Itinerary questions for first-timers to Italy: Venice, Florence, Dolomites, Rome, Cinque Terre

It is a lot. But more detail, please.

Where are you flying into and out of? When is the trip? Do you plan to use trains (I hope!)?

For 2 weeks looks like one place too many.

If flights are yet to be bought starting in Venice and ending in Rome is probably the most convenient and efficient

I agree that you should probably eliminate one place. It would work if you had a personal teleportation device; but since you need to rely (hopefully) on trains, that will eat up about half a day for each location change.

https://www.ricksteves.com/europe/italy/itinerary

Adapted from above

Day 1: To the Dolomites via Venice airport (sleep in Bolzano or Castelrotto)
Day 2:  Dolomites (sleep in Bolzano or Castelrotto)
Day 3:  Dolomites (sleep in Bolzano or Castelrotto)
Day 4:  To Venice (sleep in Venice)
Day 5:  Venice (sleep in Venice)
Day 6:  To the Cinque Terre (sleep in Vernazza)
Day 7:  Cinque Terre (sleep in Vernazza)
Day 8:  To Florence via Pisa (sleep in Florence)
Day 9:  Florence (sleep in Florence)
Day 10:  Florence, late to Rome (sleep in Rome or Florence)
Day 11: Rome
Day 12: Rome
Day 13: Rome
Day 14: Fly Home

Too much? Drop Dolomites. Add nights to Venice, Florence, Cinque Terre. You could of course drop Cinque Terre-- your choice!

Either way, I see fun- fun- fun in your future!

Those are some great destinations. I would have to agree with the others though - it does seem like a lot to squeeze into two weeks with all that travel time in between places. My vote would be to nix either Cinque Terre or the Dolomites hike to allow a little more breathing room. You'll enjoy the hiking and city visits more if you're not rushing around too much.

Fly in and out of Venice and Rome (multi-city). If you fly home from Venice, make sure it’s a later morning flight. You do not want to pay for a pricey water taxi that will set you back more than $100. Buses from Piazzale Roma across the bridge near the train station may depart for the airport as early as 4:20 but I’m not certain.
Venice deserves a minimum of three nights. A train from the Venice train station (Venezia S. Lucia) to Bolzano Bozen involves at least one transfer taking 3h 30m: https://www.trenitalia.com/en.html. Then you need to get from Bolzano to the Dolomites that will take another hour. When traveling by train it’s crucial you pack light and do laundry along the way. Don’t carry more than two pieces of luggage to avoid leaving a bag behind. This means you need to add laundry time to your already busy itinerary.
When visiting mountains, it’s best to add a night in case the weather doesn’t cooperate. With that said plan on three nights in the Dolomites. A train from Bolzano Bozen to Florence (Firenze SM Novella station) involves a minimum of two connections taking most of the day meaning you lose a day traveling from one place to another. The Dolomites is off the beaten track meaning it’s out of the way.
A train from Venezia S. Lucia station to Firenze SM Novella station is direct taking 2h 15m. Buy tickets for the Uffizi Gallery two months out to guarantee reservations. You need three nights to see Florence.
There are no direct trains from the Firenze SM Novella station to the Cinque Terre and takes 3h. The same with traveling from the Cinque Terre to Rome, there are no direct trains and takes 4h 45m. The Cinque Terre will be easier to navigate than the Dolomites and you can hike there too. If you do hike, sleep in the Cinque Terre for three nights.
You need four nights for Rome if you visit Vatican City.

Kap, please come back and tell us more. When is your trip? The Dolomites (big area and we’ll need to get specific) have definite seasons and are not always a great idea of just 2 or 3 nights as weather is even more fickle in the mountains than elsewhere.

Thank you for all the responses to my query! I have really dropped the ball (for one good reason--a new granddaughter! and an unfortunate reason--bad virus!) and am just now refocusing on planning this trip.
Ok, we've done some thinking based on the replies to date, and are now leaving Cinque Terre off this trip (unless we decide to add a week, which is a possibility...) Rome and Venice are still on the itinerary, but we welcome suggestions for in-between. This is our first trip to Italy, so it seems wrong not to see the famous places?!
We will plan to fly into Venice, spend 3-4 days in the Dolomites and fly out of Rome.
Should we do 2 days in Venice right away before we go to the Dolomites? And after the Dolomites...we're interested in Verona, Milan, Lake Como (?), Florence (?) others?
Oh, and we'd like to go in September!

