If you had 2 weeks in Italy

When considering you have some wiggle room for day trips, I think your four selected places will make for a perfect two-week trip. Do bear in mind that in summer, everywhere will be hot and crowded--so replacing one place with a lesser-visited place would not be a terrible idea, but only you know your family and what you will be up for. I am not one who thinks you must see the big three on a first trip (or even an eighth, in my peculiar example).
A car would be an unnecessary burden on this itinerary--trains are fine, but pack sensibly and plan to rent a place with a washing machine once or twice.

This sounds quite doable, and will certainly fill two weeks. Do plan on getting "open jaw" tickets, to fly into one city (Venice?) and out of the final city (Rome?). Your plan could then be: Venice, Florence, CT, Rome. You will save significant money if you also book your train trips between these locations at least 3 months in advance, also (trenitalia.com). A day trip to a couple of smaller towns, or Siena, from Florence might be a relief from the intensity of the three heavily touristed cities. Also, places to stay in CT book up many months in advance. By early this autumn, you might want to finalize at least that part of your schedule in order to get your place confirmed there, especially since you may be looking for 3-room apartments?

It’s great that you’ve given yourself plenty of time to plan your trip!

I see that you’ve picked the most crowded locations in Italy. When I’ve had friends ask me to help them plan their trip, the first thing I ask them is to describe what a couple of perfect vacation days in Italy would be for them WITHOUT mentioning any specific cities. People like to default to the Top 3 because those are the most familiar, but many times there may be wonderful options I can recommend that will get them away from the most crowded spots.

So, I’ll ask you the same question. Can you give us more info, describing what some perfect days would be? Also, any special hobbies in your family to consider, I.e. bike rides, cooking classes, music concerts, festival events, etc.?

And, usually trains will get you efficiently between locations.

Cathy - Do the Amalfi Coast and Tuscany region for 2 weeks. You will have plenty to do as a family in both locations. Since you're going during summer which will be very hot there, staying near the coastline in the Amalfi Coast and the exploring the countryside of Tuscany will keep you cool. Avoid the big Italian cities like Rome and Venice during the summer heat. Crowds and the long lines to see the sights will exhaust you mentally and physically.

Begin by counting your trip in NIGHTs not days
So do you have 14 nights or do you have maybe just 12 or 13 nights?

I think you can’t go wrong with the Big 3 but adding a few days in the middle for a more relaxed location is a good idea

I’d say
Venice needs 3 Nights minimum -especially if you fly in there (easier to fly into than out of Venice)
Florence needs 3 Nights minimum no day trips, if you want a day trip to Siena or a Tuscany town add a night here
Rome needs a minimum 4 nights

That’s already 10 or 11 nights

You can use the 'itinerary' here as an outline --- https://www.ricksteves.com/tours/italy/venice-florence-rome --- and add Cinque Terre either before or after Florence.

For the time you have and your other 'wished for' destinations, anyplace south of Rome really does not work.

You can see Pisa as a stop ( 2-3 hours) between CT and Florence

You can do it all by train.
Fly into Venice and out from Rome

I second the suggestion to fly into Venice and out of Rome and to limit your base destinations to Venice, Florence, Cinque Terre and Rome in that order. It takes a fair amount of time to change lodgings, and that time could be better spent on some day trips from your bases. Both Trenitalia and Italo offer good discounted pre-purchase fares between Venice and Florence. If you want an early start from Florence to Cinque Terre, pre-purchase tickets for the direct Freccia departing the Campo di Marte (not SMN) station at 7:28am. Otherwise, most trains are regional with a change at Pisa Centrale, and there's no advantage (and some disadvantages) to pre-purchasing regional tickets. When departing Cinque Terre, I recommend the direct Freccia train from La Spezia Centrale to Roma Termini. There's one in the morning and another early afternoon, and there should be good discounts for pre-purchase. When in Venice, consider the multi-day vaporetto pass, or at least the 24-hour pass if you plan to visit the islands (Murano, Burano and Torcello).

Fly open jaw.
Go as soon as you can to avoid crowds (somewhat) and avoid the worst heat (mid summer).
Travel from city to city by train.
If you want to explore the Tuscan region, you can rent a car in Florence. You'll see so much more by car there.

If you want to go to Rome, Florence, CT and Venice...do that. There’s no need to add other places. A well-placed daytrip is doable (Siena or small Tuscan towns from Florence, Pompeii from Rome if you are ambitious and have energy) but really the 4 places you listed are enough!

