Siena or San Gimignana
 

Still planning our honeymoon and this is our itenerary so far:

June 27th: arrive in Rome from San Francisco
June 28th: Rome
June 29th: Rome
June 30th: Rome
July 1st: Leave Rome for either Siena or San Gimignano
July 2nd: Siena or San Gimignano
July 3rd: Siena or San Gimignano
July 4th: Siena or San Gimignano
July 5th: Leave for Florence
July 6th: Florence
July 7th: Florence
July 8th: Leave Florence for Venice
July 9th: Venice
July 10th: Venice
July 11th: Leave Venice for San Francisco (sniff, sniff)

My dilemna: between Siena and San Gimignano, which one did you prefer? is this too much time at either of these places? should we spend some time elsewhere (such as CT)? and finally, because it's our honeymoon, can you recommend some hotels/B&Bs in either Siena, San Gimignano, or CT that are romantic (want to spend around $200 or so per night).

Thanks for your help!

Hi garyt, congrats on you upcoming nuptials!
Siena or San Gim....such a wonderful dilemma! You must look at some books and see which calls out to you the most.
That being said-if you are traveling by train, both places are inconvenient to the station. San Gim a bit more if you "land" during siesta time as there can be fewer taxies to be found. Siena is larger, ergo, more places to see, more restaurants. Many have said that San Gim is so much nicer after the day trippers have left.
I personally would add a day to Rome and 2 days to Florence and make Siena and San Gim day trips from Florence. OR go to Siena and make San Gim a day trip from there. Good luck and please report back!

San G. is very small and really can be seen in a day. We stayed there a couple of nights and indeed, the best time to see the city is after the tour buses leave in the evening. I would see the city on a day trip and add more time in Rome. If you do go, don't forget to climb the tallest tower (with the bell on top) to get a stunning view of the Tuscan countryside. When we did that early in the morning, we witnessed the fog rolling in and settling in the valleys and eventually covered the entire ground. It was spectacular.

For what it is worth, I really disliked being in Siena. Once you get inside those walls, there really is a feeling of enclosure. It feels very medieval and sunless -- except of course for the huge campo in the center, where all the tourists are. It's an astonishing sight, but it was not my favorite piazza in Italy. It was more like sitting in a soccer stadium.

Siena has its marvelous art treasures and historical buildings, although I found even those very dark and rather harsh and brooding. It was also extremely crowded the day I was in Siena, and that added to the sense of not having much space to breathe.

I wish I had liked it better, and I don't disbelieve the people who love it and say it's a top destination. I have never been to San Gimigiano (nor been in Siena at night) so I can't compare. I think I just happen to fan of nature and open vistas, and Siena is not the only Italian city that can make me feel hemmed in.

I loved Siena but I don't think it needs quite so much time. I haven't visited San Gim, but since it is smaller than Siena, I'd expect it would need even less time.

Free advice, maybe worth exactly what you're paying for it: Rome and Florence look about right.

But I think you're a little light on Venice time. That city oozes romance and is all about just soaking it in, and I'd move a night or two from Siena/San Gim to Venice. Especially while on a honeymoon. Heck, anytime.

And remember, I loved Siena, so that's saying something for Venice.

Since you'll be in Italy near the peak tourist season, more time in Venice will allow you the leisure to see the major sights then just wander all over the city and get away from most of the crowds. You'll love it.

If, on the other hand, you're planning a lot of day trips from Siena/San Gim, you might need the four nights scheduled in Tuscany.

Are you driving in Tuscany?

Hi Gary,
A few comments. First, congratulations on your upcoming wedding.
Second, if you're arriving in Siena on July 1st, that will be just in time for the Palio. I think it's on July 2d. Siena is very crowded, but great fun and very colorful during this time and there's much excitement over the Palio. So that might influence your decision one way or another. If you decide to stay in Siena, you'd better book soon. I suggest the Villa Santa Caterina.
Tuscany.net/santacaterina.
It's very lovely, right outside the city walls, about a 15 minute walk to the campo. Ask for a room facing the garden. They have beautiful views.

That being said, I think 4 days is too much for either Siena or San Gim. Three days are more than enough to stay in one and take a day trip to the other.
I'd do a day trip to San Gim and give the extra day to Rome or Venice.

