DAY 1: From Water to Wine (Province of Siena)
bagno vignoni
Whereas most Italian villages have a town-square at center, Bagno Vignioni, as its namesake suggests, has a giant geothermal pool at center, which might bring you closer to heaven than any duomo could hope to bring you were you allowed to swim in it. Nevertheless, free from contamination, it remains a beautiful sight to see. Before you complain about not being able to bathe in the town known for its baths, you can bathe nearby in the massive Parco dei Mulini spring, free of charge. There are no facilities here, which may be more authentic than you're used to, but if it's heaven that you seek, do bring your own towel and swimwear.
Suggested duration: 2-3 hours. Visit www.visittuscany.com for more information.
montalcino
One of two must-visit wine towns in the region (the other being Chianti detailed below) Montalcino is known for its production of Brunello red, which takes five years to age, two of the years in oak barrels, meaning that if you try it and you don't like, it's more likely there's something wrong with you than with the wine. Of course, you could just settle down for wine and brunch right away but if you like to earn your keep, you can climb the Rocca fortress for impressive views of Montalcino and Val D'Orcia - let's face it, you won't be climbing any stairs after going through a few bottles of wine. The most you'll be able to manage at this point is a meander through the cobblestone streets, without the inhibition to save you from patronizing every craft store you come across.
Suggested duration: 2-3 hours. Visit www.visittuscany.com for more information.
val d'orcia
It's not a specific place you need to see but rather the region as a whole, with its picture-perfect pastures and undulating hills, all best experienced while driving from one town to the next, assuming of course that either you're sober, or you have a designated driver (boyfriend, husband). In any case, every town has its own speciality wine worth sampling, so it's best to keep it just at that: sampling. That way you can drive from town to town to see and try all the best that Tuscany has to offer without worrying about getting into a horrific car accident, then whatever you like most, you can buy and take home with you for unhindered indulgence.
Visit www.wanderingitaly.com for more information.
BONUS: Pienza
If upon your visit here you conclude Pienza to be the perfect Renaissance-town, that's because it was designed with that intention in mind by Pope Pius II in the 15th century. This is primarily reflected in the layout of the town and the architecture of the individual structures, but all of this is perhaps justly overshadowed by the real reason for your visit - cheese. Pienza considers itself to be the capital of Pecorino cheese. While it's not quite the seat of a governing body that governs over all matters related to pecorino, they still make a mean cheese, plus there's a cheese festival on Sundays in September. Once you've finished eating the cheese, you can get extra-cheesy on a romantic walk down such romantically-named streets as Via dell'Amore (Love Street) or Via dell'Bacio (Kiss Street), where tourists are known to pack on the PDA. Unfortunately, Italy is a conservative place, so you won't see a Via della Sex.
Suggested duration: 2-3 hours. Visit www.visittuscany.com for more information.
montepulciano
In this medieval village, you'll be treated to the perfect view from Plazza San Francesco. If you've timed the day right, you should arrive just in time to watch the sunset upon the village, Templo di San Biagio, and the surrounding landscape. Now that darkness has limited the sights to see, all that's left to do now is drink and what better place to do so than the home of Vino Nobile, one of the most acclaimed wines of the region, made from grapes grown in the very landscape that you just watched the sun set upon.
Visit www.visittuscany.com for more information.
STAY THE NIGHT IN: montepulciano
DAY 2: All Along the Watchtower (Siena and San Gimignano)
Siena
This medieval town is most famous for its central Piazza del Campo, site of a bi-summer horse race, featured in the James Bond film Quantum of Solace, which is worth seeing (the race, not the film). You can also check out the Duomo, but your time would be better spent in the Museo Civico which houses the famous Lorenzetti frescoes Allegory of Good and Bad Government, the former being what all politicians promise and the latter being what all politicians end up practicing. If you've fallen in love with Siena, and wish to extend your stay, you can climb the 500-step Torre del Mangia. Otherwise, save some fuel for the rest of the day's towers.
Suggested duration: 2-3 hours. Visit www.visittuscany.com for more information.
Bonus: monteriggioni
You can see this fortified village, with its perfectly circular outer wall, from miles away in any direction. It was famously mentioned by Dante Aligheri in his poem "Supreme Poet" (how modest) comparing the village's towers to "horrific giants." A highlight of your visit will be a walk along the circumference of the outer walls, connected by 14 towers, where you pretend to be a medieval knight tasked with defending the wall, until you get distracted taking selfies, leaving the village defenseless against invading armies. The ticket to the wall also gives you access to the Armory Museum where you can further indulge your imagination by wearing armor and playing with swords, until you get tired and cranky swinging a 20-lb sword, and give up, again leaving the village defenseless. If dressing up medieval is your thing, there's a month-long Medieval festival each July.
Suggested duration: 2-3 hours. Visit www.visittuscany.com for more information.
san gimignano
What looks like a city in the approaching distance is actually a medieval village famous for its many towers, the "Manhattan of the Middle Ages," though with less attitude and more pizza, we'll take this over Manhattan any day of the month. Of 65 or more original towers, only 14 remain; you can climb the tallest tower, Monte Grosso, for an excellent view from within the village but a better view (and less of a climb) you'll find from Rocca di Montestaffoli, a ruined medieval fortress with a beautiful olive garden. While in town, try the local saffron, used liberally in most dishes, and pair it with Vernacia di San Gimignano, the local white wine.
Suggested duration: 2-3 hours. Visit www.visittuscany.com for more information.
BONUS: volterra
This town likely has a wealth of rich and fascinating history. Even more importantly, it was heavily featured in the Twilight series. Don't worry, Volterra is actually the only place in the world where you're guaranteed not to get attacked by vampires. Vampires forbid themselves from hunting humans in the confines of the city so as not to expose their presence there. It's too bad, because there's a beautifully preserved Roman-amphitheater just outside of town that would make for a perfect spot to catch the sunset, but it's probably just a tourist trap - literally - once the sun sets, the vampires attack. Besides vampires, Volterra is well known for its alabaster. If you're looking for something unique, don't shy away from the craft stores; the shopkeepers won't bite, most likely.
Suggested duration: 2-3 hours. Visit www.visittuscany.com for more information.
STAY THE NIGHT IN: Volterra or Chianti
DAY 3: Day Drinking (Chianti)
chianti
If you're following our three day itinerary through Tuscany, you've probably seen a lot of sights. You deserve a day to just unwind over a glass, or seven, of the region's finest wine varieties. Fortunately, in the Chianti region there's not much to see other than the picturesque surroundings of the various vineyards you will frequent. If you can moderate yourself while drinking, a bike ride rental would be the most picturesque way to cover multiple vineyards. If you're the type of person that can't walk straight, let alone bike straight, you should definitely consider hiring a local driver. Some vineyards even have their own accommodations, so you can kill two birds - drinking excessively and passing out somewhere nearby - with one stone.
Visit www.chianti.com for more information.