Italy... without an itinerary?

Brava for you! I miss my "no itinerary" days!

I don't use airb&b so I have no advice there, but sometimes I check a booking website the night before I depart a city and get a reservation for the following segment. My itinerary is mostly set in stone because of train ticket discounts (€9 from Milano to Venezia, for example), so I book hotels in major cities ahead, but in smaller towns connected by bus or regionale trains (no discounts for early purchase), I do some last-minute reservations for lodging.

We are thinking of doing something very similar! Train from Rome to Orvieto, hire a car and explore Tuscany for a few days dropping car at Florence Airport is easier than in the city, so I have heard. Have to beware of many speed cameras and no go zones. Was also thinking of Airbnb as we go.... Will be interested to hear of others experiences? Maybe best/must go places? Also will catch train to Venice from Florence.... Few days, then to Verona and lakes district! Any tips on best places to drive??

I've been to Italy several times also, so if it were me I'd skip Rome for the most part and pick up car at airport and head right to the countryside. (Energy Permitting)There is no way I would leave home without reservations (and I can hold my own with the language) but that's me. At the end of the day, I need to know where I'm going to lay my head for the night. I would be stressed all day just thinking about it. JMHO

A little off topic:
Spend the night (or two) in Orvieto and visit Civita di Bagnoreggio while in the area. I would also skip Florence if you've been before. (again, that's me). There are so many places in Umbria, Tuscany, etc that I haven't been to. A car in Florence doesn't make sense. Why rent the car for a few days only to take the train to Venice. Explore with your car, and maybe drop off car at Padua and train into Venice or drop off at Venice Airport and take the airport bus into Venice. If I ever get back there, we would hit the lesser visited cities such as Parma, Bologna, Padua, and maybe the Lake Regions or areas of the Veneto. I loved Venice, but if I missed in order to hit somewhere new, so be it.

Have a great trip.

You may drive into Florence even if you are faint hearted: it is not dangerous and you won't get killed. It is simply pointless: you will not allowed to park on the street and if you do not qualify for ZTL access you will get a string of automated fines. Drive into Florence if you know what you are doing - experimenting is too expensive.

Hi Meg,

We are doing a very similar trip in May / June ourselves. Flying into Rome and out of Venice 20 days later. Some people like to plan to the nth degree. Others are more spontaneous. We fall somewhere in between by making sure that we have reservations on each end. (In this case Rome and Venice) That way we know have place to rest our heads when we initially show up and a place to unwind before our flight home.
On this trip, since it is the start of the high season, we have also booked a week at an Agriturismo in Tuscany. Only because we plan of doing an lot of day trips on the surrounding hill towns and didn't want to waste time hopping from one place to stay to the next. We will rent a car for this part also.

I think going without an itinerary is very doable. We did it many years ago and I'm sure people do it all the time today. You just have to know that the busy cites and best places to stay tend to book up far in advance. You can either stay one or two train stops away in "unheardofburg" which is 10 minutes by train away and always has rooms vacant. Or just show up very early in "popularville" and start checking on rooms. You have a very good chance of snagging a vacant room due to a last minute cancellation. If you can't find a room, then enjoy the city and then try the next town over.

Case in point, many, many years we were staying in Cinque Terre. It was just when the place was getting too discovered and by late afternoon rooms were almost impossible to find. There was a "problem" at our pension and we wanted to leave but there was no other place to stay in CT. Not a problem. We just took a train to La Spezia and found a room there for the night. We then trained back into CT the next morning to enjoy the sites!

One day, one day...

...I would love to simply book the air, open jaw-like into Munich, out of Naples. Only other thing I'd do would be book a couple days lodging in Salzburg on arrival, then maybe book 2-3 days at my favorite B&B--Salerno Centro--on the other end. Everything else left to chance.

No way would I do this in high season, however, May through August, although I see that's exactly what other posters are doing or thinking of doing. To each his/her own. I just think off-season or shoulder-season would considerably open up the spur-of-the-moment lodgings available, still at decent prices. And because we don't drive in Europe and take trains everywhere, buying tickets on the spot would cost more. I don't want 'spontaneous' to be cost-prohibitive!

