We once stayed two weeks in Tuscany, one week in Volterra and one week in Montepulciano. Your time is short, so you might be best served in one area, perhaps Florence/Lucca area based on what you said. I would rent a villa with 3 baths for 3 couples. Here is one from airbnb in Vinci just west of Florence: https://www.airbnb.com/rooms/3243465...s=1&s=VQalk24h

We have found that most farmhouses and villas during the summer rent for a one week minimum, Saturday to Saturday. Agriturismos tend to be more flexible. Are you starting your trip in Tuscany or arriving from another area? If starting there, your port of entry (Rome?, Florence?, Milan?) can play a significant role in utilizing your vacation time wisely.

I think the old Saturday to Saturday scheduling has become a thing of the past for many rentals. Now that booking software offers easy to use scheduling software, and fewer travelers stay a week in one place, airbnb and Home Away have lots of flexible stays. We have stayed in beautiful homes and apartments for even one or two days. Expect a fixed cleaning fee,.

I agree with Florence as a base. Pisa is an easy train trip (double-check for the correct station) If you can arrange a tour of Pisa's Duomo, it's worth it. There is so much to see in Florence, you might not have much extra traveling time. With 3 couples, you might need 2 cars! I think you'd save money just using buses and trains. No help with cooking schools but others can provide good advice.

If you go to Uffizi, ask your hotel concierge/clerk to make a reservation for you. Bargello is a nice museum also.

Tuscany is quite a large area, not sure most people realize that. There are mountain areas, beach areas, hilltop town areas and the "must sees" (Florence, Sienna, San Gimignano, Pisa, Chianti region, ect). Unfortunately these areas will be very, very crowded in July. And 5-6 days will not do justice to truly enjoy the offers of Tuscany.

As Mike says, Tuscany is a big region, about the size of Maryland. Because much of the region is rural, travel is not usually very speedy, so there is no one base that would allow you to "see" Tuscany. You may have only a few days, if the dates you mention include travel to and from Italy.

It would be helpful if you would tell us exactly how many nights you'll spend in Italy, and where your arrival and departure points are. Also maybe you could tell us more about your interests.

Florence is a fascinating city to visit, especially if you're passionate about art, history, and architecture. I wouldn't call it a good base for visiting Tuscany, though. Many, maybe most, of the places people want to visit in Tuscany can't be reached by train from Florence, and are complicated to visit by bus. For day trips by car, Florence is probably the worst base you could find.

Last spring, we took an eight-day driving tour of Tuscany with some friends from Milan. This seems to be about double the time you have for your trip. We spent two nights in Florence, two nights in Montalcino, two nights in Pitigliano, and two nights in Volterra. We all live in Italy, and this was not the first Tuscany tour for any of us. My husband and I often visit Florence, and we once before spent four days in Montalcino. Our itinerary may give you some ideas, although you certainly couldn't do all of it.

We were able to see three very different areas of Tuscany with this itinerary, and we used the travel days to visit even more areas. Driving from Florence to Montalcino, we visited several of the Chianti towns. While in Montalcino, we visited Montepulciano, Montechiello, and Pienza. We stopped on the coast en route to Pitigliano, visiting Orbetello and Porto Ercole. While staying in Pitigliano, we visited Sovana, Sorana and the outdoor thermal springs of Saturnia. On the drive to Volterra, we stopped to visit the national park of the Maremma area, again on the sea. While staying in Volterra, we visited San Gimignano and Bolgheri.

In spite of the many places we visited, we skipped some of the more important areas of Tuscany. We didn't visit Siena, or Lucca, or Pisa. We totally skipped everything east of Florence, including Arezzo, Sansepolcro, Camaldoli, and Cortona. (My husband and I had seen this area several times before.) I would have loved to visit Carrara and the Apuan Alps, in northwestern Tuscany, an area I've never seen, but that will have to be another trip.

If you're arriving in Florence by plane or train, I suggest you spend a night or two there, and then rent a car. We took a bus to the airport to pick up our rental car. I won't bore you with the details, but don't rent from Maggiore.

Perhaps our favorite destination on this trip was Pitigliano. The view of the city from below is iconic, and the area is beautiful but not overrun with tourists. It was an Etruscan area, and there are plenty of Etruscan sites you could visit if you're interested in ancient civilizations. The thermal springs at Saturnia are delightful. Be sure to bring swim suits; we didn't because we weren't expecting it to be so inviting.

While in Pitigliano, we stayed at an agriturismo called Villa Vacasio. This was probably our favorite lodging on the trip. It's an agriturismo, a family-run farm stay lodging. They have rooms with private entrances, each with its own patio, and there's also a pool. The main building of the agriturismo has a great room with a fireplace, probably not lit in July, which is where we passed time with the other couple after a day of sightseeing. There is an optional dinner served, and the meals were superb, based on local products. The owner gives cooking lessons, and if someone wants cooking lessons in English, she has an English-speaking assistant, her son-in-law, who helps at the lodging although he has a day job. She said that if you reserve well enough in advance, she can make sure he'll be available. You can reserve this lodging on booking.com

https://www.booking.com/hotel/it/agriturismo-villa-vacasio.it.html

Pitigliano has a very interesting Jewish past. There is a museum in a historic synagogue that we found very interesting, although none of us is Jewish.

Another highlight of our trip was the tiny village of Montichiello, a real little jewel. It's not far from Montalcino. You can see it all in an hour or two, so you might want to stop over there en route to some other destination.

