Italy Itinerary Questions

Use the Italotren and Trenitalia websites to see travel times, and how to minimize.
I'd be inclined to choose either CT or Lake Como.

for 2 weeks, I would stick to at least visiting 3 cities in Italy not 5. 5 Cities in 14 days will be a rush. You will feel tired after your trip and will need another vacation. Here is the better option among your listed options.

Fly into Venice:

Venice > Florence > Rome

Fly out of Rome

Venice - 4 Days

Florence and Tuscany - 5 Days

Rome - 5 Days

That would be the most effective way to divide your 14 days for May 2020

Postpone Como and Cinque Terre for a future trip.

If you land in Italy on May 4 and depart on May 18, that gives you 14 nights and 13 full, mostly-non-jetlagged days. It takes time to move from place to place--figure a minimum of half a day each time you change hotels, and you're doing it five times unless you travel to one of your other destinations on the same day you fly into Rome (not a bad idea). Both the Cinque Terre (which town?) and Lake Como (which town?) require time on slower trains. You'll spend more time getting in and out of those places than you might expect from simply looking at a map.

It would be a more relaxing trip if you cut the number of destinations to four.

I find the Deutsche Bahn website the easiest to use when checking train schedules. When you're ready to look at fares or buy tickets, you'll need to go elsewhere, such as to trenitalia.com. For trenitalia.com you'll need to use the Italian spelling of the city names/stations:

Roma (Tutte Le Stazioni)
Firenze (Tutte Le Stazioni)
Venezia (Tutte Le Stazioni)

Have you already bought your flights? Because Lake Como is really an outlier, requiring a lot of travel time if you aren't arriving or leaving from Milan. Time that could be better spent in the other places you've listed, IMO.

Im going to suggest a different itinerary all together. If you are flying into Rome from North America, your arrival day is marred by jet lag, so I'd recommend continuing to travel - all the way to Venice. Get that leg out of the way. You could fly, or take a train that would get you there in under 4 hours. Then you can start to work your way back towards Rome at the end of your trip.

Spend at least 3 nights in Venice, then go to Florence for 4-5 nights ( perhaps take a couple if day trips to Pisa/Lucca, or Siena). Then 2 nights in one of the CT villages before returning to Rome for the remainder of your trip.

If you can change your flights to a multicity ticket, you could fly into Milan and go straight to one of the Lake Como towns for 2-3 nights before going to Venice. That would mean taking away nights from Florence and Rome, and adding a travel day.

If you fly into Rome, it is easier to take a train to Venice than a domestic flight. Quicker too.
It takes about an hour from touchdown at VCE to actual Venice.

On the premise that entry /exit must be Rome and you are determined to do ALL your destinations, this is my recommendation:

On arrival in Rome go directly to Venice

Venice to Lake Como

Lake Como to CT

CT to Florence

Florence to Rome

I agree with others that you have too many far flung places for the number of days you have.

Pick Lake Como OR Cinque Terre. Doing so gives you the time to enjoy your trip, not just survive it.

My $0.02

Maybe you just can't know until you've done it, whether you will like seeing the highlights in each place and doing a lot of packing and unpacking and checking in and out of accommodations and spending so much time in transportation. People say it's exhausting and too much trouble, but I can think of several things that are both of those things to the nth degree but also enjoyable at the very same time and not regretted afterward (newborn baby and small puppy spring to mind). You know what kind of people you are and what you like and don't like to do. And of course it is such a crummy deal that Americans get so little vacation time.

The more my husband and I travel, the less we move from place to place. I think many people on this forum just want you to imagine your trip in realistic detail (be sure to include a few snafus) and imagine how visiting five places (actually six because Rome twice) in two weeks will make you feel. Like, exhausted but exhilarated that you're seeing so much or exhausted and crabby but unable to take a break because you have to keep moving?

Joining the choir here - you have one too many stops.

And that's assuming you really do have the 4th through the 18th to play with, and assuming those are both non-flight days. If those are the days you are arriving to and departing from Europe, then that's another story.

It would be helpful if you confirm what are the actual dates (and locations) you will be arriving in Europe and departing. Also verify if you have already bought your tickets (hopefully not yet).

You didn't check in here before booking flights? You didn't check multi-city, into Milan or Venice and out of Rome? Often that is cheaper.

Trains:

https://www.italotreno.it/en

https://www.trenitalia.com/tcom-en

On the latter, Fiumicino Aeroporto to Venezia S Lucia; direct at 11:08 and 15:08 [taking 4.5 hours]; others you change downtown. Figure 4 nights there; 4 in Florence; 3 in CT [obsession by so many almost laughable] with a side trip on the 13th due to the big ship; 4 in Rome at the end.

Lake Como was eliminated by not flying into Milan.

Have to agree with rzolezi above. “ [obsession by so many almost laughable]”. Five towns, four of them on the water, Coniglia up about a thousand steps from the station.

Certainly the area is UNESCO classified, but the classification was to do with the way that terraced horticulture and agriculture is done there, and has been done for maybe a thousand years.

The towns themselves are pretty enough, but not more so than many towns in Italy.

I appreciate the feedback from everyone!! Thank you! I was actually able to change my flights, so I have an update. We will be flying out on Sunday, May 3rd (arriving in Rome next day, Monday May 4th). And we are flying out of Venice on Sunday, May 18th. Given this update... how would you proceed with an itinerary for the 5 cities we want to visit? Would you still cut out 1 city?

I would drop Lake Como if possible. Sometimes these places especially Rome and Florence will suck you in and you will want to linger and walk the streets, so you will need some flexibility or float in the itinerary.

Would you still cut out 1 city?

Will reiterate the suggestion to pick one 'waterfront' location ( CT or Lake Como). Giving yourself one less move and more time somewhere else makes for a more enjoyable vacation.

Arranging your flights as you have does make the trip much more manageable; not sure it makes trying to get to all 5 locations a good idea

And hopefully your flight out of Venice is after 11:00...not the expensive "0 dark 30""

Can you change your departure city to Venice or Milan? Otherwise none of these options are feasible. If you must fly in/out of Rome, do Opt 3 Rome, Florence, Venice then hit city/town #4 on the high speed train line back to Rome.