I just reread one or two of the earlier responses reminding me of the fact that the Dolomites are pretty out of the way. So now I'm again undecided about whether to drop the Dolomites and go to Cinque Terre or other places instead? Aargh...

We are open to using trains, and (if we go to the Dolomites) renting a car.

When is the trip? We go to the Dolomites without a car every year. Depends on exactly where in the Dolomites you want to go. You can easily fly into Venice, then visit the mountains, and wrap up with Rome or maybe even Florence and Rome, all by train with some bus. But when is an issue because it isn’t always the right season for the mountains. Things do get very busy in July and August and many things start shutting down by October 1 or so.

Please note that most of us here feel that RS suggested itineraries are too fast paced with too many 1 and 2 night stays.

Each location change takes up at least a half day so the fewer the better

A 3 night stay equals just 2.5 days in location for sightseeing etc
A 2 night stay is just 1.5 days in location

Count your trip in NIGHTs not days to give a better overall picture of the time you actually have

Should we do 2 days in Venice right away before we go to the Dolomites?

Since you appear to now be thinking of dropping the Dolomites, may I suggest you devote more time to Vincie? It is a wonderful city to use to recover from jet lag. And it is truly one of the really unique places you can go. In my opinion, you really need to spend at lest three full days in Venice; and even then you'll just scratch the surface.

I suggest that you go everywhere that you want to hike now while you have the physical capability.

Just to confirm...
It seems most people say fly into Venice, then go to the Dolomites and do our thing there, then RETURN to Venice for our proper visit. Would anyone recommend flying into Milan and going to the Dolomites from there, THEN on to Venice and the rest of our trip? I don't get why we we'd go to Venice twice....

What is the current plan of places that are on the 'must do' list?

Where to fly in and then out depends on what is between those 2 events.

Our current plan of must see places: The Dolomites (4 days), Venice, Florence, Rome. We're also interested in Pisa, Lucca, and Tuscany--if any of that is doable given those stays??

It seems most people say fly into Venice, then go to the Dolomites and do our thing there, then RETURN to Venice for our proper visit. Would anyone recommend flying into Milan and going to the Dolomites from there, THEN on to Venice and the rest of our trip? I don't get why we we'd go to Venice twice....

I don't think anyone was recommending visiting Venice twice; but to fly into Venice and transit to the Dolomites the same day; just to save time and get the bulk of the transportation out of the way on your jet lag arrival day. Then return to Venice for a visit after the Dolomites. Simply because it's the closest major airport. You wouldnt even go into Venice proper to catch your train. Milan might be an option for doing the same thing if prices, arrival times, and trains are roughly similar.

Your proposed itinerary seems to change every time you post. I think you need to nail that down, so you can soon make flight and hotel bookings. Once you figure out what it is you want to see and do in each of your major places, you can allot the necessary days. Only then will you know if you have the extra time necessary for extra side trips. However if you have 14 nights on the ground, and allotting for travel time between places, then 4 nights Dolomites, 3 nights Venice, 3 nights Florence, and 3 nights Rome =13 nights. Giving one extra day/night for your choice of Pisa/Lucca or a van tour of Tuscany as a day trip from Florence.

But if your 2 weeks includes the 2 transatlantic flight days, you will have to shorten your stays accordingly.

You're right, my itinerary does seem to change every time I post. Sigh. But thanks for the clarification on the Milan vs. Venice arrival city. I get that now. Now, back to the itinerary and hopefully further clarification.

Thank you to all for your input. I've decided to start fresh, and get my ducks in a row. SO I am ending this post, and will come back in a couple of days with a new post/more coherent plan (but surely one that could benefit from others' advice!)
Thank you all again!

Kap, thank for keeping us informed. Good luck with your planning.