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Roughly 110 miles to the southeast of Monticiano is where you will find the city of Rome.
Go north to San Rocco a Pilli, only 10 miles from Monticiano. A few of the leading sites here include Torre del Mangia and Siena Cathedral.
Remember to take a trip to Lama. When you arrive, see Abbazia di San Galgano, a popular attraction.
Nothing beats the rolling waves and that salty ocean air. Head down to Zocco Beach, 50 miles to the east. If you are not in a hurry, move ahead to Sualzo Beach, 45 miles to the east.
Pack a picnic lunch and discover the magic at Piscine Termali Theia, located 30 miles from Monticiano. Another option is Hedonistic Hiking, which is 16 miles away.
Stadio Artemio Franchi is located in Siena, 15 miles north of Monticiano. It's known as the home grounds of the A.C. Siena. Black and white are the colors of the A.C. Siena, so be sure to don some.
Ecco La Cucina and Eremo di Montesiepi in Tocchi are well worth visiting. This nearby destination is 2 miles from Monticiano. You could also stop by Church of San Nicola and Podere Ristella Vineyards and Winery in Sassofortino. This destination rests 8 miles out of Monticiano.
Castiglione del Bosco, a regional hub, is another top place to visit. It's around 10 miles from Monticiano and features a wide range of fascinating attractions, such as Museum of Brunello, Fortress of Montalcino and Civic and Diocesan Museum of Sacred Art of Montalcino. Museo della Mezzadria and Museum of Sacred Art in Val d’Arbia are additional sites if you have extra time.
Make sure you take your senses on a tour of the region's cafés and restaurants.
Pici (thick spaghetti) and steak alla fiorentina (Florentine steak) are well-known dishes you'll want to taste.
Scrumptious treats, such as ricciarelli (cookies made with almond, sugar and honey), are definitely worth trying.
Satisfy your thirst with a round of bubbly beer. Iris is right up there with the best.
Appreciate the full-flavored aromas that drift out from this region's most sought-after wines. During an evening meal, ask for a glass or two of Morellino di Scansano and Parrina.
Unfortunately, all vacations eventually come to an end. When the curtain falls on your Monticiano getaway, say "Arrivederci", spend the last of your euros, and remember all the crazy adventures you've had.
If you want to find the closest airport, it's roughly 45 miles to the north.
If you are looking for a hotel room in Monticiano itself, you may find that the list of available places isn't extensive.
If you and your travel companions are interested in booking a place to stay in the premium end of the scale, be sure to check out the Petriolo SPA & Resort, at Localita Bagni di Petriolo, or the Locanda del Ponte, at Loc. Ponte a Macereto S.S.223. Alternatively, the Da Vestro, at Via Senese 4 angolo via 2 giugno, and the Villa Vittorio, at Podere la Ripa Tocchi, are two thriftier choices worth investigating.