Hotels or B&B's in Milan, Cinque Terre, & Florence?

Do you have Rick's Italy guidebook? It's a good place to start.

Cinque Terre - spent 4 nights at the Colombo Guesthouse in Riomaggiore this July and liked it very much. It was easy to get to from the station and had "fewer" stairs than most places - by no means none, and it's a climb up from the station, but that's normal for CT. Clean, good AC, decent sized rooms, not too pricy. Though overall, we found CT more expensive than everywhere else we went.

And btw - DO NOT eat at the often recommended Ristorante dal Billy in Manarola. Most expensive meal I had in 7 weeks, rude service, only average food.

Florence - I stayed twice this summer, 2 separate 3-night stays in two different apartments from AirBnB. I don't know if that interests you, but if so, I'm happy to post links to both as they were both terrific. One was for a larger group of six and the other was sized for two. The small one was just off Piazza Santo Spirito in the Oltrarno, and I loved the area. Easy walk to the main sites across the river.

Hope this helps. I visited but didn't stay in Milan so can't help there.

I stayed at the Ciao Hostel in Florence and really loved it. Clean, modernish, and had a kitchen also a quick walk from the train station. There are two-four bed dorms and family rooms. To get a private room just book all the beds in the room.

Might be below your price point, but nice:

Milano: Hotel Berna
Firenze: Hotel Bigallo around the corner from the Baptistery, Hotel Paris a block from Santa Maria Novella.