3rd trip to Italy Sept 2013! Where in the heck to go???

Have you been to Ravenna, Ferrara, Mantova, Bologna? All close to each other by train. If you want a little of the South of Italy, sither coast would make an interesting week: Naples, Sorrento, Amalfi Coast, Paestum, even further south is Tropea. On the east coast, Puglia from Otranto north to the Gargano peninsula is beautiful and different (lots of nature parks). If you want to go to Sicily, I agree with Roberto that 10 days would be better than 7, but you could easily spend 7 days in one part of the island (eastern from Siracusa north to Taormina, perhaps even the islands of Lipari, Stromboli, Vulcano), the northern coast from Palermo to Cefalu (you could also get to the islands this way) with daytrips out of Palermo to Erice, Segesta, and Monreale; and in the South, Agrigento and Selinunte. The interior is beautiful, too, with Piazza Armerina and the nearby Villa Romana di Casale and Morgantina. Personally, I think 25 years of marriage deserves a volcano tour! Congratulations.

Pick up a copy of Eyewitness Travel Guide Italy and choose those places that appeal to you and your interests (which are.....?)

Have you considered Milan/Varenna/Lake Como region?

I'm assuming you've seen all of Tuscany already + the 5 Terre (which is in Liguria, but close enough to Tuscany). You've also seen Venice. I presume you'll have a car. During your week you are in Pienza you should take day trip(s) to Umbria, if you have never been. You could do Perugia, Assisi, Gubbio in one trip and Spoleto, Todi, Orvieto in another day trip (or more than just two trips if you like to linger longer in each town). Other areas you can do during an additional week (which are within 3 to 5 hour drive from Pienza) are the following (each number choice will take at least a week for a good visit): 1- Latium (Rome, Tivoli, lakes) 2- Campania (Amalfi Coast, Capri, Pompeii, Naples) 3- Veneto/Trentino (Verona, Palladian Villas in Vicenza, Lake Garda, and also Dolomites if you have more than a week) 4- Piedmont/Val d'Aosta (Alps, Turin, Wine areas in Langhe and Monferrato) By air: 5- Sardinia+Corsica 6- Sicily For the islands (no. 5 or 6) you would need to fly because by car takes too long from Pienza between driving and ferry crossing. You could fly to either islands from Rome or Pisa or Florence. Sicily is kind of too big and full of things to see to do all in a week, but in 10 days maybe.
Sardinia+Corsica are not so much for art/history sites, but truly outstanding for beauty of beaches and coasts.

Personally, especially if you are celebrating an anniversary, I would rent an apartment on the Amalfi Coast for a week and then fly home from Naples (or from Rome, if you spend your last night in Rome). Incredibly beautiful and romantic with lots to see and do (or not, if you are so inclined).

We stayed at a lovely bed and breakfast in Positano for a week and did day trips from there. Had a great view of water from our room and the breakfast room. It is about an hour south of SOrrento and we enjoyed it so much.

Our next trip will include a few days on Lipari, which is reachable by ferry or hydrofoil from Naples, Campora San Giovanni, Messina, Milazzo, Cefalu and Palermo. Looking forward to the night boatride around still-erupting Isola Stromboli and a daytime kayak excursion (suitable for all skill levels, they promise) through the caves of Isola Vulcano. Looking into the JFK-Palermo flights on Meridiana. If you haven't been to Paestum yet, can recommend a lovely hotel there. Great place for all ages. You could do a combination of Amalfi-Capri-Sorrento-area, with or without Pompeii and the walk up Vesuvius; hydrofoil to Salerno to catch a bus, train or rental car to Paestum; then either take the train, a cheap RyanAir flight or overnight Naples ferry to the Aeolian islands with time left over to walk around the square that was the setting for Cinema Paradiso.

I agree that for the 25th you should end a trip with the bang of a volcano. Mt. Etna is more active than the Vesuvius nowadays, but you never know. In any case it should be a romantic place and since Venice is 'done and been there', the most obvious stop is Positano. September is still good for a seaside vacation and in just over a 4 hour drive from Pienza you can be in Positano.
I'd leave Sicily for another time if you only have a week.

I heard Meridiana's JFK to Palermo (a.k.a. the "Cosa Nostra Express") is good. Let us know if the movies they show are only the "Godfather" and its sequels.

I would spend some time in Lake Como (and base specifically in Varenna) and also the Dolomites. You could fly out of Venice if you end the trip in the Dolomites or Milan Malpensa if you end in Lake Como. You could also add in another lake (Maggiore or Garda) if you'd like. Have a wonderful trip!

Amalfi coast to incl Sorrento and Capri. One of the great beauties of the word IMO. Do not miss it!!! It is stunningly gorgeous!
nearby are Heraculum or Pompeii for a side trip if you enjoy archaeology.

The Amalfi Coast is beautiful and very romantic with alot to see. We usually base in Sorrento. We flew out of Naples, via Germany (Lufthansa) to San Francisco. This last trip we tried Bologna but didn't think it compared with so many other lovely places in Italy. We totally enjoyed Sirmione off Lake Garda but we only managed a day trip from Verona.

I flew from Venice to Palermo, Sicily, a few years ago. From Palermo you can take the train or rent a car. You could fly on from Catania after touring the island. My favorite place in Sicily is Cefalu. It is medium-size, walkable, has a cathedral and a great beach. It should be perfect in September.

Thanks SO much for all of the feedback!! I totally forgot to mention we had been to the Amalfi coast, but just for a mear 4 days (2 with rain) and WE FELL IN LOVE!! We were going to save that area for a longer trip at some point, but you know, it might just be the perfect time to spend the last portion of our trip there!! Just not sure how the weather is there mid-Sept....maybe fly in and out of Rome? SO many great ideas and things to research!! THanks again!

We went to Positano/Amalfi Coast for our mid-September honeymoon a few years ago . . . I thought the weather was just perfect then.

Go North! Lake Maggiorie, Lake Garda are wonderful. Verona and Bologna are great towns.

Go to the heel of the boot! This is our 3rd trip to Italy as well, and we are visiting Puglia. In Trani right now. Absolutely love it. Coming up are visits to Matera and to the Trulli villages (Alberobello, etc.), ending in Lecce. Google those places. It's a totally different Italy. We were surrounded by Americans at Lake Como (our first stop) ... haven't seen one in the week since, and for some reason that appeals to us. :) We have been enjoying the most amazing food in all of Italy. Great wines. Wonderful people (our hotel owner took us out for 3 hours yesterday afternoon to show us the area!). Gorgeous beaches. You can get a cheap flight from Bari or Brindisi to Rome or Milan or wherever your homeward flight leaves from.

SSoo many places we want to go in Italy; like....EVERYWHERE! and we hope to do that for the rest of our lives, but i think for this trip we've decided on the Amalfi coast!!! We want to start in Tuscany and end up on the Amalfi coast; probably Positano, but will have to work out the logistics, airport, taking the train, renting the car etc...any more ideas are helpful. This is the beginning of our research now!