If you're going to be driving in Italy, you MUST get an International Driver's Permit from AAA in advance (which you carry with your US license), and you MUST learn about ZTL's. Realize that while Florence's ZTL's are the most notorious, many cities, large and small, have them.

Do you have a way to find lodgings on the fly? This will require Internet access and/or phone access in Italy.

On such a short trip, are you willing to spend time looking for lodgings?

I'm not saying you should or should not do this, but do be prepared for what's involved.

In your shoes, what I'd prefer to do is book a night in Rome, a few nights in a small town or village in Tuscany, 1-2 nights in Florence, and 1-2 nights in Venice. All would be booked in advance. Then I'd rent a car in Rome or Orvieto, explore Tuscany from my "home base," then drop the car on the way into Florence, then take the train to Venice, then fly home. I wouldn't want to use my short time in Italy finding lodgings. Just because you have pre-booked lodgings in Tuscany doesn't mean you can't explore randomly.

Again, that's me, and again, if I had more time (3 weeks, say), I'd consider your plan.

Thank y'all SO much! This is hugely helpful. I've read every post and have so appreciated the thoughts! Definitely some good pointers about driving in Florence, the international driver's license and reading up on other traffic rules. Dropping the car off at the Florence airport is a great tip, as is using the bigger cities as "home base" and exploring from there. We will have Internet/data while we travel - we spoke w/ our carrier and it was a very reasonable $10/day for a good bit of data, forget exactly how much but totally doable... as long as we aren't streaming Netflix which I feel quite comfortable saying we'll be just fine without. ;) I've looked at various cities we were thinking about staying in and found lots of options on Airbnb; I just wasn't sure how much "last minute" flexibility there would be.

I just wanted to hear the pro's and con's about traveling this way and it's super helpful to hear both from other folks who have done it/are doing it as well as those giving me the "cons" to think about. I posted on another site and basically heard this is a terrible idea/don't do it but without really specific reasons. I'm reading every response that comes in, so if anyone else has additional thoughts please share! This is a lovely community!

May is ust next month, so post back after you return and let everyone know how it turned out.

Since you have a car it is more do-able than if you are relying on a train. You might pull into a town and discover you've hit a festival weekend and everything is booked. No problem, back into the car and go to a different town.

The problem you'll face is that the internet cuts both ways; it makes it easier for you to look up information, but it does the same for everyone else. Small hotels that were not mentioned in any guidebook are readily found online. You mention you plan on using AirBnb; hopefully it is as widespread in the small towns you are visiting as it is back here in the US.

Last year I did what you are considering for about two months, beginning in late May, except that I mostly booked through venere.com and had no rental car. Only my initial stay in Rome was booked in advance. There were always single rooms available 24 to 48 hours in advance, though the cheapest centrally-located, air-conditioned options were gone. I ended up in a mixture of hotels and B&Bs, plus some apartments in other countries (through booking.com). The need for a/c made things a bit tricky in northern Italy, where many 3-star spots don't have a/c.

I have done this type of travel many, many times as I like to travel on my own schedule and want my trip to be spontaneous... it is always a choice of travel style. I tend to do this more with a car, as I can always drive on to another city to find a room if there is nothing available. I am pretty flexible with my travel plans and would not have a melt down if I cannot get the room I want. I have found some absolutely amazing places while traveling that I would have never found online ahead of time. If you can go with the flow then you can travel more spontaneously. It is more stressful for me to have an exact itinerary.
I would get rid of the car for Florence, or stay outside the city and take a bus/train in for the day, if you would rather stay in the countryside.

I will sometimes book hotels in big cities, and usually first and last night now... but, for a lot of people there is nothing as fun as a totally unplanned road trip in Europe. My first trip (I had RS ETBD, but not this forum) and my daughter and I landed in Amsterdam, had a rental car, 20 days, a map of Europe, some money and away we went....with a rough plan... best trip ever... and it has allowed me the freedom to travel the way I want to...

