Itinerary for second trip to Italy

My second trip to Italy this coming October/November will include Sorrento, Orvieto, Assisi, Ravenna, Venice and Milan, if you need ideas. You might include Sicily, since you seem to have plenty of time. In fact, you might make a flight to Palermo directly when you land in Milan, then work your way north for the flight home.

Good for you! We did the same thing a few years ago: after our first three week trip here, we immediately planned another for 4 weeks, the entire month of December 2012.

We also revisited Rome and Venice (9 nights and 6 nights respectively). We also added two new-to-us locations, Umbria and Sorrento. We stayed in Spello, Umbria, and day tripped to Spoleto, Perugia and Assisi, and also took a day tour of wineries with a guide. Our base in Sorrento launched us to Pompeii, Ercolano, Amalfi and Atrani, and Naples. We really loved our long stay in Rome as it was thru Christmas and allowed us to feel rather local by staying so long. We had a cute apartment and felt very lucky to have so much time to explore without rushing.

The Christmas lights come on in Italy on Dec 8, the Immacolata, and stay on thru Epifania, Jan 6. While Rome was busy, it was tolerable without the heat of summer. We wore jeans, merino wool layers, fleece pullovers. I had a lined raincoat. Gortex shoes, smart wool socks, scarves, gloves - easier than winter in MN where I grew up. Never used long underwear! :-) We even had some sunny days around 60 F!

We saw Pompeii on a sunny 45-degree day when there was only a handful of people there. We hiked from Amalfi to Atrani in 55 degree sun and ate lunch outdoors with a view of the sea. Be aware that many Italians travel between Christmas and New Years. Set up your lodging as early as possible. We tried to go to the Dolomites near Sesto last December, and by early November everything was booked for Dec 26- New Years. When we checked out on Dec 23, we were told by our hotel in Sorrento that they were sold out the 24th-Jan 6.

If you like winter activities, don't overlook the possibility of some time in the Dolomites. Even if you do not ski, there's winter hiking on groomed trails, sledding, or just riding the lifts for fabulous views. We are spending this Christmas in Ortisei to partake of the winter wonderland after having spent 3 Christmases in Rome.

Great advice so far. I would look at some time in Bologna and Ravenna. Central Italy is beautiful in winter (Assisi, Gubbio, Cortona, Todi, Siena). Sicily deserves a couple of weeks if that goes onto your list.

Thanks Angela and Laurel, never thought of jumping straight on a flight to Palermo after arriving in Milan! Interesting.
i wanted to spend Christmas somewhere special like Bolzano but i guess Rome would be nice also.
My wife fell in love with the place.
It is interesting how perceptions change after you experience a city. In preparing for our last trip after reading all the reports about Venice I was not looking forward to it at all.
However with careful planning it turned into my favourite place on the trip!
In contrast I was looking forward to Paris and so dedicated 6 nights.
Sadly after 3 nights I was ready to leave! We had seen everything one would want to see.
Just a big city really, we were there for Bastille day and most Parisians vacate the place.

How about this then...
4 nights in Milan (is that too long?)
3 nights in Verona
4 nights in Bolzano (arriving on the 23rd of Dec with a possible day trip to Innsbruck)
3 nights in Venice
3 nights in Siena (arriving on 30th of Dec)
4 nights in Spello (base to visit the area Orvieto and Assisi)
4 nights in Rome
5 nights in Sorrento (base to visit Naples, Herculem and Pompeii is that too long?)
4 nights in Palermo

4 nights in Milan (is that too long?) Yes. You can see everything in 2 days
3 nights in Verona I love Verona. 2 full days is enough to see the sights, so 3 nights sounds right.
4 nights in Spello (base to visit the area Orvieto and Assisi) I haven't been to Spello. I spent 1.5 days in Assisi (1 night) and then 4 nights in Orvieto. In Assisi I left my suitcase at the train station and just took a small back up to the town. Orvieto has some very good restaurants. I'd recommend at least 2 nights there. I loved wandering . . . and just enjoying the cathedral facade.
5 nights in Sorrento (base to visit Naples, Herculem and Pompeii is that too long?) I don't think so.
4 nights in Palermo Sicily needs at least a week. Consider flying to Catania and staying in Ortigia/Syracuse and/or Taormina, then renting a car and visiting Piazza Armerina (Villa Romana del Casale), Agrigento, and Selinunte for the ancient Greek temples, ending in Palermo (1 to 1.5 days to see the sights).

