First trip to Italy

Cars cannot be driven in large portions of Rome's and Florence's city centers. Also the car is of no use at the Cinque Terre where it will stay parked the whole time. Be aware that only Monterosso and Riomaggiore have parking facilities, whereas the other towns, such as Vernazza, have a maximum of one hour parking for non residents.
If you arrive in Rome, I would take the train to Monterosso at the Cinque Terre. Then I would rent a car at La Spezia, next to the Cinque Terre and keep the car for visiting Tuscany. If you visit Florence from some Tuscan location, you could keep the car, however you need to park it outside the city walls while visiting. If you intend to stay in a hotel downtown Florence, you should return the car before doing so, unless you stay in a hotel outside the city center, which is not what I would recommend for fully enjoying your stay in Florence.

Day 1 Arrive in Rome (3)
Day 2-3 Rome
Day 4 Train to Florence (2)
Day 5 Florence
Day 6 Pick up rental car and drive to Siena (2) (or near countryside)
Day 7 Excursion to San Gimignano (& Volterra)
Day 8 Drive Siena to Cinque Terre (2) (via Pisa or Lucca)
Day 9 Cinque Terre
Day 10 Return rental in La Spezia (or Pisa) & train to Venice (3)
Day 11-12 Venice
Day 13 Train to Milan (1)
Day 14 Depart from Milan

What luggage? Take only one carry-on bag each. Follow dimensions posted on your airline website. Pack below airline weight rules and pack only the weight each can manage at all times whether you are walking, going up and down stairs, carrying, or hoisting. And you will do a lot of all this in Italy.

Trains are ok if you go First Class where you will find other people your age. Reserved Second Class is ok too. Trains are ok if you have only one carry-on bag each to manage.

At times you may have to take Regionale trains. If First Class is offered on your Regionale, take it. Otherwise you may have to stand in the vestibules for the trip. The coaches can get really crowded with local workers and students and young travelers who bound up the coach steps and sit down before their duffel lands on the overhead rack.

You can do the trains and buses if you are smart about your luggage.

Day 1 Arrive in Rome (3)
Day 2-3 Rome
Day 4 Train to Florence (2)
Day 5 Florence
Day 6 Pick up rental car and drive to Siena (2) (or near countryside)
Day 7 Excursion to San Gimignano (& Volterra)
Day 8 Drive Siena to Cinque Terre (2) (via Pisa or Lucca)
Day 9 Cinque Terre
Day 10 Return rental in La Spezia (or Pisa) & train to Venice (3)
Day 11-12 Venice
Day 13 Train to Milan (1)
Day 14 Depart from Milan
This itinerary would work fine if you want to spend half your time driving around Italy and be exhausted all the time. And most of the other time packing and unpacking.
Pick three places that you can train to easily, and explore. Stick to Rome, Florence and Venice. Three days each, training all the way and time your arrival in Milan to get to your plane, or maybe spend one day in Milan.
At our age, unless you've been training for marathons, relaxed is best. And there's plenty to see in those three cities.

BTW, I agree with the poster about using just a carry on. take enough for five days, 5 tops, 5 pants, 2 pr of shoes(at least one a walking shoe), light jacket and a hat. you can hit a laundromat in each of those cities or you can use your sink to rinse out undies, etc.

Everyone has there preferences but I avoid first class on trains. Second class is every bit as comfortable and rarely so full that you have to stand, although it does happen. I just don't get the point of first class on a train and I am in your age group.

Hi Kathy,
I'll be 60 this fall.
How limited is your husband's mobility? Can he climb stairs easily? How far can he walk? Staying the majority of your time in cities allows you access to taxis vs buses/underground which may be helpful for you husband as well as hotels with elevators. (Be sure to check when you book).
Personally, even not having COPD, I think you should concentrate on 2 or 3 locations. Except for rural Tuscany, I have been to all the locations you have listed. Each is beautiful. I would not consider a car unless you are planning on staying in rural Tuscany.
How about:
Rome - 5 nights
Train to Orvieto- 2 nights
Train to Florence- 5 nights with day trips from there via bus or train
Train to Milan - 1 night prior to flying home
If you want to add CT, take one night from Rome and Florence. But consider that 2 night stays can feel really rushed.

I don't think you can include Venice with the time you have, plus it would involve significant walking. Some on this sight have said the CT from Florence can be done as a long day trip. I haven't tried it but may this fall.
As for luggage, I second the recommendation that you travel with one carry-on size bag per person. You can check the bag.

Sorry, I just tried to fulfil the brief ...
"We will be flying into Rome and leaving out of Milan. Definitely want to spend time in Tuscany, Florence, Cinque Terre, possibly Venice."
Only you know how mobile you are to cope with the level of activity you take on.
If you wanted something really simple I would do the train ... Rome (4) Florence (4) Venice (3) Verona (1) Milan (1)
Book hotels close to the station and you can't go wrong as they are all very central in these cities.

Thank you all - great suggestions!

I would book a hotel in Roma in the historic center, just take a taxi from the station. Make sure your hotel has an elevator.

Tuscany, in my opinion (and I know many will disagree), is overrated. The Cinque Terre is really unique and ranks high on the must experience list. Florence also has a lot to offer and Venice is a city unlike any other. With the time you have available, and the fact that going from one place to another seems to always use up more time than planned, you might want to consider just Rome, Florence, and Venice. Perhaps you can work in the Cinque Terre. Better to experience a few places well rather than so many places that it just becomes a blur.

There is no right or wrong answer to your train vs. car question. In my opinion, it depends so much on what you want to see and get out of your trip and your travel style. You have the added consideration of a health concern to think about, too. Both a train and car will get you to see most of Italy quite conveniently. Although some more rural areas, such as parts of Tuscany, won't be as easy by train/bus. As you say, cars create more difficulties in cities. Especially in Italy where many cities have limited traffic zones. Then again, with trains you are confined to a schedule.

I would start by considering your husband's health concerns. Think about what your trip will be like. Will he be able to spend the better part of a day walking around city centres? The 'yes' or 'no' answer to this will determine how much time you may want to spend exploring cities vs countryside. When he gets tired, will he want to be able to hop right in the car and go where he needs to or will he be comfortable waiting for the next train to take him there?

As other posters have said, pack in a carry on (I did it for the first time on my last trip and it made life so easy) and luggage will be easy whichever way you choose to travel.