2 weeks in Italy - minimizing hotel moves

Amalfi too far as a day trip from Rome

Venice is too far as a day trip from Florence

CT Needs more than a day trip

Can you fly in to Venice and fly out of Rome?

In a word NO, I don't recommend it. You can do a day trip from Rome to Naples/Amalfi Coast/Pompeii/Capri, but you won't see that much. You could probably take in Pompeii, but forget the rest. If you want to go to the Naples area, suggest staying in Sorrento and stay for 3-4 days.

Venice is a special city and doing on a day trip from Florence is like just going to Paris to see the Eiffel Tower.

Also, Cinque Terre is good, but Venice, Florence, Rome and the Naples area are a step above CT. Between CT and the Amalfi Coast, I go with Amalfi.

You can do a day trip to Sienna from Florence, or Orvieto from Rome.

Because of the extreme crowds and the heat, I'd drop Clinque Terre, and maybe add Lake Como, which is an hour train from Milan [Milan to Varenna]. I found the area to be beautiful and charming, and want to return. I wasn't there in July, however, so can't speak regrading the heat.

For your time frame, I'd suggest flying into Rome, to Florence, to Venice, and then Lake Como [flying out of Milan]. I'd save the Amalfi Coast for the next trip, because of the logistics getting in/out, and the time to travel around the winding roads in the area, accompanied by the summer heat.

Enjoy a wonderful family vacation!

There is, or was, a school of travel thought that said only unpack once and take daytrips. That seems to have fallen out of favor, since it involves a lot of travel time each day.

You can't really do the Amalfi coast easily, but the rest should be doable by train, bus or car with driver.

If you have not already purchased air tickets, look at starting in Venice and ending in Rome.

Check out the "Itinerary" here-- https://www.ricksteves.com/tours/italy/venice-florence-rome -- to use as a blueprint for inspiration.

You could easily add a day a Venice and Florence and the 'extras' to Rome. From Rome you could easily go to Ostia Antica, vs a mad dash day trip to Pompeii

Another option is the above tour and sandwich in a couple night at Lake Como (OR Cinque Terre) between Venice and Florence.

The tour works because it has a dedicated bus for door to door service and a guide so there is no getting lost or figuring out how to from point A to B

2 weeks is not a lot of time. Do you have 14 days on the ground, or are you counting your arrival and departure days in the 14? Even if you are to arrive early in the day, by the time you get out of the airport, get into town, and get to your lodgings, quite a few hours will have passed.
Rome should be allotted 6 nights (5 full days) minimum if you want to include day trips. Two great ones without excessive traveling are Ostia Antica and Orvieto.
You need to devote several days to Florence itself. Siena can easily be done from there as a day trip. Tuscany is where a guided day trip might be a wise investment. A very pleasant day with a knowledgeable guide might include a town or two (0r three) and a winery visit.
I wouldn’t spend any time in Milan on this trip. You could go straight to Lake Como or consider Maggiore. Ferries can take you to see the sights. When it’s time to say, “Arrivederci Italia,” you can stay at a hotel near MXP the night before. There are many. I’d get one with a free shuttle to the airport.

With only 2 weeks, and for a first visit, you already have too much on your plate. Add in summer crowds and the heat, then the smart move would be to skip anything south of Rome and do them on another trip.

None of the places are easy day trips from Milan, except for Como. I'm assuming you added that city because you got a cheaper flight home from there. Too bad, since starting in Venice and ending in Rome would have made better logistical sense.

Visiting Venice from Florence as a day trip makes about as much sense as visiting Paris from London as a day trip. Much of the day sitting on trains, and little time seeing anything once you're there. The same thing goes for seeing the AC and Naples from Rome. Yes, you could see ONE of the sites in a day trip, but it would be rushed.

I'm also going to assume your 2 weeks includes travel days from and back home, so you'd only have 12 nights on the ground. If you cant change your flights, then I'd suggest 4 nights in Rome, 4 nights in Florence, with one or 2 day trips to other Tuscan towns, 2 nights in Venice, and 2 nights on Lake Como. But if you have an early flight out of Milan, you'd have to find a hotel near the airport for that last night.

I'll confirm what others have already said, Sorrento and the Amalfi Coast are way too far for a day trip. The first time I went to Rome, I did a day trip to Naples/Pompeii. Most people on this forum probably would have scolded me for it, but because I like you didn't want to have too many home bases, it made sense to at least get a taste of Naples/Pompeii and then I could return later for a longer visit (which I did this past summer).

