Highlights
There is no better way to explore Italy than by car. The breathtaking views will captivate you as you explore the beautiful countryside of Italy’s most famous regions Umbria and Tuscany. Indulge yourself in this 10 day vacation that will give you an authentic experience Umbria & Tuscany. Start in Rome, a couple of days to overcome your jetlag. Retrieve rental Vehicle and head to the central Italian regions, two of the most popular tourist destinations in the country. Populated with sloping hills covered with vineyards, luscious green woods, magical medieval villages, and spectacular valleys. This area of the country is famous for its long tradition in producing some of the best Italian wines, olive oils, cheeses and cured meats. Start off in the famous Chianti region, where wine is a religion, before passing through the beautiful town of Siena – home of the famous and Palio horse race. Head south reach the romantic Val d’Orcia to admire its Tuscan landscapes, dive into its woods to hunt for truffles, and then learn how Italian “Nonni” make the local “pici” pasta. Top your experience off with an indulgent visit to the Perugina chocolate factory in Perugia: the icing on the cake for this astounding adventure through central Italy.
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Itinerary - click for more
10-Day Italy Itinerary: Rome – Umbria – Tuscany – Chianti
Day 1 – Arrive in Rome
- Activities:
- Meet your driver upon arrival at Rome Fiumicino Airport.
- Private transfer to your hotel.
- Time to relax and recover from your journey.
- Overnight: Rom2
Day 2 – Vatican & Rome Highlights
- Morning:
- Breakfast at hotel.
- Hotel pick-up for small group tour of the Vatican Museums & Sistine Chapel.
- Afternoon:
- Free time to explore Rome’s highlights (e.g., Colosseum, Trevi Fountain, Piazza Navona).
- Overnight: Rome
Day 3 – Rome → Todi (Umbria)
- Distance: 135 km – approx. 2 hours drive
- Activities:
- Pick up rental car.
- Depart Rome, drive north into Umbria.
- Arrive in Todi, a charming medieval hilltop town.
- Explore on your own and enjoy traditional Umbrian cuisine for dinner.
- Overnight: Todi
Day 4 – Explore Todi & Spoleto
- Distance (Todi → Spoleto): 45 km – approx. 1 hour each way
- Activities:
- Morning: Discover Todi’s medieval streets, walls, and panoramic views over Val Tiberina.
- Afternoon: Drive to Spoleto, famous for its Roman theater, arches, and Romanesque churches.
- Return to Todi for the night.
- Overnight: Todi
Day 5 – Todi → Assisi → Perugia → Lake Trasimeno → Montepulciano
- Total Distance: approx. 170 km – 4 to 5 hours with visits
- Suggested Route & Stops:
- Assisi (65 km) – Visit the Basilica di San Francesco and medieval center.
- Perugia (25 km) – Explore the historic center and Gothic architecture.
- Lake Trasimeno (35 km) – Scenic drive around the lake.
- Continue to Montepulciano (45 km) through rolling Tuscan hills.
- Overnight: Montepulciano
Day 6 – Montepulciano & Cortona
- Distance (Montepulciano → Cortona): 35 km – approx. 45 minutes each way
- Activities:
- Morning: Stroll Montepulciano’s Renaissance streets, piazzas, and viewpoints.
- Afternoon: Visit Cortona, famous for its Etruscan roots and the film Under the Tuscan Sun.
- Overnight: Montepulciano
Day 7 – Montepulciano → Val d’Orcia → Chianti
- Distance: approx. 120 km – 3 hours with stops
- Suggested Stops:
- Pienza – the “Ideal City” of Renaissance urban design.
- Montalcino – home of Brunello wine.
- Abbey of Sant’Antimo, San Quirico d’Orcia, Bagno Vignoni.
- Continue to the Chianti region.
- Overnight: Chianti area
Day 8 – Discover Chianti
- Activities:
- Scenic drive through the Chianti Classico Wine Route.
- Visit local villages such as Greve in Chianti, Castellina, and Radda.
- Stop for wine tastings and a traditional Tuscan lunch at a countryside estate.
- Overnight: Chianti
Day 9 – Chianti → Siena → Hills near Rome
- Distance: 250 km – approx. 3.5 hours total
- Activities:
- Morning: Drive to Siena (40 km).
- Visit Piazza del Campo, the Duomo, and historic contrade neighborhoods.
- Afternoon: Continue south toward the Roman countryside for your final overnight stay.
- Overnight: Hills outside Rome
Day 10 – Departure
- Distance (to Rome Fiumicino Airport): approx. 60–80 km – 1 to 1.5 hours
- Activities:
- Drive to Rome Fiumicino Airport.
- Return rental vehicle.
- Board flight home with unforgettable memories of Italy!
- Activities:
Included
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Vehicle Rental Details - click for more
Car Rental Includes:
- Unlimited Mileage
- Third Party Liability (RCA)
- Collision Damage Waiver Reduction (CDW)
- Theft Protection Reduction (TP)
- Personal Accident Insurance (PAI);
- Super CDW – Super TP
- 18% Airport Charges
- 14% Railway Fee
- Road Tax
- 22 % VAT
Car Rental Does Not Include:
- Administrative cost of invoice
- Administration fees in case of accident (GMU) and fines (GRV)
- Whatever not mentioned in the inclusions
Not Included
Hotels or Similar
As a general rule the scheduled hotel for each departure will be one of the above listed. The final list of the hotels will available 15 days prior to departure.
Rates (From)
| 2026 | Per Person Double | Single |
|---|---|---|
| 02 Apr-30Apr | $3100 | On Request |
| 01 May-30 Jun | $3200 | |
| 01 Jul-02 Sep | $3500 | |
| 03 Sep-30 Oct | $3550 |
The CAD ($) rate is indicative of Euro price and subject to change.
Price per person in CAD $ Dollars.