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KSWinograd Aug 2nd, 2014 01:29 PM

Itinerary help in Tuscany!
My friend and I (both of us are foodies and wine lovers) are planning on extending our trip of a week cooking in Umbria to explore the Tuscan region. We'll be checking in to a hotel in Greve in Chianti for 2 nights on September 13, to enjoy the Chianti Classico Wine Festival. We will be in Tuscany until 19 September. We leave out of Rome that day at 2:45 pm. So far that is the only plan we've made. While in Tuscany we would like to tour some wineries, go on a Hot Air Balloon ride, explore San Gimignano, visit Sienna, check out the many Renaissance museums and churches, and hike the Cinque Terre. I am overwhelmed by all of the wonderful options and need help in planning our itinerary. Do we need a car in the region, or should we book day tours instead of driving ourselves? What order should we consider travelling to these towns? I've read so much about Vinci, Cortona, Montepulciano, and Montalcino - too many places, too little time. Which of these towns would you recommend we spend time visiting? We want to see as much as possible without spreading ourselves too thin. Our budget leaves room for private tours. Any information or guidance you can lend is greatly appreciated, such as where to stay, where to eat, which wineries we should visit, where to explore, and in what order. Also, we are not planning on going to Florence or Pisa this trip since we've both been there already.Thanks in advance!

annhig Aug 2nd, 2014 02:05 PM

<<too many places, too little time. >>

sadly you are absolutely right.

this is what you have so far:

Sept 13 - arrrive Greve. stay 2 nights.

Sept 15 - travel to ??

Sept 19 - depart Rome at 2.45 pm [which means you'll want to be there by about noon]

So you've got just 4 nights to fill in. looking at your preferences you could drive to the CT [will take you about 2 1/2-3 hours and stay there for 2 nights, followed by a night in San Gim [much nicer when the tourist buses have left so a good place to overnight] and then another closer to Rome.

alternatively spend all but your last night in Greve and use it as a touring base - you can easily see San Gim, Siena, and Arezzo from there; the CT is a bit harder as it's at least 2 1/2 hours drive each way which IMO is a bit far for a day trip.

another alternative would be to explore the south of Tuscany around the Maremma - you could head south to Siena and then go west to Massa Maritima, and Orbetello, or further inland to Pitigliano and Viterbo. Both Orbetello and Viterbo are about 2 hours drive from Rome so they would make good last night stops.

kybourbon Aug 2nd, 2014 03:07 PM

Yes, you need a car (and probably for Umbria too, but you didn't mention where). You can't reach much from Greve by public transport. There are buses to Florence, but not much else.

It's been a few years since I was at the Chianti Festival. It was quite hot so you didn't feel like drinking much wine. You get a certain number of tastes (different wines can take more than one off your card)with the fee, but you can pay it again if you want to taste more.

I would head to San G and Siena after Greve. Then head south/east (Montepulicano, Cortona although it's much closer to Umbria and would make sense to visit on your transfer from Umbria to Greve)or south (Montalcino, Pienza, etc.). You can't do all the places you listed as you simply don't have time. If you make it to Montalcino, sample the Brunellos. In Pienza, the various Pecorinos.

If you plan to book tours, you would probably be better off basing in Siena as there are a lot of tours operating from there. Small towns don't have as many on offer.

annhig Aug 3rd, 2014 03:30 AM

oops - I had missed that you were querying whether to drive or not.

How were you intending to get to Greve? by bus?

As you say that your budget will stretch to some private tours, you might want to look at these people who get consistently good reviews both on TA and here:

SkipHudgins Aug 3rd, 2014 02:58 PM

All the folks that have responded so far have been a big help to me over the years so let me give it a try. Just set up a similar vacation for some friends for 5 weeks later than your trip.

