Place your deposit now for our May 2026 escorted tour. Exact dates to be determined. This tour is designed for the new to Italy traveler who is looking for a different experience. See itinerary for activities in the tour. We must sell at least 1 spot (1 fully booked room) in order for this tour to happen. Tour space is limited to 6 people (3 fully booked rooms).
Escorted Umbria and Tuscany May 2026
Itinerary
This escorted tour includes the following activities:
Fluent Italian and English speaking tour director joining you on each outing.
Tastings at 5 local vineyards (you pay the vendor directly)
2 lunches (you pay the vendor directly)
Private transport to and from the places on the itinerary
Private tour guide for each medieval city we visit (subject to availability)
DAY 1
Quick 12:00 pm check into your room then jump on private transport to a local vineyard for a tasting session. Enjoy the winery for a few hours before heading back to your room for an apertif at 5 pm.
DAY 2
Wake up and enjoy cook to order breakfast at 7:30 am. By 10, you board the bus and head to the first stop, Castiglione Del Lago, where you can explore for 2 hours before heading to a local vineyard. There, you will enjoy a private tour and tasting with a light lunch. You will be at the vineyard for 2 hours before boarding the bus to Passignano. You can explore the city and take the ferry to Isola Maggiore where you can explore the island. By 5 pm be back on the bus and on your way back to your room for an apertif.
DAY 3
Wake up and enjoy cook to order breakfast at 7:30 am. By 10, you board bus and head to the first stop, Spello, where you can explore for 3 hours and enjoy lunch on your own before heading to a local vineyard. There, you will enjoy tasting the wonderful wines made at this vineyard. By 5:30 pm you board the bus back to your room for an apertif.
DAY 4
Wake up and enjoy cook to order breakfast at 7:30 am. By 9 am, you board the bus and head to the first stop, a local vineyard. There, you will enjoy a private tour and tasting of the wonderful wines and cheeses made at this organic farm. You will visit this agriturismo for 90 minutes before boarding the bus and heading to Pienza, where you can explore for 3 hours and you will have lunch on your own. By 4:30 pm you will be back on the bus and on your way back to your room.
DAY 5
Wake up and enjoy cook to order breakfast at 7:30 am. By 10, you board the bus and head to the first stop, Cortona, where you can explore for 2 hours before heading to a local vineyard. There, you will enjoy lunch and tasting the wonderful wines made at this vineyard. By 4 pm you are back on the bus and on your way back to your room for an apertif.