Traveling solo of Italy seeking some advice on planning my route

Are you staying in La Spezia for budget reasons? Otherwise there are direct trains with resered seats going from Milan to Monterosso. You could land in Venice, hike in Ortisei, go to Milan, then hike in the Cinque Terre etc. etc.

The Pinacoteca di Brera ("Brera Art Gallery") in Milan has a Caravaggio, quite astonishingly it's not the most important piece of the collection. Somewhere in Milan there is also a Pietà by Michelangelo.

PS Unfortunately, you can't see all the Caravaggios in Rome. One of The 2 "Conversion of Saint Paul" is still in private hands and Mrs Odescalchi hasn't been accepting tours in her living room for years. But if you succeed in seeing it... please let me know how you could do it.

Oh, do not forget to see the only remaining fresco painted by Caravaggio in the Casino (aka Villa) Ludovisi.

I've been researching Milan and other northern-Italian cities for a future trip. The more I dug into Milan, the more time I felt I would need there. It's true that many people hit the highlights (Duomo, Last Supper, maybe Galleria Vittorio Emanuele II) on a very quick visit, but the city also has:

• over a dozen art museums
• seven additional churches interesting/important enough to have been discussed in the guide books I've read
• quite a few museums with decorative arts from different eras
• dozens of Art Nouveau buildings--probably over 100.
• great fashion window-shopping

I doubt that you'll be bored there, but your personal interests should govern how you divide your time. There are always sights--and even entire cities--a traveler would enjoy but doesn't have time for.

I think 3 nights in Venice is the minimum even for folks who aren't interested in the out islands. Murano and Burano will take the better part of a day, so I think you'll be short on time there.

If you are interested in Caravaggio paintings, I believe that the Pinacoteca di Brera in Milan has the Supper at Emaus (and maybe others by Caravaggio) and the Biblioteca Ambrosiana in Milan has the Basket of Fruit painting.

I think this sounds like a wonderful trip. I don't have much advice regarding renting a car, but relaxing in an agriturismo for a few days after your hiking sounds like a good idea to me. Since you're finishing your trip in Sicily, why don't you just fly home from either there or Naples rather than having to go all the way back to Milan just to fly home?

Minpal,

This sounds like a good itinerary. Just a note: The Dolomite/Ortisei area is large and takes a bit to get to each hiking area but I think you have enough time planned for it. You might want to add another day for Cinque Terre since there are 5 towns that are all worth visiting while hiking.
Good Luck!

Thank you for your great sights.
I booked flights to and from Milan because I really did not think I would visit Venice this time but somehow misinformed that Milan is the best airport to visit Dolomites. I also couldn't resist a chance to see Last Supper and yes a couple of Caravaggio in Pinacoteca di Brera and Duomo. So, starting from Venice and traveling westward is not an option at this point, I am afraid.

La Spezia is not the best destination to explore Cinque Terre but it is where the train station will be. So If I am coming from Venice by train, I guess I can take a local train and decide to stay in one of the villages. I was planning with a possibility of renting a car and parking issues in small villages but if I take trains, this might not be a concern at all or I may find an agriturismo in 1-2 hour distance from major attractions in Tuscany and will take a day trip to Cinque Terre. This is the hardest part to decide.

I hope to see all Caravaggio but alas, I will just have to do what it is possible and maybe that can be an excuse to come back to Rome sometime soon. :)

I have been to Naples 2 times and this is my favorite city in Italy. It is not pretty but there is something very special about the city. But, frying out of Naples means 2 more connection to come back to Indianapolis, rather than one connection in NJ. So, I had to make a choice. Also there are many nonstop flights from Palermo to Milan early in the morning for me to fly directly to US.

I wish I researched a bit more before I booked my flights but I got too excited about the idea and without having the flights booked, I think I might have chickened out and decided not to go because of anxieties over Covid.

Your insights are so helpful in revising my plan. Thank you so much.

Are all your flights on one ticket? I would not risk spending my last night in Palermo if flying home from Milan unless it's all on a single ticket. If the Palermo-Milan flight is canceled or seriously delayed and you miss the transatlantic flight, you'll have an expensive one-way ticket to purchase.

La Spezia is not the best destination to explore Cinque Terre but it is where the train station will be.

There is a train station in all the Cinque Terre 5 villages, on trenitalia.com choose one and put its name into the "to" field. Use Venezia S. Lucia as departure station if you are leaving from the "floating" district, otherwise pick Venezia Mestre.

As I wrote above, long distance trains from Milan call at Monterosso, but there are local trains stopping in all the villages. The train journey from Venice to Monterosso via Milan is a little longer, but there is only one change.

Note that when travelling between the Cinque Terre villages the trains are 3 times faster than cars. Parking problems aside, you'd also need a ZTL permit.

This looks like a wonderful itinerary! A couple of suggestions: four or five nights in Venice might be better, especially since you want to visit islands in the lagoon. In addition to Burano and Murano, I highly recommend Torcello. When you’re up north in the mountains, you might want to visit the Archaeology Museum in Bolzano, either on the way to or from Ortisei. You’ll need to change there from the train to the bus and vice versa, and the train station has a left luggage room. The Museum features poor Ötzi the Ice Man and his belongings. Anyhow, though, great plan!

I am also planning a trip to Italy. With your time frame, don't bother with Cortina. Stick with Ortisei. Otherwise, you'd waste too much time transiting from one place to another. Less is more.

