Itinerary for May 2020

That's a lot of moving around. And traveling100% by trains is difficult, especially to so many places--and in the mountains. Have you considered staying in 2-3 locations and doing day trips from them?

It's not entirely clear whether some of your destinations are day trips or changes of location, but there does appear to be a lot of moving around and multiple one-night stops. Your biggest detour is Liguria (Genoa, Cinque Terre, etc), so you might consider replacing that area with extra days at your other locations and a couple of nights in Verona on your way from the Dolomites to Venice. You may be able to day trip to Mantua from Verona, but not sure whether there's a train. You could also day trip to Lake Maggiore and Bergamo from your Milan base, both about an hour each way by train.

Do you know from your previous trip that you are not wiped out by the overnight flight? I would nor be able to handle what you plan on your arrival day.

This doesn't feel like a relaxing itinerary to me, but I guess it's doable with the possible exception of seeing both Portofino and Santa Margherita on the same day you relocate to Genoa. I'm concerned that you're going to be spending a good bit of time on trains/buses/boats, but I haven't researched the schedules, and it may not be as bad as I fear.

Rather than a very short visit to Lake Maggiore (how frequently do the Borromean Isle boats depart from Stresa in May? Will you be limited to seeing just one of the islsnds?) and a very short visit to Lake Garda, I would choose a single lake.

I would visit Bergamo as a day-trip from Milan to cut one hotel change. I think the trip from Bergamo to Genoa would route you back through Milan anyway. Bergamo's an atmospheric place, and it would be nice to spend the night in the upper town, but for me it wouldn't be worth the hotel change for just one night on a trip when you're moving around this much.

My plan is to stay in Milan for 4 nights and do a day trip to Bergamo one day, and one day to Lake Maggiore and Borromean Isle. I read that it is doable as a day trip to both places. The on-line review said that the islands can be visited in a day albeit a long day. I believe in doing touring as soon as we drop off our luggage and have done so every time. Mantua is perhaps the longest day trip and might have to be dropped. I have been to Verona and seen the sights there and do not want to go back. The train from Milan to Genoa is about 3 hours. From Genoa we would take a local train to either Rapallo or Santa Margerhita depending on where we get accommodation. WE might just stay in Genoa and do the other areas as day trips. Again I have read that they are very short train rides away. I would spend the remainder of that day in that local. The next day we would get a cruise to one of the Cinque Terre towns and perhaps another boat to a second one or the local train. One day would be spent touring Genoa. So we would be in Milan for four days and the Genoa area for three days. We would be in Riva del Garda also for about 3-4 days and then stay in Bolzano for the remaining time, about 4 nights. We have both been to Venice and could just go there to fly back as it is the closest airport to the Dolomites. I found in the past that the train from Milan to Garda was about 2.5 hours so from Genoa it would be about 5 hours, the only really long day of train travel. Does this make more sense?

Bergamo is not a long trip at all. I have always stayed in Stresa to visit the Borromean Isles and don't know whether you'd be better off getting the boat from one of the other towns on the lake.

I want to be sure, though, that you realize there are three islands there, not just one. I can't inagine you'll have time for all of them.

I had read a post that allowed an hour for one island and two for another and the fihermen's island a stop for lunch. I will have to research more and if you are right that we can't do all three in one day then we will have to pick what is the most interesting for us. Thanks for pointing this out to me.

Caryn, have you considered flying into Venice and out of Genoa. (edited for exit airport) This would put you on more of a straight line path without crisscrossing thru Milan. It would look something like this.

Day 1. Arrive Venice.

Day 2. Venice.

Day 3. Venice-Bolzano, train 2H41m.

Day 4. Day trip. Ortisei, bus 31m.

Day 5. Day trip. Merano, Train 37m.

Day 6. Bolzano-Riva, train 2H17m.

Day 7. Day trip. Rovereto, bus 42m.

Day 8. Riva.

Day 9. Riva-Desenzano, Ferry 2H25m. Evening train to Milan 52m.

Day 10. Milan.

Day 11. Day trip. Bergamo, train 48m.

Day 12. Day trip. Stresa, train 56m.

Day 13. Milan.

Day 14. Milan-Rapello, train 2H08m. Staying here or Santa Margherita puts you equidistant between Vernazza and Genoa.

Day 15. Day trip. Vernazza, 58m.

Day 16. Day trip Santa Margherita, ferry 15 minutes. Train 03m.

Day 17. Ravello/ SM- Genoa. Train 52 m.

Day 18. Travel.

Edited for timing.

Thanks for this suggestion. I like the itinerary. Flying to Venice may mean making a stop in New York and then in Rome but I will have to check it out.