Any comments on the San Gimignano/Florence stay?

After looking up hotels on the internet I've decided to stay at Hotel Bougainville in Positano. The hotel is on Via Cristoforo Colombo. Has anybody ever stayed in that hotel? Is it well located?

Looking up a hotel on Capri has been a little more complicated. I'd like to stay in Anacapri. So far, Hotel Mediterraneo is the only place that seems to be inexpensive and reliable. It's on Via Caposcuro which seems to be near the historic center of the town.

Has anybody stayed on any of these hotels? Can anybody recommend a hotel in Positano/Anacapri which accepts credit cards, is decent, well located and that doesn't cost more than 110 Euros?

Re: your San Gimignano/Siena stay, I'd certainly organize it the other way round: stay in Siena, and make a daytrip to San Gimignano. Both towns are beautiful, but San Gimignano may be even more cramped with tourists (in fact, crazily cramped), and it is tiny. Siena is several times bigger, and for me, several times more interesting.

Thanks Franco, I know there's much more to do in Siena, but, since I am spending the night mostly in cities (Rome, Florence and Venice), I'd also like to spend the night in a town for a change. If it's tiny, I guess no more than a day is enough.

I'd just like to know if half a day in San Gimignano spending the night is enough to visit not just the two main squares, two main churches and two main museums, but wander through its streets camly without feeling there's much to see in so little time.

Certainly, half a day is perfectly enough. I'd choose the second half of the day, in order to spend the evening there, when most of the tourist busses will already be gone.

Thanks again Franco, so I'll stay 2 nights in San Gimignano with a daytrip to Siena.

I also have a day off in Florence which I'd like to spend in another Tuscan town. I was thinking of Cortona, but Montepulciano seems very lovely, too. Any comments on that?

I would definitely do a drive through the chianiti region, even if you don't like wine. Very close to Florence. Also, you may want to check initaly.com for some interesting out of the way places. Did you book for Florence? Can't remember your budget, there are some really big apartments in a residential area close to everything and great inexpensive trattoria's around. There is a price break if you stay more than three nights. Ciompi apartments through initaly.com They also have a lot of useful info. Visit David in the late afternoon for shorter lines.

I checked the tour website and they are a little bit out of my league. If I were doing a shorter trip, maybe I'd consider doing of those tours. Thanks for information, though. I really appreciate it.

Thanks for the "David" advice. I was also thinking of visiting La Accademia in the late afternoon.

I'm still trying to decide whether to visit Cortona or Montepulciano.

Since I can't make up my mind on whether to go to Cortona or Montepulciano or any other Tuscan town, I've decided to use that day off to do a daytrip to Bologna. It's an hour away by train and, according to many posts I've read and my bookguide, the city can be visited in a day.

lonely, if I may be honest with you, this leads back to the headline of this thread - it's your first decision so far that is really insane. Most Americans are constantly underrating distances in Italy, or all over Europe, and underrating the diversity of regions: a one-hour train ride can take you into a completely different world, as in this case. Bologna is in Emilia-Romagna, which bears not the faintest resemblance to Tuscany; before you'll get orientated and before you'll understand anything of the new and different flair around you, you'll already be on your train back. A daytrip from Florence to Bologna, that's a bit like a daytrip from NYC to Mexico City.
It can't be so exacting to decide between Montepulciano and Cortona - just stay in Tuscany! (I can't help much, as I don't unfortunately know Cortona. It's reportedly a wonderful old town without any single important sights, but with a great atmosphere. I know Montepulciano, which is pretty and has one really important Renaissance church, but also much of that over-polished Tuscan flair that makes me prefer Umbria to Tuscany.)

Thanks for your opinion Franco. I guess you're right.

In my original itinerary, I thought of doing a daytrip to Assisi from Rome, but I guess I'd better do it from Florence and spend that extra day in Rome. I was in Assisi once, but it was on a tour which combined Perugia and Assisi on the same day. I have to admit that was a frustrating daytrip. We only visited the Basilica di San Francesco and spent like two hours having a mediocre lunch at a busy restaurant. We had no time to visit the town because we had to continue to Perugia. The little I got see of Assisi was gorgeous, though. That's why I want to go back. Perugia was OK. I think it was an ordinary medieval city. I didn't like it that much.

I know that by the time I get to Rome I'll be kind of tired and I'd really would like to visit Rome without feeling rushed even though I've been there before.

Wait a second, franco - what's insane about a one-hour train ride? And what's the big problem with it being "a completely different world"? Bologna is a great town with a wonderfully walkable center. The food is out of this world. You may be right that it 'bears not the faintest resemblance to Tuscany", but neither do Rome nor Venice nor Campania. lonelyplanet is already planning on a daytrip to Naples - if he can get a flavor of that sprawling wonderful city in a day (and I think he can), why not do the same for Bologna? Visit a few specialty shops, stroll the covered sidewalks, enjoy a couple loooong meals...sounds like a wonderful vacation day to me.

Insane? No, I wouldn't say insane. Lucky is the first word that comes to my mind.