If you can fit it in, spend 3 nights in Bologna between Venice and Siena. Bologna itself is worth a day and it's a good place for a day trip to Ravenna to see the superb 5th-6th century mosaics.

Plan to dress in layers. It can be in the 60's-maybe even 70's and sunny, with a bit of luck (based on my experiences in February).

After rereading your new itinerary, I suggest you skip Milan, as being the least interesting of all your destinations. You can fly into Milan and train straight to Verona, then use the "extra" days for someplace like Sicily. Then fly home from Palermo via Rome.

i wanted to spend Christmas somewhere special like Bolzano but i guess Rome would be nice also.

It's all pretty special, Paul. :-) Bolzano is not quite "in" the mountains but it does have the famous Christmas market. Personally if you want snow, I'd give up Bolzano and head deeper into the mountains like Ortisei as I mentioned above. Rome or Venice will also make great Christmas headquarters. There's a lot to do here even on Dec 24, 25 and 26th. If you like, PM me and I'll send you some of the to-do list in Rome those days.

Well after pooling the comments and reflecting on them and negotiating public holidays, being tied to the train system etc this what i come up with.
I am going to sacrifice Milan for some more time in Sicily, this is because we land so early in Milan it might be an idea to use the time to head straight to Verona rather than wandering the streets in poor weather waiting to get into our hotel.
I have also shorten the list of cities to occupy in effort to slow the trip up.
Therefore...
4 nights in Verona (time to adjust to the cold and timezone coming from Australia)
4 nights in Bolzano (with a possible day trip to Innsbruck)
3 nights in Venice (arrive on the 24th of December)
4 nights in Siena
8 nights in Rome (arrive 31st of December and explore the towns of Orvieto and Assisi from there. even though we spent 5 nights in Rome last time there are still places we did not see yet. Rome is like a messy antique shop. I will take Rome of Paris anyday.)
5 nights in Sorrento (explore the area from there)
(off to Sicily, take the ferry from Naples or train to the toes and ferry?)
4 nights in Catania
3 nights in Palermo

what do you reckon?

Just a couple of comments. Four days in Siena without a car for day tripping seems like a lot to me. We were in Palermo for New Year's Eve once. The whole city was out having a street party with musicians, clowns, jugglers, folk singers and dancers. Great fun! That same year we were in Taormina on Jan. 6 (or maybe the evening of Jan.5). The cathedral had a concert by an amateur, but not amateurish, choir, which was quite lovely. If you can be in either of those places on those dates, I think you'll love them. By the way, it wasn't terribly cold in Sicily; but I would certainly be prepared with some layering options like a fleece vest, some gloves, a scarf, and a hat.

Hi Paul, Verona is a wonderful city for the beginning of your trip. We stayed at Hotel Aurora, located on the Piazza Erbe - great location. Also, the town has a Verona Card to maximize your experience.

Great itinerary but I would take one or two nights from Verona and add it to Venice. Verona is nice enough but Venice has so much more to offer, and two of your otherwise 2 full days in Venice (24 and 25) will have a lot of closures.

Consider flying to Catania. The trains and ferries eat up a lot of time. I flew Meridiana (budget airline) and it was fine. I would not stay in Catania. Split that time between Syracuse (stay in the oldest part - Ortigia) and Taormina, both of which offer much to see and do, though I wonder if Taormina would be a good choice considering the possibility of poor weather. Perhaps others will chime in, who've been there then. You might enjoy an overnight in Cefalu before Palermo. Although it's touristy, it's not kitschy.