Tuscany is really only accessible from Florence and not really that easy to get to by public transportation (expect Siena, which makes a good day trip). You might find a good tour company that would do a car/van day trip for your family around the parts of Tuscany that are closer to Florence. If you really want to stick with public transportation from Florence, I would do Siena (by bus), and Lucca/Pisa by train. Lucca and/or Pisa (on the same long day, or two separate days) are great options from Florence. Way better than trying to get to Cinque Terre, which needs a visit on its own.

Venice IS possible as a very long day trip from Florence. Most argue against it, because it rightfully deserves its own stay. But I have done it as a day trip before with relatives that were in Italy for the first time and didn't want to miss it.

From Milan Lake Como (either Como or Varenna) are possible by train. Varenna is a little more idyllic, but Como is very nice and there is plenty to do there as well.

Finally, plan the trip that YOU want to do. You don't have to listen to all the nay-sayers on this forum. Read their advice but don't limit yourself to staying in every place you want to go to for a minimum of three nights if that doesn't work for this trip. Balance what you want to see in two weeks with the pace of trip that works for you.

You're going to have so much fun!!

As everyone else has said, skip the Amalfi Coast and go another time. You could include Sicily when you do go. I would remove the Cinque Terre too since it’s the outlier and not that convenient to get to.
Fly into Rome and sleep in the Trastevere neighborhood. If you can’t find an affordable place to stay, check out the nearby Hotel Smeraldo across the River Tiber. Spend a minimum of four nights in Rome and that includes a day at Vatican City. If you’re not interested in visiting St. Peter’s Basilica and the Sistine Chapel, make it three nights or take a nonstop train to Naples (1h 15m) for the day.
From Rome’s Termini station take a direct train to Florence SM Novella station (1h 45) and sleep there for five nights. Buy tickets for the Uffizi Gallery two months out to guarantee a reservation. On day three take a direct bus to Siena (1h 15m) for the day. On your last day in Florence get up early and hop on a direct train from the SM Novella station to Venice (2h 15m) and a train back to Florence that evening. Long day but it’ll be worth it.
The next day take a direct train from the SM Novella station to Milan’s central station (2h) and sleep near the train station. You can take an early morning direct train from the central station to Varenna (1h 15m) and explore Varenna before hopping on a 15-minute ferry to Bellagio and walk around there before ending your day in Milan. I would sleep in Milan for three nights.

So Day 1 is board the flight and Day 2 is land in Rome? Or is Day 1 land in Rome? Day 14 is probably a morning flight.

That gives you 11 (or 12) full days on the ground plus about a half day in Rome on arrival, jetlagged and sleep-deprived.

Rome has tons to see. I have spent around a week in Rome more than once and not run out of sights to visit. The best day trips are Ostia Antica and Orvieto. Ostia as old as Pompeii, though not as extensive or impressive, but July heat in Pompeii is brutal. At least there's a beach near Ostia that you could end the day at, and it's easier, cheaper and much faster to get to Ostia - and probably not nearly as crowded. Orvieto is a lovely hill town with a beautiful duomo (especilly in the late afternoon sun) and fascinating underground caves (the hill it's on has been described as swiss cheese).

Florence is chockfull of Renaissance sculpture, painting and architecture. Day trips include Siena (full day) by bus and Pisa & Lucca by train (about 1/2 day each).

Venice which you didn't mention, is magical and unique. It would be a sin to skip it. (Okay, I'm prejudiced in her favor). Though is has more than one great sight, the best thing to do in Venice is relax and enjoy - ride the vaporetto along the Grand Canal (at least once during the day and again after dark) and across the lagoon to Burano (worthwhile for the ride even if you don't spend time on the island itself. Walk through the back canals and get a little lost . . . it's easy to get lost, hard to stay lost.

Those are the 3 biggies for a first trip. You have to spend your last night in Milan. You can leave Venice early on your last full day and spend most of it in Milan. See the duomo (be sure to walk around on the roof), then walk through the Galleria Vittorio Emanuele II and tour La Scala or continue to Castello Sforzesco. OR take the train from Venice to Verona, check your luggage at the train station, spend the day in this charming city (don't miss the Arena) and get to Milan at night.

Everyone here has given great advice. I would just like to add that the 2 best pieces of advice I received when planning my first trip to Italy:
1. Experience a smaller town at night. Living in an urban area, I'm so glad that I didn't spend a 2 week vacation going from city to city in Italy. Over the years we have stayed in Lucca and Orvieto, Bellagio on Lake Como for example.

2. Be honest with yourself and your group about how much energy/mental concentration for museums/churches/history in Rome, Florence and Milan. Ours is 2-4 hours every other day, otherwise everything just starts looking the same and just dragging along from one big building to another. Have a wonderful trip!

You're forgetting Rick's first rule of travel - assume you're going to return so don't overdo it