Suggestions on an Italy "Loop" Trip
 

What are your favorite day trips from Florence, Bologna, Venice, Ravenna, San Marino and Assisi? Am reading a lot about these places but the more I research, the more confused I become.

Also, we usually book through AirB&B and stay in independent en suite rooms, small apartments or studios, but with the incidents happening through AirB&B, I am open to suggestions of other websites that are good, reliable options for lodging. Since we'll be renting a car part way we will need lodging with free parking or parking less than ½ mile away.

Any suggestions, advice or input are greatly appreciated.

When is the trip? How long is the trip? How many people, children, etc.?

Below is link to my 2018 trip report ... Might give you some hints ... lots of photos, too.

3 Nights Milan
5 Nights Bologna (day trips to Padova and Ravenna)
4 Nights La Morra (Piemonte wine country ... if you go in October you'll hit white truffle season ... divine)
3 Nights Turin
2 Nights Orta San Guilio
https://travelswithmaitaitom.com/italy-2018/

You can research lodging on booking.com.

Without the additional information sassafrass requested, it's hard to know what suggestions, advice or input would be helpful to you.

Some cities are best visited by train, and you need to learn about limited traffic zones and how not to received a citation for driving into one.

https://www.italybeyondtheobvious.co...with-ztl-zones

You already have six stops without including Rome . Unless you're looking at more than a month I'm not sure you should be thinking about adding day trips.

From Florence I like Siena (by bus), Pisa/Lucca (by train)

From Bologna I like: Ferrara, Modena, Palma, Ravenna (you have it as a separate night, I think it's fine as a day trip from Bologna). All those are easy by train

From Venice you can do Padua, Vicenza, Verona, Treviso - all easy by train

So your outliers are San Marino and Assisi. I assume that's when you'll rent the car. I spent two nights in San Marino and did San Leo as a day trip. You do want to do a day trip from there as it gets horribly crowded mid day with people day tripping in so seeing it early morning and late afternoon/evening and getting out mid day makes sense.

Well, you've named 6 places, some of them fairly random, but haven't even mentioned how much time you're planning on visiting. I would be looking at at least two months to cover these places, and wouldn't even be considering "day trips." You need to give us a whole lot more information before anyone can help you sort this out. You've got a whole lot more planning to do before you start thinking about where you're going to park!

Why does this have to be a loop? Surely you've heard of multi-city fares.

Florence, Bologna, Venice, Ravenna, San Marino and Assisi?

lovely places all of them, but each of these is surrounded by equally lovely places, these are just the ones that are hyped and part of a tick list from a company or companies. If you must do this list you'll find that Bologna is the central train station for just about them all so you could base in Bologna.

Trip isn't until next September, but I need to use our FF miles and book in a couple of weeks, so I want to get an idea of our itinerary so I can book round trip. There are 2 adults travelling.

You really can't get an idea of an itinerary until you know how many days the trip will be. I presume that will be determined by your success booking with FF miles, but don't overlook the possibility of flying into one city and out of another.

I would book the flights and fill in the dates in between.

"lovely places all of them, but each of these is surrounded by equally lovely places, these are just the ones that are hyped and part of a tick list from a company or companies."

I agree.

Like maitai, we did a loop but larger and to different cities. Definitely go to the cities that interest you the most.

The suggestion to fly into one city and then out of another is a good one. That's what I did with my FF miles.

We flew into Florence, visited, then rented a car and used a wonderful (inexpensive) villa for a base for a week. I'll share the name if you are interested. During that week, drove to the train station to take the train to visit the Cinque Terre (without checking out of the villa). We really enjoyed that slow week. Then returned the car to Florence, train to Venice for 3 days. Flight to Naples, and then off to Capri, Amalfi coast and then Rome for 3 days. But those were the cities that appealed to us. Perhaps you could find a location that you like to use as a base and do day trips - by train or by car.

But personally, I'd lock in the FF dates for low point miles and figure out the order of things in between. I'm pretty frugal with my FF points though.

Forget day trips BY CAR from Venice or Florence!

I rechecked DL site to see about doing a multi city FF reservation. If we flew RT SFO-FCO or multi city SFO-FCO and Milan to SFO, it is 50,000 FF miles. Using Florence or Venice airports would cost waaaaay too many more miles. So if we RT SFO-FCO we have the choice of doing the loop one way or the other, it doesn't matter a whole lot.

So right now, this is what it looks like: (the total time of trip is at least one month)
Train FCO to Florence (3 days) We've already been to Florence, so we can plan a day trip from here
Train to Bologna (3 days) and we can do at least 1 day trip from here
Train to Venice and take the cruise
After cruise, explore Venice for about 3 days (already been to Venice) Do a couple of day trips and just meander
Pick up car and drive to Ravenna for 1.5 - 2 days
Drive to San Marino for 2-3 days (lots of day trips I found from there)
Drive to Orvieto and stay about 2-3 days including Civita di Bagnoregio. Drop car off when we get to Orvieto
Train to FCO and stay somewhere close to airport the night before we go home.

We can jockey amount of days we stay in each place....nothing is written in stone yet.

You want to keep the car for the Civita di Bagnoregio day trip from Orvieto. It is possible by bus but it's a pain, car is better for that.