I am a car guy. Partly because we go to Tuscany just about every year since 98 and it is the easiest way to enjoy the countryside that is Tuscany.
Sept 13--arrive Greve. (Two suggestions if you are not sure about your hotel. Villa Vignamaggio for higher end or Le Centinelle for B & B). Attend wine festival that afternoon evening. We had some much "fun" eating and drinking all afternoon that we cancelled dinner plans. Also nightly events at the Festival.
Sept 14--drive around Chianti area. Make a winery stop like Volpaia or Castello di Ama.
Check out Badia Coltibuono for lunch and their wine shop. Visit Radda or Panzano. See Dario the butcher in Panzano. (Alternatively drive just a little and do hot air ballon).Eat dinner at Ristoro Lamole in Lamole. Best in Tuscany, not just my opinion but most other sites agree like Tripadvisor. Filippo and his partner will take care of you for food and the view is exquisite on the top of a mountain about 7 km above Greve. Lamole di Lamole Chianti Classico Riserva is perfect wine for the setting.
Sept 15--short drive to Siena. Sightseeing all day in Siena. Lunch on Campo. Suggest stay at Hotel Santa Caterina or Palazzo Villi on south side of town. Parking for car. Splurge would be Certosa di Maggiano in the same area.
Sept 16--more Siena and Hot air ballon or spend the day visiting San G and Volterra. The two together make a nice day trip.
Sept 17--Montalcino and wine, wine, wine. Stay both nights at Hotel de Capitani. Get a valley view room and you will be happy. Easy to drive to. Parking. On the way to Montalcino visit Buonconvento or the Abbey Monte Oliveto nearby. Or stop at a winery like Altesino which is on the road to Montalcino.
Have lunch at Taverna Barbi (Fattoria Barbi) just outside Montalcino and get a quick Barbi tour/tasting. Then head down around the Abbey S Antimo and if still going strong make another winery stop in afternoon. Walk thru Montalcino after you check in. Check out the little square with a great 1880s bar opened by the guy who invented Brunello. Say hi to Stefano the nice bartender who speaks virtually no English, but who carries on a great conversation with you. Dinner at ReMacchia, S. Giorgio or Buccon di vino (just outside town).
Sept 18--visit Pienza nearby. Add Montepulciano (Vino Nobile) for a full day. Or leave Pienza and drive thru the Val D'Orcia. Stop at Ristorante La Porta for lunch in the little town of Montichieello (sp?) and then work your way back to Montalcino stopping in Bagno Vignoni. Stroll thru Montalcino again in late afternoon early evening, stop at the bar, then dinner at one of the other restaurants. Or just sample wine and have a brief meal at one of the enotecas.
Sept 19-- (after making advance reservation for Betty Ford upon your return to states after your fun wine tasting week in Tuscany) get in car and drive like mad back to Rome airport. Go by way of Grosseto and the coast autostrada. It is an easy trip and avoids Rome traffic. Leave plenty of time to get thru airport assuming you are going to US for car drop off, airport checkin, airport bus ride to another terminal, lines to go thru passport control and security and finally escalator up to terminal.
Any part of this and whatever anyone else suggests will be great fun. Enjoy. Don't worry about getting lost. Some of the best places we "found" in Tuscany were discovered when we were technically "lost".

zoecat Aug 3rd, 2014 03:10 PM

Great suggestions from Skip!

zoecat Aug 3rd, 2014 03:13 PM

Rent your car from car rental broker Kemwel. They have excellent rates and customer service. Be sure to check deductibles when comparing prices.

Have fun!

bvlenci Aug 4th, 2014 10:37 AM

I would forget the Cinque Terre. It's not in Tuscany and it's not worth going there if you don't spend at least two nights. It's also very crowded in September, almost sinking under the weight of the foreign tourists. Many of the easier hiking trails are closed because of the risk of landslides.

San Gimignano also gets far more than its fair share of tourists at that time of year. We've been there several times but only once by car. That was in late April, and they were turning cars back on the approach road, it was that crowded. We parked on a country road and walked in. Once we were there in the winter, and it was very nice.

I particularly like Montalcino.

I can't imagine why you'd want to take a hot air balloon ride in Tuscany. The best way to see the countryside if from the ground, and it it's just for the experience, you could have that at home instead of eating up your really limited time. Anyway, they can only operate in ideal weather conditions.

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