Tuscany surprise trip itinerary

Sounds good as long as you have some time to spend in Lucca, it's a lovely little town. Not sure how far Volterra is from San G,if not too far just spend a 2nd night in Volterra as it's time consuming and a pain (imo) to keep changing hotels a lot. You'll have to make sure to buy her some leather for the b-day too!!

That's so great that you want to give your wife a trip to Italy for her birthday. Clearly you're a thoughtful guy. Since you said "Any advice would be appreciated" I hope you don't mind me asking if you're sure that doing this as a surprise is the way to go. Again, I know your motivations are perfect, but if she's at all like me, at least half of the fun of such a trip is in the anticipation. There was an excellent article in the NYT about this recently: How Vacations Affect Your Happiness. Here's the money quote: "In the study, the effect of vacation anticipation boosted happiness for eight weeks. After the vacation, happiness quickly dropped back to baseline levels for most people." Knowing that the trip is coming will also give her the chance to plan what to wear, make sure she's got good shoes, etc. And who knows? There might be some specific place in Italy that she's dying to see that's NOT on your itinerary. Venice, for example. So my advice to you is to give some thought as to how to surprise her with this. She might want to be part of the planning. Happy travels.

Michael, Appreciate the thoughts, but I know her very well and she will be just fine with being surprised. I will tell her sometime before the trip the dates we are going and what clothes to wear/pack, and she will obviously know once we check in the airport where we are going, but I have no doubt that she will be tickled pink that I planned everything.

San G is only 40 kilometers or so from Volterra. Easy day trip in the car. Some nice scenery between the two. Some Volterra tips:
Web&Wine has some awesome zucchini bruschetta and prices are decent. Also, across the street there's a cool little bronze workshop. Owner is friendly and will BS with you. Prices are about average with the rest of town. Montagnani Spartaco I believe is the name of the shop. Both on Via Porta del Arco. The Etruscan arch is a couple hundred feet down the street. Avoid buying food/caffe in Piazza dei Priori. Expensive and not as good as other parts of town. Parking: Besides the #2 lot that the RS book has as a free lot, #6 is free also. Just be sure you don't park in spots reserved for emergency vehicles. There are signs in English. If you'll be there on a Sat. don't park in lots 4 or 5. Market day. Inside Chiesa San Francesco there is the Cappella della Croce with some interesting frescoes. Teatro Romano- it's not much $ to get in but you don't get a whole lot more than you do from the view above on Via Mandorlo. Some informational plaques and a bit closer view is all you get. The one hour RS walking tour. It was ok. Pretty much all the same info you get from the tour book. There's an alabaster shop right across from the alabaster museum that features (functional) guitars, drums, flutes etc made from alabaster. I thought that was pretty cool. Nice departure from all the usual plates, statues etc. Also, shop around for the alabaster souveniers. Prices vary.

Stan, you are such a romantic. I love it. Do you have a brother (like you)?

Yes I do. And he's single. :-)

Nice Stan. Did that for my wife for our 30th anniversary. She thought we were going to Bahamas where we have a second home and instead we went to Amalfi to her favorite hotel. Keeping it a surprise is hard. Now on to your schedule. Looks good. I would spend 2 nights in Volterra and just visit San G. one day. They are very close. We stayed in Volterra last year and picked a highly rated place, and very reasonable place from TripAdvisor and were very happy with it. It is called Villa Porta all ' Arco. Currently number 3 on their list. Ask for a room in the back with a view.

Okay. Why hasn't anyone suggested a great agriturismo for the entire time? Or two different ones in different locations? Every time we go to Italy, our best experiences come from having a home base. The agriturismo can be upscale with dinner/cooking lessons....and would be a great present ! Then you can drive to ANY town you wanted instead of packing every day or two. And you could choose your cities based on how you feel when you wake up instead of choosing them now and having lodging planned. My husband and I are in our mid 50's and will drive into 2-3 towns in one day to explore, eat, and wander.
I know readers have favorite places they could suggest !!

Thanks so much for the great suggestions!

Agree with Carla... lots of driving around Tuscany can be fun, but not when you are repacking and moving all the time. How about one move in the middle?
Sounds like a wonderfuo surprise no matter what you do. You could just skip Florence since you have already been there unless you really want to revisit. How about more time in wine country and little villages?