Also, mountain weather is totally unpredictable. Further, it's a rainy region. So, five days in one location isn't much because there will likely be some days with bad weather. Use these days to recuperate. You have a long trip--it's good that you will see a lot, but you will also be exhausted.

I just did almost all of your trip so I can comment on my experiences in each place:

Milan: for me, there's not a lot of interesting things to see, I think you can do it all in 2 nights easily
Ortisei: only place I didn't go, so can't comment
Venice: 3 nights is possible if you plan really well
La Spezia: I might do three nights as you have an option just in case of bad weather (which I had several times). Also, I would stay in one of the towns, not La Spezia. The trains are very easy and run often. I stayed in Vernazza as RS recommends and loved it. I would not take a car to Cinque Terre, it's just a headache you don't want to deal with. It does take a few changes to get to one of the CT towns, but it's not a problem.
Siena: I did two nights also and felt it was just right
Rome: I had 10 nights in Rome and felt like it was too much for me (I know other people will find this impossible to believe), but if it's your third time, I'm sure you know what's best for you
Sorrento: I think you can get everything done in three days
Sicily: I preferred the eastern side of the island much more to the western side

1. I don't think it's too busy for public transportation
2. I did three road trips this summer in Italy: Tuscany, Sicily and the Northern Lakes. I would highly recommend getting a car and driving around Tuscany. That was the best road trip by far and the countryside is beyond belief beautiful.
   
3. I would stick with what you have planned in the north.
4. I picked up a rental car at the Pisa airport after visiting Cinque Terre and drove through Siena down to Rome. I dropped off my car at the Termini train station, but you can also drop it off at either airport.

I will comment only on Ortisei as I fancy myself a bit of a specialist in that area. Take a night from Milan and add it to Ortisei. You can keep yourself busy hiking in the Val Gardena for a month!

another admirer of caravaggio! there are 3 in sicily you should not miss. 'the resurrection of lazarus' and 'the adoration of the shepherds' in messina at the museo regionale. 'the burial of santa lucia' in siracusa at chiesa di santa lucia al sepolcro. you seem to have palermo covered. i would suggest segesta, pizza armanina (villa romana del casale) and at least noto and ragusa among the southeastern baroque towns. in my opinion trapani is meh but nearby erice is a must-see.

(Is 3 nights in Venice sufficient?)

Three nights really gives you only two full days and (depending on arrival time) part of another. Having been there a number of times, my opinion is that three nights is barely sufficient -- and that will be at a fast pace. The trip to Murano and Burano will take the better part of a day, and the other full day will just scratch the surface. On of the best things about Venice is the chance to relax, wind down, and enjoy the city at a slower pace. If possible, add a fourth night. You'll not regret it.

Thank you all so much for providing your insights and recommendations on my planning.
Here are some modifications I am going to make and I will probably post a separate question later.
1. I will spend 2 nights (9/6-9/8) in Milan instead of 3 nights
2. I will add a night to Ortisei (9/8-9/13) and will definitely check The Ice Man. It was on my list to see there.
3. I will add a night to Venice (9/13-9/17): I booked doge's secret itinerary and traveling opera ticket for La Traviata!
4. I will skip Cinque Terre hiking this time to allow more time in rural areas
5. After Venice, I will rent a car and explore Prosecco, Tuscany and Umbria regions (9/17-9/21): Car rental return in Rome Termini Station in the afternoon (I would need recommendations as to where would be a good place to stop by or stay. Would love to do some truffle hunting and Chianti and Prosecco tastings too. )
6. I will shorten my Rome stay (9/21-9/26) and definitely will check out every possible Caravaggio
7. I will take train to Napoli and then Curcumsversus train to Sorrento and explore Amalfi area from Sorrento (9/26-9/28): A full day boat tour to Capri, and full day Amalfi coast Boat and walking tour.
8. Depart to Catania in the morning of 9/29 and stay in Sicily until 10/6 evening. I did see the carravagio painting in Siracusa last year but hope to see the rest during this trip! I will definitely add Erice! For my next visit to Sicily, I would like to do the east side with Cerafu and Stromboli island, etc. I love this island so much.
9. Take a night flight to Milan and stay near the airport for the night for 10/7 departure back to US.

How does this sound as the final plan?

Thank you all so much!!

This sounds wonderful--two quibbles:

1. After Venice, I will rent a car and explore Prosecco, Tuscany and Umbria regions (9/17-9/21): Car rental return in Rome Termini Station in the afternoon (I would need recommendations as to where would be a good place to stop by or stay. Would love to do some truffle hunting and Chianti and Prosecco tastings too. )

This seems like a lot for four nights, but I'm sure it is just because it has not been fleshed out yet. I wanted to learn more about the prosecco region, and in my reading I found this helpful post: https://indianajo.com/prosecco-tour.html

1. I will take train to Napoli and then Curcumsversus train to Sorrento and explore Amalfi area from Sorrento (9/26-9/28): A full day boat tour to Capri, and full day Amalfi coast Boat and walking tour. (8. Depart to Catania in the morning of 9/29)

Just making sure--you will have two full days here, right?

Thanks for the suggestion, valadelphia!
I actually came upon the same website for my inspiration for Prosecco trip and will take a day in the region.
I do have 3 full day in Sorrento for my planned tours. Thank you!