Any Itinerary suggestions for a 15-17

to start .... http://www.lifeinitaly.it/italiasegreta/Italia_Segreta.htm

As far as the Amalfi coast, and also for the perfect opportunity to spend time with the locals, I highly recommend Sorrento. It was one of my favorite cities during a 2-week tour that we did. It's also in close proximity to day trips in the area, including Capri. Enjoy your travels!!

We've only been once and it was a 2-week tour. We went in July (it's been 10 years already!) and saw Rome, Florence, Milan, Sorrento, Capri, Venice, Verona, Pisa, Assisi, Lake Maggiore, Pompeii, Siena ... and stops along the way. For me, the highlights were Venice, Sorrento and Lake Maggiore. The museums in Florence were amazing. We saw the Vatican and colisseum in Rome, and had some great food there in that City. Pompeii is a wonder! If you do Pisa, don't make a day of it. Make it a 20-minute stop and then be on your way. That's all you need there. There are lots of little towns everywhere in Tuscany and along the way. Get to northern Italy (northern lakes region) if you can. We even went into Lugano Switzerland one day. It's just beautiful up there.Believe what people tell you about theft. Don't carry a purse on your shoulder and I'd use a wallet or zipper pouch that you can tie around your waist or under your shirt. My sister in-law set down her camera for a split second to pay for something at an open market and it was gone in 2 seconds.The Italian people are just wonderful. I was so impressed at how friendly they are and how much pride they take in their jobs, etc. Granted, we were with an Italian tour guide the whole time, but people seemed genuinely happy there with their work and happy with visitors. July was hot, for sure. If you struggle with heat, that might not be the best. The one day it did really get to me was the day we were walking around Pompeii. Now, 10 years later, it might affect me more than it did then! We loved every moment though. We plan to return in 2 years when we retire, and we are planning to stay for a month - maybe do a tour again for the first week or so (going with friends who have not been there), and then maybe rent an airbnb or something centrally located and try to fend for ourselves. We need to start our own planning!We stayed at hotels throughout our stay, but my brother in-law and his wife go every few years and they also like the agriturismo as an option now and then - kind of like a B&B, but on a working farm, so you get to eat what they prepare from there.Enjoy planning. The anticipation is fun. Embrace it all!! 

I respectfully disagree with what was said about Pisa, spending 20 minutes on it. After all, the Piazza dei Miracoli is a UNESCO World Heritage site and it's not just because the Leaning Tower is there. I don't know if it's worth a full day in Pisa (though there are certainly museums worth visiting, if you are a museum junkie), but certainly it's worth a morning or afternoon spent there to visit the cathedral and the baptistery. I spent over an hour at the cathedral and would have spent longer but was with a group of friends that wanted to move on. It's pretty spectacular. Tickets are free but they come with an entry time. The Baptistery is also worth a visit, I think tickets are €3 for that (maybe €5?). I think you can do it in a half hour. On the half-hour they close all the doors and one of the staff demonstrates the amazing acoustics by singing some sort of chant. There are probably videos of this on YouTube if you are curious.Frankly, I don't think the tower is worth the cost and trouble to go up in it. But, do that too if you're dying to, at least you can say you did it! And the cemetery ("Camposanto Monumentale") is also worth a visit. These are all in the same area, so as I said this can all be done in half a day and possibly still leave time to have lunch before or after, before moving on.I am a big, big fan of Lucca, which is only 15 min from Pisa by car or train. The old town is inside massive defensive walls that date from the 16th century. You can walk on the walls or rent a bike to ride around the walls and the town. €12/day at most places but the luggage deposit at the train station has them for €10/day. So, you could take a train from Pisa, get a bike at the train station in Lucca, and ride around the walls and Lucca itself. They will want to photocopy your passport if you rent a bike, FYI.Do some online searching for festivals and sagre. It depends on the weather from year to year, but you might be able to participate in the vendemmia (collecting the grapes) if you are there at the right time.Montecarlo is a charming hilltop town a short distance east of Lucca, and all around there is wine country.Other than this, I am highly partial to Umbria. However, it is advisable to hire a car to really enjoy it. There are trains but the drives through the countryside are unforgettable, and there are places you'll want to go where the train is not convenient. Orvieto, Perugia, Assisi are all worth a visit. Assisi can be a bit of a PITA because everyone goes there; try not to go on a weekend and get there first thing in the AM if you can. Spello is nearby Assisi and very charming. I used to highly recommend Castelluccio but it was devastated by the earthquake a couple years ago, so I am not sure if it's a good destination right now. Same story for Norcia. There is a lovely drive to be had from the Marmore waterfalls up through the valley of the Nera river, all sorts of typical Italian villages to visit. This area is renowned for its black truffles, if you like that sort of thing go to Scheggino which is right by the Urbani truffle "factory".In fact, a great itinerary would be to do western Tuscany as I mentioned (Pisa-Viareggio-Lucca-Montecarlo), then hire a car and drive through southern Tuscany, the Val d'Orcia. I have been here many times and it always takes my breath away. Try to spend a night or two somewhere in that area, so that you may properly enjoy the wine tastings :-) , this is some of the most famous wine country in Italy. Make sure to stop in Pienza as you make your way to Umbria. Pienza has a fascinating history, great views, and is renowned for the pecorino cheese. Other towns in this valley worth a visit: Montepulciano, S. Quirico, Montalcino.Finally, a secret I love to share: at the Bettolle exit on the A1 is a store that is like a supermarket of local wines, cheeses, and cured meats. It is absolutely stupendous. It's called the "Bettolle Consorzio Agrario". You can buy meats and cheeses and some bread here, check out... then at the right of the checkout are some tables where you can have your lunch with the stuff you just bought. They supply oil and vinegar and utensils and napkins and cups. They even have boxed wine to have with your meal, I do not recall if it is free or there may be a very modest charge for it. I promise you will have one of the best meals you'll have your whole trip, for maybe €5 a head.PM me if you want to know more, I know quite a bit about this area and  am happy to share but I have gone on too long already!

Cindy,You are in for the time of your life and October is a wonderful time to be in Italy.  My one caution is to avoid the temptation to see everything in one trip.  Sorrento is wonderul and Capri is a worthy trip.  Consider visiting Anacapri and goint to the top of Mount Solaro.  The view is one of the best in the world! Skip Naples on this trip. It is very busy and a bit overwhelming. Don't miss Rome.  At least a few days there, so much to see. Post if you deside to got to Rome and I will recommend a few things to do. Then off to Florence; my favorite place in the world. From Florence you can do day trips to Milan (The Cathaderal), Pisa (The Tower) and Lucca (love the city, consider at least one night). I suggest you skip the car.  The trains are wonderful and go to most of the places I would recommend.Enjoy!Jeff

I have been to Italy five times.  Either April or October.  I loved them both.  The advantage of October is that it tends to be harvest time in Tuscany.  Touring a vineyard that time of year is extra special.  If you go that rount check out Tuscan Wine Tours (https://www.tuscan-wine-tours.com).  I have done three tours with them (different friends/family members) and loved each one.Jeff