Bob: the difference to lonely's Naples trip is that he will be in Campania for 9 days or so. The important thing is not to be IN THE CITY for several days, but in the region. If you can already "feel at home" in Campania, then one day may be quite enough for Naples. But if you come for one single day to a region that you don't know at all, I think that day will be lost, as you simply need to get orientated first.
I absolutely agree that Bologna is a wonderful city, and if he'd stay in, say, Modena/Parma/Ravenna/Ferrara, I'd absolutely recommend to go there. And I even agree that it's worth visiting only to have lunch (we've discussed that on another thread with nessundorma, and I fully supported it) - but that makes sense if you can make Bologna a stop while traveling by (like the OP in the other thread I mentioned). You won't get a feeling for the city, but you'll have a splendid meal - well done! But going there from Tuscany, just to enjoy a meal? No.
What I've learned from my many, many trips to Italy is that you shouldn't mix regions excessively. On my first trips, that was exactly what I did - this was my first northern Italy itinerary: Cividale del Friuli, Aquileia, Grado, Venice, Padova, Vicenza, Montagnana, Pomposa, Ferrara, Bologna, Marzabotto, Modena, Ravenna, Rimini, S. Marino, Urbino, L'Aquila, Cerveteri, Tarquinia, Tuscania, Viterbo, Orvieto, Todi, Spoleto, Trevi, Spello, Assisi, Perugia, Gubbio, Pienza, Montepulciano, Siena, Volterra, S. Gimignano, Florence, Fiesole, Prato, Pistoia, Lucca, Pisa, Cinque Terre, Parma, Fontanellato, Mantova, Verona - and I'm sure that I don't remember everything (it's quite a while that I made that journey). We had five weeks for it, so believe me, I know what's insane!!!!
What I've learned since, however, is that you don't really get a "flavor", or better: you get a flavor, but it isn't the flavor of the region through which you are rushing. It's only the flavor of your own "amazing race" schedule. You have your checklist, visit whatever is artistically important (we did 108 churches in that holiday, if my memory is correct) - but as soon as you come back, you'll discover that your first impression was entirely wrong. You've seen the churches. You've not seen the places where they are. And the same is true if you go for restaurants or specialty shops instead of churches...
One of the most amazing features of Italy is its incredible diversity (there is no "Italian cuisine", e.g. - just Umbrian, Roman, Tuscan, Sicilian and so on cuisines). And I think you're doing yourself a favor if you give this regional diversity its due, and limit your itinerary to few regions which to explore with more attention to their particularities.
But of course, everyone as he or she wants.

Thanks for your comment PoohGirl. I've never been on a trip this long. That's why the title of this post. I'm very excited about this trip now and not so worried anymore. My mom was born in Italy, so, for me, this trip means getting to know a little bit more about her homeland.

Thanks Franco and BobLudLow. I've decided not to plan anything for that day off in Florence. I'll have a couple of plan B's and decide what to do that same day when I wake up depending on the mood I am for.
Of course, I always take into account other posts' advice; otherwise, what would be the point of asking for it if I'm going to ignore it?

To be honest, I have that extra day in Italy because my travel agent couldn't get me an inexpensive airplane ticket to come back a day before. That's why I don't know what to do with it. I decided to add it to Florence because that's where I felt I'd have the most choices for a daytrip, and because I felt I was dedicating too much time in Campania.

I still think that maybe I could spent 7 or 8 days in Campania instead of 9, but doing that would mean not to overnight on Ischia and I'm already excited about it. I'm kind of hyperactive. I can't be in a place with nothing to do. That's why arrival days are resting days for me, because those are the only ones that I like doing nothing but rest at the hotel/convent or sit in a square and do nothing. Besides, my Campania part of the trip is kind of tight and I am definitely going to need those 3 resting afternoons.

I already booked all of my hotels/convents. I decided to book Hotel Bougainville in Positano since it seems to be the only inexpensive and decent place there that accepts credit cards. As for Capri, I booked Hotel Mediterraneo in Anacapri. According to many posts I read on Tripadvisor, all of the other inexpensive and decent hotels that I found on Capri lied about accepting credit cards (and where not really that decent). On Ischia, I'm staying at Albergo Il Monastero, which is housed at the Aragonese Castle.

I'm staying at a convent in Venice (Casa Caburlotto), Florence (Villa Agape) and Rome (Fraterna Domus), and at Hotel La Cisterna in San Gimignano.

Thanks again for all your thoughtful comments!

reduce your days in venice, 3 is plenty, it will be hot crowded, smelly and expensive, maybe spend more time in umbrian countryside eg Orvieto

I agree to lessen your time in Venice. Also Positano...not 3 days. Hopefully you have your hotels booked for Ischia and Capri...you are travelling during high season. It will be hot! Enjoy your trip!

Thanks Fisches and Woodsie.

I'm staying in Positano for 3 nights because I'll do daytrips to Pompeii and Amalfi/Ravello.

Venice is my favorite city in Italy. I can't get enough of it even though I've been there twice. I'm always looking for an excuse to go back.

lonelyplanet - you know that you owe us a trip report in August as soon as you'll be back? Have a nice journey, and greet Italy!

insanley wonderfully lucky! and Im insanely jealous! Have a trip of a lifetime!