La Dolce Vita Wine Tours

Tuscan Trek

Walking the Wine Roads of San Gimignano and Montalcino

Trip Notes:

Hiking Level of Difficulty

This is one of our easiest hiking tours, for two reasons. First, there’s a support van that accompanies us every day, so you can jump in the van if you get tired. Second, for the majority of the time, we’re walking on gravel country roads. That means there’s no tricky scrambling on rocky trails, no mountain steps, hardly any hilly vineyards, and just an occasional dirt path in the woods. But there are hills (this is Italy, after all), including a couple of steep ones. But as we say, piano piano, take your time, and you’ll be at the top before you know it. Be prepared to walk 3 to 4 hours every day, except the shorter warm-up hike on Day 1. That’ll let you enjoy an extra gelato guilt-free!

Airport

Florence or Pisa (continental), or Rome (intercontinental nonstop). To land in Florence or Pisa, you’ll need to connect somewhere in Europe. From the Florence airport to the city center, it’s a 20-minute taxi ride. If arriving in Pisa, the airport has its own train stop and is only an hour from Florence. Rome is the closest intercontinental airport, with direct flights to the US. If arriving in Rome, you’ll need to take a train from the airport to town (30 min.). Then from Rome’s main train station, it’s only 95 minutes to Florence on the fast train (EuroStar); the latter requires reservations.

Pre-tour

Plan to land in Italy at least a day before the tour begins; that’s necessary to be at our starting point on time. Most people spend the preceding night in Florence. For hotel suggestions, email us or consult a good hotel search engine, such as TripAdvisor or Venere. If you’re spending just one night, we recommend staying near the main train station, Stazione Santa Maria Maggiore, since that is our meeting point. Otherwise, take your pick of neighborhoods. Florence is not a huge city, and it’s very walkable. In fact, we encourage you to get out and walk around; the streets are a living museum!

Meeting point

Our meeting point is Florence, at the main train station, Santa Maria Novella (details will be indicated in your information packet). From here, we shuttle to Chianti (about 1 hour), where the tour gets underway. (We cannot pick up from individual hotels because only taxis and permanent residents are allowed in Florence's city center.)

Departure day

On our final day, we’ll have you back at the Florence train station by noon.

Italian train schedule

Click here for the Trenitalia schedule in English. Be aware that the schedule is posted only several months in advance, so if you’re looking for long-range dates, try something sooner, just to get an idea of departure frequency and trip length.

Trip extensions

Because TUSCAN TREK does not include any time in Florence, we recommend spending a few days in this fabulous art city, either before or after our tour. Florence is easy to navigate on your own. But there are also excellent thematic walking tours offered by our friends at ContextTravel. If you’d like to explore other small-sized cities in Tuscany, Florence is well connected with Lucca (1 hr, 20 min) and Arezzo (1 hr) by train. And it’s just a hop and a skip to Rome on the EuroStar express train (1 hr 35 min).

Weather

When packing, check check www.weather.com. Go to “San Gimignano, Italy” and “Montalcino, Italy” to get a general idea of temperatures and forecast. By mid-June, we’ll be experiencing nice summer weather, with daytime temperatures averaging 80º and nighttime dipping back to 60º. In October, fall weather has commenced. Daytime temps average 60º and nighttime 47º, with a chance of sporadic showers.

Reading

Articles by La Dolce Vita Wine Tours cofounder Patricia Thomson:
"Vernaccia: A Medieval Wine for Modern Times"
"Castello Banfi: Transforming Brunello"
"Supertuscans for Mere Mortals"
"Wines in Florence: Frescobaldi and the Rise of the Wine Bar"