22 days in Italy, planning our first trip

What's your lodging preference? We like B&Bs and boutique family-run hotels. For our first time in Italy starting November 1, our Florence leg will be six nights. We're staying at a highly recommended Trip Advisor B&B, south of the Arno, near Boboli Gardens, but approx only a 20-30 minute walk to historic city center. Our goal is to make day trips around Tuscany with our B&B as our base. Where we tour will be based on weather ( e.g. if it's really storming at Cinque Terra, we'll pass). But a day trip is easy to Pisa/Lucca, Siena, etc. We'll relax in the evenings, mingling with the locals, maybe even take a rest day. We prefer small restaurants recommended by locals, rather than those that cater to tourists. You're in San Diego, we're in LA, so we both have plenty of restaurants to go fancy at home. We'll do the same with 4-5 nights in Rome, at a Trip Advisor endorsed family- owned boutique hotel. and 3-4 in a - you guessed it - Trip Advisor recommended Venice B&B. What sights we miss will give us a reason to plan a second trip. Besides, what I have found in our travels, is that the best memories are those of people we met along the way. And I want to make this trip lesiurely paced to do the same. Just my 2 cents. Have a great trip.

You might want to rethink Cinque Terre that late in the year, there isn't much to do there when the weather is bad and many hotels and restaurants will be closed. Besides, you will get plenty of lovely Coast towns further south. Train and bus will get you most places cheap and easy. Only rent a car for Tuscany if you want to drive to hill towns and wineries, everywhere else it is an expensive and useless pain in the neck. Pisa and Siena can easily be done as day trips from Florence.

You can find train schedules and even buy tickets on trenitalia.com.

You have almost as many cities listed as you have days in your trip. I would suggest cutting some locales, so you're not spending most of your trip in trains and cars. Also, each time you change location, you're going to lose hours of touring time checking into and out of hotels, packing and unpacking, etc.

In the amount of time you have, I would pick no more than three or four places to stay, and make day trips from those locations.

I would drop the CT at that time of the year.

Orvieto is an easy day trip from Rome -- about an hour by train.

I would do Siena by bus as a day trip from Florence. And Pisa is easy as a day trip from Florence by train. While I think Assisi is worth a few days, if you want to visit so many cities, you could also do Assisi as a long day trip from Florence.

Ravenna is definitely worth at least an overnight if you're interested in Byzantine art. You could do it on your way from Florence to Venice by train.

And given the possibility of unfortunate surprises in transportation, definitely spend your last night in Milan so you can make your flight on time.

We are in Florence right now for 4 nights and after a bunch of 2 nighters, it is wonderful to stay in one place for awhile. There is so much to do here (and eat!) And there is a Monday in the mix when a lot of museums close. Short stays can get old after awhile.

Rome 3 nights doesn't give you enough time in Rome. It's 2.5 days when you're jetlagged and after a long-haul red-eye flight. Rome is big, bustling and confusing. Give it another 2 days. If you haven't found enough to occupy you, take a day trip to Tivoli.

Sorrento I found Sorrento to be a good base, train to Pompeii, Naples, and buses to Positano and Ravello. It will take several hours to get there by train. If it's in your budget, consider hiring a driver and car for a day from Rome to Sorrento. Stop for a couple of hours to see the archaeology museum in Naples, then Pompeii and finally your hotel in Sorrento. It will take most of a day to get from Sorrento to Tuscany/Umbria. I would not spend less than 4 nights here, probably 5. Paestum is not far by car but it's a hassle to get to otherwise, especially at that time of year when there are fewer hours of daylight. I think a car would be more trouble than convenience in this area. For instance, Sorrento has a system of one-way traffic that loops around the town.

Umbria (Orvieto/Assisi) I visited in May and loved both towns. I wonder though how enjoyable they'll be in November with the real possibility of rain and cloudy skies. The historic centers of both these towns are up on the hilltops while the train stations (and probably car parking) are down below. That adds a lot to your travel time. If you do go, spend a night in each and allow 1/2 day to get to Assisi and 1/2 day to get from Assisi to your next stop.

Tuscany What do you want to do here? If you really love Renaissance art and architecture, 3 full days in Florence is barely enough. If not, you can see the highlights in a day trip. I'd base in either Florence or Siena and day-trip to the other. You can day-trip to San Gimignano also. Or rent a car for a few days and stay at an agritourism. Just be aware that you have to leave the car outside the historic centers or incur fines of hundreds of euros.

Cinque Terre I'm with Angela. Wrong time of year, forget it.

Bologna is a good base for day trips to Padua, Ravenna, Ferrara and a lovely town to boot. Ferrara might be a good base too.

Venice 3 nights, 2 full days. That's the minimum. Don't plan on day trips from Venice.

Verona is one of my favorites. It's between Venice and Milan, not a day trip from Venice. Also, it is best experienced as an overnight stay.

Milan Plan to spend one full day to see the sights, possibly two. Then you never have to go back.

You will have to cull from this list. There are several more than your 21 nights and days (don't count Dec. 6 at all - with an early afternoon flight, you won't have time for more than a leisurely breakfast before heading to the airport). Figure on 1/2 day used for each hotel transfer - more if you include the Amalfi Coast. Even if you have a car, you still need to pack/unpack, check in/out, and park the car.

Keep in mind that sunset is around 4.30 p.m. at that time of year, so you will want to be in places that have enough to offer after dark.

Lynne, I love southern Italy but with the list of places you have named, I would take Chani's advice and make it a short trip. I go to Paestum every year but it is out of the way with so little time.

Skip Cinque Terre this time. Assisi and Orvieto (and many other hill towns) will be beautiful in November/December.

I like a minimum of three nights per city, but that's not always possible. A word about daytrips: I do them sometimes, but there are cities that are better after the daytrippers are gone. These are fine for a two-night stay, or even an overnight if you have longer stays planned around them.

If you have a car or can arrange trips with your hotel or TI, Siena is a great base for Southern Tuscany (especially Montalcino and the southern Tuscan wine areas). Florence has a completely different vibe, and is a good base for daytrips to Lucca (can be combined with Pisa if you have to go there). Bologna is great as a base because of transportation links (Modena and Parma). I would overnight or spend two nights in either Ravenna or Ferrara.

Can you fly into Venice and out of Rome? Do you want to nail down reservations, or be more flexible regarding how long you want to spend somewhere? Booking.com and other booking services can be helpful in finding same- or next-day accommodations. Your travel dates should show plenty of available rooms.

Yes, Florence is an excellent base. You won't want to leave. We love trains- great transportation with a great view and someone else is driving. I would suggest hotels but we stay at luxury hotels only and I don't know your preferences.

lynne, sent you a PM