Ciao! We are coming to Tuscany the last two weeks in May to celebrate our 30th wedding anniversary. I have thoroughly studied your entire website to help plan our visit and appreciate the wealth of information you have provided. We have already visited the big tourist cities in Italy, so this time we want a more relaxing trip to experience the Tuscan countryside and local culture, cuisine, and of course, the wine! We will be staying in a farmhouse apartment, relatively close to Castellina in Chianti. We still have some questions: Will the countryside be in full color during this time, or will we be a little early? Do you have some suggestions, in addition to your website content, for some off-the-beaten-path areas we might visit to make our visit this time more unique and memorable?
Visiting Tuscany in May
- Thread starter rtmgigem
- Start date
lots of places off the beaten track as well as som better known ones..
Ciao rtmgigem,
Congrats on the upcoming anniversary, you will have a lovely time spending it in Tuscany and Castellina in Chianti is a great central location from which to visit the smaller towns/villages that you've likely not seen yet.
May will be a great time, actually there is lots of flowering and green to be seen at the moment and you'll see more of that in May as the weather is also pretty nice.
I assume you will have a car so you will be able to get around easily to the small towns.... as you've seen on the site, we highly recommend Siena. It is a city but somehow with its closed off center and medieval look, the feeling is of being in a small town where time has stopped.
So I recommend Siena but other places in the vicinity you will have to explore include:
Castellina, Radda in Chianti, Panzano, Monteriggioni, Colle Val d'Elsa, the small castle at Staggia (it is very close to Castellina), San Gimignano, a day trip to Volterra, another to the Abbey at San Galgano, Certaldo, San Gimignano, San Miniato. Have you been to Pisa and Lucca? Have you already booked the two weeks at one place? Because an option would be to spend a week there, then move toward the coast for the second week. That way you can explore the coastal area, from Piombino to Livorno. Bolgheri, Castagneto Carducci, Rosignano.... maybe even Elba! May is still a bit cold as far as the temps of the sea so bathing is up to what you're used to.... but at least for Elba, it is the border between low season and high season which makes it the perfect time to explore the island.
I hope some of these suggestions just get you thinking.... there are so many off the beaten track but very lovely to discover. You can mix some of the more visited (such as San Gimignano) in with the smaller ones. You won't be bored and am sure you'll have a memorable anniversary vacation!!
Let me know if you want more suggestions
Ciao rtmgigem,
Congrats on the upcoming anniversary, you will have a lovely time spending it in Tuscany and Castellina in Chianti is a great central location from which to visit the smaller towns/villages that you've likely not seen yet.
May will be a great time, actually there is lots of flowering and green to be seen at the moment and you'll see more of that in May as the weather is also pretty nice.
I assume you will have a car so you will be able to get around easily to the small towns.... as you've seen on the site, we highly recommend Siena. It is a city but somehow with its closed off center and medieval look, the feeling is of being in a small town where time has stopped.
So I recommend Siena but other places in the vicinity you will have to explore include:
Castellina, Radda in Chianti, Panzano, Monteriggioni, Colle Val d'Elsa, the small castle at Staggia (it is very close to Castellina), San Gimignano, a day trip to Volterra, another to the Abbey at San Galgano, Certaldo, San Gimignano, San Miniato. Have you been to Pisa and Lucca? Have you already booked the two weeks at one place? Because an option would be to spend a week there, then move toward the coast for the second week. That way you can explore the coastal area, from Piombino to Livorno. Bolgheri, Castagneto Carducci, Rosignano.... maybe even Elba! May is still a bit cold as far as the temps of the sea so bathing is up to what you're used to.... but at least for Elba, it is the border between low season and high season which makes it the perfect time to explore the island.
I hope some of these suggestions just get you thinking.... there are so many off the beaten track but very lovely to discover. You can mix some of the more visited (such as San Gimignano) in with the smaller ones. You won't be bored and am sure you'll have a memorable anniversary vacation!!
Let me know if you want more suggestions
Thanks so much for the great suggestions! We have been to Siena and San Gimignano before, but we liked them so much, we will definitely be spending some more time there on this trip. We'll definitely be adding some of your suggestions to our itinerary. Thanks again for your help!
Siena is a must 
Siena and San Gimignano definitely merit a return visit, especially if you went there really fast the first time. San Gimignano turns into a quiet village around dinner and afterward, I'd suggest going out to dinner there once ;-).
Siena is often also just visited from the outside but if you have time, take a whole day there and buy the Siena Pass offered by the cathedral to get in to see the duomo, the Piccolomini library, the baptistery and then go into the museum and climb all the way to the top of the "facciatone" which is that one wall built in the 13th century as Siena prepared to expand the size of the cathedral (and then stopped after it was hit by the Black Plague). You get a stupendous view of all of Siena from up there.
If you also have the energy, a visit to the top of the Torre del Mangia tower (and a visit to the Palazzo Pubblico) are worthy of doing. So many people with limited time give too little to Siena but it has many treasures. I'm writing more about Siena to add to the section on the main website so hope to give you more suggestions soon as to what to see and do and where to go eat ;-).
We stop in Siena at least for lunch anytime we are passing by on our way to somewhere else, generally down to Maremma or to the Val d'Orcia.
Siena and San Gimignano definitely merit a return visit, especially if you went there really fast the first time. San Gimignano turns into a quiet village around dinner and afterward, I'd suggest going out to dinner there once ;-).
Siena is often also just visited from the outside but if you have time, take a whole day there and buy the Siena Pass offered by the cathedral to get in to see the duomo, the Piccolomini library, the baptistery and then go into the museum and climb all the way to the top of the "facciatone" which is that one wall built in the 13th century as Siena prepared to expand the size of the cathedral (and then stopped after it was hit by the Black Plague). You get a stupendous view of all of Siena from up there.
If you also have the energy, a visit to the top of the Torre del Mangia tower (and a visit to the Palazzo Pubblico) are worthy of doing. So many people with limited time give too little to Siena but it has many treasures. I'm writing more about Siena to add to the section on the main website so hope to give you more suggestions soon as to what to see and do and where to go eat ;-).
We stop in Siena at least for lunch anytime we are passing by on our way to somewhere else, generally down to Maremma or to the Val d'Orcia
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