Fall in Tuscany: Medieval towns and the Chianti wine country

Upcoming Tours > Upcoming Tours 2026

If your image of Italy includes cypress trees, red tile roofs, wine and pasta, this is your trip. We’ll spend half our time in the Chianti countryside at a beautiful villa and half in the medieval town of Lucca. We’ll visit gems like Siena and the Cinque Terre, join a truffle hunter and his dog in the woods, and cook alongside a world-class chef in his convent-turned-cooking school. We’ll visit wineries and see the grape harvest in full swing. September is Wine Festival time – lots of music, celebrations and toasting!

This small-group trip includes:

Accommodations, private drivers, train tickets, most meals (with wine, naturally), wine tastings, private guided tours, cooking lessons, private boat along the Cinque Terre, and exclusive local experiences. And your own private, 24/7, Italian-speaking guide.

More details here.

Price: $4,550 per person, double occupancy (based on ’24 pricing; waiting on vendors for ’25)

$5,915 per person, single occupancy

Dates:

September 5-15, 2026