I agree with Chani, fly to Sicily. You will give yourselves an entire day by flying roundtrip.

Regarding staying in Sorrento for 5 days as a base to see Naples/Pompeii/Herculaneum: I'd suggest taking a train from Rome to Pompeii/Herculaneum, and then hiring a private transfer to stay in Praiano. It sounds like you guys are really trying to get a feel for Italy, and I'll be honest, Sorrento is very touristy and doesn't have the same charm as the smaller locations on the Amalfi Coast. We just got back from a trip to Italy, and we rented a house in Praiano (town near Positano) for 3 days through AirBnb. Having a house was fabulous- we were able to cook our own meals, eat out on a beautiful terrace with sweeping views of the Mediterranean, and really spread out in a way we couldn't in a hotel. It would've cost the same amount to rent a hotel room in Sorrento or Positano, but we got such a unique, incredible experience.

I'd also highly suggest doing the Walk of the Gods hike from Praiano to Positano - I've done Cinque Terre, and I've done a lot of hiking in places like Ireland and New Zealand, but this Walk of the Gods was incredible and unlike anything I've ever done. (Do a Google image search and you'll see!) Plus we only saw 4 or 5 other tourists in the 3-4 hours that we hiked! Halfway through the hike, you reach this beautiful, centuries-old whitewashed church.

We also did a day trip to Capri from Praiano, and it was worth every cent. I know you'll be there in the winter, so it may not be the same, but you may want to check it out while you're there!

Personally, I would skip Naples. There really isn't much to see there, it's gritty and not much fun. Save that time to spend on the Amalfi Coast or further south!

My favorite places in Italy at this point are Praiano, Bologna, and some of the smaller north-central cities like Parma and Modena. Hope you have a great trip!

Hi, thank you for all your advice so far. I have been a bit side tracked with work etc but here is the latest itinerary. Mark 10 i think?

Fly into Milan on the morning of the 16th of December and catch the train straight to Verona - 3 nights.
Train to Bolzano with a day tip to Innsbruck 4 nights (christmas markets etc).
*Train to Venice (arrive on the 23rd of December) 4 nights (yes it's long but there are a lot of churches and museums we want to see).
Train to Bologna 2 nights.
*Train to Florence (a day trip to Siena) 3 nights. (Spend new year eve, arriving on the 30th)
Train to Sorrento 4 nights (use as a base to visit Pompei etc)
*Train to Rome 6 nights ( two day trips, one to Orvieto and the other to Assisi).
Fly to Palermo for 5 nights (day trips from there)
Fly to Milan 2 nights.
fly out of Milan.

What do you guys think?

• indicates we visited here in the summer of 2013

While you are in Venice, daytrip to Padova to see the Scrovegni Chapel (frescoes by Giotto). You need a timed-entry ticket so get that in advance.

Too bad you are skipping Milano, there are a couple of world-class museums, the Duomo, and Leonardo's Last Supper (again, advance timed-entry ticket needed).

If you can squeeze Ravenna into the mix, you won't regret it. It's a quick train ride from Bologna.

A second for Ravenna - the mosaics are incredible. I could also make other suggestions, but - although 5 weeks sounds like a long time it sounds like you're having the problem we all face when planning a trip. It sounds like a long time and then when you start to make your itinerary it always seems there's not enough time to do, see, and visit what you want. The trip sounds great but if I were a betting person I'd bet you will want to return to visit the places you had to cut. We've been to mainland Italy 3 times for 3 - 4 weeks each time and Sicily once for 4 weeks, and still have a list of towns we'd like to visit or re-visit on our next trip, whenever that may be. Have fun making your choices. You will enjoy your trip regardless of the towns you choose!