First trip to Italy

I would recommend going to the library, borrowing some Italy books (RS is a great one), reading as much as you can, and then narrowing down what region (cities) you'd like to see based on your interests (then you should come back here and post an itinerary, which folks will gladly help fine-tune). Italy has blockbuster attractions in every region (the extreme south and southwest is arguably very underrated), but some may appeal to you more than others. The number of sites you can see will depend on the time you have as well as your budget. The best advice I could give to a first-time traveler is to build slack into your itinerary to account for jet lag, travel time (typically by train) and to pick a region to minimize travel time and maximize touring time (lots of folks don't give themselves enough time and yet try to cover a huge geographical area, which is often unrealistic). I'd also say no less than 2 nights in one place, unless it's a day trip. Key cities (Rome, Florence, Venice, etc) deserve at least 3 full days, preferably more.

It's also very helpful to look at train schedules (Trenitalia) to estimate time between two cities and plot out your itinerary logically to avoid backtracking, etc.

The cruise option will shortchange the interior of the country - I would do a pure land-based trip.

And forget the "cruising" part if you really want to see Italy. Cruising gives you a few hours in port at various sea locations - that's not the way to see ANY country.

I think you need to provide more information before the readers will be able to help you. How many days have you allocated for the land portion of your vacation? What ports of call will your cruise ship be docking at? Do you have to take a cruise or are you open to seeing Italy by land? If so, how many days?

There is no best way to see Italy for the first time. Cruising with an extended trip is an excellent way to go. We do that frequently and add a week or two are either end and sometimes both. But you really need to firm up your travel schedule before this site can be very helpful. Otherwise we are wasting our time and yours.

Forget the cruise! The only way to "see" Italy is by land.

First, get some books and/or videos to see which areas appeal to you. Enlist your sons help in planning, they may have totally different ideas than you do.

Many people start with the big 3 - Venice, Florence, and Rome. Depending on the amount of time you have you could also do day trips from there.

I would also suggest flying open-jaw, into one city and out of another. This will eliminate needless backtracking back and forth.

Why would land be the only way? After all, most of the great cities of Europe and Italy are or were great seaports - Naples, Venice, Rome, Genoa. Five hundred years ago the sea was the only way to get to a lot of those cities. There is an anti cruising bias among some posters here so recommendations against cruising should be taken with a "grain of salt." We have always found European cruising to be a very economical way to see a lot of Europe conveniently.

I suggest choosing which places you want to see then build on it. For my trip this summer, I narrowed down my chosen destinations to Croatia (because I had seen a beautiful photo and thought I must go there), Ephesus (husband wants ruins), Santorini (doesn't everyone want to go here?), and if I could work it out, Lake Como, Italy. Here is what I ended up with:
Day 1 Arrive Milan
Day 2 Train to Lake Como ( 3 nights)
Day 5 Train to Venice (1 night)
Day 6 Leave for 8 day cruise to Dubrovnik, Ephesus, 4 ports in Greece, including Santorini
Day 15 Back to Venice (2 nights)

As for Italy only, if you are interested in cruising, then there are plenty of places in Italy to see along the coast. I would north to south and extend the end in Rome. And eat gelato every single day.

Enjoy!

I don't know as there's a wrong way to do it: all depends on what sort of trip makes you happy. I personally wouldn't choose a cruise for a first visit to Italy for the same reason as Tim: the ships dock too far away from some of the star cities, and one-day tours from those docks are not enough time to really experience them. But again, that's just my own preference, and others may feel differently.

I feel a bit the same way about only allowing a "few" days for land exploration: devoting it ALL would be my choice for this adventure.

Where? Again, people are going to have very different preferences but many of us agree that the classic, first-timer's itinerary is the 'Holy Trinity': Rome, Florence and Venice. Why? All three are very different cities with their own individual histories, architecture and cultural heritages so it's not as if you've seen one Italian city, you've seen them all. There's also easy, efficient train transport between them; they're all close to international airports; they're all used to hosting tourists from all over the world; day trips are also easy to do by train/bus to any number of smaller villages.

What to see? What are your interests? Rome, of course, has the crumbling vestiges of what was once one of the most sprawling, powerful empires on earth. Florence was the cradle of Italian Renaissance art. Venice was once the wealthiest seaport of an age, with the exotic influences of the far East reflected in its architecture. Art museums, gorgeous churches, parks, atmospheric backstreets and lively piazzas abound in all. Possibilities are endless: which of those to choose is entirely up to you and your young people (involve them in the planning; have them do some of the research!).

I'll throw out a minimum length of 10 nights - more are better - with an itinerary order of Venice>Florence> Rome with open-jaw flights (into Venice; out of Rome). May - June lands you in high season in Italy so all three cities are going to be VERY busy but breathing room, when needed, is usually easily found by wandering just steps off the Tourist Route.

It would help to know how many nights you have for your trip. It also depends on how you like to travel - cruise or land. I would consider a cruise to the Caribbean, but I would feel like I would miss too much of Europe's history, culture and sights if I cruised there. By the way, I've never been to the Caribbean, so that's my anti-cruise bias, but it's strictly personal choice.

You and your family might have a great time with 8-10 hours in port. You would not have to feel responsible for everything 24/7.

Whilst a cruise can make for a great holiday, keep in mind you will only be 'in' Italy for approx one third of the time, with the remainder 'at sea'.
Having said that, you could take a cruise from Venice to Rome, with time in each before and after, as well as additional time after Rome for Florence.
Look at Celebrity Constellation 12 day cruise departing Venice on May 19.

My first trip to Italy was with my brother, SIL and their 2 20-something sons in 2013. I didn't want to do all the planning and I was concerned that getting the guys up and going in the AMs would be a chore, so we chose the Rick Steves Heart of Italy tour. Our time frame was limited as the oldest could only take off a certain amount of days from work. The air travel days cut out 3 days for travel to begin with (Days 1 and 2 flying over as you usually arrive the day after you depart the US) plus the last day for travel back. We were able to add 2 nights on to the beginning and one extra night in Florence at the end. This worked perfectly for our family. The guys had a wonderful time with the tour, the guide and the other tour members. We went in May as soon as the younger one finished his exams. I would do this again in a heartbeat.

https://www.ricksteves.com/tours/italy/heart-italy

Have a great time with the guys!

Bgiannini

Last May, we flew to Venice 3 nights, trained to Florence 2 nights and trained to Rome 5 nights. We then did a Western Mediterranean cruise for 7 nights out of Rome and then flew home. If we could change one thing, it would have been to add an extra night or two in Florence. This was our first real cruise, and it was enjoyable even though that was not my preferable way to travel

In your post, you said you are considering a cruise with just an extra few days at the beginning or end. If you do that just spend those extra few days in the major city next to your port (e.g. Venice for East Med or Rome for West Med) and forget about trying to visit anywhere else. You will not have the time or energy. I don't know how other cruisers do it, but i found our cruise to be exhausting.

Tim, the OP is thinking about combining a land trip in Italy with a cruise, not a cruise-only vacation. That said, I would only recommend traveling that way if the land portion is limited to one city. A good option would be one week in Rome, then cruise out of Civitavecchia that includes mostly Italian ports. But yes, a land trip would be a much better way to see Italy than a cruise.