Within 3 to 5 years, wife and I expect to re-locate permanently from US to Italy. I have citizenship and speak fluent Italian, while the wife does not speak Italian yet.
Thank you all for the great comments and suggestions. My preference would be Umbria but the requirement for an English-speaking expat community is to help my wife transition (my Italian is quite good) and I am all too aware that a car is almost essential in Umbria, especially if one wishes to fully enjoy it!
I have been there four times, always in the northern region of the island (Gallura). I envy you. I am dying to return, I think I love it more than Tuscany and Umbria which is saying quite a lot, especially since these are the regions of my ancestors.Some random thoughts:September is a wise choice. Still fantastic weather but the Italians on holiday have mostly gone home. The sun can be so intense in July and August that the beach is too hot to walk on barefooted. In Sept. there is a slight chance you may catch some bad weather and when it happens, the rain can be torrential.You will likely want a car. Public transit - at least in Gallura - is lacking and there is SO MUCH TO SEE that you won't ever see without a car.I cannot give any advice about 4-star/5-star resorts, we always booked an apartment as part of a package deal. While there I did see a number of nice looking resorts along the northern coast of the island between Santa Teresa and Porto Cervo. So I think you could search that area and come up with something acceptable.Sardinia is well-known for roast suckling pig (porceddu). Seafood can be had as well but it's not as well-known for this. Sardinia is also well-known for pecorino cheese. In fact quite a bit of pecorino romano cheese is actually made in Sardinia. "Seadas" is a popular dessert in Sardinia, it's a ricotta-stuffed fritter coated with honey.Around Porto Cervo (center of the "Costa Smeralda" where the wealthy come to play and stay) you can get by with English; elsewhere it may be difficult because the bulk of the tourists are Italian-speaking and German-speaking. A couple of times we wandered the marina at Porto Cervo and goggled at the incredible yachts and sailboats. These boats don't belong to the 1%, these are the 0.01%!!!We bought umbrellas and lounge chairs ("ombrellone" and "sdraio") at one of the numerous shops that sell beach goods, loaded them in the car and just drove around finding beaches at random. This worked out incredibly well and I highly advise it. Much less expensive than renting each day, and far fewer people around than at the private beaches or resort-owned beaches. We found somewhat remote beaches that had stocked snack bars as well!!! If you PM me I can tell you exactly where some of these places are. Most bookstores and beachware shops also sell paperback books in English that show you where all the beaches are. It is very hard to find a bad beach in Sardinia, and the water is Caribbean crystal-clear everywhere. The only bad beach I found, there were big rocks in the water instead of sand, so it was hard to walk. Unlike most beaches on the mainland, very few of the beaches in Sardinia are private beaches owned by resorts or hotels where one has to pay for the privilege of using them.There are marvelous snorkeling opportunities in Sardinia. You may want to bring some sort of underwater-capable video camera like a GoPro or still camera. I have photos and video of octopus, all sorts of schools of fish, and even amazing colorful jellyfish.I have a few specific recommendations for restaurants that I can share via PM.There is a bookstore in Palau called "Libreria dell'Isola" and another in the main square in Santa Teresa which have an adequate selection of English language books about the beaches, culture, archaelogy, and people of Sardinia. (the one in S. Teresa is much better though as far as the selection of English-language books.)All over Sardinia there are the ruins of the Nuragic people who were a Bronze Age culture that built impressive structures using the plentiful granite. I believe some of the most interesting and vast ones are further south than Gallura. Sardinia also has a fascinating history of banditry and kidnappings of wealthy tourists, even some as recently as the 80s and 90s. It was very much a sort of "wild west" place for quite some time until modern transportation brought the island somewhat closer to the mainland.There are various 'Green Train" lines that run across Sardinia, I haven't done this but I've seen the stations from where they depart. Everyone who's done this highly recommends it. Great way to see the countryside.On the central-eastern area of Sardinia is a vast natural park and mountain range called Gennargentu, also highly recommended if you have the time.An interesting day excursion might be to take the ferry from Santa Teresa to the Corsican port town of Boniface.A particularly popular beach on the western end of Sardinia is at Stintino, and justly so. But if you go, arrive early because it's very well-known and parking is limited. If you take a drive in the area of Tempio Pausania, you can see the groves where cork is harvested from the trees.The local beer is "Ichnusa" (the Greek word for "Sardinia"), it's pretty popular there and there's a couple different varieties. Sardinia is known for "Cannonau" wine, a hearty red, and also for the liquer (sp?) "mirto" which is made from the berries that grow on bushes. I don't particularly care for mirto but the Sardi are very proud of it.Surprisingly, there's not much to see in the way of churches unlike mainland Italy. Maybe I'm wrong about that, but I don't recall spending much time at all visiting churches there.DH Lawrence wrote a short story about a visit he made in January 1921 to Sicily and Sardinia called "Sea and Sardinia". Most of it is set in Sardinia and many of the observations he made can still be recognized today.The Sardinians are an amazingly hospitable hosts, I cannot recall a single instance of encountering locals who were rude or annoyed with tourists. It's just a marvelous place with wonderful people and it has played a significant role in Italian history, particularly in the unification of Italy into a country in the mid-19th century. It's a shame that it is such a poor place, historically the Sardi have lived in desperate conditions due to the primarily agricultural nature of the economy, their history of being ruled and exploited by foreigners, and its isolation from the continent. The advent of tourism has helped to some extent but it's still a place where many young people move away to find better prospects.HTH, buon viaggio!
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!
October is fine, just fine. The weather can still be great and the tourists have largely gone home. It's a great time to go. November is the month that can be tricky, it is commonly (but not always) rainy in the first two or three weeks of November. However we went on our honeymoon during the first two weeks of November in 2014 and it was fantastic weather. It was very fall-like and there was little rain. The winter weather begins to set in around early December.April is OK, depending on the year it might still be the last bit of winter before it gives way to spring. Also if you can time your visit around Easter there's a lot of great stuff going on in April, such as the Explosion of the Cart in Florence ("Scoppio del Carro").I do realize I didn't really address your desire to tour the Amalfi Coast! I don't know that area all that well. Feel free of course to borrow my ideas to build your perfect trip.