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Tuscany Help

My husband and I are planning a Tuscan holiday for May next year. We were originally thinking of late April/early May but I'm a little worried about the weather, so we are looking at pushing it out to late May - unless any comments sway us otherwise! (we live in South Africa so like warmth, although hot is not needed!)

This trip for us is about countryside scenery, exploring, walking, food and wine. We've earmarked some destinations, but there are others we like - but of course we can't do everything without rushing (which I definitely don't want to do)! I'd love some input from those with experience of the destination!

Our thoughts are:

Fly into Florence and spend 2 or 3 nights there. Pickup a car and head to Chianti, maybe stay at Locande de Piazze, where we would spend 3 nights. Then head to Montepulciano / Val DÓrcia / Pienza and spend 3/4 nights. We love the look of Borgo San Vincenzo, if I can convince my husband that the price is worth it! Then back to Florence for the flight out.

But then we also saw the Maremma, and thought it looked lovely! We found a charming hotel called Locanda Rossa. Is it worth substituting one of the areas earmarked for this rather? There is a possibility of flying out of Rome if we need to.

Does anyone have any other area or hotel recommendations? We like lovely boutique hotels with a bit of charm but still stylish.

For reference, this is my 2nd trip to Italy, first was Rome, Siena and Elba, and my husband has been to the various Lakes a few times.

Posted by
1884 posts

My flowering cherry tree index says that anytime after April 23 would likely be enjoyable weather and my experience is that the first 3 weeks of May are the sweetest of all. Of larger concern practically are the long holiday weekends of Liberation Day (April 25) and Labor Day (May 1) which in 2026 will likely be a big deal as it falls on a Friday. I'd suggest starting your visit on or after Tuesday, May 5.

Posted by
6222 posts

May is indeed a wonderful time it be in Italy. Only once in a decade+ of travel did we encounter terrible weather (the flooding rains a few years ago).
Your itinerary sounds lovely. It is more what I call "classic Tuscany" -- where I have not really explored, but the Maremma is nice, too. I guess I would compare the two stops in Tuscany and see if they are varied enough for you or if you want to head south to see some of that area. I would only do so if you could fly out of Rome and not have to backtrack.
What I love about the Maremma is the nature, like the wild beaches, and the Etruscan heritage sites like the vie cave.
I tend to stay in towns so I don't have any recommendations for hotels similar to those you have selected, but I had this place bookmarked for some reason--https://www.parrina.it/en/
You might want to check it out if you are interested in being closer to the coast.