First time Itinerary

Ok, first, 12 days total means, depending on flight times, at most 10 full days "on the ground."
So 10 days of sightseeing is what you start to work with.
Likely you are like most of us and will be somewhat slowed down from your usual energy level, by jet lag, the first few days, more so the first day or two. You're going through 7 or 10 time zones.

Because this is your first trip, assume you'll be back and first arrange your list in terms of your priorities, must do destinations first and so on.

Unless you hate world class cities, art, and attractions--I'd suggest you seriously consider prioritizing several days in Rome.
For many travelers, Florence and Venice are high priorities.
And there's your ten days.
Make sure you are careful not to under-estimate real travel times.
No rental cars in: Rome, Florence, or Venice. That means take trains, because those 3 destinations are well served by reasonably priced and regular trains.

Is my original plan too much?

I think you already know the answer to that one! Especially if you're going to be working, because WiFi is not always a sure thing while traveling from one place to another. So you need to cut the number of destinations.

You have to be in Rome for the flights anyway, so you should take advantage of that, and in mid-May Roma should be absolutely glorious, right before the onslaught of tourists. Lose Cinque Terre, good instinct there, and Milan as well. So here's how it could look:

Arrive Rome, immediately train to Florence (1 hr, 31 min), even though it's going to be late and you probably won't get there until 21:00-22:00. But it's important to start your trip there and finish in Rome.

Nights 14th-17th: Florence
Train Florence/Lake Como 3 hrs, 14 min
18th-20th Lake Como
Train Lake Como/Rome 4 hrs, 47 min
21st-24th Rome

I think this makes a lot more sense. Enjoy your planning!

I would remove Milan and Lake Como from the itinerary and save it for a future Italy trip. It would be too much travel to include both. You can adjust your trip in the following order:

Rome - May 14

Florence - May 15 to May 18 (Day Trips to Sienna or Lucca)

Cinque Terre - May 19 to May 21st (Hike around the Vllages)

Rome - May 22 to May 25th (With a possible Day trip to Ostia Antica)

This is more manageable and less hectic to rush on your vacation.

You should not hop on a train to Florence from Rome immediately after a Trans Atlantic flight. You will be exhausted. It' s better to get a good night sleep and head to Florence on May 15th.

Yup, too busy I think. If Tuscany and the lakes are the priority, then go there. Too bad you're stuck with the time and cost of returning to Rome to fly home, instead of flying home from Milan.

I would follow the recommendation to take a fast late train to Florence the night you land. The Leonardo Express from FCO will put you at Termini, just walk to the platform where the train leaves for Florence, validate your tickets, and get on. If you can catch an hour's sleep on the train so much the better. Get a hotel near the station in Florence and crash. Next morning you're ready to start in Florence, then eventually make your way to the lakes. Return to Milan, then fast train to Rome. Just in case, you might return to Rome May 24 and spend a night near Termini, giving yourself a few hours for sightseeing the next morning. Looks like you've already planned that.

Yes, Rome is great and so is Venice. CT is also supposed to be great, though probably not for me. But this is your trip, not other people's.

This has helped answer some of my questions and raised more!

Kent - We're not apposed to Rome, but we get a bit overwhelmed with cities after 2-3 days..
RJean & Jay - I like both of your itineraries - Milan is out! ;) I'll share them with my husband and see if he agrees - We haven't looked at going to Sienna, Lucca, or Ostia Antica. Will need to research them -
Dick - We chose flying in & out of Rome because it was a direct flight otherwise flying out of Milan would have been nice! I traded more train time for less airport time.
I like the idea of getting to Florence on the first night there, but struggle with the probability of being over tired. We leave LAX @ 22:00 after a long day (Disneyland for 10 hours with grandson) Yes, we are a bit crazy!! It'll either help us sleep or kill us! I can do crazy for 1-2 days, but then we need to rest! So I will be simplifying this itinerary!!
Thanks again!!

I like the idea of getting to Florence on the first night there, but
struggle with the probability of being over tired. We leave LAX @
22:00 after a long day (Disneyland for 10 hours with grandson) Yes, we
are a bit crazy!!

Ya think?! Geez, for my overseas trips I'm gearing up for a week!

OK, since your flight home from Rome is not until 16:00 on the 25th, you can conceivably leave Florence that morning--plenty early enough, mind you--to Roma Fiumicino. You'd have to arrive at the airport no later than 13:00. I believe you have to go through Termini station but there might be a way to accomplish this by changing at the Roma Tiburtina stop. Others, chime in please on this. With so many Florence/Rome trains over the course of a day, it probably isn't that much of a risk. But leave early!

If you do that, you can start your trip in Rome for 3-4 nights. Then...I'd opt for Cinque Terre (a 3 hr, 6 min train ride) instead of going to Lake Como (6 hrs, 11 min) for 3-4 nights. Then your train from La Spezia to Florence (2 hrs, 27 min) is pretty easy for the rest of your time.

Actually, that looks like a pretty good itinerary, and you'll only have--hopefully--one day of jetlag rather than be a walking zombie for the whole first part of your trip! BTW, our first trip to Italy in 2010 was for our 30th anniversary as well (Sicily, Florence, Rome) and have been back twice since then.

