When I said the places are hard to navigate I was thinking about transporting luggage
and what Sandra said about elevators.
Please don't be discouraged ...crowds are unavoidable in such popular , small cities,
but on can manage.

There are 2 kinds of train stations: terminus stations and through stations. In terminus stations the tracks end at the station, so are all on ground level and it's easy to walk around them and into the station. Through stations are stopping points on the train line. So to get to another track or to the station proper you may have to go over or under the tracks, usually by way of a stair.

Fortunately Venezia Santa Lucia, Firenze Santa Maria Novella and Roma Termini, the main train stations at your 3 stops, are all terminus stations, and should be relatively easy for your parents to get around in.

Lifting their luggage on and off the train and up into the overhead racks might be difficult. But you can work out a system for that -- especially if someone else is along to help. And there may be other options than the overhead racks: racks at the end of the car, between seats, on seats.

Thanks again guys for all the advice. I spoke to someone I know who has travelled to Italy before, and he suggested to rent an apartment at least for Rome. He suggested 1 week for Rome in an apartment, and to split the 2nd week between Florence and Venice. I guess Rome is pretty big so it needs more time and its size makes it easier to find an apartment. I wonder however if it's as easy to find apartments in Florence and Venice. If not, then maybe it will be a B&B or hotel for these 2 cities.

I think not only we would save a lot of money because apartments are cheaper than hotels, but with my mom there we will also save a lot of money with the food because of the full kitchen in an apartment. lol Plus it will be more relaxing and we will have more space. Is Airbnb the best site to find an apartment? Either way, it's still not decided the amount of people who will be on the trip as well as the exact dates, but the apartment idea is looking very appealing for both relaxing as well as money cost.

It just depends. Apartments are not always cheaper than hotels. And the savings on food just depends on how you eat, where you eat, where you shop, how much time you want to put into cooking.

The trick about Florence and Venice would not be in finding the apartments, it's that you are renting for such a short time.

Be sure to find out all the requirements for renting an apartment. It's not like walking into a hotel and checking in.

You have to make an appointment to meet the agent, and confirm the time when you arrive at the train atation or airport. Will you have a phone that works in Italy?

You can usually pay a deposit by credit card, but have to pay the balance, in cash, on arrival. (AirB&B doesn't require this.) Will you be able to get enough euros and are you willing to walk around with such a large amount of cash?

If checkin time is later than your arrival time, what will you do with your bags while you wait? At a hotel, you can drop them off and do a little sightseeing.

You also have to do very thorough research when renting an apartment. There are some scammers, even on AirB&B. Make sure not to wire money to the owner, but just pay AirB&B.

Some people have negative attitudes about apartment rentals. I have positive ones, and you definitely should be able to find one cheaper than hotels that are nicer than hotels. I think it is a HUGE plus to have a kitchen available in Italy, not just for saving money, but to get one's preferred breakfast and to get a break from the rituals of eating in Italian restaurants.

Here is the agency I like to use for Rome. You can pay by credit card for the entire stay and they have excellent customer service.

http://www.romeloft.com

You should carry a couple of cell phones anyway for your travels, but even if you don't, thousands of people have rented apartments in Italy and met the landlords to pick up the keys without having a cell phone. You can work with the agency. They all speak excellent English.

I wish I could give you a similar link for Flrorence and Venice, but it is not hard to rent apartments there for less than a full week. If you go to the Slow Travel website you can get lots of help finding a reputable, secure apartment rental within your budget.

We rented great apt. In Venice through VRBO.
Only canh required was 150 euros to the agent who met as at the vaporetto stop.
We did have to phone the agency upon arrival. Many rental apts do not have a land line. ....I always take a phone that works in Europe.
Checking in. and out of hotels is easier ..you can leave the luggage.
Also, if you don't speak any Italian, the hotel staff is there to help.

Thanks for the tip about apartments vs hotels... I figured that hotels would be easier for check-in and check-out, I guess i'm going to compare both options as soon as I have the dates. Maybe I'll find a good deal for a hotel or B&B, with a mini-bar or fridge to store some food. That way it will probably be easier since we are not very experienced travellers as I'm sure the hotel staff could offer a lot of help and advice for exploring the cities.