I will definitely come back and share how the trip goes. We're going mid to end of May. Thanks for the recent additions - very encouraging to hear from y'all! I think I'm going to book at least our first and last night as others have said they've done.

Hope Meg is having a wonderful trip. My husband, myself, and 15 year old son are also considering the open-end no itinerary plan. We fly into Rome 5/31/16 and fly out of Rome 6/14/16 - about 14 days total (not including travel days). We are debating rail or car; but are leaning towards car. I've looked at all the pros and cons. We have been to Rome, Florence, Cinque Terra, Siena - in 1999 (without son) - and we rode trains then. So we thought we would be more looking at other parts of the countryside and be more flexible, but also want to visit Florence. I am very concerned about the parking outside the city for a few days - it seems like such a hassle. How complicated is it? If we do not have reservations - can we still park and go in? I think we still want to keep the car. So the dilemma is keep the car for the whole trip, but when we visit the cities (for a few days sometimes) we may have to pay for parking outside. We are also considering going to Venice, but since we fly out of Rome (didn't think to do the fly in one town and out the other), we have to make a loop, and Venice is far up there.
I'm also wondering about the eastern coast of Italy that not too many people mention - is it worth a visit over there? I know there are a lot of questions here - but primarily it is the no-itinerary question, and rail vs car question too! :)

Puglia is fabulous, but it's not only east, it's south, so maybe not a great idea on this trip. The Gargano Peninsula (the spur of the boot) is interesting. There are some beaches that are certainly not secret, but I imagine most of the folks who go there are Italian. However, to the extent that a lot of the accommodations are positioned for folks going to the beach and possibly spending a week there, I don't know how easy it would be to drop in and find a place to stay for a night or two. Maybe it would be fine since you're earlier than peak beach season. And with a car, you can always move on. Much harder to do if you're depending on public transportation.

There are many fascinating cities not too far off your direct path, of course--Assisi, Perugia, Ravenna...

Hi everyone! I wanted to drop in and update on our trip ... which was wonderful! We ended up booking places via AirBNB a few weeks before we left, so we didn't leave the itinerary completely open ended. We were a tad reluctant to lock ourselves into a set schedule but it ended up working out just great - we were happy with the amount of time we had given ourselves in each spot and it was nice to know we had a place to rest our heads each day. I just wanted to share how FANTASTIC our experience with AirBNB was, in case anyone was on the fence about using them. We stayed in some truly lovely spots, in really great parts of the city at a fraction of the cost of the hotels we had looked at. But the best part was having a "host" in each city as a contact - every host we interacted with met us in person at the apartments, gave us restaurant recommendations and some "insider scoops." A few booked reservations for us and one even texted us one day while we were walking around to let us know a little wine bar he was hanging out had live music playing. It was just a comfort to feel like we knew someone in each city we stayed in. Highly recommend! We spent 2 nights in Orvieto, 2 nights in Montepulciano, 1 night in Florence and 1 night in Venice. Loved the small town feel of Orvieto and Montepulciano - it was a totally relaxed pace. We returned the rental car outside of Florence which was definitely the right call and trained from Florence to Venice then Venice to Munich. It was an awesome trip and I loved the contrast between our "countryside" visit for the first 4 nights and the big city of Rome, Venice and Munich. Happy to share any other thoughts but I just wanted to touch base and reply that we didn't end up flying by the seat of our pants (probably good for our marriage, as navigating the highway with a KNOWN destination was a fun enough challenge) but we did have a great experience w our airbnb lodgings. Thanks for everyone who gave their input and experience before we left!

Hi Meg--

So in the end, you kind of did a 'half-spontaneous' trip. Sounds like something we'd do for sure. We only did VRBO once, for 5 nights in Florence on Piazza Santa Maria Novella near the SMN station. The 'host' met us at the apartment as well, but after giving us a few tips, taking our cash rent and happily waiving our 200 Euro security deposit, that was the last we saw of her, which was OK.

We are possibly doing Rome in February--I really like off-season--because we only have 9 days and were there for only 2 days six years ago. If we go, absolutely we will use VRBO or AirBnB, and may even visit Orvieto, which is only a little more than an hour away by train from Roma Termini station.