Siena would make a great base for your 5 days in Tuscany
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As you've already discovered, it isn't easy to move around the smaller towns in Tuscany with bus. Since the majority of your destinations are in the central area closer to Siena, I'd think Siena would be a better base than Florence. Consider
Volterra, San Gimignano and
Pienza are
towns while
Chianti is a
region so you need a more precise destination in Chianti when trying to get there/move around.
For
San Gimignano and
Pienza, as both are within the province of Siena, you can go to
http://www.busfox.com/timetable/ to check bus timetables.
- Bus from Siena to San Gimignano (bus 130 from Via Tozzi) - about an hour ride and costs 6 euro each way.
- Bus from Siena to Pienza (bus 112 from Porta Ovile) - about an hour and 10 min, costs 4,40 euro
Volterra is in the province of Pisa so requires a little bit more info, this is where I can be of help
From Siena, you get to Colle di Val d'Elsa (bus 130, same one that goes to San Gimignano) - takes about 30 min and costs 3 euro. Then from there, you need to catch another bus, line 770 ran by CPT (the company that runs service around the province of Pisa) that goes from Colle to Volterra - you can see timetables here:
Line 770. As you can see, the latest return bus from Volterra runs at 13.15 so you really need to do Volterra early morning to be done by then to head back to Colle! Once in Colle, bus 130 gets you back to Siena and since there are several buses in the afternoon, you can actually take the time to see the small charming town of
Colle as well before heading back to Siena!
If you really want to see the wine region of
Chianti, since there are small towns spread out all over the area, the best solution here might be to actually do an organized tour. They usually focus around wine tastings, so you're driven around, stop at 2-3 wineries, including a light lunch with typical Tuscan products in the middle and then driven back. Many of these run out of Florence but I know
Vinaio also offers tours out of Siena. From Siena you can do a tour of Chianti which falls to the north of Siena, or to the south toward Pienza and Montepulciano and Montalcino - these last two are two different important wine regions in Tuscany as well.
Ask if there are tours already planned that you can join up with so that the cost of the tours cost less... generally the more people on the tour (although try to be less than 20 for it to be better organized), the cost per person falls.
As for where to stay: there are some nice hotels in the center of Siena that will make you feel like you are in the countryside. Siena is very different from Florence. The center is mostly closed off and there is hardly traffic, it is more quiet and relaxing.
You can find a wide range of hotels that are within the same price range but that range from more basic to much nicer, I really encourage you to take a look with a price range in mind so that you can see what comes up. Look at their location and stay a little further from Piazza del Campo so that you're closer to the bus stops you'll be using (for example, Via Tozzi is where bus 130 leaves from and that is near the Siena stadium so the B&B San Francesco below is really close by.) Here are some you can look at to start your search:
B&B San Francesco
Il Casato
Cannon d'Oro
Il Chiostro del Carmine
Hotel Italia
Consider staying a double room with your friend so that you can divide the cost - single rooms will cost more. Since you don't say what period of the year you're thinking of coming, consider that June-August is the high season so everything costs more than if you come in September-November or March-May. Lowest season is from November-February (excluding the Christmas and Easter holiday period).
Hope this information helps you in your plans!! If you have any further questions, don't hesitate to ask!!
