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train travel July early August

We are traveling from Milan(overnight from New York) to La Spezia, 2 days, Florence, 2 nights, and train to Rome for 3 nights. July 29 to August 5th. Do we need to reserve 1st class train seats during this time?
Then August 5-8th we are in Positano and have to get back to Milan for our flight back to NY early morning on August 11th. I wanted to possibly go to Venice for a night, but think we may be trying to fit in too much. Should we try to fly from Naples to Milan and just relax in Positano for one more night?
We are a family of 4 and I wanted to plan a nice trip to Europe before my oldest son goes off to college, but it seems my husband is so stressed with all the details that are needed. I would love some advice. I thought going to Italy would be a relaxing trip, but so far it's been a bit overwhelming:)
Any help is so appreciated!

Posted by
4152 posts

You don't really need first class for any of your trips as second class is very nice. You have about 13 days and have listed 5 cities (areas) that you plan to visit. That's not a lot of time in any of them. Personally, I would drop at least one stop and spend more time in less places so that you can really enjoy these wonderful cities.

Donna

Posted by
23270 posts

You don't need first class at any time. It is rare for second to be full at anytime except for a rare event. Some of your travel may be on Regionale trains where no reservation is required. If your flight is depart early am then you need to be in Milan the night before.

Posted by
16893 posts

For longer-distance and faster trains, seat assignments will be built in when you buy the tickets, but there is no deadline to buy them. You can buy the ticket departing Milan in Milan, rather than trying to predict around your flight arrival time. Trains from La Spezia to Florence are either entirely or partly by unreserved regional train; that's another good ticket to buy at the station. (Regional train tickets are more restrictive if purchased online, and also not sold online more than a week ahead.)

If your hotel plans firm up and you're more prepared to book tickets ahead for Florence-Rome, Rome-Naples, or other big-city connections, then you can get nonrefundable advance-discount tickets as early as 3 months before those travel dates at www.trenitalia.com. For flights within Italy, see www.skyscanner.com.

Posted by
11613 posts

Fast train tickets for Italy are available up to 120 days in advance, with super-economy discounts, not three months ahead. By three months out, that super-economy fare may be gone on the most popular routes.

Plan to spend the night of the tenth in Milano.