Hotels: Milan, Venice, Florence, Cinque Terre, Florence, Rome

For Venice, Florence and Rome, try Cross-pollinate.com. An American couple living in Rome who own the Beehive hostel (which gets great reviews) has many b and b type lodgings. We have used them numerous times in the past 10 years and have been very happy with them.

They are upfront with the pros and cons of their places. Check reviews and photos. 10 years ago we traveled with our teenage son and found triples. We were in Italy last month and stayed in Oltrarno in Florence, Trastevere in Rome and Castello in Venice which were a close walk to everything but with a more neighborhood feel and out of the main tourist crush of people. Well within your budget.

Send me a PM if you want specific places we stayed.

If you go to www.booking.com, you can find listings for lodgings, along with the types of rooms they offer. By putting in your dates, you can also get the prices. Many places have triples, family rooms, or small apartments, in addition to regular hotel rooms. Some people advocate doing the actual reservation directly. I'd at least check to see if there is any significant difference. I like using the site because you get instant confirmation. It includes reviews from people who actually stayed in the listed places, as well as other useful information like wifi availability, credit card acceptance, etc.
You didn't ask, but in my opinion, you have too many destinations for a 13 day trip. Is Milan in there because that's where you land? If so, I'd get to Venice as soon as possible. Otherwise, I'd cut out all but the big three, Venice, Florence, and Rome.

Thanks for the suggestions! We are only flying into Milan and then going to Venice. I also realized i listed Florence twice in my title by mistake. We might consider going to Cinque Terre for just a day trip

Hotels can be expensive in these cities, but Rick Steves' Italy guidebook does list at least several places with triple rooms around €150, such as Pensione Guerrato in Venice. Finding something that meets your budget is a good reason to book ahead.

I'm not sure about their triple accommodations but we recently stayed at the Hotel Al Ponte Mocenigo and really liked it. Away from the craziness of San Marco, in the San Polo area. Just get a vaporetto pass when you arrive and you can jump on and off the vaporettos to get where you want to be, saving your legs for all the walking and wandering (and getting lost!) you will be doing anyway. Check the reviews of this place- I'm not sure if it's in RS, but it gets well-deserved high marks on other travel sites.

Cinque Terre is too far from Florencefor a day trip unless you want to just go for a couple of hours. It's not the distance, it's the numerous train connections. It would be doable if you are driving.

Cinque Terre is too far from Florencefor a day trip unless you want to just go for a couple of hours. It's not the distance, it's the numerous train connections. It would be doable if you are driving.

Cinque Terre is too far from Florencefor a day trip unless you want to just go for a couple of hours. It's not the distance, it's the numerous train connections. It would be doable if you are driving.

Cinque Terre is too far from Florencefor a day trip unless you want to just go for a couple of hours. It's not the distance, it's the numerous train connections. It would be doable if you are driving.