Hi!
We made reservations for a gorgeous place to spend our 20th anniversary, it's about 14 minutes SE of Cortona - is this too far out to do day trips to wineries and towns? Any info is appreciated!
14 minutes by car is nothing provided you have a car.
You will be within 2 hour drive from most of Tuscany and most of Umbria. There are hundreds of wineries and towns around, some within a few min drive.
Near Cortona you can visit (in alpha order): Anghiari, Arezzo, Assisi, Castiglion Fiorentino, Castiglion del Lago, Lucignano, Montepulciano, Perugia, Pienza, Siena, Spello.
And I'm mentioning only some of the most famous towns you can reach in less than one hour drive.
Great! Thank you so much for your input!