I like to use this website because it has a great search filter and user reviews. You can select to search for specific amenities like a pool, a restaurant, a hill location -- whatever you like. I like a farmhouse with its own restaurant, because usually they grown there own food (and often produce their own wine and oil), and it is nice not to have to drive home after dinner.

I would recommend you search in the area on the map marked "Lucca' and the area marked "Siena" to start out.

http://en.agriturismo.it/tuscany/index.jsp

I always google up the names of places I like to see their websites to contact them directly, and also to see if I can find other reviews -- although my experience of most family-run establishments in Italy is that they are spotless and wonderful.

Tripadvisor is also a great resource for "specialty lodging" in Tuscany -- meaning farmhouses -- with current reviews. Check the webisites to see if they have restaurants.

http://www.tripadvisor.com/Hotels-g1...ny-Hotels.html

http://www.tripadvisor.com/Hotels-g1...ny-Hotels.html

Whit out taking away anything to the splendor of Tuscany I dare to say that Tuscany is not Italy and Italy is not Tuscany. In your first visit of Italy I can't understand that you are worrying to visit the Cinque Terre and not Rome or Venice, to mention the two major art-history centers. But its your decision and I respect that.
For the best hill town I would go for Abbadia S. Salvatore, Montalcino, Montepulciano, San Casciano Bagni, Poppi, Anghiari, Barga, Cetona, Collodi, Montecarlo, San Gimignano, Suvereto, Sorano.

Check my blog for more info www.travelingtoitaly.com/blog

I ignored my instincts, as well as what I was outright told, and went to CT as a day trip. Could not resist the impulse. I don't think you would need to worry about October, but in May it was horribly crowded. The towns were overrun as well as the path. Gorgeous, just not my thing.
If I were to return to the area, I would stay in a town nearby and visit only to walk the upper, more challenging paths.
10 days is a nice amount of time--somehow time slows when you travel, if you let it. Sounds like it would be good for your to pick two bases. Enjoy!

I have read comments like gti-travel's many times on Fodor's, and I "dare say" that Tuscany is more Italy -- historically -- than gti apparently realizes. Who does he or she think Etruscans were? And where did they live?

A blockish, textbook approach to a "first-time" visit to Italy has sent millions upon millions of travelers fleeing Italy's art sights in droves and turning Venice into a mindless playground of hyper-consumption.

Rather than finger wagging, I encourage people to approach Italy as they would any other country rather than castor oil to be gagged down when you'd rather be exploring italy's extraordinary richness of natural beauty and charming village life.

Italians often speak quite disparagingly of Rome, and many throw up their hands at what has happened to Venice. There is profound history, beautiful art, deep Italian culture wherever you enter Italy, and wherever you stay. Don't be fooled into thinking you need a travel planner to tell you some formula for visiting one of the most open and welcoming cultures in Europe.

I went to Italy for 10 days and fit in Florence, Venice and Rome with a day trip from Florence to Tuscany. I agree with others, Venice is a must visit. It's not that far from Florence by train (approx 2hrs). I was in Florence for 3 days and I LOVE art and felt that was enough time. I took a day trip to Siena and San Giminiano in Tuscany, and one evening in Florence we took a train to Pisa to see the tower etc. I haven't been to Cinque Terra, so I can't advise there. Wherever you go, have a great time!

zeppole, lets clear first I'm "he," then that in your history lecture you forgot that, in Southern Tuscany, before the arrival of Etruscans there were the Umbrians and their territory was stretching from the Po River down South Pompeii.

You talk about "hyper consumption" as bad disease for Venice, when it was last time you were in Florence? Travel is a "hyper-consumtion" leisure activity and that's why Airbus Industries is building 800-seat airplanes. And Florence is not the "happy island" you would make your readers believe. The town, like it or not, is over crowed, noisy, expensive and over run. Still the most beautiful in the world.

I might understand you allergy for travel consultants, that is what I'm, but nobody invested you with the authority to give lectures about traveling philosophy. Of course chat rooms are full of experts that traveled a couple of times to a place and know every thing about that.

And are right these "chat rooms" experts that give the wrong information to people that do not need history lectures but just simple information on where to go, what to, what to see and fully taking advantage of their experience, and money. that they can better appreciate and remember the places they visit, the places they see and experience the culture of the visiting country personally without the lenses of chat room experts.

Happy traveling!

