Next September for my 60th birthday I want to vacation in Italy. I’m figuring 10 to 14 days. There are a few places I’ve always wanted to see (Pompeii, Herculaneum, Florence, Tuscany, Pisa and Milan) and of course, Rome. I will probably go with my brother and possibly my daughter. I don’t think I’m up to brazening out traveling without guidance but I would prefer a tour that wasn’t really rigidily planned. Anybody have any advice?
You’ll probably want a car. Put a lot of emphasis on Tuscany. Consider Ravenna (home to some amazing mosaics from around 1000 years ago). Expect to eat some of the best food you’ve ever encountered.
Do you want it guided by a tour company or self guided? Must know that before continuing this dialogue.
There are plenty of internet cafes around in most towns. Using sites like Hostels.com and Hostelz.com it’s possible to book a place only a couple of days in advance. (I recommend my ‘two night minimum’ policy - even if you hate the hotel, you still need a bit of time to find somewhere else.) So, hole up in one town, choose the next online, book ahead, then explore, then drive to the next place with hotel already booked. It gives you a lot more leeway.
Also I recommend www.viamichelin.com for driving planning - it does pretty good estimations on route times and planning, and has a good restaurant guide (naturally!). Though do get it to choose “shortest route” rather than “recommended”, which perversely makes you go out of your way to drive on freeways.
I’d also recommend Tuscany - it’s within a few hours of Rome, and you’ve got Florence, Pisa, and the marvels of the Tuscan hills.
Skip the car completely. Only an madman drives in Italy, and that includes all Italians! Get a train schedule and use that to get around. Stay up north and day-trip around to where you want to go. Rome is worth a day or two, but not more than that. The best food is in Tuscany.
There are any number of short, two-day or so tours that leave out of Rome and Florence. Talk to AAA about them. In fact, let AAA do as much of your booking as possible.
I am a complete “tyro” when it comes to European travel. So are my traveling companions. Perhaps a guided tour would be the best way for us to go for our initial foray into travel outside the US. That’s the main purpose for this thread…to get some feedback. Is it difficult to drive around on your own if your grasp of the language is limited to pizza and tiramisu? What about budget? A tour gives you an upfront price but can you really do it cheaper on your own?
Don’t believe it about the driving - I’ve driven in Italy and it was fine. Rome was teeth-gritting, and the Tuscan hills involved ignoring the other drivers, but largely it’s not as mad as people make out.
I really think you’ll have a more interesting time if you do it yourselves. Otherwise you’ll be in a coach with lots of people like you and not really experience the country. I have no idea which way would be cheaper, though.
Buy the Lonely Planet guide to Italy - it’s geared towards independent travel.
We rented a car and had a wonderful time. We had no reservations at all except the car & the plane. Had no trouble at all finding affordable rooms (there were 5 of us). The traffic was not bad at all compared to where we normally drive (LA freeways!) except for the lack of street signs. We actually bought a map which had all the roads and streets, but no names, just lines…but we never got so lost that we couldn’t find ourselves! I agree that you will have more fun if you do it yourself. We spent 14 days and visited Milan, Venice, Florence, and Pisa. If you really want Rome you should probably do that & nothing else tho. Pisa was my favorite, followed closely by Padua. Have fun! The food is the best part.
Most people in tourist areas speak reasonable English; and in the non-touristy areas, sign language is good fun and a great icebreaker. Armed with a good travel guide, you shouldn’t have many problems in restaurants deciphering the menu. Also, before you go it isn’t so hard to review a pronunciation guide and then learn a few key phrases, including numbers 1-10, please, thank you, and how to order your favorite beer/wine/soda/coffee - and the most important one: “where is the toilet please?” (dove il bagno perfavore).
Man dopers are quick. In the time it took me to look up and old thread, 5 posts.
I’ll agree with some of what has been said. Driving in Italy can be hit or miss. In Sicily for example you really need to be an alert driver. Signals are almost totally ignored, and stop signs are even worse. I’d suggest just taking trains between major cities and walking or using the public transportation in the city.
Here is an old thread about Venic and Rome with some good advice. If you get to my post on the last page, I link to some older threads that also have a lot of good advice. One good thing about going to Italy is that most of the major things you’ll be seeing don’t change much over the years.
Yes you can do things cheaper if you do them yourselves vice booking a tour. If you’re an experience traveler. You don’t have to have been to Italy specifically, but if you’re used to making your own arrangements and getting around in different countries on your own, then you’ll do fine. I tend to dislike tours mostly because I’d rather do things on my own than be forced to fit into someone else’s schedule. But really there are enough Italy-familiar dopers here that you can probably almost plan the entire thing just by asking us about different locations.
For your first trip I’d suggest starting in Rome. Spend about 2 days in Rome after you arrive. That should let you hit most of the major sites without having to fill every moment of every day. Then you can do Pompeii and Herculineum as day trips from Rome. I’m not sure that seeing both sites is the best use of time. Each has it’s own pros and cons, but they are similar enough that seeing one will get you by. When we went the first time, we took an overnight train from Naples to Venice. That way we didn’t lose a travel day. So think about that option. When you can travel at night between destination, think about doing it. But only if you can rest on a train. If you can’t sleep at all, then you’ll just get to the hotel and crash and lose the day anyway. A day or two in Venice is probably enough. Same with Florence. Pisa really doesn’t have much to offer except for the Tower. So that is an easy day trip from one of the other locations. Try and fly into and out of the same airport…it’ll save you money, and the pain of figuring out mulitple airports.
