First time in Italy

I think your itinerary makes good sense. You won't be too rushed.

I would tend to stick with outdoor activities on your arrival day in Rome, because moving around in the sunlight will help banish jetlag.

Try to include Lucca on the day you go to Pisa. Lucca's charming and less touristy. You can walk or bike on top of the wall.

You will not have trouble filling your time in Venice. Just get lost! The forgotten corners of Venice are great places just to be. You'll definitely want to take a vaporetto ride down the Grand Canal. A lot of visitors like to do that once in the daytime and again at night. Many also like to ride out to the islands in the lagoon. I found Burano (lace) more picturesque than Murano (glass--and be careful about buying).

Most visitors find Milan considerably less engaging than many other cities and towns in Italy. The big sights are The Last Supper (tickets very hard to get; many end up taking some sort of tour as a means of seeing the painting), the Duomo (magnificent--you can walk on the roof), the historic Vittorio Emanuele II shopping gallery and the Brera District. I think fashion is a very big thing in Milan, so your daughter may be very happy there. I think you could fairly easily cover all the sights I've listed in a day, so you don't necessarily need to rush away from Venice on June 18. On the other hand, you might want to make a side-trip from Milan to Bergamo to see the atmospheric hill-top town. Or--if you can find a luggage-storage service--you could stop on the way to Milan in Padua, Vicenza or Verona.

The advice not to rush to buy train tickets was probably related to arrival-day travel. For the rest of your trip, if you know when you want to travel and are willing to commit to non-changeable/non-refundable tickets, you definitely should buy early. You'll probably save quite a lot of money by doing so. The cheapest tickets get snapped up first.

You have made the right decision regarding Le Cinque Terre.

You planned well.
Only problem is that I see you only have three days in Rome. You need more, but not sure you want to cut our Orvieto or reduce your time there.

I have been to Rome twice and spent a total of 12 days there and still haven't seen all that I wanted to see.

Rampart Stroll

I thought the movie was based in LA, not in Orvieto! What's a Rampart stroll?

Your first day in Rome seems to me the National Lampoon's Version of Bataan's death march, but you know your limits. I see an overall lack of free days when everybody does what happens, but again it's a matter of personal tastes.

June 17 - ??

Itvcould be the day to actually see Venice, getting lost for a couple of hours without a schedule that must be adhered to.

Hotel Berna by Rail Station

The Hotel Berna is close to Milano Centrale railway station, I bet your 14 years old daughter would rather stay close to Milano Cadorna station.

Your plan looks good. We did a partially similar route in Aug-Sep 2019. We stayed two nights in Rome -- seeing much the same sights as you -- and then trained to Orvieto. (We stayed Sicily--Sorrento--Rome--Orvieto--small agriturismo near Montepulciano--Siena--Cinque Terre--Milan with day trips to Florence, Amalfi Coast, Pompeii, and Naples.)

Orvieto was wonderful. I don't know the restaurant you mention, but one of the two restaurants we most liked during our trip is in Orvieto: Hostaria Posterula . I posted a review on the forum here: https://community.ricksteves.com/travel-forum/italy-reviews/orvieto-excellent-restaurant-hostaria-posterula .

We did a daytrip to Florence from Siena by bus. Uffizi in the morning, and Accademia in afternoon. (Both with advance reservations). We had a good LUNCH at Caffeteria delle Oblate, on the terrace with view of Duomo dome a few meters away. This place behind the Duomo was recommended to us by a friend whose daughter had attended university in Florence, and who himself had lunch there while on a business trip. The cafeteria is inside the university grounds. Uncrowded, close view of dome, friendly fast service, surprisingly good basic Italian food at economical price. https://www.facebook.com/caffetteria.delleoblate/

After Siena we went to Cinque Terre, and then like you stayed near the Milano Central Station in Milan for one night before flying home. We arrived in Milan about 11am and checked into our hotel (NYX Hotel Milan). Before walking from station to our hotel we confirmed the location of the departure platform for Malpensa Express to the airport; we were glad we did as it is located alongside the other platforms BUT it is farther "back".

While in Milan for that one night there was plenty of time to take subway to Duomo and walk the Galleria and nearby streets of the "fashion" area. That evening we dined at a restaurant one subway station away from the Milano Central Station (though it could be walked in 15 minutes). Found the restaurant in the Italian book "osterie d'Italia guida 2019". It was quite good, and open on a Sunday. The name is Ratana on Via De Castilia, 28. Unexpectedly when we left the restaurant, there was a free classical concert taking place in the park next to the restaurant, on the walk to the subway.

June 5. Are you landing at the airport at 12.15? Allow about 2 hours to get through the airport and take a taxi to your hotel, check in and drop your bags. By then you'll probably want lunch. Do you mean just the Baths of Diocletian or one of the other 3 sites of the museum as well? That's a lot to absorb in what could well be a jetlagged haze.

June 7. The Forum, Palatine Hill and Colosseum on a hot sunny day is a lot to cover before lunch. Consider going to the forum first, when it's a little cooler and where you'll be more exposed to the sun.

June 14. Are you going as a day trip from Florence? Consider combining it with Lucca. Someone recently wrote that he started in Lucca, got to Pisa in well into the afternoon and there were very few tourists by then.

Venice. Look at rowvenice.com which should be fun for all and cheaper than a gondola ride, though it could be in addition to it.

Amy,

I think you've done a good job with your homework and come up with a good plan that could improve with some tweaking.
Cut back your plans on your arrival day. It will take longer than you anticipate to get settled. Keep moving, though.

I think a great way to start your trip would be to take the Walks of Italy Welcome to Rome Evening Walking Tour. You'll walk through the heart of the city. Our tour guide was wonderful and they limit the number of participants to a handful.

I also agree with the suggestion that you steal a little time from Orvieto and add it to Rome. I also agree with adding Lucca to your Pisa day, there's really not enough in Pisa to fill up a full day when you are limited in your total time.

Finally, your mention of your 14 year old daughter and a trip to Italy made me smile. When I was in high school, a local group of 4 boys and 4 girls took a People to People tour of Europe. There was this cute 14 year old girl on the trip and we began hanging out together. By the time we got to Italy, we were an "item". It took us going to Venice, Assisi and Rome before I worked up enough courage to kiss her one evening in Florence. This August we'll celebrate 50 years of marriage!

Thank you so much to everyone's input.

Doug Mac, your story is so romantic and thank you for sharing it. I am not sure if my husband will let anyone kiss his 14 years old princess yet. My husband kissed me when I was 14 too and I have been married to him since we were 20 years old.

I will see how my First Day in Rome go. Definitely try to go by how exhausted we are on that day. There is so much to see in Rome and I will be okay if we don't get to see everything. We have a good half day on our last day and we may just go to National Museum on our last day in Rome. My husband is not a big museum fan so it will be only my daughter and myself. He likes to rent a bike and explore the city.

And yes, I have included Lucca and Pisa together. It is a brilliant idea to go to Lucca first and then Pisa in the later afternoon when it is not as crowded.

Baths of Diocletian is just a small portion of the old bath. There should not be a line and we can finish it very quickly.

I have purchased my train tickets already to Orvieto and I won't be able to change it unless I am willing to forfeit it. We will see how it goes and play it by ear.

thanks again for all of your inputs.

Amy

Great job planning. I think the first day is ambitious. I am a planner and get disappointed when my nonplanning wife and kids put a wrench in the plans but I have learned to plan what is necessary and go with the flow for the rest. I suggest ristorante del Carlo in Orvieto.