Tuscany & Umbria Insider
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!
- Inside connections and rare cultural experiences
- Meet author Dario Castagno, who shares insight into the Palio bareback horse race
- Exclusive chocolate-making class with Italy's premier chocolatiers
- In-depth visits to Florence and Cortona led by area experts
- Paint ceramics with a local master in Deruta
The Day-to-Day Itinerary
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.
Jeff Cantarutti, Our Man in Chianti
Jeff draws on a passionate Italian heritage to create unforgettable Insider experiences: "My father was twice knighted by Italy's government for his efforts to promote Italian culture in the U.S. And I can show up at the homes of my Italian cousins anytime." Now our Regional Manager in Italy, Jeff has led Tuscan trips since 1994. "From the first moment, I knew I'd be coming back forever. And thanks to the local friendships I've cultivated over the years, our trips have an authenticity that can't be matched."
- Premiere Inns: These lodgings possess both elegance and authentic regional flair.
- Casual Inns: These lodgings are comfortable and appropriate to the area with such characteristics as authenticity, scenic settings and proximity to our activities.
- Deluxe Family Camping: We set up the tents (and take them down), handle every camp chore and perform culinary magic.
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Look at what other guests are saying about this trip!
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 More about this Trip All Guest Reviews
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Tuscany & Umbria Insider
ITALIAN GRACE: Premiere Inns
Relais Borgo Scopeto
Vagliagli (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
Cortona (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
Collevalenza (2 nights) Tradition blends beautifully with modern comforts at this stylish hotel, set in a 14th-century manor on a hilltop with sweeping vistas.
Tuscany & Umbria Insider
Daily Mileage Options & Cumulative Elevation Gain
Routes For All Abilities
Every Backroads trip is designed to appeal to a wide variety of interests and fitness levels. We know your pace may vary from one day to the next-and your traveling companion's may differ somewhat from yours. So we present a range of mileage options, and each day you decide exactly what and how much you want to do.
| Activity Level | Average Time | Biking Average | Walking Average |
|---|---|---|---|
| Insider Trips | Explore at a leisurely pace—on village walks, market strolls, art history excursions, hands-on cooking classes and more. | ||
| 1 | 2-3 hours | 10-20 miles | 2-5 miles |
| 2 | 2-4 hours | 21-30 miles | 5-7 miles |
| 3 | 3-5 hours | 31-40 miles | 7-9 miles |
| 4 | 4-6 hours | 41-55 miles | 9-11 miles |
| 5 | 5-7+ hours | 56-75+ miles | 11-13+ miles |