It's official. Just purchased 2 Cheap Tickets flights, from LAX to Rome arriving Sept. 10th, flying out of Bologna back to LAX Sept. 21st...We plan on a couple/few days in Rome, and then renting a car to drive through Tuscany, making our way up to Florence over the course of a few days. Then ending with a few days in Florence. Somebody had suggested flying out of Bologna, as it's pretty close to Florence.

Any advice? Also, is travel insurance a good idea?

For our personnel trips, husband & I, we do not use travel insurance. Only one of our trips, which included Mom & Niece, did we purchase the insurance, strictly due to Mom's fragile health. Depending on your age/health, you may want to save the money for the outstanding wines in the region.

Good for you !
Here are some places to stay in Tuscany. I would train to Chiusi to get your car---see Autoeurope.com.


BOB’S FAVORITE DIGS IN TOSCANA

A. RURAL LOCATIONS: All have parking and good food options nearby

1. Relais La Saracina www.lasaracina.it 230 to 300E
Fabulous country home near Montepulciano—helpful owners

2. Cretaiole Agriturismo http://www.cretaiole.it/ Good value for families

3. Terre di Nano www.terredinano.com 100 to 155
Both rooms and apartments at rural Agriturismo near Monticchiello

4. Hotel Pescille www.pescille.it Good value at a rustic hotel only 3 km from famed San Gimignano with great views---100 to 130E

5. Fattoria Tregole www.fattoria-tregole.com 110E to 180E
Has both B&B and apartment accommodations. Near Castellina in Chianti

6. Agriturismo apts. near San Quirico— www.poggiolo.info/ About 110E


B. IN-TOWN LOCATIONS: For walking convenience to shops & ristorantes.

1. Palazzo del Capitano www.palazzodelcapitano.com 130 to 180E
Very nice small hotel in center of San Quirico—perfect location to explore.

2. Vecchia Oliviera www.tuscany.net/oliviera/ 130 to 180E
Nice 4 star hotel at the gate into lovely Montalcino---has pool.

3. Palazzina Cesari www.montalcinoitaly.com 80 to 110E
Lovely small B&B in heart of Montalcino—great value—2 night stay minimum.

4. Locanda di San Francesco www.locandasanfrancesco.it 180 to 200E
New boutique B&B in a lovely location in Montepulciano—great reviews !

5. Palazzo Ravizza www.palazzoravizza.it 130 to 180E
Very nice & popular hotel in Siena with parking.

6. Fattoria Vignale http://www.vignale.it/eng/ Four star hotel in Radda in the heart of Chianti. About 230E for double

Why not just fly out of Florence if you will be there on your last days. We did. Also we purchased travel insurance because we have elderly parents so we wanted the trip cancellation insurance.

Do not even think of travelling without insurance. Consider the risk of a traffic accident.
Hospital.
Air fares for parents or carers to join you.
Medical evacuation.
Vehicle repair costs.
etc.

If you can't afford insurance, then you can't afford to travel.