Most flights from abroad land to Roma Fiumicino International airport, as those coming from the USA and Canada. At the beginning or at the end of your trip you’re going to spend some time visiting the wonderful city of Rome, so full of incredible sights! Needless to say, Rome is a must visit for anyone!

On the route from Rome to Tuscany…

Supposing you’re renting a car directly in Rome and had planned to visit Tuscany, the Cinque Terre or other fantastic destinations of Italy, here is my travel advice as what to visit on your way from Rome to Tuscany and back. The route is literally full of wonderful sights and unexpected gems…not just in Tuscany, but also in Lazio and Umbria regions.

An itinerary from Rome to Siena, Florence and Cortona in Tuscany

What I’m going to suggest here is a route on your way to Siena and/or Florence in Tuscany; there are a lot of stops along the way, so I suggest to pass some nights here and there in the hill towns before reaching main art cities.

On leaving Rome and its traffic, go north running on the Autostrada A1/E35 in the direction of Siena.Your first stop may be the beautiful Etruscan hill town of Orte, still in Lazio, that is rich in natural springs. Particularly suggestive is the visit to the subterraneans of Orte, a tour through the tunnels of the ancient pre-Roman aqueduct, with fountains, cisterns and wells drilled into the tuff rock.

From Orvieto and Civita di Bagnoregio to the magical countryside south of Siena

Once you’ve left Orte, drive on the A1 to get to Orvieto; we are in the wonderful Umbria region. Orvieto rises on a very hill-top of tuff rock and is simply spectacular! The view you enjoy from Orvieto is stunning as is its Duomo, one of the most beautiful of all Italy. You may consider having lunch in Orvieto, where food and (white) wine are excellent!

Leave Orvieto and the Autostrada to reach the amazing Civita di Bagnoregio, in my opinion one of the most beautiful and suggestive villages of Italy! Suspended in the air and inevitably destined to fall down as time goes by, Civita di Bagnoregio is actually unique in itself! 20 minutes west Civita you may want to visit the beautiful Lake of Bolsena, that offers a lot to any visitor…any kind of sports and activities, great food, great sights and breathtaking views.

This time I suggest you don’t run on the highway to reach Siena, but ride through the ancient historic Via Cassia (SR2), that is curvy, panoramic and incredibly beautiful! It runs across the typical Tuscan landscape, enchanting especially in the south of Siena, passing through the wonderful villages of the Crete Senesi, like Monteroni d’Arbia and Buonconvento, and the ones of the fabulous Val d’Orcia, like San Quirico d’Orcia and Radicofani.

You may first stop to visit Radicofani and its imposing fortress, enjoying a neverending panorama, continue to reach San Quirico d’Orcia and then head west to visit Montalcino, so famous for its precious red Brunello wine and finally get to Pienza, incredibly beautiful and known for its tasty cheese called pecorino.

All this area in the very heart of the Val d’Orcia park is a world to explore, and the food here is fantastic! You may want to sleep in one of the charming villages of the Val d’Orcia, like indeed Pienza or the near Bagno Vignoni, simply enchanting!

Pienza, one of the most charming hill towns of Italy, stands up on a hill offering breathtaking views all over the valley! simply wonderful! In its small town center there are many characteristic restaurants (Osteria Baccus for instance) serving exceptional Tuscan dishes made with pecorino. While there, also visit Montepulciano, a real beauty! That’s also one of the most renowned areas of Tuscany for its fine wines!

From the Val d’Orcia and the Crete Senesi to Siena…

Leaving the Val d’Orcia towards Siena, you may decide to spend a full day visiting the Crete Senesi, a peculiar and suggestive area of Tuscany different from any other. You finally get to Siena, what a beauty! a fabulous medieval art town with a unique atmosphere. The famous Palio horse race is just one of its many treasures, so I suggest to pass at least an overnight here; find my suggestions for chic hotels and apartments in Siena’s center.

