I convinced Tyler and our friends, Geraldine and Grant, to go to Montepulciano for the day while we were lounging around the villa one day. I had gone years ago and was itching to show them what a cute town it was. After they relented to my less-than-subtle nudges, we hopped in the car and drove an hour and a half. When we got there, I soon realized- I had actually been to Montelcino and had never been to Montepulciano before. Oops.
The good news for all of us was that this town was WAY better than I had expected to show them. Lucky for them (and me!), we got to spend a wonderful day exploring this charming town once run by the Medici family and still known today for its world class wines.
Plus, rolling the word "Montepulciano" off your tongue is one of the funnest things ever said.
To drive from Florence (which is the best way, since it's really complex to reach otherwise), you'll take an easy 90 drive south, past Siena. Park in one of the paid lots and wander in through one of the various city gates. We parked in lot #1 and it was a great starting point.
You can walk straight from the parking lot and into town. From there, it was a windy and colorful stroll up through into the city center. Along the way, expect fruit stalls, tiny artists' shops and touristy stops full of leather purses and ceramic goodies.
WHAT TO DO
This isn't going to be a day-trip that has a big bullet-point list that comes with it. Your main objectives for the day are to relax, catch some great views from the endless alleyways and vistas, and eat/drink well along the way.
You can make it up to the Piazza Grande (admittedly, a tiresome endeavor with a baby stroller) and enjoy the piazza life from there. Grab a cup of (delicious artisan!) gelato from the tiny cafe right in the square for a real treat. Or if you're feeling more energetic, you cna pay €4 to climb up to the top of the Terrazza del Palazzo Comunale for sweeping views of the Tuscan hills surrounding you.
WHAT TO EAT
If wine is your game, then you've got countless vineyards surrounding the town you can visit as this is the home of the famous vino nobile. The larger vineyards offer amazing lunches in gorgeous settings... along with pricetags that pair well with such an opulent experience. Some of the most famous vineyards in the Montepulciano area are Avignonesi and Contucci Cantine.
Tuscany is a great place to take day trips- really for any type of traveler. If you're young and looking to explore- these small, friendly towns are nearly fail proof adventures. If you're a couple looking for some romantic spots and lonely cafes, these towns offer it. If you're a family craving some culture, but feel exhausted by big cities- small towns like Montepulciano are a great middle ground. (Plus so many of the streets are pedestrian only, you don't have to worry about cars. Let those kids run free!)
*images original to aspiring kennedy by grant schol