It's true that you might need more than one car for your group. If you rent a van, make sure it will have enough room for all your luggage. There are 7-passenger vans, but some of them have two extra seats that fold up from the luggage area, leaving little room for suitcases. In any case, make sure all of you pack light. Having two cars allows the group to split up sometimes, but, to me, it takes away a lot of the fun of a group road trip.

If you share the driving with some of your friends, make sure you have a talk about tickets before you begin the trip, and then keep track of who was driving when. One of our friends was constantly driving well over the speed limit. We often told him to slow down, but he couldn't keep his foot off the accelerator. I rented the car in my name, so all the tickets came to me, complete with the fees tacked on by the rental company for their assistance to the police in tracking you down. This man has been a friend of my husband since university, and my husband wanted to just pay the tickets rather than bring it up after the fact, especially since we couldn't prove who was at the wheel when the infractions occurred.

Also be aware that almost every town and city in Italy has limited-driving zones (ZTL), where only residents, delivery vehicles, and the like, can drive. It's best to just assume that all towns have these zones and park your car outside the town center. Usually you'll see signs directing you to parking areas as you approach a town. Look up ZTL before arriving in Italy to familiarize yourselves with the signs. However, there is no uniformity in signage. and some signs have additional instructions only in Italian.

Finally, unless you have an EU drivers license, everyone who will be driving needs an IDP, the International Drivers Permit, which you have to carry along with your regular license. It's really just a translation, but it's required by law. Some rental car agencies will refuse to rent a vehicle to you if you don't have it. Most police officers will want to see it if for any reason you're stopped. (In Italy, there are often random traffic stops to check documents.) You can get the IDP at an automobile club in most countries. It doesn't cost much, especially if you bring along your own passport-sized photos.

We have been to Tuscany twice for a two week period each time. We went with friends and rented a villa in Pienza. We had a Chef come and make us dinner a few nights each week (loved it). We loved the area so much we rented the same villa the second time we went. It is a beautiful area in the Val D'Orcia area of Tuscany and I don't think you can find a more beautiful part of Tuscany. We did many day trips from there over the time we were there. We went to Florence for one day each trip. For me that was enough due to all the crowds. I'm sure if you stayed there overnight you would get a different impression of Florence. We visited Sienna and San Giminano also. We liked seeing them but again they are very crowded. All the day trippers from Florence take busses there.

We enjoyed the smaller hilltowns much more. We loved Pienza, San Querico, Montelpulciano, Montichiello, Montalcino, Bagno Vignoni. Be sure to go to Radicofani. There is an old fortress at the top that you can go to and the town itself it beautiful. We had dinner one night here at La Grotta. We did not know it but the food was family style. We ordered so much food that it covered the entire table. The wait staff did not speak much English and did not stop us from ordering so....The food was very inexpensive so we had no way of knowing. We never laughed so much at a dinner. It wasn't the best food we had in Italy but it is one of our most memorable meals. We returned on our second visit and ordered more sensibly.

One day we took a trip to Sorano, Sovana and Pitigliano and as bvienci said Pitigliano is stunning. It is a must visit. Another day we drove to Orvieto and Civita (google image it as it is amazing). Another day we went to Avignonesi, which is a winery. We took a wine tour and had a wine paired lunch. It was AMAZING! We then visited Cortona.

Stu Dudley has an amazing driving itinerary of the area. Hopefully he will chime in. We got some great ideas from him.

As you can see there is a lot to do in the area and you are not contending with quite so many bus loads of tourists as you would be in Florence or Pisa. I guess it depends on what you are looking for.

This was the personal chef we used. We loved Alessandro! https://www.tuscan-chef.com/ He will come to your villa for cooking classes too.

We went hot air ballooning near Montisi too.

Hot air ballooning. It was awesome!

I've cycled and car toured over most of Tuscany.

1) July will be hot, city centres will be hotter
2) https://www.agriturismo.it/ offer a range of interesting places to stay often with a pool but a real opportunity to meet Italians and to see the sites but they tend to be outside cities in the countryside
3) if I was doing this thing I would focus on one of the smaller towns and find an agriturismo on the edge, this allows you access to a range of restaurants which will not suffer from the "big draw" of the big sites in the evening but still the opportunity to dine outside in the country and watch the twinkling stars that are the pearls of the area against the big velvety ski.
4) despite the heat and in some cases air-conditioning, you will find that the traditional farms often just use thick walls and windows that open to the north to keep them cool, be prepared to either be shocked or amazed that it works. But it will not work for your car, open top or air-con will be a must. Rent your car from AutoEurope. Italian car rental practises make the Pirates of the Caribbean look like boy scouts. Having a broker between you is a good idea and the prices will be good.
5) The trick to using a car during these sort of holidays is to get up early and hit the cities you want to visit early before the coach parties turn up. Lunch is often a "crap shoot" though good selection and booking will work wonders. Afternoons to the Pool. You will also find that many of the towns have a time (6 pm 7 pm) when people just wander around the main town squares saying hello etc. This can be lovely and is a good time to be in your local town

Thanks to everyone who sent me ideas and suggestions. I'm meeting with my fellow travelers tonite and will review everything with them

We have a hard enough time coming to agreements with only 4 people in our travel group - good luck with 6 - you have a lot to discuss. I hope you come back and post what your group decides they would like to do. A timeline with potential dates and all the different places in addition to Tuscany and the Amalfi Coast that you want to see would allow more accurate suggestions. Again, good luck.