Cortona tours

Most popular Cortona tours

On each of our guided tours, you’ll enjoy a balance of sightseeings led by locals and free time to follow your interests. All our tour packages include an expert Tour Director, breakfast daily, select lunches and dinners, comfortable transportation, and accommodations hand-selected by our staff.

Food & Wine: Flavors of Tuscany & Umbria

Canadian WWII History: The Italian Campaign

with Sicily extension

Talk to a regional expert to narrow in your perfect tour

Start planning

What travelers say about their tours

Bucket list expectations exceeded!

4/16/2016 by first-time traveler Jenny

The beauty of traveling with a group is that the logistics of your trip are worked out for you: hotel stays, ground and air transportation, and daily tours. Traveling with Go Ahead Tours allows you to skip lines at the sites visited.

True professionals in vacation planning!

7/27/2018 by first-time traveler Diane

Such a value! Every day offered us opportunities to see and do so much with the group, as well as opportunities to tour on our own. Each destination had a city tour with excellent professional, knowledgeable local guides who not only shared their passion for their city but also the cities history.

How it works

Planning a trip is a breeze with the help of Go Ahead Tours’ experts working behind the scenes.

Work with our in-house experts

Choose from 175+ tours all around the world. Need help narrowing down? Call our regional experts at 1-800-590-1161 to talk through how you like to travel.

Sit back & get ready for your trip

Your tour package includes handpicked hotels, breakfast daily and other select meals, comfortable transportation, an expert Tour Director, guided sightseeing, and more.

Take off on an adventure, stress-free

Your local Tour Director will meet you and your group on the first day, and be your go-to for the best sites, flavors, and stories of the region.

Browse all our Italy tours

See all