First time going to Italy, would like some opinions

The timing is fine, though obviously heavy on Rome. (If you had not already booked, then we would suggest flying into Milan or Venice and out from Rome.) I consider Venice to be more romantic than Milan. Your central location in Milan will be very convenient and the Piazza del Duomo provides good people watching (especially of the scruffy gypsy variety). I would also usually like a smaller town in this big-city mix. The hill town of Orvieto is easily accessed from the central train line; if you don't stay overnight, it can also be visited en-route back to Rome or as a day trip from Rome (1h 15 m each way). A coastal stop like the Cinque Terre would be another popular option. I hope that you have Rick's Italy book, but if not, see an overview at https://www.ricksteves.com/europe/italy.

How to Look Up Train Schedules and Routes Online gives you the DB train schedule link and tips for using it or www.trenitalia.com is the one that sells tickets (from 3 months ahead). Schedules for slower regional trains (including to Orvieto) are not yet published for next year but also don't change much.

So it's your first time in Italy.
What's in Milan that you need to see before even considering Venice?
If this were my trip, I'd go to Venice upon landing. Spend 3 nights there. Then to Florence for 3 nights. Lastly 3 nights in Rome before coming home.
Scratch Milan off.

I agree with Roberto. While I liked Milan, I loved Venice. Venice is unlike any other city in the world.

Trains will move you rapidly between the cities you are considering (and also to/from Venice), but be aware that the fares will probably go up a lot as you approach your travel dates. The best deals usually need to be purchased soon after the tickets go on sale, and the cheap tickets are non-refundable and non-changeable. You'll have to weigh the cost savings against the loss of flexibility. Regionale ticket prices, however, are not date-sensitive, and you can take regionale between Rome and Orvieto.

I stayed in Trastevere in May 2015 and liked the location. There are more Italians than tourists out and about. One thing to keep in mind is that it can be quite hot in June. You won't know until shortly before arrival what the weather forecast is, so I advise being sure that you have air conditioning.

Thank you all for the quick responses. I'm not sure how to directly reply to comments but I'll address as much as I can here:

We had originally considered Venice. We had read in various places, mostly on Reddit's /r/Travel, that while Venice is incredible, it can be skipped. We heard Milan was very nice and had a great nightlife. It's a tossup between the two, to be honest.

We've researched train times and fares on raileurope.com which seems to be pretty reliable and the costs seem reasonable.

Assuming my current itinerary doesn't change, (20th-23rd in Rome, 23rd-25th in Milan, 25th-27th in Florence, and finishing back in Rome the 27th-29th) would you take that last day in Rome, the 28th, and do a day trip to Naples/Pompeii? That seems like a really great tour.

Would drop Milan personally, think there are better places you are passing over to see it. Either choosing a new 3rd location or adding onto Florence or Rome. I think Siena, Orvieto or some other hill town in between Florence and Rome would be more romantic, I am certain Venice would be more romantic. Cinque Terre may even work but would require a little shuffling. I admit though, nightlife is not a consideration for me.

Totally agree with others who said to skip Milan. With only 9 days, less if those include air travel days, I would strongly suggest you split your time between Florence and Rome. You could spend a month in either place and still have more to see and do. These two cities would also provide some wonderful day trips, very easy to Orvieto from Rome, very easy to Siena or Bologna from Florence. There is great night life in both cities. If you add a long trip to Venice, splitting 9 days among 3 places, you will barely get a taste of any of them. You can always return to Italy in a future year.

would you take that last day in Rome, the 28th, and do a day trip to Naples/Pompeii?

No, because it will be 6 hours spent on the train going back and forth, which makes for too little time on the ground. In other words, a very long, tiring day mostly spent in transit. It's best to see that area with an overnight trip. Pompeii itself can take half a day to see. In terms of your plans, I would substitute with a much shorter side trip from Rome..you won't run out of things to do, don't worry.

I wouldn't use Raileurope for train tickets...just buy them from Trenitalia (Italian rail service) itself.

I've always just bought my train tickets in Europe, paying the freight for the extra flexibility, but others here report quite convincingly that RailEurope's fees (embedded in the cost you see) can be substantial, and it doesn't show all the options, skipping some of the less expensive ones. I urge you to check the fares on TrenItalia so you'll be an informed consumer. My bet is that the inexpensive regionale tickets to Orvieto are not offered on RailEurope.