I was looking at some day trip options from either Rome or Florence into the countryside of Umbria and Tuscany. What interests me most is a small town but where I can have amazing views over the countryside. I saw some pictures in Orvieto where people are standing on the side of the town with great views looking down over the countryside. But once in Orvieto (by bus or train?), is it easy to find this area where you can look over the countryside? Is it near the main square with the duomo or can you tell me where on a map would it be? And what are other towns easily reached by train or bus from Rome or Florence that offer such landscape views over the countryside and the hills?

Italy has so many beautiful places, it's so fun to discover and read about all these towns and places....

Views like this:

https://www.youtube.com/watch?v=fzvHqlfOBlI

https://www.youtube.com/watch?v=wjqGaoAQNb4

Is there a place to sit down and enjoy this like a park or terrace? or is it mainly a street? are areas with such views close to the main square and the duomo?

What other towns in Umbria or Tuscany easily reached by public transportation from Florence or Rome would offer such views?

I know there's Fiesole, do the views compare? What else? :p

Some thoughts

Orvieto, and surrounds are hilly, as defensive measures a lot of towns are built on or into hills. So yes you can look out onto lots of stuff. Tuscany, for instance is famous for its hills.

To help choose you can make Google maps show isoclines and of course there is street view so you can see the actual view.

Appartments, I've rented in Rome, Florence, Venice. If you don't need a concierge then appartments for say 4 days min make a lot of sense, you will find that good prices appear as you move away from the main drawer and into the residential area. So I've stayed twice in the Vatican neighbourhood in Rome, in Florence, on the unfashionable side of the river and in Venice a few streets back from San Marco. The good thing is that you get to access local shops, the bad news is you end up with a bunch of foods that you may have to wade through on the last day :-) in my case I always buy too much wine.

Smaller towns have fewer appartments but for fine views I'd also look at Pienza, Montepuliciano and possibly Siena. Both the last two are very steep, while Pienza, which was not built for military purposes is dead flat though with fantastic views.

I don't think I have a negative attitude about apartments; I often rent one myself. However, my experience has convinced me that, compared to a hotel, it requires much more effort to find a good rental; that it is a riskier proposition; and that it entails many little inconveniences. If I'm traveling with three or more people, or if I'm staying more than four days or so in the same town, I prefer an apartment rental. Otherwise I prefer the convenience and services of a hotel.

I suggest that you purchase Trip Insurance. It is important that if your parents have any pre-existing conditions, that you read up on how TI works and time frame for buying it.

We have rented apartment. In Spain , Italy and France.( for space, not cooking)
I am not saying it is a must, but speaking the language of the country
makes it easier .
Often, apts. have been in buildings without an elevator. It might present a problem
for travellers with a lot of luggage or mobility issues.

I'm with you bvlenci

<requires much more effort to find a good rental; that it is a riskier proposition; and that it entails many little inconveniences.>

That is absolutely my own experience as well. I would never rent an apartment for less than one week.

Hmmm after reading the comments maybe I'll stick with hotels and B&Bs... Lol

Apartments CAN be nice. But there's a lot more that can go wrong with your arrangements than staying at a hotel. It's also a lot harder to find reviews for specific properties. Just a lot more unknowns in apartment rentals.

I would only do one in a place I had stayed before and knew fairly well, or if it was a long stay (like a month or more).

Yeah, maybe since I'm bringing my parents, it's better to stay on the safe side and book hotels with tons of reviews... I don't want stress or surprises, and I guess with hotels there's less risk for that...

I have always found that true. It's easier to research hotels. PLUS if something goes wrong at a hotel it's a lot easier to get it straightened out than in an apartment where the owner is not even in residence. Another plus is that the front desk staff at a hotel can be very helpful, say if you need help translating something, making a dinner reservations, figuring out local transportation, etc. You don't get any of that in an apartment.

I also like to return at the end of the day and find the bathroom cleaned and the bed made.