My suggestion is that you do a loop. Start at Rome, a few day trips south to Pompeii/Herculineum then to Venice for a few days…train to Florence. From Florence you can get to Milan without too much trouble. Then back down to Rome for the last day or so. You can stop by Pisa on your way to Rome to see that.
Most important? Have fun! Italy is just an amazing place. More to see and do than you can fit into a lifetime. If you try and let us know what you’re interested in seeing, we all may be able to suggest specific sites.
Excellent idea…and I even have a gift certificate for Barnes & Noble!! 
Oh, and thanks for “dove il bagno perfavore,” too! 
Is Italy using the Euro?
I lived in Italy for 2 years.
My recommendation: Land in Venice, stay there for a couple days. Get a car and drive south. Stop in Rimini and Ravenna. Stay there a night each. Drive down the coast to Pescara, stay there for a day. It’s truly beautiful. I was stationed at Aviano AB (~40 clicks west of Venice) and probably 15 times had to make the drive to a small base on the tip of the ankle of the boot. I loved it. It was a 10 hour drive. But I digress. From Pescara, go southwest to Rome. Stay there for a few days. Check out the Sistine Chapel, Vatican City, the Colosseum, etc. To me, Milan was nothing special. It was a big and very busy European city. Pisa is tiny and the leaning tower was kinda lame, not worth seeing IMO. Anyway, on your way back to Venice, go through Florence and Bologna. Stay a couple days each.
Don’t believe what these other posters are saying about the food. Just like here in the US, I had some crazy-delicious food but then I also had some very shitty food. And to be honest, you never know.
Also a recommendation: Try every restaurant’s house wine. It’s usually very cheap and very tasty.
Also: When driving, if a Caribinieri or Polizia, hold the lollipop (a round target looking sign on a stick) out and are looking at you, pull over immediately. If you do not, they will shoot out your tires. They do not chase people.
Yes Italy uses the Euro. We were there right after the switch and many prices were given in Euro and lira. Many people had not gotten used to so many coins either. At a small hotel we stayed in the owner said where am I supposed to put these coins, they’re worthless. Speaking of 5 Euro coins. I guess by now she knows they are not worthless.
The driving can be crazy… especially in the cities. Even where I lived, small city Pordenone, it was sick at times.
The Autostrade can also be crazy. One thing that makes the road especially dangerous is the big trucks. They will be lined up all along the right shoulder and they constantly are passing one another. Oftentimes they’ll pull into the left lane without much notice.
They are worthless, as they don’t exist. (I think you mean €2 coins - the largest denomination in ciculation.)
Worst advice ever. Unless you’re doing all your driving in the countryside… and even then.
I would be very happy to work with the OP to plan out a travel schedule. If they PM me I’ll link you to some photos from my recent trip and I can offer some advice. Also, Lonely Planet’s “Thorn Tree” forum is a good source for travel advice.
Good thing I’m starting a year in advance to plan this. I will definitely check out Thorn Tree, Spezza.
Eh. I lived in Sicily for two years and only had one insurance claim. 
If I go to Italy again, I’d probably either do it by bike and train or car. I likely would self tour - it is an easy country to navigate, once you work the basics out.
I probably wouldn’t do a guided tour. I don’t like to be pinned to someone else’s schedule.
I have only ever been outside the U.S. once [del]for 20 minutes in the 1960s…[/del] in the 70’s and that was to Ireland where my ex-husband and I drove around and stayed in B&Bs. That was a long time ago so I’d say I’m not at all experienced.
Pompeii is a place I have wanted to see since I was in grade school. I saw the traveling exhibit in Boston years ago and that only whet my appetite more. I’ve read or watched everything about these two sites but seeing Herculaneum isn’t a deal breaker.
Good idea. How’s the security doing that?
That’s about what I had in mind.
Well, in addition to Pompeii, the Vatican is on the list, and I would like to see “The Last Supper” before it crumbles off the wall although it may be a disappointment. More generally, art, ruins, beautiful scenery. I’ve noticed that Padua, Assisi, and Capri seem to be on many of the tour destinations.
re: the car/train question.
If you don’t have a car, then the only places you see are the ones with a train stop, which tend to be the big touristy spots. In Tuscany, you want a car, so you can drive out to the goat farm and buy cheese, or to the farm house restaurant on the olive oil farm, or go to Montalcino and taste the Brunello. None of those spots have a train stop.
In Rome or Florence you don’t want a car.
One way to do it is to start in Rome, rent a car there on your last day, drive directly out of town, and head up to Tuscany. Stop for lunch in Orvietto. Stay in one of the small towns in Chianti, and spend a few days seeing the sights – Sienna, Pienza, Montalcino, etc. Then find a convenient spot to drop the car in Florence and go by train the rest of the way.
Train to Venice - you don’t need a car there. Train to Milan - you don’t need a car there. Fly home out of Milan so you don’t need to back track all the way to Rome.