And I agree with all the others: Milan instead of Venice is really odd. Yes, Venice can be skipped. So can Rome, Paris, London, etc. It's a matter of what you skip it for. It's true that Milan's Duomo is lovely. But instead of Venice?

If you're thinking of seeing the Last Supper, you need to check into that right away, because there have been reports that tickets sell out months in advance.

By all means go to www.seat61.com for all you'll need to know about train tickets in Europe. Never use RailEurope but use Trenitalia. We booked direct with Trenitalia I think maybe 120 days in advance but maybe 90. Be sure and use the Italian spelling for the cities -- Venezia, Roma, Milano, Firenza -- or the response will be no tickets available. I second the advice to trade Milano for Venezia. You can book some tours of the Vatican in advance since some of them fill rapidly. Send me a PM for special behind the scenes viewing at the Vatican.

First of all, congratulations!

It's a good thing that you're getting an early start on planning. As this is your first trip to Italy, you'll need to get up-to-speed on the specifics of travel there, which include some potentially expensive "pitfalls". My first suggestions would be to read Europe Through The Back Door and then pick up a copy of the RS Italy guidebook. Those will provide you with a lot of good information to help your trip go smoothly.

I agree with the others that it would have been preferable to use "open jaw" flights as that's more efficient and allows you to maximize sightseeing time. Does your time frame include your two flights days? It would help to have some idea on where you're flying from, as forum members in your area may be able to provide some good tips. Also, what time does your flight arrive in Rome? Limiting your trip to three destinations with some day trips would be ideal.

I also most definitely agree that it would be a good idea to skip Milan. While it does have some interesting sights, IMHO your very short travel time would be better spent elsewhere. As you don't seem to have much interest in Venice, I'd suggest arranging your Itinerary as a "loop". When you land in Rome, don't stop there but immediately go to your first destination (Florence?). That's going to make for a long travel day after a long international flight, but a more efficient method.

Someone else mentioned the Cinque Terre, so I was also going to suggest that you have a look at that. While it can be crowded at times, that would be a great area to spend a few days while recovering from jet lag. If you decide that might like a few days there, you'll have to decide which of the five towns you want to stay in. The C.T. is a good possibility as it's easy to do a Rome > C.T. > Florence > Rome loop. While in Florence, you could also take day trips to Siena (by Bus) or Lucca, as those are both easy. Venice is also possible as a day trip, although it will be a "longer" day trip due to the travel times involved.

Good luck with your planning!

I would also concur with others that whatever you read that said Venice can be skipped is completely different from my opinion. Venice is one of my favorite cities that I have been to. Admittedly I have yet to see Milan (other than the airport and train station) but it does not usually make the top of the list for first time visitors.

If you want to see some ruins but do not want to go all the way to Pompeii, then Ostia Antica is very close to Rome and a much shorter day trip. The ruins are a similar time period but were not covered by ash due to a volcanic explosion. It is a former port city and the city died out when the port shifted locations over time.

May I suggest something a little different?

You arrive in Rome on the 20th. Coming from the States, I'm guessing your arrival time is in the morning. I would take the Leonardo Express shuttle from Roma Fiumicino airport to Roma Termini station, then hop a train--which takes under 3 hours--to Verona. It's picturesque, historic, more scenic than Milano & not as urban, and its location allows you to visit Milano or Venice on a daytrip should the mood strike--a little more than an hour by train to each place.

Stay until the 23rd, when you'll take the train 90 minutes to Florence, where you'll stay until the 25th, when you'll take the Freccia train 90 minutes to Rome. Having 4-5 uninterrupted nights in Rome allows you to get the feel of the Eternal City over that time, or do a daytrip to Orvieto (1 hr, 10 min each way) or even possibly Pompeii (2+ hours each way). BTW, I've been there and it's worth the trip. Or, as Jen says, Ostia Antica is a shorter distance to traverse than Pompeii and contains similar ruins. And you're still finishing in Rome, where you need to be the night before you fly home.

This is a little less backtracking and one less hotel/B&B stay than your original plan.

Enjoy your planning!

Let me add my congratulations.

But I'm going to dissent from the Milan naysayers. I've been to Venice, and yes, it's great to "see." But in a lot of ways, it's not a living, vibrant city. Milan is. It's got a lot of nightlife, it's got terrific restaurants, it's got tons of great shopping. And people there are terrific--funny, kind, fashionable.

