Place your deposit now for our May 2025 escorted tour. Exact dates to be determined. Final pricing to be determined 6 months prior to trip. Trip is historically priced around $2450 per person but cost increases may change this pricing. Please let us know if you want to bring a friend, spouse, partner, etc., and we will get you shared room pricing (about $500 less for that guest). Sorry, no kids allowed on these tours. Please let us know if you require an ADA accessible room. We are a full service travel agency. We can assist you with flights, transfers, pre and post stays, and more at no additional cost. This tour is designed for the new traveler and includes 2 nights pre or post stay in either Rome or Florence (unescorted portion) and 5 nights stay at a rustic agriturismo. See itinerary for everything included in tour. We must sell at least 6 spots (3 fully booked rooms) in order for this tour to happen. Tour space is limited to 10 people (5 fully booked rooms).
Escorted Umbria and Tuscany May 2025
Itinerary
This escorted package, priced per person, includes:
Fluent Italian and English speaking tour director joining you on each outing (not pre or post trip though)
2 nights pre or post stay in Rome or Florence at a hotel of our choosing (3 star or higher). This is unescorted but we provide all the info you need for a great stay.
5 nights at a rustic agriturismo
5 breakfasts
5 dinners with one bottle of local wine per room per night
One aperitif each night per person (wine or Aperol Spritz)
Tastings at 5 local vineyards
2 lunches
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 at a rustic agriturismo then jump on private transport to a local vineyard for a tasting session. Enjoy the winery for a few hours before heading back to the agriturismo for an apertif at 5 pm. Dinner is a served at 8 pm and includes a bottle of wine for each room.
DAY 2
Wake up and enjoy cook to order breakfast at 7:30 am with a brief mindfulness session at 9 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 the agriturismo for an apertif. Dinner is served at 8 pm and includes a bottle of wine for each room.
DAY 3
Wake up and enjoy cook to order breakfast at 7:30 am with a brief mindfulness session at 9 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 the agriturismo for an apertif. Dinner is served at 8 pm and includes a bottle of wine for each room.
DAY 4
Wake up and enjoy cook to order breakfast at 7:30 am with a brief mindfulness session at 8:30 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 the agriturismo for an apertif. Dinner is served at 8 pm and includes a bottle of wine for each room.
DAY 5
Wake up and enjoy cook to order breakfast at 7:30 am with a brief mindfulness session at 9 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 the agriturismo for an apertif. Dinner is served at 8 pm and includes a bottle of wine for each room.