10 days in Tuscany

We had a wonderful stay at Agriturismo Cretaiole, near Pienza, last June. During peak season (which includes May) they require a Sat. to Sat. stay. It's not a B&B. Breakfast is on your own, but if you purchase the optional Dolce Vita package, you'll have an amazing array of food in your apartment and can easily provide all your own breakfasts without any additional shopping. It includes fresh eggs, bread, meat, cheese, yogurt, cereal, honey, jam, etc. The apartments are beautiful. The property accommodates a total of about 20 guests. We traveled there as a group of 10 people, age late 50's to early 60's, but there is a wide range of ages among the guests. One apartment was occupied by a young couple on their honeymoon, and there was another couple in their 30s. You'll love the family that owns and operates this agriturismo! Some great group activities are included in the Dolce Vita package, or if you prefer to just do things on your own, rest assured you will get wonderful information about all the best things to do in the area, from Isabella (daughter-in-law of the farmer/owner) and Carlotta and Marta (employees who provide expert consierge-type services, including making reservations for you, providing directions to places, and handling any emergencies that may come up). Check out Cretaiole's website, Facebook page, and the blog posts by Cameron Hewitt on this Rick Steves website. Everything that everyone raves about is true! A beautiful place, in the most beautiful part of Tuscany, very convenient for day trips to all the wonderful Tuscan hilltowns. You'll be warmly treated like family during your stay. Our time there went too fast and we wished we had another week!

Spend 3-4 nights in Chianti anywhere along the SP222 between Greve and Radda, then 4-5 in the Val d'Orcia. Between Montalcino and Montepulciano. The area we focused on last fall was south of Pienza toward Bango San Fillipo.

We rented an apartment outside of Montepulciano one time and a house in San Quirico another. Both trips were two weeks. We found plenty to do in the surrounding areas. We took day trips to the towns you mentioned plus a day trip to Rome.

Hello!

Tuscany so unique... The best region in Italy for sure!

When in Lucca, don't miss the the Leaning Tower of Pisa and Maddalena bridge. Head to Riserva State Orrido di Botri for a canyon tour. If you are a foodie, you might like to have dinner in prison... check out the Fortezza Medicea in Volterra, near Pisa.
Taste truffles in San Miniato, take a day-trip to Cortona, get to The Uffizi (if you like art you'll love it!), wander the streets of San Gimignano, visit the Garden of Bomarzo (also known as the Park of the Monsters) in Viterbo. At Castellare de’ Noveschi you can have a winebath (!!!) for two... Also check out Bagni San Filippo is a small village known for its thermal waters (southern Tuscany)
Eat wild boar covered in chocolate, you can find it in most restaurants.

When in Lucca, don't miss the the Leaning Tower of Pisa.

When did they move it?

Recommend checking out the DK Eyewitness Backroads Northern Italy guide. They have great suggestions for scenic routes and sights. I bought a used copy via Amazon, but many libraries also have. They give itineraries for different areas. As for a restaurant suggestion, we really liked Ristorante di Lamole. They are open for lunch and dinner. Up a very small road in the tiny village of Lamole in the Greve in Chianti region. They have great food and an outdoor patio. Reservations recommended.

What are your interests?

We had a wonderful stay at Castello di Verrazzano, which is just outside Greve. They are reasonably priced. The rooms were clean and tidy. The furniture was homey, you didn't feel like you were staying in a hotel. Isabella lives on site and is happy to help in any way she can.

The accommodations are in a farm house on the private road that leads up to the winery. There are just 7 rooms, so it feels intimate. You take breakfast up the hill at the winery. Breakfast is a wonderful spread, including local bread and cheeses and wild boar salami. Marco was very attentive and we had a lot of fun with him teaching us a little Italian and him practicing his English.

Whether you stay there or not, be sure to do their winery tour and food and wine experience. You start with a tour of the winery, then sit down to an incredible lunch. You start with an appetizer and prosecco. You then have a pasta dish with their Chianti, a meat dish with their Super Tuscan, then another dish with their Chianti Reserva. You also get to sample their amazing Balsamic Vinegar. Dessert is biscotti served with Vin Santo. Eat a light breakfast and plan on skipping dinner!

We loved the hill town of Radda. Plan to spend at least an afternoon in Volterra. Stay for the evening promenade and the spectacular sunset.

We also had a great afternoon visiting the Abbey of Monte Oliveto . We had a wonderful dinner at the adjacent restaurant, then attended Vespers at 6:30, which is held using Gregorian chant. Other than one local woman, we were the only guests. We were invited to sit up with the monks and given materials to follow. We also participated in the responses. The sanctuary is stunning and it was a memorable experience to be in the still of the evening worshiping with the monks.

We just spent 5 nights in October 12 km southwest of Siena at the La Bagnaia hotel (we used Hilton points). It's a neat hotel consisting of multiple medieval era buildings that have been updated. I'm not necessarily recommending that you stay there so much as giving you a point of reference where we based. If I were paying $$, I'd find a nice agritourismo in that area or maybe a little further south like San Quirico. We had a rental car and the RS Florence and Tuscany guidebook. Within the guidebook, there are 3 driving tours (pages 512-513 give you an overview map) you can follow; 1) Heart of Tuscany tour, 2) Brunello Wine Country tour and 3) Crete Senesi tour. We spent a day on each of these and really enjoyed them immensely. The guidebook shows points of interest and some great photo ops. We also spent a day driving to Cortona and Assisi and another day trip covering Volterra and San Gimignano. That covers 5 days at a slow enough pace that you don't feel like all you did was drive. If you get the chance, stop into Montechiello for lunch at La Cantina de La Porta. The wild boar pasta was the best I have ever had!

Word of caution on driving: The roads are fun to drive but your GPS may take you some places you don't want to go! Our GPS took us to Monticchiello through a narrow, curvy gravel/dirt road. I have no idea what we would have done if we approached another car because there was nowhere to pull off! Just go with it and enjoy!

We stay in Montepulciano. Wonderful hilltop town and short drives for day trips to Pienza, Montalcino, Cortona, Assisi, and others. The countryside is a beautiful drive. We stayed at Hotel Duomo. Nice B&B hotel with elevator and breakfast. We also stayed at Camere Bella Vista. No breakfast but wonderful views. Both are in the upper, historical, center of the town, right by the Piazza Grande.
http://albergoduomomontepulciano.it/?lang=en
https://www.camerebellavista.it/en/

Thank you all for the great info!!! Much appreciated!

Bologna is a very cool town - not in Tuscany but a fast train ride from Florence. If you like food - it is the food capital. Also Ferrari & Lamborghini museums are nearby.