LouisTraveler - Zeppole has a valid point: no matter what the rest of us think has been an epiphany during our travels, these are still only personal favorites for reasons particular to ourselves. You should research the areas you think have inspired you to go there, and then choose a base that is sensible to explore as much as you can of that region. For example, I can never go to Italy without at least having 3 days in Florence somewhere during my travels, but that's because I always leave knowing I haven't seen everything I'd like to see. Similarly, for hill and fortified towns, I didn't like Siena at all, finding it too crowded even in November, but I loved San Gimignano which at least allowed me to step away from the modern day hustle and put myself back in time. Many go to Venice and only see the endless shops along the calli, but I look past and over them to see the jewel that it really is despite all that.

I enjoyed Montepulciano, Montecatini, Monteriggiano, Val d'Orcia,Montalcino, Pienza, and even the tiniest Lucignano and we based out of Pozzo, in the Val di Chianna. Radda in Chianti was also lovely, with a perfect little inn on the outskirts for a leisurely lunch. Cortona was charming and Lucca was lovely, but I didn't care much for Pisa - it will all come down to your own personal quest during your travels. For me, it's history and architecture, and some places appeal more than others. Further east, the small but beautiful San Sepolcro was lovely, as well, and if you manage a visit there, you will be very close to wonderful places in Umbria, such as Citta di Castello, Assisi and Gubbio within easy reach.

I understand your time constraints; I usually go for 4 or 5 days because of that myself, but I go often. Just don't cram too much in to what you finally decide may hold the greatest interest for you so that you can really soak in what it is you went to see.

Travel is meant to be a joy, not a chore or a test of fortitude, so you should pick places that intrigue you.

Sandra

Ignore some of the comments about Florence - it is well worth your time and the key to seeing it is getting tickets ahead of time to the museums, Duomo, Santa Croce etc. All should be seen and tickets will mean not having to stand in line. Also the Bargello and San Marco are must-sees and were my favorites. Give yourself a few days to see the sights and do spend a day in Fiesole - it is lovely and the views are wonderful. While in Florence, go up to the Piazzele Michelangelo to see a spectacular view of the city.

I have not been to the Cinque Terre but have been to some hill towns. My favorite is San Gimignano followed closely by Sienna where the cathedral is amazing. I also loved Lucca even though it is not a hill town. You might also want to check out Volterra.

Once you have seen Tuscany, plan a trip to the Amalfi Coast. As it is a very romantic place, perhaps an anniversary trip is in order. Must-sees are Ravello, Positano, and of course, Capri. I recommend staying in Amalfi as it is centrally located and the town itself is very nice.

Have a wonderful trip!

We just returned from Italy in April with 5 days in Venice and a week in Tuscany. During that week we drove up to Cinque Terre, parked at the train station in Levanto and took the train - based on recommendations online. What we found was that yes, it was mountainous, but nothing we could not handle driving ourselves. So the next morning our guys headed back to get the car, and they drove it to our B&B in Corniglia. We only stayed one night, but it was amazing.
Walking between Corniglia and Riomaggiore is a breeze (except for the 382 steps up the mountain back into Corniglia) and the paths between Corniglia and Monterosso progressively get more difficult. A beautiful place we are so glad to have visited and perhaps one day will return.

Our rental in Tuscany was just south of Firenze off the SR2 in a village called Badia de Pasignano...just west of Greve in Chianti. These villages are little jewels dotted throughout the province. We had a couple wonderful meals in the restaurants in town. We found it very central to many other towns, and close to Firenze altho we never spent any time there. We did a cooking class in our own home and another hilite was Magic Dinner at Castello di Verrazzano. A fantastic evening where we got more than our monies worth! www.verrazzano.com
On our last day we drove west to the coast to the city of Follonica - it was quite a drive, but we saw the beautiful Maremma countryside and enjoyed Ponente Beach in town.

We squeezed every moment out of our 2 weeks in Italy, including suntanning around the pool for 1/2 a day, but hey, I didn't go there to sit around! Make your vacation everything you want it to be.

I loved Pienza, with a side trip to Cortona.

I'm planning our 8th trip to Italy, traveling on a budget (time and money). We have learned something new each time. The most important lesson is to plan well, then release your attachment to everything going according to plan and enjoy whatever comes your way. On our first trip, we stayed at Relias San Pietro in Polvano, a lovely inn located remotely between Cortona and Arezzo. A car would be necessary for this as it it 7 km from the nearest train station. Driving in Tuscany is the best way to experience the area, but avoid driving into the larger cities (Florence and Sienna). Favorite hill towns: Cortona, Volterra, San Gimignano (off season), Pienza (day trip), and just south of Tuscany - Orvieto (with a day trip to Civita di Bagnoregio). We love Florence, although after our first visit we swore never to go back, because we made the mistake of scheduling it as a day trip and drove into the city. Now that we have discovered the treasures of Florence beyond the Uffizzi and Academia (David), we have a new list of things to see on our next visit. If you are there for two days, include Santa Croce on your must see list and spend an evening in Piazza Michelangelo, watching the sun set over the city.

