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  1. Hi Scarlett

    We are planning a Italy road trip for 10 days for September 2025, which we are planning to drive ourself. We would like to to make sure we throw Rome and Pisa in with everything you suggested, could we get that all in 10 days? We want to see the wine country and all the beautiful land/towns. Rome is one of the special places that we want to visit because my Mother always wanted to see it but never had the chance to go. Our daughter-in-law told us that if we fly into Rome and make our way up north and end in Florence to turn the rental car in there and take the train back down to Rome to end our visit. Any suggestions would be appreciated.

    1. Hi Lisa,
      It is never too early to start planning! That would be a very rushed 10 days, in my opinion. I haven’t been to Pisa in forever, but I didn’t think it was that special honestly. It all depends on your style of travel, but I would suggest 3 days in Rome, 4 days in Tuscan countryside, 2 days in Florence and a travel day.
      And yes, that is an excellent suggestion from your daughter-in-law. The train from Florence to Rome is fast and direct. Just be prepared that sometimes a rental car company can charge a one-way fee (sometimes it is reasonable, but other times it can vbe ridiculously expensive).
      Let me know what you decide!

  2. Kate – Thank you for the wonderful itinerary tips. We will be in Tuscany for 7 days in May 2023 and are looking for an apartment with full kitchen and 2 bedrooms. Do you have any to recommend? Appreciate your knowledge and help.

  3. Hi, we have just used your guide to book our trip in late May! We’re going for a week and staying just outside Pienza for 3 nights to visit Pienza, Montepulciano, Bagni vigorous & maybe Cortana. Then a night in Siena, a night in a winery a bit north (this wasn’t on your list but we had to squeeze in a winery stay!) then Florence. Thanks for the blog, it’s so helpful!!

  4. Thanks so much for recommending Borgo Pignano and Lupaia. These 2 places absolutely made our trip to Tuscany unforgettable.

  5. Thank you so much for your informative and inspirational posts on Tuscany!
    We will be there in October for a week.
    Can you recommend accommodations in Montepulciano?
    Thanks so much!

  6. Hi, Scarlett, thinking of heading to Tuscany this September, hiring a car and visitng many of the places you have suggested here, which area would you suggest staying in Southern Tuscany as a base to explore the surrounding areas? Before heading North for a few nights in/around Florence. Also, myslef and my partner are big wine fans and would love to visit a couple of vineyards whilst there (white wine ideally), any recommendations.

    Thanks so much for all the info

    1. Hi Jules, September is my favorite time to visit Tuscany. Southern Tuscany is absolutely beautiful. I really like Pienza and Montepulciano (slightly closer to the freeway for easy day trips). You can’t go wrong with wine in this region. There are wineries everywhere that you are sure to enjoy.

  7. Heading to Italy in 3 weeks (June 2022).
    Itinerary Rome (3nights)-Florence(2)-Bologna(2)-Modena(1)-Venice(2).
    Renting a car when we leave Rome and planning on driving and returning car @VCE. Having a difficult time deciding stop(s) between our longest trek…Rome- Florence. So many choices. We love wine, food etc. There are 4 of us. I’m overwhelmed by choices.

    1. Hi Karen, That sounds like a wonderful itinerary! The road from Rome to Florence is filled with many gems. Orvieto and Montepulciano are two great stops not too far from the freeway. Enjoy your trip!

  8. Hi Scarlett,

    This is wonderful and very helpful post. My friend and I will be visiting Tuscany in spring of 2023. I did consider fall, but the days are so much shorter. We are considering staying in Villa a Sesta for maybe the entire 7 days and day doing trips from there. Is that feasible? How do we handle transportation for winery tours when we stay in a rural location especially in the Montepulciano area?
    We will start our trip in Venice, and include Siena and Florence.

    Thank you,

    1. Hi Kathy,
      Honestly, I am not as familiar with the area around Villa a Sesta as I am with the Val d’Orcia area. It does seem centrally located though and feasible for day trips. Depending on your interests, you might want to think about splitting it up. Half in Florence and half more towards Montepulciano.
      You could look into winery tours that offer transportation. Group tour and private drivers are available in the area.
      Spring will be lovely. Have a nice trip!

        1. I personally have never used a private driver in Tuscany because I lived there and had my own car. However, a quick search on google will find you companies that arrange drivers and tours. You can also look on Viator or Get Your Guide. Lastly, depending on your hotel, they could probably arrange one for you as well.

  9. Love all your Italy posts they are the most helpful. We will be traveling to Italy this fall for the month of Icyobwr. I want to stay in the Tuscany area for a week have a rental car and just see as much as possible each day. About how many places can I see in this time by car? PS I may just skip bringing a camera and use my iPhone

    1. Hi Toni, You can easily see a town or two a day if you have a car. You can also break it up (three nights in Southern Tuscany and three nights more north like Florence). iPhones take pretty amazing photos these days and are more than efficient for the everyday user. Enjoy your trip 🙂

  10. Hi Scarlett, this is such a great post on Tuscany, thank you so much for sharing! My husband and I are going to Tuscany and I can’t wait! We’re thinking of going to Siena, Chianti, and Lucca – we’ve found it difficult to find good resources for tips, so I’m glad I stumbled upon this via pinterest! I really love your photos! What camera do you use?

    Thanks again for sharing!


    1. Thank you Kate! You will love Tuscany. It is so beautiful! I’ve also heard great things about San Gimignano and its award winning gelato. I use a Canon Rebel T5 for my DSLR, but a lot of photos on my blog are taken with my iPhone too ; )
      Don’t hesitate to reach out if you have any questions about the area!!
      Ciao ciao!

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