And to me, it's the people. Sights are ok, but to see modern Italy, it's good to get off the tourist path for a bit and see what life is like. Hang out with the crowd in the bars and restaurants of the Navigli. See what sushi is like in Italy (Italians are really warming up to it, and Milan has more foreign restaurants than most Italian cities.) Check out the bookstores full of art coffee table books. There are museums and churches too, if you're into that kind of thing. But it's got a great hangout culture, and it's very different from the more touristy places in the country.

Nothing wrong with Milan, but hands down Venice is where I'd send you. You can find nightlife and good food wherever you go, but the beauty and uniqueness of Venice makes it the first choice. You have to read closely at what people say they don't like. All the places you're considering will have crowds. Watch some videos and read some guidebooks.

We had originally considered Venice.
And you should still consider it. It's a must, especially on a honeymoon. Way more romantic than Milan.

We had read in various places, mostly on Reddit's /r/Travel, that while Venice is incredible, it can be skipped.
Anything can be skipped. But if given a choice between Milan and Venice, I'd choose the latter 100% of the time. Hands down.

We heard Milan was very nice and had a great nightlife.
Compared to Venice, Florence, and Rome, it's no comparison. Milan would come dead last.
Nightlife? Not sure what you are looking for, but you will be there on the last weekend of June. If it's hot, many Milanese will be skipping town and go to the lakes or to the seaside. I think you'll find as much nightlife or more in Venice at that time of the year.

We've researched train times and fares on raileurope.com which seems to be pretty reliable and the costs seem reasonable.
The website you should be looking at is www.trenitalia.com, which is the actual operator of the trains. Raileurope is a travel agency which will add their commission to the price.

would you take that last day in Rome, the 28th, and do a day trip to Naples/Pompeii? That seems like a really great tour.
It's up to you. As long as you have at least 2 or 3 full days in Rome.

Since you are flying into and out of Rome I would suggest a circular route taking in Tuscany and Umbria along with Rome. Would skip Milan and add Florence and some hill towns. While I love Venice I don't know if you have enough time. Congrats!

I have been to Italy four times and always gone to Florence at least for a couple of nights, but never Milan. Venice over Milan is an obvious choice, based upon my years of research for various trips, and personal experience with how great Venice is. If there is a way to have your Rome stay in a single stay, you should do it. You are probably younger that I am, but urban Italy and the mass tourism that goes along with it is exhausting and you might want to try starting in Orvieto. Fresh off the plane, Rome is like taking a firehose in the face. June will be very, very busy. Venice embodies romance like no city in the world that I have been to, and I've been to lots. The tourists crowds will be very crazy there too, but easier to find a quiet place. Actually I did watch Rick Steves on Milan recently though and it does look more interesting than I thought. All of this said, if Milan calls to you then go for it. As Rick says, assume you will return.

I agree with the others and skip Milan in favor of Venice. When you arrive, head straight to Florence, so this would mean buying your ticket at the train station, then Venice, then Rome. Use www.seat61.com for detailed rail info. Buy tickets at www.trenitalia.com.

My last trip to Rome we stayed in Travestre and loved it. It is a great safe neighborhood with lots of locals eating at resturants surrounding a square!

You may want to think about air conditioning in Rome. June was very hot when we went.

Hi George -

We had read in various places, mostly on Reddit's /r/Travel, that
while Venice is incredible, it can be skipped.

"Incredible" and " can be skipped" don't work in the same sentence, IMHO. :O)

We enjoyed our (short) time in Milan but I wouldn't have done it at the expense of some other locations. I'd go along with dropping that one in favor of Venice or adding those days to Florence and making day trips to some smaller Tuscan towns.

If you can change your reservations in Rome, I'd also go directly to Florence on arrival day (and on to Venice from there if you choose to make the switch from Milan) and putting ALL of your Rome days on the back end instead of splitting them. Grouping those days would allow you to unpack, relax, catch your breath and enjoy some more leisurely sightseeing before heading home. Tons to see in Rome!

Yes, use Trenitalia for researching trains. Take a look at Italo as well as it has competitive rates between larger cities. Some members have been happy with www.trainline.eu (used to be Captaintrain) for ease of use but I haven't yet used that one personally.

I would drop Milan and just spend the days in Rome and Florence/Tuscany. My wife and I did it in 2010 and it was really a great time. Remember, you don't have to see everything in one trip, once you go do the first time you'll go back.