Tuscany & Umbria Insider
This trip is currently only available as a Private Trip. For a trip like this one, please see Tuscany Walking or call 800-462-2848 to speak with a Trip Consultant.
From Classic Tuscany to the Green Heart of Italy
Ageless scenery, rich history, and stellar wine and cuisine make Tuscany and Umbria ideal destinations for culturally curious travelers. This Insider Trip showcases our very best collection of special events and encounters - from a behind-the-scenes exploration of Florence to fun-filled cooking classes - giving you the most in-depth Italian experience possible. Spend time with our local friends who know the area intimately and can peel back its layers to reveal its passionate heart. Meet artists, chefs and residents who share their stories and expertise. When you return home, don't be surprised if you've become part of an extended famiglia internazionale!
Vagliagli
Meet in Florence and get an insider's view on a guided walking tour 
Join Jacopo and Ana at their apartment for an informal cooking lesson and lunch Meet Dario Castagno, author of Too Much Tuscan Sun, who's brimming with fascinating information about the Chianti region Explore Siena's handsome medieval center with our local guide, learning about its 17 fiercely competitive contrade (districts) Swirl, sniff and savor fine vintages at a wine tasting.
Cortona
Accompany charming Cortona native Giovanni Adreani through Cortona's Etruscan tombs, ancient streets, piazze, churches and neighborhoods, gaining insight into the town's storied past Put your culinary skills to the test as you create (and devour!) piatti tipici Toscani (typical Tuscan dishes) under the tutelage of our good friend Viviana.
Collevalenza
Celebrate your arrival in Umbria with an exclusive chocolate-making lesson with a chef at the Perugina School of Chocolate Stroll through Todi's majestic medieval Piazza del Popolo Discover the atmospheric hill town of Deruta, an ancient ceramics center Unleash your inner artist during a ceramics painting class at the prestigious Scuola d'Arte Ceramica Relax by the pool or venture into Assisi, birthplace of St. Francis, the patron saint of Italy Cap off the trip in Carsulae with a guided visit of one of the most important Roman ruins in Italy.
ITALIAN GRACE: Premiere Inns
Relais Borgo Scopeto (2 nights): You'll feel as if you're in a medieval stone village at this elegant welcoming hotel set amid classic Tuscan scenery, and featuring two heated swimming pools, tennis courts, a jogging track, immaculate gardens and superb views of Siena.
Villa di Piazzano (1 night): Located just outside of town, this 15th-century manor house offers a swimming pool, beautifully appointed guest rooms and an expansive formal Italian garden.
Relais Todini (2 nights): Tradition blends beautifully with modern comforts at this stylish hotel, set in a 14th-century manor on a hilltop with sweeping vistas.
Guest Trip Reviews
Especially enjoyed Dario Catagno's presentation about Il Palio and Giovanni Adreani's enthusiastic "insider" tour of Cortona. Giovanni took us to places that I would never have dreamed of entering like standing on the altar and inside the rectory! He had so much knowledge about art and the history of Cortona.- Newcastle, WA
Backroads is really excited to add our latest way to explore the world - Insider Trips - to our award-winning biking, hiking and multisport vacations. These are experiences you cannot have behind the wheel of a car, or on a train or a tour bus, or in a few excursions from a cruise ship or a secluded resort.- Backroads President and Founder