Soon a holiday in Tuscany? Wondering on the best Tuscany itinerary?

Find our itinerary ideas for Tuscany🙂

Chianti as a base to explore Tuscany

Tuscany tourist attractions are so many that planning a good Tuscan itinerary all depends on the length of your stay. That’s why I’m going to suggest 3 possible itineraries, for short and long stays.

1. Best Tuscany Itinerary for a short stay, 3-4 days using public transportation

3 or 4 days are few but you can still enjoy amazing Tuscan sights. The best solution is you base in Florence and do day trips from there! Florence, cradle of Renaissance art, is a must visit in Italy! considering its central location in Tuscany and the possibility to take advantage of public transportation right in the town’s center, that’s the best way to enjoy the region when you’re not willing to rent a car. You will appreciate some of the best sights while staying in one of the most beautiful art towns in the world.

You can choose one of the many Florentine charming hotels and accommodations in its historic center.

From Florence SMN Train station you can reach fantastic destinations and enjoy great day tours; here is a possible 3 days itinerary in Tuscany:


Note, however, that there can be a lot of other great day trips to make from Florence, so give a look at the link to have an idea; you may be particularly inspired by one destination and decide to go visit it in place of one or more of the above!

The great thing about traveling is also a question of feeling free to explore an area without following a too strict scedule 🙂

2. Best Tuscany Itinerary for a short stay, 3-4 days moving by car

Having the car, base yourself in the heart of the Chianti area of Tuscany: scenic landscape, verdant forests, imposing castles, wineries… the typical Tuscan countryside that will make you feel the real essence of Tuscany. Chianti is a great home base to discover Tuscany.


3. Best Tuscany Itinerary for a longer stay, one week or more with the use of a car

You have more time to spend in Tuscany, take it slowly! Here follows a list of the very best sights and destinations in Tuscany, of course from my point of view! The best thing to do would be to split your days in 2 or 3 different locations to use as your base to start exploring the region. I always suggest spending half the trip in Chianti and the other half in the Val d’Orcia. Here is a dedicated post!

Have a look at the pictures of the various places to choose the ones that you most like to see during your trip!


Get further ideas for your next Italian holiday from our 1 week Tuscany itinerary and our 2 weeks itinerary in Tuscany.

For a customized travel plan ask me here 🙂 It’s free!


  • Kate ha detto:

    Hello! We are planning a trip to Italy for Sept-Oct 2015. We will be spending 2 nights in Florence, then plan on renting a car and driving to the countryside for 2 more nights. From there, we will be driving to Rome and dropping off the car. Do you have any suggestions for a base ? We enjoy great food and wine, and hope to explore the shops and restaurants of smaller towns.


    • elena nacci ha detto:

      Ciao Kate!

      You love great food, wine, shops and restaurants of smaller towns…your base should be the Valdorcia region of Tuscany, located south of the beautiful medieval town of Siena. In Val d’Orcia there are a lot of small and amazing hill villages with lovely shops! This is the area renowned not only for its scenic fields but also for its great wines: Brunello of Montalcino and Nobile di Montepulciano.

      Siena itself is a major art town but retaining all the charm of a small medieval village, here are beautiful shops, do visit Siena.

      A good alternative to the Val d’Orcia, is the Chianti, located between Florence and Siena in a territory famous for its beauty and again for its wines. Take a look at the links of the 2 areas of Tuscany and choose according on what you most like! This blog post will actually help to make your decision.

      I remain at your disposal!
      Happy Planning!

  • Greg ha detto:

    Hey Elena,

    We were hoping you could help us plan our trip in Sep-Oct this year. My wife and I are in our late 20’s/early 30’s and love good food and wine, we are real foodies and love doing road trips through beautiful sceneries.

    We have 14 days in total and fly into Rome from Sydney Australia. We are thinking of doing both Tuscany and Sicily and starting our trip by hiring a car and driving from Rome to Sicily, via the Amalfi Coast for approximately 7 days. Is this a beautiful drive?

    From Sicily we were going to fly to Florence/ somewhere in the tuscan region and spend approximately 7 days in tuscany and maybe visit cinque terra and spend a night there.

    Should we be spending 9 days to get to Sicily and spend time there and 5 days in Tuscany/ Cinque terra or is this too many places and are we over stretching our time? Your advice would be really helpful.

    We were hoping you could help us plan an itinerary and suggest what we should do, where we should stay, how long we should stay in each place, where we should hire a car from, what airline we should use to fly from Sicily to Tuscany.

    We love accommodation that is quaint/ bed and breakfast style places that offer luxury and a real italian experience so your suggestions would be very helpful.

    Looking forward to hearing from you. Your website is so beautiful and it sounds like you are so passionate about your blog?