Into one, out of the other. I’d suggest fly into Venice, train/bus around, fly home from Rome. When booking flights look at “multi-city” or similar search category-NOT 2 one-way tickets.

I have found that four places is about right for a two week trip. It becomes wearing after that.

So much great advice! Thank you all. It sounds like into Venice and leaving from Rome is the way to go. We were in Greece last summer and it looks like it was hotter then than these parts of Italy are right now. I think as long as we have AC where we stay we'll be ok. The excitement of the trip overtook the heat most of the time. We are limited to summer for now because of school schedules, but do look forward to the times when we can be there off season.

When I went many years ago I remember doing a day trip to Pisa from Florence and that seemed to be just the right amount of time to be there. I remember worrying about getting back to our pensione that evening though since it had a strict curfew - I think it was run by nuns :)

A perfect day - We are happy just wandering around looking at the architecture, people watching, eating good food, maybe a cooking class since that's something we've all talked about trying. Then maybe a museum. Most of our memories from other trips involve just walking and seeing what we find along the way. We've usually had a destination, but have always allowed ourselves to let the plan change if we find something interesting to see or do.

Since it seems like many of you have been to Cinque Terre - do you have a favorite town to stay in? We all don't mind doing walking, but probably not hiking (although my oldest would probably rather do that). Have you booked through Airbnb, VRBO, hotels? I'm going to be getting the RS Italy book and check out the places he's got listed in there too.

Definitely would love to be able to go the Amalfi Coast and stay in Tuscany, but that might have to be for our next trip to Italy.

We are planning far out because to me the planning is half the fun :)

If you enjoy walking and food consider a Food Tour
Do a search for “eating Europe” here or on google
We’ve done several of their food tours and they have all been fantastic

Also do a search for food tour discount

In Venice, we stay in the Cannaregio area, which is very quiet and uncrowded, and SO peaceful in the mornings and evenings. It is such a welcome break from the crowds of St. Mark's Square. It is also the area where Row Venice meets, if you want a reasonably priced adventure on the canals , as your group receives rowing lessons [89 Euros TOTAL for 90 minutes for a group of 4.] They're easy to Google.
Safe travels!

Me and my spouse and our two older teens went to Italy for 16 days a couple of years ago. It was in July and it was VERY HOT, but we were told it was one of the hottest summers they'd had in a while. We visited Rome, Florence, Sorrento, Capri (an Island right off Sorrento), Pompeii, Venice, and some of the hill towns in Tuscany (Siena, Motelcino, Montepulciano, San Gimignano, Pienza).

Without a doubt all of us said our favorite area was Tuscany. However, there are two parts to Tuscany...The Val d'orcia and Chianti. We went to the Val d'orcia because it was what I have always admired in artwork, on post cards, etc. Chianti, as the name suggests, is a wine region. The food was delicious all over Italy. The scene in Tuscany was very pastoral and "laid back." If you go, don't miss Siena. Venice was also interesting to see and I'd allow at least 2 full days there. We also loved Sorrento for the beach vibe and huge lemons (which I was told aren't actually lemons, but haven't investigated this).

Least favorite for us personally were Rome and Florence, although other people love them.

My best advice is get a good guide book and read online about the places you think you may want to go and get any tickets you need ahead of time, read about hours and tips for experiencing those places, and keep good notes to reference on your trip.

Our day in Pompeii is the closest I think I've ever come to a heat stroke. Be prepared with water, hat, sunscreen, etc.

ALSO, BE ALERT FOR PICKPOCKETS EVERYWHERE YOU GO. DON'T BE AFRAID, JUST AWARE.

I think you'll love Italy. We did and can't wait to go back someday.

My tip is in relation to dirty clothes! Our 18 day trip to Venice, CT and Lake Como last May was the longest we had taken, so doing laundry was necessary. We stayed in Monterroso in the Cinque Terra, and that was about 1/2 way out. In Ricks guidebook, he listed laundromats in different places. I chose one in the old town part of Monterosso since that is where our B and B was. ( Affittacamere Da Cesare which I recommend. Small, quiet, great hosts and amazing homemade breakfasts. Reserve early.) In the laundromat, all the washers and dryers were already in operation. However, a woman who presided over the laundromat said she would wash, dry and fold my load for 15€. I thought it was was a fair price, AND it would free us up for the afternoon. I left the laundry and returned later in the day to get it. It was wonderfully done! Clean, dry and folded. I can't remember the name of this laundromat, but was on the main street in old town Monterosso on the right.