To really experience the Cinque Terre, stay in one of the villages. We love Vernazza. Being there for at least two nights allows time for hiking the trails (which are amazing and various levels of physical challenge, from the easy path between Rio Magiore and Manarola, to the most challenging between Vernazza and Monterosso). Buy a Cinque Terre card, which gives you unlimited trips on the train between villages, as well as access to the trails. We stayed in Lerici and commuted the last time we were there and found that the commute took far too much time out of our days. I do not recommmend a car to get to the Cinque Terre - getting there is a huge challenge. If you do drive to the area and have a GPS, you can park near the train station in La Spezia and take the train from there to the Cinque Terre. Of course, if you are staying for a few days, the best choice is to travel by train to La Spezia. Your Cinque Terre card can be purchased at the La Spezia train station and is good from there to beyond the 5 villages.

Whatever your choices, revel in the experience and don't worry about all of the things you won't see on this trip - you will return.

I am surprised that none of you have mentioned that St. Francis of Assisi's (patron saint of Italy) feast day is October 4th. Assisi (although in Umbria - the "Heart of Italy") is not far from Sienna that buts up to Umbria. There is plenty of hiking because when you cross the street you are 50 feet in the air. A beautiful Medieval town with a lot of history. If you go down into the valley to the Basilica of Santa Maria di Angeli, you will find the small church called the Porciuncola (small portion) that Francis himself rebuilt. It is located inside the Basilica, as it is very small. If you go to confession, receive Holy Eucharist, and offer prayers for Il Papa, you will receive a great indulgence. This happens on no other day, but October 4. your birthday, and the feast of St. Francis. If you have a car, you can visit the "Hermitage" up in the mountains, where St. Francis went to pray. The Basilica of St. Francis houses the most famous frescos of Giotto, a brilliant Siennese artist. The Etruscans also inhabited various parts of Umbria, and there are small museums, such as Colimancia, a hill visable from Assisi and about 13 kilometres (6-7 miles) away.
There are many quaint towns and villages all around, both in the vallies and mountain hills, and a nice drive from Sienna.
October can be very nice, as sometimes September is molto caldo, but carry layers for the evenings.
No matter where you go, you will love it. The people, the culture, the food, the scenery and the wine are the best!

October is a great time to go to Italy, that is when my husband I prefer to go. Less tourist and the weather is great!!

If you love to hike, the Cinque Terre is the best place to go. The villages are lovely and the seafood is awesome!!! Vernazza is a great home base there. I recommend staying at Gianni Franzi (http://www.giannifranzi.it/index2.html). It is a bit of a hike up to it but the views are amazing (ask for a room with a view when you book it). There is also the Pirate Cafe (Il Pirata delle Cinque Terre). Great sweets for the morning & later in the day and dinner is incredible. Depending on how much hiking and down time you want there 2- 3 days.

Florence is a must do!!! Depending on how much of the art you want to see: 2-3 days but you really should take the opportunity to see the David's (Donatello's @ Il Bargello & Michelangelo's @ Accademia - make reservations for the 2nd one). Wander the streets and look at the amazing architecture. Must dos: Piazzale Michalengelo, Piazza della Signoria, Ponte Vecchio, Boboli Gardens, Baptistery, Orsanmichele, Duomo, Giotto's Tower, and the market.
Some of the best restaurants: Yellow (across the street from Il Bargello), Da Il Latini (Via dei Palchetti 6/r - a little hard to find but so worth it), and gelato (many places around)!

As for Tuscan villages: Volterra is so beautiful. One of our favorites. So few tourists go. There is an amazing theater is ruins there. San Gimingnano is great. On the way to the Cinque Terre, if you are driving, you should stop in Pisa (do plan on a long time there - a couple of hours) and Carrara (just drive through and see the huge marble slabs - Michelangelo's marble for David came from here).

Someone mentioned Assisi, which is great but Umbria is a bit of a drive. If you go on parton saints day, keep in mind there will be fairly large crowds and it is fairly crowded even in the off season.

No matter where you go, you will have a great time. You can't go wrong. You have plenty of time to figure out what you want to do.

