Trip to Italy

Welcome! You're going to get lots of wonderful advice here. You just need to help us with some details. Let me start with a basic question: what do you see/do/experience while you are in Italy? To answer your 'basic' question: getting to Venice from Milan is only a couple of hours by train. If you can deal with jetlag, that would mean getting to your hotel in time to unpack, freshen up, get out for a walk before dinner. Venice is not really a 'late night' city, so you won't really be missing too much if you retire on the early side. You'll get lots of suggestions about details for a Venice stay. My favorite hotel: Hotel Ala (hotelala.it).

From Venice you should take the train (trains in Italy can be a wonderful way to get around) to Florence. It's only a couple of hours. You need to decide what to do/see/experience in Florence and how much time that will take.

Then, on to Rome. Again by train (trenitalia.com), and again only a pleasant, short ride. There is more variety of experiences available to you in Rome since its history/culture covers lots of centuries. Get tired of one, just turn the corner.

Now the less than good news: any chance you could fly into Milan (for the cheaper fare) and out of Rome (to save you a vacation day)? Remember, you'll have to pack, train to Milan (not a short trip!), do the 'hotel thing' (check in, unpack, pack, get to the airport). Your last day in Italy is basically lost. Getting to the Rome airport from the city of Rome is very easy and your already short vacation just gained a full day! We're all looking forward to joining you enthusiastically while you do your planning. Remember, you can plan your next trip to Italy while you're on the plane heading home!

I know that a few years ago the air fare to and from Milan was so much less than flying open jaw out of Rome we could spend an extra day in Italy and still be money ahead.

Thanks so much for your response! I was thinking maybe to go straight to Rome after landing, my first day will basically be just relaxing. Thinking to stay in Rome 4 nights or so, with a possible day trip to the Amalfi coast. (Does this sound doable?) After Rome head up towards Florence stay for 2 nights, then make my way to Venice, stay a couple of nights, with day trip to Verona. My last two nights I would like to be close to the airport (back in Milan), with a day trip to either Lake Como or Cinque Terre.

Amalfi coast is too far as a day trip from Rome

Venice is a very nice way to ease into Italy, with no cars and a more relaxed atmosphere, especially compared to hustle-bustle Rome. The train takes you right to the Grand Canal and from there it's all sidewalks, bridges, and boats. I was enchanted. It definitely checks your "somewhere near the water" box, especially if you get to some of the lagoon islands or to the Lido.

If your round trip airfare to and from Milan is really low, it's probably worth the time and cost of backtracking there at the end of your trip. But I hope you explore the possibility of flying out of Rome instead, to get an effective extra day of sightseeing. It looks to me like you have ten full days in Italy, and if the last one has to end in Milan you really have only nine for sightseeing. See the itinerary for the Rick Steves Venice-Florence-Rome tour, not as something you'd necessarily follow, but for an idea of how busy you'll be with just those three cities. Day trips to other places, especially outliers like Amalfi and Cinque Terre, would really eat into your time. You don't want your vacation memories to be of stations and trains and highways if you can help it. Each day you change locations takes time and energy away from what you're going to Italy to see.

Have a great time planning this trip and keep in mind our host's advice: "Pace yourself. Assume you will return."

I count 14 nights
4 in May
28, 29, 30, 31
10 in June
1-10
Depart on 6/11

Two nights is a painfully short time for Venice. That's just one full day and some extra hours. There are parts of Venice that are hyper-touristy and overcrowded; with too little time in the city, you will end up spending a lot of your time in that environment, seeing things around Piazza San Marco and the Rialto Bridge. Don't set yourself up to dislike Venice. Allow yourself some extra time to see some of the hidden corners of the city.

It is not a good plan on a short stay in Venice to day-trip to a secondary (much lesser) destination like Verona. If Verona is a must, you should stop there on your way to or from Venice. It's right on the rail line between Venice and Milan. Alternatively, if you approach Venice from Florence, detouring to Verona adds only one hour to the total train time--though you still have to get yourself from the train station to the historic center.

The Cinque Terre do not work well as a day-trip from Milan. There's an 8:05 AM train taking 3 hours, but all the other morning departures are 3 hr. 49 min. or longer. It's not much faster from Florence. And keep in mind that your travel time is substantial in both directions, so you're giving up a huge chunk of a sightseeing day in Venice, Florence or Rome to spend six to eight hours sitting on trains. There's the additional problem that the Cinque Terre are overrun with daytrippers, making for a less-than-great experience. If you want to see the Cinque Terre, you need to spend at least one night in the area. That will give you a few peaceful hours in the early morning and evening.

I like your original thought to go to Rome on arrival day. With where the rest of your trip takes you, Amalfi Coast is not practical.

