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Trip to Italy May 2020

Hi, I am returning to Italy in May 2020 for 16 days including travel days. My daughter and I are flying in and out of Milan. We have already been to Rome, Venice, Florence, Pisa, and Tuscany. This time I really want to see more of Italy. I was planning the following itinerary:
May 13 arrive Milan
Stay in Milan through May 17 - (5 nights) Take day trips on Bernina Express to St. Moritz; Lake Como; Verona
May 17 travel to Siena
Stay in Siena through May 19 (2 nights)
May 20 travel to Naples
Stay in Naples through May 22 - (3 nights) Take day trips to Pompeii and Amalfi Coast
May 23 travel to Cinque Terre
Stay in Cinque Terre through May 25 (3 nights)
May 26 travel to Milan
We depart May 27 in the morning at approximately 11:00am so I was thinking of going straight to airport and staying that night at the airport.
I would appreciate whatever feedback you can provide on this itinerary; if it is feasible, train connections and any recommendations on the places planned to visit. Also suggestions on where to stay in each city. I prefer to stay in center of town and good hotels, but reasonably priced, since it is my daughter and I traveling alone.
Thank you so much!

Posted by
5472 posts

Regarding your leaving from Milan and staying the night before at the airport: I heartily agree with that plan. Last April, we stayed in Milan, by the train station, the night before our flight. The morning of our flight, our original train was cancelled at the last minute, and we had to take the next one, about 40 minutes later. We had extra time, and did make our flight, but the stress was incredible. If we fly out of Milan again, we would stay by the airport, and avoid the train commute stress.
Safe travels and have a wonderful trip.

Posted by
2 posts

That is what I was thinking when I thought we should stay the night before leaving by the airport. I do not want to have to wake up really early and have the stress of getting to the airport on the morning of the flight. I want to avoid what happened to you. Thank you Pat.

Posted by
3112 posts

If it were me I'd head straight to Cinque Terre, then to Siena and on to Naples (although Sorrento might be a better home base for your intended day trips), saving Milan for the end of your trip. You could stay in Milan and take a taxi to the airport the morning of your flight home. You'd be going the opposite direction of rush hour traffic so it should be easy.

Posted by
7674 posts

Just throwing out some thoughts since I’ve been to Italy multiple times.

Looking at your itinerary and the past cities you have visited, you are still going to the heavier touristed locations. Any interest in something like Bergamo or Torino - both quick train day trips from Milan instead of Verona? Torino has the Savoy history, royal palace, the Superga, several museums, great chocolate. Bergamo has a funicular up to the oldest section of town that would give you some nice variety in your itinerary.

When picking locations for overnights, I try to pick locations that are special in the evening, especially if it’s going to be multiple nights. Cinque Terre and Siena were that way to me, but Milan wasn’t (haven’t stayed in Naples).

Otherwise, I would move the first two nights to stay at Lake Como - a nice place to get over the jet lag and enjoy.

For train info, check www.trenitalia.com. Use the Italian names: Milano for Milan. You can save money by purchasing your train tickets a couple of months ahead on-line.

Posted by
5472 posts

I would also vote to spend the first two nights in Lake Como, in Varenna . It's an easy one-hour train ride, but if it is a weekend, I'd get First Class train travel, to guarantee a seat. [That train can be like a crowded commuter train, with many folks standing the entire hour. ] If you book 6 months out, First Class is cheaper than regular fare, but there is a very limited number of First Class seats at the price.

Posted by
105 posts

I agree with the previous commentators. Stay in Varenna and/or Lecco and do your trips from there, Milan is too far away. Lecco has good shopping, dining, and Italians with regular jobs (other than tourism).

Posted by
481 posts

We had a business trip in Torino this summer, and extended our stay - 4 nights in Torino, 1 night in Milano, and then train to Stresa for 3 nights on Lago Maggiore. We flew in and out of Milano. The Piedmont region is beautiful, and if we'd had a car, we would have loved exploring the areas outside of Torino. Torino itself was interesting and pretty, with lots of arcades to stroll, great historic cafes, the Royal Palace, the largest Egyptian collection outside of Cairo, excellent chocolate as mentioned...it was also not overcrowded with tourists.

We only had one night in Milan, by design, as we were eager to get to the lakes region. The one thing we really wanted to see/do was visit the Duomo and go up onto the rooftop. I'd highly recommend that experience - it was really beautiful, and memorable to be in the "marble forest" above the Piazza del Duomo. We also went to the Navigli canal district for aperitivo, and took a tram back to the Duomo area, seeing cool sights along the way in our less than 24 hours there.

We chose Stresa on Lake Maggiore instead of Lake Como, mainly for hopes to be less touristy, and to see the Borromean Islands. Either of the lakes are about an hour or less by train from Milan - easy access. Stresa had the benefit of being close to the Malpensa airport for our return by bus...we didn't have to go back to the Milano Centrale for a fourth time! Although we did get gelato from Venchi each of the three times we were at that station, because it was super hot, and gelato was necessary. :-)

Another reason we chose Stresa was the chance to go to neighboring Lago d'Orta and see Orta San Giulio and visit the Isola San Giulio - both really beautiful, and again, not overloaded with tourists. We were there in July. There's also a mountain in Stresa that you can take a funicular to the top of for spectacular views of the mountains and lakes...the weather didn't cooperate for us, but the pictures we saw were gorgeous. Plus, being on the lake and traveling between the islands was a highlight for us, too. The palace and gardens on Isola Bella were memorable, and we saw Chinese white peacocks strutting around the gardens there!

So there are some other places for your to consider for your trip. We traveled by train or tram in the cities, and were only using carryon luggage, so it was easy to get around.

Have a wonderful trip with your daughter!
Laurie