Three stops or Four?

Where are you flying in to and out of?

In and out of Rome, but out of Venice could be an option

Flying in to Venice is decidedly easier than flying out of Venice
But Venice seems to be the outlier here
Fly in to Rome go immediately to Florence for 3-4 nights
Then way down to Capri for 3 nights?
End in Rome

Or
Rome 4
Capri 3
Florence 4
Venice 3

Fly home from Venice and try to get a later morning flight out
Capri to Florence is going to take most of the day

If you can drop Capri and fly in to Venice I would do
Venice 4 nights
Train to Florence maybe 5 nights with a day trip or 2
Train to Rome for at least 5 nights

Depends if you’ve been to any if these locations before

What were your priorities? Do you think you'll get back?
I'd consider saving Venice for a future trip to eliminate any long train rides. But much depends on what you want to be doing. Capri is not a city, and it can be nice to break up intensive sightseeing with natural beauty on the water.
If you decide seeing the big three now is more important, I'd look at heading to Venice immediately and then working your way back to Rome.

I would drop Capri, and focus on Rome, Florence and Venice.

The train ride between Rome and Venice takes about 5 hours. I personally enjoy long train rides in Italy, so even if you fly round trip from Rome, your longest train ride doesn't seem too daunting,

Rick Steves offers a 10 day Venice, Florence and Rome tour. You could use that itinerary as a starting point to craft something to suit your interests and time frame.

https://www.ricksteves.com/tours/italy/venice-florence-rome

Hi wpayos, I recommend flying into Venice and out of Rome if possible and skipping Capri. If I added another stop, it would be the Cinque Terre if you haven’t been there yet and sleep in Monterosso if traveling by train.
I would spend approximately three nights in each place. Following is a sample itinerary and if you buy Rick Steves, IT guidebook, it will help you get around.
Day 1 - arrive in Venice / sleep in Venice
Day 2 – ride vaporetto (water bus) between the train station and San Marco square (or ride it until the end of the line) at twilight so you can see the interior of the palaces that line the Grand Canal with their large ornate chandeliers fully eliminated showing off its interior. This way you won’t notice the decay on the exterior of the buildings. It took me back in time / sleep in Venice
Day 3 – get lost / sleep in Venice
Day 4 – take direct train to Florence (2h 15m) / sleep in Florence
Day 5 – visit Uffizi Gallery followed by a trip to Accademia / sleep in Florence
Note: buy your Uffizi ticket when you buy your plane ticket. This place sells out quickly because only 200 are allowed inside at a time.
Day 6 – sleep in Florence
Day 7 – day trip to Siena by bus / sleep in Florence
Day 8 – take a direct train to Pisa (1h) and store bags the at train station and see the leaning tower of Pisa and Field of Miracles. Have lunch before continuing journey onto Monterosso (1h 15mn) / sleep in Monterosso.
Day 9 – take a boat to Riomaggiore and work your way back to Monterosso by train stopping along the way / sleep in Monterosso
Day 10 – finish seeing the Cinque Terre towns or do some hiking in between towns / sleep in Monterosso
Day 11 – take a 6h 45m train to Rome that requires one connection. Have picnic on train / sleep in Rome
Day 12 – sleep in Rome
Day 13 – sleep in Rome
Day 14 – visit Vatican City (closed Sun) / sleep in Rome
Day 15 – fly home

I'd skip Capri but that's based on my interests for a first trip to Italy. I wouldn't miss Venice, which I unexpectedly fell in love with a few years ago, but your priorities may be different.

The reason flying out of Venice can be problematic is because getting from your hotel to the airport requires water transportation at least part of the way, and water introduces uncertainty not found with pavement. Early morning departures, necessary to connect with same-day flights to North America, can be stressful -- unless you spend your final night at a hotel near the airport. There are several of these with airport shuttles.

Early morning departures, necessary to connect with same-day flights to North America, can be stressful -- unless you spend your final night at a hotel near the airport. There are several of these with airport shuttles.