From Siena to Florence passing through Chianti…

It’s then time to head in direction of the amazing city of Florence driving through the scenic Via Chiantigiana (SR 222), that crosses the famous and idyllic Chianti area, renowned not just for its wines but also for its lush landscape, medieval castles, and enchanting hill villages, like Castellina in Chianti. You may want to spend a night or two in the heart of Chianti in a fairytale castle or a charming hotel.

Once in Chianti I suggest a visit to the famous medieval village of San Gimignano and its stunning slender towers. You may visit San Gimignano and possibly also Monteriggioni also before joining Chianti on the Chiantigiana road.

Finally you get to Florence, the cradle of the Renaissance and the greatest art town in the world! Florence is simply beautiful, its treasures are countless, a surprising open air museum, not to mention its wonderful shops. You’ll find Florence is very different from Siena, Florence is more chaotic and tends to be overcrowded, while Siena is more peaceful, while both towns are amazing!

From Florence to Cortona and Rome passing through Perugia and Todi in Umbria

From Florence start your way back to Rome but passing through Cortona, where again you may spend one night in some chic hotel, while visiting the wonderful Trasimeno Lake and its lovely villages facing the lake on the following day.

You may end your trip running along a different path to reach Rome from Cortona, you may drive though the Umbria region passing through Perugia and Todi, both incredibly beautiful!  You can have lunch in Todi before continuing on your way to Rome and then back home 🙂

11 Comments

  • Gurpreet ha detto:

    Hi Elena

    Fascinating read- im raring to experience this! I am from India and planning a 17 day trip to Italy this Sep 23- Oct 10 with my wife. Want a good mix of road drives like the above and beach experience at Sicily island. How long will this round trip on road take approx from Rome-Florence-Rome with decent stopovers in middle? I see its about 500 km one way so may be we can land in rome, do a round trip over next 8-9 days exploring 2 different routes as suggested by you- and then fly to Palermo from Rome for a week- fly back to Rome connecting back to India. Would you recommend driving further south to Naples? Also we will possibly miss Venice as it looks out of the way and may plug it sometime next with a Europe trip.

    • elena nacci ha detto:

      Hello Gurpreet,
      Thanks for contacting me, I’m glad to give some advice for your trip to Italy:-)
      I think that 8-9 days of exploring starting from Rome is the right time to enjoy the area. For scenic drives in Tuscany also see these suggested routes. I would recommend driving further south to Naples and the enchanting Amalfi Coast, so unique and beautiful!
      As you’re staying in Sicily for a week, I fear you’ll not have time to fit Venice in; that’s a pity as Venice is magical 🙂
      This suggested tour of Italy I usually recommend can be of some further inspiration,
      Happy planning,
      elena

      • Gurpreet ha detto:

        Hi Elena

        Thanks for your advice last year. Unfortunately, the trip got postponed and now we are thinking about doing it from July 1-16. (15 nights).

        Here is what we are thinking. Land in Rome. Rent a car for rome-tuscany-rome road trip as suggested and spend 7 nights in any good base in tuscany. (Any specific countryside accomodation recommended?)

        Out of remaining 8 nights, we probably would do last 3 nights in Rome and see closer cities on daytrips.

        We are left with 5 nights which ideally we want to be in a nice relaxing beach location- Should we spend that down south- naples/amalfi coast by extending our road trip or fly to Sicily from Rome or Naples..

  • sumeet ha detto:

    Hi Elena,
    i am visiting italy with my wife in september end for 8 days and would like to start from rome 2 days and then move to amalfi coast visit positano, capri, ravello and amalfi for 3 days and then proceed to florence and do tuscany for 2 days and 1 day in venice and then take a flight back . please let me know places to visit with accommodation and do i need to change the circuit of starting from rome or florence to have a better iternary as i would be on train journey and travel by car tuscany area. please suggest best possible mode of transporaion and iternary.
    regards,
    sumeet

    • elena nacci ha detto:

      Hi Sumeet,
      Your plan include quite a lot of destinations for 8 days! But of course it can be done. I think the order starting from Rome and ending with Venice is the best option. There will be quite many things to see, so you may skip Venice, though that’s a pity, and let it for a future holiday in Italy.
      Amalfi Coast is stunning, don’t miss it! As for Tuscany I would visit Florence for a day, and then base at some relaxing location in the countryside, possibly in Chianti or San Gimignano and make your day trips from there.
      Please take not of some nice accommodation suggestions in Chianti and in San Gimignano.

