Ciao Florence Tours · Florence
A Mercedes with driver picks you up at your Florence hotel, gives you about three hours in Assisi and two in Cortona, and brings you back. Pick it if you want two hill towns at your own pace and door-to-door comfort matters more than cost.
Ciao Florence Tours runs this as a private car day: driver, Wi-Fi, water and USB chargers, about 2.5 hours each way to Assisi by one guest's count, and Cortona on the way back. The itinerary allows about 3 hours in Assisi, with short stops at Santa Chiara, the Basilica of St Francis and Santa Maria degli Angeli, then about 2 hours in Cortona.
The driver drives. If you want Assisi explained, choose the "English + Assisi Guided Tour" option, which adds a 2-hour guided walk; a guest who took it called it the best decision of the day. Without it you get free time and the listed stops. One guest flagged the headset charge at the basilica (2.50 to 3 euro). Entry itself is free.
Price: from $624 per person, with tiered pricing for 1 to 8 travellers, so the rate per head drops as the group grows; enter your party size to see the total. It is the most expensive way to see Assisi on this site, against $107 for the coach from Florence. One March 2026 guest left at 9:00, reached Cortona around 17:00 and was very tired. Leave early.
About 2 to 2.5 hours to Assisi, with a break to stretch your legs.
Santa Maria degli Angeli on the plain, then Santa Chiara and the Basilica of St Francis; with the guide option, a 2-hour walk.
West across the Umbria-Tuscany border.
Free time in the hill town of Etruscan origin above the Valdichiana.
Drop-off at your hotel.
★★★★★We opted for the two hour guided tour of Assisi and that was the best decision. She was so knowledgeable and helped direct us on what do with our free time. Would have liked more time in Cortona.
★★★★★Great low stress experience! Our driver Valentin was exceptional and professional. [...] Our guide of Assisi was knowledgeable of St Francis and St Clare and the two cathedrals.
★★★★★Stellar service, easy way to see historical sites. Plenty of time to spend in both places and the private driver was professional, timely and a pleasure.
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Only with the "English + Assisi Guided Tour" (or Spanish) option, which adds a 2-hour guided walk in Assisi. The basic tour is a private car and driver with free time.
About 3 hours by the itinerary, plus about 2 hours in Cortona.
Viator shows a from-price of $624 per person with tiered pricing for 1 to 8 travellers. Enter your party size to see the total.
Much cheaper: a direct regional train from Florence to Assisi takes about 2 hours 45 for 17.60 euro. You lose Cortona and the door-to-door service.
Ready to book
Hotel pickup in Florence and a private car to Assisi and Cortona, with time to wander in both.
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