You could look at this as a planning tool and just go in reverse. ( check the "itinerary" tab) Add/subtract days as your interests dictate.
https://www.ricksteves.com/tours/italy/venice-florence-rome

Cinque Terre is too far for a day trip. Lake Como would be the best option for a 'waterfront' experience given your time constraints and Milan as your entry/departure point

For a first trip to Italy of 14 nights most people would do Rome, Venice and Florence with a few one night or day trips to smaller towns. But you didn't mention Florence and there is nothing wrong with skipping it. I'm actually a big fan of Florence but I didn't go there until I'd done several trips to Italy - no rule says you have to go there on a first trip.

But Rome needs at least 4 nights. If you are bored you can always do a day trip to Orvieto. It's a quick and easy train ride and will give you a taste of a small hill town. The Amalfi Coast is NOT a day trip from Rome. But if you are skipping Florence you could do a few days there. In that I'd do: 4 nights Rome (with day trip to Orvieto), 4 nights Amalfi Coast, 4 nights Venice (it will take a whole day to get from Amalfi Coast up to Venice), 1 night Verona, 1 night Milano.

There are lots of other places you could go but I wouldn't do more than 5 different hotels in the two weeks. If 'somewhere near the water' is important then I'd keep the Amalfi Coast. If not I'd skip it (it's further away, more time on trains) and include Florence with day trip to Siena, and/or Pisa/Lucca.

I recently booked a trip and also opted for RT to and from Milan. We normally book open jaw but the return flights from Rome were exorbitant and Venice also. Anyway, I agree with Roberto on adding a stop in Florence. You also should see at least one hill town in Tuscany, which you can do as a day trip from Florence. For a first trip, it’s fine to hit the high points and get a sort of overview, with 3 days in each location. Some will argue more days are needed, but we did the overview for our first trip and found that Venice was our favorite and where we’ve returned 3 more times and counting. Focus first on the types of sights that interest you most, whether it’s history, art, architecture, food, etc., and then you can branch out, and plan to return because I’m sure once you’ve experienced Italy, you will want to visit again!

You’ve listed
Rome
Florence
Venice
Verona
Milan
with a possible day trips to CT, Como or Amalfi.
Como makes the most sense- others are too much travel time for a day trip and you don’t have enough time to give either AC or CT the time it deserves

Arrive Milan- continue onward to Rome (about 4.5 hours so you arrive Rome 7-8 pm)
Rome 4 nights- give you 3 full days
1.5 hr Train to Florence 2 nights
2 .5hr Train to Venice 3 nights
1.5 hr train to Verona 2 nights
3 hr train to Lake Como- Varenna 2 nights
Return to Milan- 1 night
Fly home from Milan

That’s 14 nights

How about including Varenna and Bellagio on Lake Como. Here’s an idea with the minimal number of nights in each place:
May 28 – if flying into Malpensa take a direct train to Milano Centrale and transfer there to get to the Venezia Santa Lucia station (Venice; 4h). It would be easiest to sleep near the train station, otherwise you’ll need to hop on a vaporetto (water bus) just outside the train station.
If flying into Linate, take a bus or taxi to Milano Centrale
May 29 – Venice
May 30 – Venice
May 31 – take a train to Padua (Padova; 30-minutes) and store your luggage at the train station while you tour the Scrovegni Chapel. You’ll need to reserve tickets before leaving home for the chapel. Afterwards stroll through the town before collecting your bags and going to Florence. You want to take the train to the Firenze Santa Maria Novella station (1h 45m).
Jun 1 – Florence
Jun 2 – day trip to Siena by bus (1h 15m). Check out Il Campo square and the duomo, sleep in Florence.
Jun 3 – take a train to Orvieto (2h 15m) and store your bags at the train station and explore Orvieto for the day. Afterwards get back on the train to Rome (Roma Termini station; 1h 15m).
Jun 4 – Rome
Jun 5 – Rome
Jun 6 – Vatican City, sleep in Rome.
Jun 7 – take a train from Roma Termini to the Varenna-Esino station (5h 15m) that requires a transfer in Milan.
Jun 8 – Varenna
Jun 9 – day trip to Bellagio, sleep in Varenna.
Jun 10 – take a train to Milan (1h 15m).

I like MaryPat's itinerary as far as Florence. I'd skip Orvieto and go straight to Rome. Then go to the Cinque Terre for 2 nights and last night in Milan. I haven't counted the nights, but if there's one "extra", you could spend your final 2N in Milan and see the sights there.

Venice is, indeed, the best place to get over jetlag. Rome is noisy and hectic. Venice is quiet. It's easy to wander a few meters from the big tourist draws just soak up the atmosphere. In the early mornings and in the evenings you can relax on a vaporetto as you gently cruise on the Grand Canal and watch this magical city glide by.

If you are flying to Milan and already at the airport, are there commuter flights down to Rome? I always like doing the longest leg first and working my way back. Although some destinations don't logistically make sense, listen if they are calling you. On our first trip, we took the night train from Venice to Paris. In retrospect, it was a crazy thing to plan. However, Paris ticked the list and thoughts of it and Italy were a sustaining comfort during the pandemic lockdowns. We loved Rome, Florence (2 days was not enough), Cinque Terre and Venice. Paris was icing. Listen to your heart.