      San Gimignano, still in the Chianti region, is beautiful and renowned for its medieval towers, you may visit a lot of interesting places from there, take a look here.
      Chianti is the wine region between Florence and Siena, famous for its wine and its scenic countryside, here are my tips fro using it as your base in Tuscany.

      Do not hesitate to contact me again for any other suggestion,
      Elena

  • Aarti ha detto:

    Hi dear,
    We are in Italy for 5 days,arriving at Rome and departing from Venice .Will 2 days in Rome to begin with and a day in Florence and last 2 days in Venice ok? What should be the mode of transport? I can miss Florence but would like to see countryside in a private car.where should we pick a self drive car….I mean which city? Please guide as you sound genuine and a lovely person

    • elena nacci ha detto:

      Hi Aarti,
      Thanks for coming here 🙂
      Your plan is ok, 2 days in Rome, 1 day in Florence, and 2 days in Venice, good!
      You can move from town to town by a fast train (check for “Frecciarossa” or “Frecciargento” trains on http://www.trenitalia.com), while I would rent a car while in Florence so to see the scenic Tuscan countryside. Then drop the car off again in Florence and take a fast train to Venice.

      Feel free to contact me again at anytime,
      elena

  • Lydia Comito ha detto:

    Hi my husband and 17 year old son and I are visiting Italy in July . Landing in Rome 2 nights . Then debating if we should drive to cortona? Or train or get a driver ? we are staying at the villa dipiazzano for 3 nights I want to see Florence , also go to a winery and then just explore maybe go see the sirrinouse . Or anything else you think I can do. Then going to Venice for 2 nights leaving from there . How do you think we should travel to see the most !

    • elena nacci ha detto:

      Ciao Lynda! thanks a lot for asking my help 🙂
      Of course touring around with a car is a great way to fully experience Italy and also have more freedom. The car can also be convenient for you while in Cortona, as the beautiful Villa di Piazzano is in the countryside, a car will be necessary to explore the area.
      The fact of using the car or not much depends on you; the route from Rome to Cortona offers a lot of beautiful destinations, like Orte, Orvieto, and Civita di Bagnoregio, all spectacular. In case you’re not willing to drive yourself, you could also get a driver. Once at Villa di Piazzano, you should make day tours to the wonderful Val d’Orcia Park, with its amazing little hill villages, and its countless and famous wineries. Montepulaciano and Siena are also not to be missed. Florence can be conveniently reached by train from Cortona train station, as the train station of Florence is in the center. This way you will avoid all the traffic of the city.
      I understand that this is quite a lot to see, so in case you’re thinking to a more relaxing vacation, you might also consider reaching Cortona by train from Rome, and once there get a driver to explore the surrounding territory, mainly Montepulciano, the Val d’Orcia (Montalcino, Bagno Vignoni, and Pienza), and possibly Siena.

      Please contact me again for any further suggestion,
      Have a great day,
      Elena

  • linda ha detto:

    HI Elena,
    Wo e are planning to visit Italy in the summer for about 5-6 days, getting off in Rome and driving from Rome to Milan where we will be taking the plan back. We would like to visit Florence, Siena and from there up to Milan, possibly through the cost. What would you recommend? We would love to enjoy a night or so in Tuscany but not sure where to base ourselves. We have a 12 years old with us and would also like to make the trip enjoyable for her. Thank you

    • elena nacci ha detto:

      Thanks a lot for coming here Linda 🙂
      So your plan is to visit Florence, Siena and from there up to Milan, possibly through the cost. As you will have a 12 years old with you I think basing in Florence would be a good idea, there are a lot of activities and attractions to enjoy you all. And then passing on the Coast you may stop for a day to enjoy the sea of Tuscany, maybe in Viareggio, that again offers many attractions,
      Let me know if you have any additional question 🙂 elena

Leave a Reply