How would you go about deciding on places to stay? Would you book in advance, or just wing it? What internet sites are there to find lodging, Airbnb, VRBO...?
Probably traveling in September or October. How difficult is it going to be to find lodging at the last moment during that time of year?
Should we be using a travel agent to make these decisions for us?
We book, but that's mainly because my partner prizes that certainty.
September/October usually a good time for accommodation and less tourists, though early September may still be busy in some places.
Plenty of options for accommodation:
- Chain hotels, which are useful if you're a points gatherer, but having experience hotels for work too often, they don't feel anything like a treat now.
- Independent / boutique hotels do exist, and should still be in the aggregator listings
- B&B isn't big in Italy, but is growing a little
- Apartment rental has been a preferred option for us, well before airbnb came along. It forces you to get into the local community more, buying groceries, shopping in specialist food shops, alimentari and gastronomie (like delis) and sharing the block with some locals. You typically get more space, with more facilities / freedom than a hotel, but for cheaper! It does however lack the hotel 24/7 support.
- Aparthotels / Residences: These form a halfway house between private apartment rentals and hotels, and well worth considering.
- Agriturismo: Another favourite of ours, staying on working farms, typically in modern or historic accommodation, and with the food they serve being local, home-made, plentiful and tasty, yet often stupidly cheap for what you get. Eating here often has you sat in a room with groups / families of Italians, so a cool window into that world.
We always book things ourselves, but going back to my first trip in 1990, 2nd trip in 1995 and 3rd trip ~ 2001, I went through a travel agent. It's much easier to tailor your own trip now, than back in the 1990s, but experience of the country (and a basic understanding of the language) helps for sure.
Trenitalia site will sort train transfers / day trips and booking in advance on a set train save a lot of money, on what start off as good value trains.