cinque Terre, where you need no car. You should return your car in the city of La Spezia, next to the Cinque Terre. After you return your car take a taxi to the la Spezia Central station and from there take a train to the Cinque Terre town of your choice (10-20 min). I recommend Monterosso, as it has more accommodations and restaurants.

After the Cinque Terre you would take a train to Civitavecchia. There are several trains that run along the coast from Genoa to Rome and stop in Civitavecchia along the way. From the Cinque Terre you will likely need to take a regional train back to La Spezia to catch those trains as they travel through the Cinque Terre but they don't stop in those small villages (maybe only in Monterosso, but I haven't checked).
To rent a car use a consolidator, such as:
www.kemwel.com
www.autoeurope.com
choose the no deductible full coverage insurance (aka No Insurance Excess)
For train schedules see:
www.trenitalia.com
enter from Monterosso to Civitavecchia and a date in the next week.
To rent a car in Europe you need an International Driver Permit (IDP), basically a translation of your US driver's license which you also need. Any AAA office can get you the IDP for $20 and two passport photos. It takes 10 minutes. It lasts one year, so get it as close as possible to your trip date.

You are such a big help Roberto. Thanks so much~! This is going to be one amazing trip~!