A couple other options would be lodging within easy walking distance of Piazzale Roma to catch a bus, and (admittedly pricey) a water taxi.

wpayos, as you didn't express any previous interest in the Cinque Terre or Pisa, I don't think you need to include them. Capri will require some transport time, and I'm not sure I'd do it unless you have some interest in, and time for, other parts of the region, such as Pompeii, Sorrento or Naples.

You haven't told us how you prefer to travel? Do you like to have more versus less time to browse around your cities of choice, or hit the highlights (those being of your choice) and move along? And what sorts of thing do you wish to see?

Without having answers to the questions above, if you can fly into Venice and out of Rome, I might do this:
Day/night #1 - overnight flight to Venice
Night #2, 3 and 4: Venice
Nights #5, 6, 7: Florence
Nights #8, 9, 10; Capri
Nights #11, 12, 13, 14: Rome
Day 15: Fly home

If you are a "slow" traveler and can leave out Capri (which is what I'd recommend), I might do this:
Day/night #1 - overnight flight to Venice
Night #2, 3 and 4: Venice
Nights #5, 6, 7, 8, 9 Florence with a day trip (Siena and/or Lucca)
Nights #10, 11, 12, 13, 14: Rome
Day 15: Fly home

Having made two separate day trips to Capri from Sorrento, I question the wisdom of going there without seeing Naples, Pompeii, and Sorrento, and Positano. Because of the time to get there, I suggest doing those southern towns on a separate trip. We combined them with London because of the air options London-Naples. It’s virtually impossible to sleep in Capri or Positano and fly home from Rome the next day.

This is personal opinion, but as “beach resorts”, I do not find Capri (or Positano) to be superior to the Caribbean. Better food and history maybe.

Having been to all of your destinations, I agree with Tim and others who suggest skipping Capri, and combining it with Naples and the Amalfi Coast on another trip.

Thank you all...I think your advice is great!

If I do Rome, Florence & Rome...should I try to get to Bologna?

Oops...I mean Rome Florence and Venice

Seems to me you have enough time to visit all four - so why not?

Bologna would fit perfectly but best if you fly in to Venice
try to give Venice at least 3 nights.

Do you have 15 NIGHTS in Italy? Your post says “days”
Count your trip in nights on the ground

Venice 3
Bologna 3
Florence 4 with 1 day trip to Siena
Rome 5 (or 4 if you really have just 14 nights)

Try to avoid any 1 or 2 night stays
Although a 1 night stop in Orvieto on your way to Rome would work well

Also wanted to add that if you can’t get flight in to Venice don’t fret about it
While a bit more trouble to depart from Venice it is still manageable
(We did it without difficulty)

You just need to know your transportation options, so come back here and ask for help when you know your flights

I second Mary Pat's suggested itinerary. Although I haven't been to Pisa, Cinque Terre, to me, is a must. Big cities wonderful, but you would miss so much by not seeing other locations such as Cinque Terre and Sienna (Tuscany a must).

I've been to the Cinque Terre three times. I liked the area a lot, but it has apparently changed a great deal since my last visit, which was in the 1990s. I assume it's not as crazy in September as in the middle of the summer, but I'd still encourage anyone contemplating a trip there to do some research on current conditions.

I'm curious about how recently folks who consider it a must-see have been there. I believe there have been quite a few negative comments on the forum from fairly recent visitors.

It sounds like this is your first trip to Italy, so I’m with those who say 3 stops, the Big Three. There are plenty of day trips you can take from any of them, should you so desire, and you’ll avoid losing time to checking in and out of another accommodation. Some suggestions: Orvieto, easy by train from Rome; Siena, easy from Florence; Vicenza and Padova easy from Venice.

I’ll also side with those who nix the Cinque Terre. I believe they are boring, over-hyped, and likely to be overcrowded, even in September. The Amalfi Coast (Capri) is stunningly beautiful, but too far from your other targets to be included on this trip.

Trust that you will return to Italy. It’s addictive. We’ve been there around 16 times and have another trip planned, covid developments willing.

I was in Capri for a day to see the Blue Grotto. High surf and we couldn‘t see it. A day wasted for us. If you really want to see the island, go ahead. We visited Assisi for two days and enjoyed it.