More time in Venice,no more than 2 days in Sienna and stay outside of the walls. We stayed at the Garden Hotel, very nice. San Gim is a good day trip, wouldn't stay there.

check out relais and chateaux website. there are also ather choices for Tuscan countryside feel in Chianti region. That will contrast well with your sicy visits to Rome, Floreece and Venice.

Having been to Italy quite a bit, we like to go to a true Italian spa for a few days. Don't know if you have thought of that. The Termi di Saturnia is not far from Rome.

In case it helps, we'll be leaving for Italy on Sept. 1st. Arriving in Florence for 4 nights, then 2 nights in San Gim and 3 nights in Cortona, then 4 nights in Venice.

My brother has been a couple of times and he thinks that Seina is more like Florence (bigger, more comotion) and suggested that we skip it all together this time. He recommended that San Gim (enjoy it at night after the throngs of tourist slip away) and Cortona would be a slower pace, more relaxing and we can do easy day trips to Volterra, Pienza, Orvieto, maybe Montalcino or Greve. Sienna is only an hour from either San Gim or Cortona, there abouts. I'd be very tempted to see the Palio if I was there during that time.

This will be my 2nd trip to Venice and I'll add to the side that says you won't regret spending extra time there. It's THE most Amazing place I've ever been.

With 3 major cities in your itinerary, you might be glad you slowed it down for a little while.

If the Palio is July 1st and you think you might want to stay in Siena, book a room immediately. Even if you later cancel. Waiting to book could cost you the option.

If it is Palio, also be prepared for the possibility of a minimum stay and elevated prices.

A lovely hotel in Siena is the Palazzo Ravizza; ask for a room over the garden at the back and looking out on the rolling green hills of Tuscany.

Garyt: First of all, congratulations on the upcoming wedding.

As for the Siena - San Gimignano matchup I love both, but I'd agree that four days in either one might be a bit too much, although exploring all the nooks and crannies of Siena could take you that long. Siena is a medieval city and San Gimignano just a medieval town, so both are worth seeing. The closed in feel of Siena is part of its beauty; many people lived here in medieval times. I understand nessundorma's feeling about being closed in, but I happen to think that exploring those rabbit warren streets is part of Siena's charm. One big difference between Siena and many of the Tuscan hill towns is that most all of those towns are small enough so that you could wander a block or two in almost any direction, and that wandering would take you to some dramatic vista at the city wall. You can do that in Siena too if you follow the outer wall, but you might have to go a way to get there. It's sometimes a bit hard to avoid getting swept into the Campo in Siena, but exploring outlying areas is certainly worthwhile.

If you are indeed going to be in Siena during the Palio (run twice, once at the start of July and once in mid-August), you will see a different city than you would at other times. Bands of flag twirlers and singers from the different contrada (there are seventeen, each with a different flag and different colors) roam the city, and associations in the contrada set up outdoor dining (I assume just for the locals; I wasn't brave enough to ask). The Campo will be set up for the race, so it won't have the same feel as it ordinarily does, ringed by stands just for the Palio. It will be a busy, loud, and colorful time. Indeed, it may be hard to get reservations even now. We were there last year in the days leading up to the Palio (first weeknd in July in 2005), and it was exciting to wander the streets and come upon all the celebrations.

With its towers rising over the Tuscan countryside, San Gimignano is a very different sort of place, seeming to have more of the fortress mentality and less of the marketplace bustle of Siena. It is certainly worthwhile spending one night in San Gimignano, however, since it can get overwhelmed with daytrippers during the summer months. Things slow down after 5:00, and it is great to wander the streets in the evenings. Indeed, I think that one of the most romantic aspects of Tuscany is wandering through the small hill towns. Volterra, Pienza, Montepulciano, and (a bit farther afield) Pitigliano are all places you could spend a good chunk of the day watching the people, seeing some history, and sampling the cuisine.

I hope you will be driving, since it's difficult to visit the hill towns of Tuscany without a car. If you leave Rome on the 1st, it will take you about three and a half hours to drive into the heart of Tuscany. If you want to experience the Palio and can get a place in Siena, that should be your first stop for a couple of nights. I'd suggest spending the other two nights in San Gimignano and devoting one day wandering through the countryside, visiting one of the towns I mentioned (or even some smaller ones like Casole d'Elsa or Monteriggioni), looking at the sunflowers, and maybe visiting a fattoria (winery) in the Chianti region. Reverse the times if you want to avoid the Palio or can't get rooms in Siena on Saturday and Sunday, since it will be over on Monday. You could certainly add more time in the big cities, which are also wonderful, but I think (my wife agrees) that the romance of Italy is in the small towns of Tuscany. We spent a week exploring them a few years ago and have been back twice since then just to wander in rural Tuscany

Midnightsun,

Your descriptions are beautiful! I am looking forward to a brief visit to Siena on our way to Venice. Thanks for the info.