We loved Venice, but we avoided St. Marks Sq and the Rialto Bridge from mid morning to about 4 pm. (Our hotel there was Hotel al Ponte Mocenigo at the San Stae vaporetto stop. Another great place. Quiet location, spacious rooms and fantastic breakfasts. The best part for us was walking back along the side canals, getting LOST! (seemingly a given in Venice) and finding lovely campos where children played and old folks sat on benches sharing stories. Cicchetti bars are fun also. Rick lists some good ones in his guidebooks. We also took a sunset trip up the Grand Canal on a vaporetto to Lido and back that was lovely.

You are going to have an amazing time. Happy planning!

When weighing whether to drive or train in Italy, consider car sizes. I've driven frequently in Italy and consider a car essential in Umbria and Tuscany, but the biggest cars I've ever found to rent were Alfa Romeos seating four adults with light luggage, and the fourth roll-aboard had to share the back seat. The trains easily connect all the cities, and if you buy tickets far enough in advance, prices are reasonable, even x5. My favorite train line is Italo. Once you've unloaded in a city, i.e., Florence, you could rent a car to explore Tuscany.

It's kind of a pain getting to the Cinque Terre by train (lots of changes) but it can be a nightmare by car. Even parking in La Spezia isn't simple. Driving there in the way off-season isn't bad, but I've got a great tragicomedic story about being pushed into a stone wall by a box truck above Vernazza, and that was in 2005 in May, when it wasn't even too crowded!

We flew into Venice and out of Naples. We had 14 nights and made the most of the time and allowed some downtime in Rome.
It wasn't my first time, but it was my first time planning an independent trip to Italy , not to mention planning a trip for another couple who had never been to Europe. No pressure, right?

Venice 3 nights at apt. booked with Views on Venice. (highly recommend)

trained to Florence for 3 nights at another Apt. Since we did not want to eat away our hours in museums, we took day trips.
One was with Walkaboutflorence. https://www.walkaboutflorence.com/tours We took the Best of Tuscany Tour which included a nice lunch with free flowing wine, Sienna, San Gimignano, and Pisa. it's a long day but we got to see those place on this sampler tour.
They also have the Cinque Terre Trek, but it was not yet available in late March when we went.

We also took a public bus to Castello Verranzano from Florence. The website will give bus directions. I told the bus driver where we wanted to get off. For those who are not comfortable with Italian, just show the bus driver the name of place and he'll tell you when to get off. It's a hike up to the winery, but we later found out that they could pick you up from bottom. We did get a ride down. One of our best days in Italy. A wonderful tour, view and we opted for one of the wine with food packages.

We hired a private driver to transport from Florence to Rome and stopped in Orvieto and Civita de Bangoreggio en route. Both amazing towns that we would not have been able to visit independently. Arrived at about 7pm at our Rome apartment.

5 nights in Rome. (one full day spent with family and Palm Sunday with Pope Francis in front of Basilica)

Train from Rome to Sorrento. Pompeii en route. 3 Nights in Sorrento (Hotel Antiche Mura as recommended by RS.--a short walk from train station.) From Sorrento we did a day trip to Capri and hired a private taxi (in advance) for half day tour and also hired Aldo limo for an all day tour of Amalfi, Positano and Ravello.

So, we had 4 bases over 2 weeks and the first 3 had washer and dryers! Apartments are so much more comfortable than hotels.

Flew home from Naples...also used Aldo limo for airport transfer from Sorrento. We didn't want to backtrack to Rome so we opted to fly home from Naples with a connection in Munich to Newark. We live closer to Philadelphia, but would have meant another connection so we had a longer drive home from Newark airport.

Months of planning and fine tuning paid off. Wouldn't change a thing. Next trip will explore the deep south and Sicily and maybe some rural areas of Abbruzzo where I have a host of 2nd cousins to meet.

Christine - the food tour sounds amazing!!!

So many great tips and ideas. I'm going to print these all out so I don't forget any of them.

Laundry is also good to know about, we did something similar in Chania and it was so nice not to have to spend half the day in a hot laundromat.

You've all got me so ready to go already :)

Hi Catherine, my favorite cooking classes in Italy have been:

Rome - www.cookingclassesinrome.com with Chef Andrea

Lucca - Extra Virgin cooking class.

Thanks Jean!

Unless the Summer is the only time you can travel, avoid avoid avoid.... toooo hot & toooo crowded. We always go to Europe in October...we fly into one city & depart out of another; saves time.

Cheers,
Jean