Trains don‘t take that long between the 3 main cities.

Backing up, I didn't mean to shoot down MaryPat's well-meaning itinerary at all but for a first trip. I don't know as I'd do the CT or Pisa. I honestly wouldn't do Capri either: I'll vote with the others to save it for a future trip when you can explore more of that region: the towns of the Amalfi Coast, Pompei, Herculaneum, Naples, etc.

LOL, we didn't go near the Blue Grotto during our stay on Capri. Better things to do, IMHO.

What's great about your situation is that you have time to make some very nice day trips from city bases. Not having to pack up, move, locate, and check in and out of hotels can save time and energy, and allow for some flexibility as well. Raining? Stay in town and explore indoor attractions. Sunny and dry? Hop a train.

Just a few suggested trips, some of which were previously suggested:
From Florence: Fiesole (just minutes by local bus), Siena (by bus or train), Lucca (by train)
From Rome: Orvietto (by train); Ostia Antica (local train)
Venice: a number ofthe smaller islands (by vaporetto) such as Burano or Torcello. There are other options as well but it all depends on how much time you devote to Venice.

If I do Rome, Florence & Venice...should I try to get to Bologna?

We went to Bologna as a day trip from Florence. I have to say that after two trips to Italy, Bologna has been my biggest disappointment, and I regret wasting a day there that could have been better spent in or around Florence.

With that said, there were some issues that probably color my feelings about Bologna - we went there for a traveling exhibit that turned out to be disappointing; a mime tried to steal my husband's hat; and an old woman tried to pick his pocket.

Thank you all!

My interest in Bologna is based on that I’m an Executive Chef. The visit there would be culinary focused. Any comments on the food there?

We have a trip to Italy planned for OCT 2021, but I feel it is unlikely due to the poor vaccination rates in Italy.

Regarding your question with 15 days, you can do all four. Sorry, we did Bologna once, it was OK but nothing to cheer about compared to the places you listed above.

Venice 2-3 nights
Florence 3-4 nights
Rome 5-6 nights
Capri (if you do Amalfi Coast, Sorrento and Pompeii) 4 nights

Is this first time to Italy? There's always the tension between depth and breadth. If there's a reasonable chance you can return, I opt for more time at less stops.

On our last trip to Italy we stayed the entire time in an agriturismo in Tuscany. From there we took day trips. On our last trip to Europe, we spent one week in Loches, France visiting our grandson and one week in London which was partially a business trip for my wife. In the past we've done trips where we move every couple of days. There's no right or wrong, but slowing down gives you more time.

Remember moving from one place to another can be a real time suck. You can spend most of one day, if not more, checking out, moving, then checking in.

I also recommend for the length of your trip to schedule in two down days, where nothing is planned. You may discover something special that was unplanned and an unscheduled day gives you a chance to take advantage, or you might want to just spend a day knocking about.

I am not a food expert, but the experts say Bologna's food is exceptional. I liked the city a lot, but it is true that it isn't Venice, Florence or Rome. What it is, is a city with perhaps Europe's largest medieval center. It's fabulous for wandering around (and scouting out delis and restaurants). Most of the streets are arcaded, so if you're unlucky with the weather, you have some protection. The tourist office offers a good walking tour.

There are also some top-flight side-trips from Bologna, some of them food-related: Modena for balsamic vinegar and Parma for ham and cheese. Alternatively, you could day-trip from Florence to Bologna if you have only one day to spare. There are frequent trains taking only 38 minutes. They are Frecces, so the fare will be pricey unless you buy a ticket (for a specific train) well in advance.

wpayos, regarding Bologna, I think there might be a difference in appreciation between dedicated foodies and the general tourist.

You might start here?
Go to the top of this page, with the word "Search" and magnifying glass icon.

Type "Bologna, food" into that box and hit "go"
Hit "Travel Forum" under " Filter by type"
Under " Filter by date" choose" 2 years and newer"
Explore previous forum suggestions.

One caveat? The problem here with linking some past posts for epicurean resources in Bologna is that we don't know what curveballs COVID has thrown them. They may or may not have survived the shutdown.