Another Itinerary help request!


New member
I know there are hundreds of these requests, sorry! But it's our first time to Italy and I REALLY need advice please. We will have close to 5 weeks beginning in May 2015. Flying into Rome and spending 3 nights. The idea is to pick up a car and slowly wind our way north, so we end up in Milan to fly home in the middle of June.
So far I have booked accommodation in
Rome, then we pick up our car and head to
Montefiascone (booked) for a few nights to explore, then
Assisi for 4 nights (booked) explore the area
Then the idea was to find another town and spend another 4 days to take and explore the area further north of Assisi....I was thinking
San Gimignano, but some people have said it's way TOO touristy, but I thought if we stayed in the town we'd get to see it without the day trippers. And it would be a good base to use to explore the western side of Tuscany.
Florence - 4 nights
Then Levanto in an agriturismo in order to explore the Cinque Terra.
Then.....I'm stuck.....I would like to see the lakes and the Alps but don't want to spend our whole time in the car....what about
I'd really appreciate others thoughts and input, ideas and recommendations.
Is it unrealistic to try to get to Venice?
Many thanks

Pro Loco Sovicille

Well-known member
Itinerary help

for you 4 days near San Gimignano: San Gimignano is certainly a very beautiful and antique is one of the most well known places of the province of Siena, this is probably the reason why it is always very crowded....You could consider staying at about 13 kms from Siena, in Sovicille. It is a little and nice village with a lot of charming places. It is a good base to reach the wonderful town of Siena, the Chianti area, San Gimignano, the Val d'Orcia....if you need some help for this part of your itinerary, get in touch with us, we'll be happy to help you!
Tourist information office of Sovicille


The Tuscan Expert ;-)
Staff member
Don't worry, we try to help out as much as we can since everyone's itinerary is slightly different... and offer tips and suggestions to make it better!

San Gimignano would make a great base and is beautiful, and while it is true that it has become a popular destination, this is mainly in the day. If you're interested in it as a base for seeing the area, it would still make a great place to stay at - you see the area in the day and enjoy San Gimignano in the evenings when most of the crowds are gone. I'd also suggest not staying within the town itself, but just outside - so you'll enjoy the beautiful view of the medieval town as well.

Make sure to also visit Volterra and Certaldo in the area :).

I've actually been to Stresa and it's beautiful - I highly recommend it. How many days will you have for the lakes and Alps by then? The Alps stretch all the way from one end to the other of northern Italy, so you will have a lot of choice. If you go to the Lakes and Stresa, you could always then head east toward Bolzano and Trentino Alto-Adige for the Alps. Or maybe the Alps first, then the Lakes so that you're closer to Milan at the end for the trip back home.


New member
Thanks Lourdes for your reassurance regarding San Gimignano. I was trying not to be put off staying there as I thought we'd mostly see it in the afternoons and evenings after our daily jaunts! And I just love the look of the town itself. In saying not to stay in the town but just outside in order to enjoy the view, how does that go with getting to restaurants etc and not having to drive (we like our wine!)? I looked at Hotel L'Antico Pozzo which is I gather right in town. We don't necessarily want to self cater, as we'd enjoy others company and their tips and insights into sights etc. but B&B's is fine. Any recommendations close by?
Thanks also for the Stresa reassurance. We will have 9 days before we fly out of Milan. I have found an apartment right in town that is a good weekly rate and thought perhaps we could base ourselves there and do day trips. Thoughts?! I think now we'd both like to see if we can get to Venice as our last stop before flying home, so that takes a chunk out of the Stresa stay. Perhaps 3 nights in Venice, so that leaves 5 nights in Stresa and our last night near the airport in Milan before flying home.
Any other input and recommendations will be gratefully received.
Many thanks again.


The Tuscan Expert ;-)
Staff member
Yes, that's what I meant with staying just outside of town - take a look at the places we recommend on here:

There are several labeled as Agriturismo Niccolai - those are within walking distance from town, 2 to the south and one to the north. We went hiking in May around San Gimignano and noticed exactly how close they are! Two of these offer rooms - which are as a B&B option. Generally when you see apartments with their own kitchen is when you know they are self-catering... but if you see rooms available, those always have breakfast offered.

The Hotel Antico Pozzo is right inside the town, so during the day you might feel it is a bit crowded. Before booking there, ask about parking - parking in quite expensive in San Gimignano so if the hotel offers it as included, it might be a great chance to enjoy the town in the evenings with the comfort of having your car nearby to use during the day as you explore... but if it is not available or extra, take that into account. Parking in San Gimignano can be as high as 16 euros per day, if I remember correctly. Basically you pay by the hour but once you've passed a certain amount of hours, there is a default set fee.

Dividing Stresa and doing Venice would be a good idea - Stresa is on the left side of the lake, the islands within the lake are beautiful and a must while you're there and there are lots of charming towns all around (and across). I don't really know the lakes area that well, so can't recommend specific day trips but do know you're really close to Switzerland at that point... ;)