    • elena nacci ha detto:

      Happy to hear from you again,
      I’m glad to give some help in planning your Italian trip 🙂

      The drive from Rome to Sicily via the Amalfi Coast is a beautiful drive but it’s also very tiring and with quite a lot of traffic! You say you intend to do it in 7 days, of course it is doable and in that case I would recommend around 3 stops on your way. 9 days to get to Sicily and then 5 days in Tuscany/ Cinque terra…honestly I think it’s too many places and you are over stretching your time.

      If I were you, I’d spend 2 days in Rome, then hire a car and drive from Rome to the beautiful Amalfi Coast and stay there 2 days, then I would take a plane from Naples to Palermo or Catania and once there explore Sicily for about 3 days. You might also consider skipping Sicily. I suggest you pick your rental car at a location outside the historic center of Rome, like “Rome-Eur Downtown”, the better for your way south. A week is done!

      After Sicily, fly to Florence in Tuscany via Alitalia airline and spend one week there. Make 2 or 3 days in Florence from where you can also reach the Cinque Terre on a day trip. I would suggest you base in Chianti, in Val d’Orcia, or better in both areas of Tuscany, take a look here for that. In Chianti you can consider Villa Bordoni and Villa Vignamaggio, in Val d’Orcia Relais la Saracina and Lupaia B&B.

      Let me know about your thoughts and if you wish accommodation suggestions for your other destinations in Italy.
      Enjoy planning your trip 🙂

  • Greg ha detto:

    Hi Elena,

    After chatting about our trip I agree and think we are trying to fit too much in. We have proposed a different itinerary, let me know what you think. We have been to Rome and Florence before so don’t want to spend too much time in those two place.

    What we have proposed:
    1. Rome – tuscany drive to tuscany and spend 5 nights in Tuscany in total (2/3 places) + 1 night Cinque Terre.

    2. Fly from Tuscany – Sicily and spend 4 nights in Sicily.

    3. Fly from Sicily – naples and spend 3 nights in Sorrento / Positano.

    4. Get the train from Naples – Rome and spend the night in Rome before flying back to Australia.

    • elena nacci ha detto:

      Dear Greg,
      Here I am! sorry for the delay.

      I second your itinerary, very well planned 🙂

      I suppose you’re now soon leaving Rome via the car to direct toward Tuscany. The number of nights in each place is ok! Definitely spend one night in the Cinque Terre. With this plan you’re going to spare a lot of time!

      You will fall in love with Italy, especially Tuscany and Amalfi Coast!

      For any other help just ask!
      Enjoy your weekend,

  • Danielle ha detto:

    Hi Elena,

    I am really enjoying your website so far and all the helpful information you provide.

    My mother and I have booked a trip to Italy. We will be starting our trip on Monday September 21, 2015 arriving around 4:30 pm. We are staying at a B&B in Via Cantagallo, Prato, Tuscany, Italy for 4 nights and 5 days, leaving in the morning to Florence on Friday September 25, 2015 for one day/night then leaving for the Amalfi coast by train on the morning of September 26, 2015. My mom has already been to Florence so one day is all she needed/wanted. We have a rental car from September 21 till September 25, 2015.

    I am not sure where to start with the planning as we have to return to our home base everyday in Prato. I know I am interested in the scenic drives you suggest and visiting the chianti region but am not sure what else.

    Any help you can be would be greatly appreciated.

    Thank you,

    • elena nacci ha detto:

      Hello Danielle,
      many thanks for contacting me, I’m happy to give some advice 🙂

      Actually Prato is not the most attractive Tuscan town to stay, and not the one I would recommend as the base where you have to come back everyday. The location, also because of the traffic, is not particularly recommended. I would first think about that.
      As you’re moving with the car you might certainly choose another place as your base, the scenic Chianti area itself or the beautiful area of San Gimignano. Follow the links to see as they can be great as a base n Tuscany,

      Get back to me for any further question,
      Have a nice weekend,

      • Danielle ha detto:

        Hello Elena,

        Thank you for your advice. We actually cancelled our stay in Prato as you mentioned it just didn’t work for us and lots of driving back and forth. So we ended up booking a B&B near Greve for first two nights. First night arrive around 5pm have dinner and explore Greve. Next day explore the chianti region, go wine tasting then staying in Greve. Check out in the morning the next day hoping to see San Gimignano, Monteriggioni (if have time) and Siena on the way to Montalcino. Sleep here one night. Next day explore Montalcino and the Val d’Orcia area. Sleeping in Montepulciano. Then take the A1 back to Florence. If have time stop in Arezzo.

        I know we are now staying in multiple places but my mom didn’t want to drive back and forth everyday. How does our new plan sound? Any other suggestions?

        Appreciate your help!

        • elena nacci ha detto:

          Hello Danielle,
          Here I am!
          I’m happy to hear you’ve changed your plans.
          Your new plan sounds very good 🙂 and full of beautiful places to see. I second the idea to stay in multiple places, that would make all easier and less tiring. On your way back to Florence, if you have time, you may visit the lovely Cortona and then Arezzo 🙂

          Do contact me again for any other suggestion,
          Enjoy your stay in Tuscany!

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