I've only been to Italy twice, both times with a very similar itinerary (taking group of students on a tour) and this is my impression: I love love love Florence (art, architecture, the bustle, and yet the REALNESS of it once you get out of the main areas), and my students all felt the same. The Baptistry is more appealing than the Duomo, and the Boboli Gardens were a real delight, and better than the Pitti palace they are part of. I was the only hardcore art lover amongst these travel groups, so I'm giving you a general consensus -- I LOVED the Uffizi, and seeing the masterpieces in person changed the way I felt about Renaissance art forever. The Botticellis left many of my group weeping at their beauty. Teenagers. That's saying something.
Venice has its charms, but feels a little like Disneyland to me, with lots of shopping. Try as we might to get lost in the backways and byways, we kept stumbling upon what were essentially marketplaces. So, mixed feelings - the charms didnt outweigh the drawbacks.
Hilltowns: Pienza - loved it alot - full of good food, artisans, and charm. quietish. Siena - has a magnificence, but also a sense of being crowded at close quarters with tourists. San Gimignano - we all like it - we went up to the very outskirts and climbed the old castle walls - the little courtyards around that area were restful and charming - away from all the shops. Had GREAT gelato here.
But hands down, outside of Florence, my favorite place is Orvieto. In Umbria, not too far from Assisi, which we didnt have time to visit, alas. Orvieto has the most beautiful duomo inside and out, with spectacular Signorelli frescos and a "jewel box" exterior that will take your breath away. Etruscan ruins, little side streets, relatively few tourists...all in all, soooo much worth a visit.
So, there are my two cents. We also went to Verona on the way to Venice and overnighted there, and found it charming --
Though I wouldnt go out of my way, I enjoyed the little squares in the evening - music, food, farmer's marketplace, etc.
Hope that helps somehow!

I haven't read all of these responses but I know that going off the beaten path in Italy is definitely worth it. Many Italians (and tourists) acknowledge Venice and Florence as museums instead of cities, as they have few inhabitants that aren't involved in the tourist industry and stand as monuments of the past. I think a few days in each is sufficient, as you're not going to learn a lot about language and culture there in the droves of tourists... Most of Tuscany is so, so SO touristy that it's worth it only because it's almost obligatory.
For a more intense, interesting and educational experience, I recommend an itinerary that includes Rome for at least a week, Naples for a few days, and Sicily if time permits..

I second all those who mentioned Montalcino, Florence, Siena and Volterra. I would add Abazzia Monte Olivetto Maggiore between Siena and Asciano. We spent 7 days on a farm outside of Asciano and made day trips to these and other places. We took the train into Florence and returned the same day–bad decision: we should have stayed a couple of nights!

Also the towns just over the Tuscany-Umbria border (Orvieto, Perugia, Assisi).

We started our 2 weeks in Italy with 3 days in Venice (should have been 4-5) and left Tuscany for 4 days in Rome (again should have stayed longer).

It has been 3 years and my husband who was my reluctant fellow traveller cannot stop raving over our time in Italy to all and sundry—they may be bored but we are not.

Buon viaggio!

My husband and I are also planning our first trip to Italy in October to celebrate a special anniversary. We are planning on two weeks, starting in Florence, traveling through Tuscany, then to Rome and finishing in Sorrento. We have been thinking of hooking up with a tour for the Tuscany part of our trip but after reading the comments here it almost seems like we could do our own thing in a car. True? Any thoughts/recommendations for Tuscany food/wine tasting tours?
Also, any suggestions for Sorrento/Amalfi/Positano?
Grazie!

Count me as one who's lukewarm about Siena. It's just one of those "I don't get it" times for me.

Thanks to all for taking the time to offer opinions....

Question....I couldn't possibly imagine driving without a GPS navigation...any suggestions here???...I have one built into my 'Google' Droid phone...not sure about available service with it.
I've learned allot....fyi...I stayed 4 days in Roma and then 4 in Positano....very nice combination the week after Easter when most all had left.... with flowers out everywhere and the temps so nice... wouldn't have missed the day long Vatican tour or walking 'ancient Rome' for anything...likewise for Positano and Capri area.

Nice spirited thread here. First time to Italy I can certainly agree with the suggestion that missing Venice and Florence is not a sin but i think Rome for 5 days is a must and 10 days... why not?

I like marroma's idea of heading down to Naples for a few days. Another fantastic city.

As for tour versus going it alone - seems to me this thread shows that Italy is so loaded with things to do that it is easy to get it right and just as easy to get it wrong. Regardless of whether the traveler decides to join a tour or go it alone, or do a combo I think a travel adviser is an excellent resource. The travel adviser knows the tours, knows how to travel alone, has probably done much of it so can help you just like many do here. Why not use a pro?