Have you flown from LAX to Europe before? I hope you’re flying first class, because that’s about the only chance of getting decent rest. Do you live in L.A. or are you there for Disneyland? Have you factored in time to get to LAX? I have traveled through Orange County and had our Garmin report “one hour delay has been added to your travel time”.

Also, plan on around three hours once you’ve landed to get your luggage, get through customs and get to Rome. I’d look hard at staying at the Hilton at the airport on arrival, then head to Florence first thing in the morning.

I’m concerned you are going to arrive exhausted, take longer than normal to get over jet lag and then pursue an over aggressive schedule.

Jay - We're leaning toward the itinerary you suggested because my husband really, really wants to go to the Lakes. We may stay one more day there and head back to Rome on the 23rd.

Will probable stay first night in Rome as well. We hope to return there as well. This whole planning has been an enormous eduction and there's so much more to Italy than we originally thought! Definitely want to explore more regions!!
DougMac - Have never flown to Europe from LAX, but have flown to Thailand a few times and Israel from there; and some shorter trips...not my favorite airport, but best option for this trip.

We're giving ourself 2 hours from Dland to LAX. We'll also keep WAZ app on to see if we should leave sooner. We don't live in SoCal, but my son does and we're down there for grandson's birthday. I used to work near LAX when I lived there so I do have some anxiety about the traffic issue which may have us leaving the amusement park earlier. We're planning on arriving 2-3 hours before take off (depending on traffic). It's "supposed" to be a 45 minute drive. I appreciate your reminder!! I forget the night mare traffic can be down there! I've been away from the area for 25 years!! I can only imagine it's gotten worse!
Any suggestions on nice/romantic restaurants in the Lakes area for our actual anniversary night? (20th)

Also, no checked luggage - we're light travelers :)

Sorry, this is one of the worst planned itineraries that I have seen in a while.

Why so little time in Rome, it is amazing?

You are trying to cover too much territory and wasting a lot of time traveling. Florence is wonderful and deserves more time.

Forget the Vespas, with the way the Italians drive they are better know as organ donor machines.

Getting around Florence on foot is easy.

CT, Milan and Como are great, but you have little time there.

Milan and the Italian Alpine area is great, but I would stick with Rome, Florence and Venice for a first trip to Europe. CT is a nice stopover place, but you have too many places on your list. You have 10 days, divide up your time by three, pick three places (or even two) and really enjoy where you go.

I stayed walking distance to Disney a couple years ago and was amazed by the traffic to and from the airport. And I live in south Florida with lots of traffic. It took much longer than 45 minutes. I took a red eye home at about the same time you are leaving. It was bumper to bumper as we approached the airport at about 8 pm.

I would consider skipping Disney this time and do something much lower key before traveling overseas. My husband has tended to do too much and then gets sick. And he is not going to Disney.

So, resarenees, this is what you're proposing now:

Night 14th: Rome
Train Rome/Florence 1 hr, 31 min
15th-18th: Florence
Train Florence/Lake Como 3 hrs, 14 min
19th-22nd Lake Como
Train Lake Como/Rome 4 hrs, 47 min
23rd-24th Rome

Not optimum (and you'll get as many opinions on this forum as Carter's got pills, as they say) but doable. And no checked & light baggage is a time saver on the plane and much easier to maneuver on the rails.

Well, a little time in Rome is better than none, I suppose. For that first night, stay in the central district, so you have the thrill of waking up on the morning of the 15th (only a little jetlagged I hope) in Roma. And then you'll still have a couple more days at the end of the trip, even the morning of the 25th, to savor the Eternal City.

Good luck, and make the itinerary not like running around like chickens with your heads cut off, but allowing time to just sit back and enjoy, no matter how Type A you may be!

BethFl - Not doing Disney isn't an option, but leaving earlier is. It's our only grandchild's first time and we really don't want to miss it. However, we may leave much earlier than originally planned. That would alleviate the stress and we'd get to have a nice dinner before hitting LAX.
Jay - Yes, I think it's looking like that's going to be the final itinerary. I'm eager to get our accommodations settled.

I'm sure after this first taste of Italy we'll be eager to return. Perhaps then, with a little experience under our belt, we'll have a stronger desire to see Rome. For now I'm confident that we'll enjoy the trip immensely!

Thank you again for all of the wonderful insight and advice! You've all been very helpful with narrowing down some of my choices. I've sensed a great passion for travel and for Italy among you and hope to catch that passion.

Happy 2019 to you all!
Reas

We live in Florida and so have been to Disney many times. The first time we went (after moving here) our youngest was 5. He was totally intimidated. Much to his 11 year old suster’s chagrin, the first ride was a familiar merry go round!

When our children were young, we always went first thing in the morning and left before dinner. That is as long as any of us could enjoy the parks.

BethFL -
I totally agree!! I think our little guy will be done before dinner!! And if not he can stay with mom & dad while the great grandparents take us to LAX!! If he's not ready they will be!!
If we lived closer I'd be there once a month (at least) while my husband would say once a decade is too much! It's amazing how grandchildren can change perspective - My husband is the one who planned the Disneyland trip!