Save yourself too much moving around...I have stayed ay both several times, and I prefer the San Jimmy area...it can be the base for visiting all the hghlights of Tuscany on day trips, coming back to SG after the tourist busses leave at 4 pm...the town is lovely at night. We prefer the Hotel Pescille about three miles out of town surrounded by its own vineyards and great views of the towers of San Jimmy..reasonable, about 130 E's, pool and lovely grounds.
Stu T.
http://www.pescille.it/pescille/index_en.php

gosh, you all have great advice! thank you all!!! i tried booking the hotel santa caterina, but they don't have any available rooms until the 3rd (probably after palio)...bummers! the hotel looks absolutely gorgeous!!!

i'm leaning toward avoiding the crowds in siena especially after coming from rome. are there other beautiful areas and hotels in other areas of tuscany that would be just as great? i would tend to not go from florence and then back to siena and then head to venice...seems like we would be back tracking. what about the possibility of heading from rome to cinque terre instead first (or is this too much moving around)? by the way, we are doing this all by train.

thanks again!

I think moving further west to Cinque Terre would be a mistake. If you are looking for a break from the Roman hordes, why not stay someplace just a bit beyond Firenze where you can easily day trip in but also not have to deal with the mobs of people who are in Firenze in the summertime?

I've never stayed in Fiesole, which sits just above Firenze and has marvelous views. (Has anybody stayed in Fiesole?) Or perhaps there is another very lovely spot within an easy bus or train ride to Firenze and San Gimigiano that would work just as well.

So maybe the answer to giving you some peace and relaxation after the stress of a wedding is:

5 nights Rome
5 nights Tuscany somewhere close to Firenze, with day trips if you feel like it
5 nights Venice

(am I counting right?)

Just brainstorming here but I've sometimes heard that Prato is a really underrated, charming place - one train stop away from Firenze.

Any chance this is true and that there is a great or charming hotel there?

You might want to read this, garyt:

http://www.tripadvisor.com/ShowUserR...o_Tuscany.html

And here's their website:

http://www.toskana.net/villarucellai/english/index.html

For what you'd be saving in the cost of a hotel room, you could afford taxis to drive you to the train/bus station for your day trips.

Hmmm. And I see Karen Brown recommends it too:

http://www.karenbrown.com/property.asp?propid=10600

We'll be staying here after Florence:

San Gimignano: Antico Pozzo www.anticopozzo.com

and here before Venice
Cortona: Villa Marsili Hotel http://www.villamarsili.net/eng/index.html

We plan to have a car in Tuscany to allow us the freedom to move around.

We stayed in Montecatini Terme. It is very popular with Europeans "taking the cure of the waters" if you look it up, you will understand. It is very different, often described as the "Palm Springs" of Italy. It is just west of Florence and there is a great hill town to have sunset dinner. Has anyone ever eaten at Pietre Cavate? I cannot believe I even remember the name its been years.

I agree with the thought of visiting towns and not all cities and using San Gim or anothr town as a base. I wouldn't do Fiesole, too close to Florence. Many towns like Greve, Castellina, Orvieto can be a half-day trip. We had a routine of heading out to see a town, then a great winery, pick up a bottle or 2, grab a nice lunch, then maybe 2-3 hours of R & R at the hotel pool (we always try to pick a place in the countryside with a really nice pool). Maybe another place later in the day and have dinner there. Some of them may take longer to get to than you think. It can seem like FOREVER, first you wind up the mountain, then you wind down the mountain. Try to stay more on the main roads if you can.

This is my recommendation by San Gim if you can get a room, it may be pricey though.
http://www.lacollegiata.it/

By Sienna take a look at: http://www.certosadimaggiano.com. But I have expensive taste and I don't know your budget.

If you are driving from Rome to Sienna, Orvieto is a good place to stop and visit and have a nice meal.

Sometimes if I find an amazing place to stay I use that as a base.