TASTE Series Italy’s Mid
Tour of Tuscany and Umbria
September 27-October 4, 2025
Experience the Essence, Italy at its finest!
Destination: Val d’Orcia to Florence
Price: $4,895 per person
Duration: 8 Days/7 Nights
Style/Level: Point to Point, Classic, Intermediate
Average Temperature: High: 73F Low: 54F
Daily rides:
Shorter routes of 20-30 miles. 1000-1800 feet elevation
Longer routes of 30-55 miles 1800-3000 feet elevation
Extended options are available each day upon request.
A $200.00 deposit is required to secure your spot. Remainder due in 3 installments.
Have questions or need more details before deciding? Click learn more.
Experience the beauty of Tuscany as we journey from the Western border of Umbria to the beautiful region of Florence. Explore the charming towns of Chianti, Montepulciano, Siena, and San Gimignano before ending the journey in the beautiful city of Florence. You will find yourself surrounded by rolling hills adorned with vineyards and olive groves, leading you to the historic towns of Montepulciano. Savor local wines and traditional cuisine. Enter Siena, renowned for its medieval architecture and vibrant piazzas. In Florence, the cradle of the Renaissance, visit iconic landmarks like the Duomo and Uffizi Gallery. This cycling adventure offers a perfect blend of stunning landscapes, rich history, and delightful Farm to Fork culinary experiences. For non-cyclists, the daily itinerary will feature tailored options such as scenic walks or hikes, historic tours, and engaging activities like cooking and wine classes. Each experience is customized to suit the group’s preferences, ensuring an enriching and memorable adventure for everyone.
Tour Highlights
Bike through quiet roads weaving through vineyards to scenic family-run estates
Accommodation will be in 4-5 star hotels and ‘UNESCO villiages’ giving you a real taste of local life.
Experience Tuscany when its culinary treasures are ripe for the picking
Harvest olives or hunt for truffles.
Enjoy award-winning wine made from native Sangiovese grapes.
Pedal through the postcard-perfect hills of Val d’Orcia, the vine-lined climbs of Chianti, and white gravel roads of the Strade Bianche, for some of Italy’s most unforgettable cycling experiences
Cook with our friends enjoying hand-rolled pici pasta
Enjoy the regional agricultural farms growing earthy beans and tender artichokes.
Savor renowned Chianina beef complemented by the bold elegance of Chianti Classico, the refined richness of Vino Nobile, and the world-famous Brunello.
ItinerarY
Day 1: Saturday September 27, 2025: Welcome to Italy (Florence FLR)
Upon your arrival, our guides will be waiting to greet you at Florence Airport (FLR). Two scheduled shuttles will depart beginning at 1:00 PM and last shuttle at 4:00 PM, transporting you to the charming region of Cortona, Italy. After checking into the hotel, each participant will undergo a bike fitting and short test ride. In the evening, we’ll gather for our first dinner together, providing an opportunity to meet your fellow travelers and guides while savoring delicious local cuisine. We will conduct a safety briefing and discuss the details of our week-long tour and plans for Day 2.
Hotel: Il Faconiere Wine Resort
Meals: Light Lunch, Dinner
Day 2 Sunday September 28. 2025: Warm Up Ride Val di chiana
Today's adventure takes us to the hill town of Cortona in Umbria, perched above the picturesque Val di Chiana, famous for its legendary Chianina steak. Our ride begins in Cortona, where you’ll see the rolling hills give way to the wide, fertile plains of Val di Chiana. We’ll pause at a local farm to meet the iconic Chianina cattle, the stars behind Italy’s best beef. After a charming agriturismo lunch on the farm, featuring of course, Chianina steak and seasonal sides, we will work our way back to the hotel with a stop at Lake Trasimeno for a nice treat. Tonight, a a beautiful dinner in Cortona, with its roots as an Etruscan town dating back to 600 BC, is the perfect introduction to Central Italy. Its Medieval charm and character remain beautifully intact, making it a delightful spot.
Hotel: Il Faconiere Wine Resort
Meals: Breakfast, Lunch, Dinner
Day 3 Monday September 29, 2025: Val d’Orcia
Today’s ride through Val d’Orcia offers one of the most evocative experiences of our entire tour of Umbria. We’ll pedal through breathtaking landscapes, with stops to photograph iconic sights like the Vitaleta Chapel, timeless farmhouses, and some of the most celebrated hills in the world. As we head west, we’ll pause in small towns including Montepulciano and Bagno Vignoni, a unique village where the central square is occupied by a large, ancient 16th-century thermal pool. Pienza—famous as the birthplace of Pecorino cheese—we’ll savor its rich flavors at a local hot spot for dinner. Tonight, we’ll rest like locals in the heart of a UNESCO World Heritage village, surrounded by the history and charm of San Quirico d’Orci
Hotel: Townhouses, Capitano Collection
Medievale Borgo, San Quirico D’Orcia
Meals: Breakfast, Lunch Dinner
Day 4 Tuesday, September 30, 2025: siena and chianti
We kick off the ride along the scenic Strada del Brunello, weaving through rolling hills and vineyards with fields and cypress trees as our backdrop. We will enjoy exploring the Siena and Chianti Region through some of Tuscany's most iconic landscapes, blending rolling hills, vineyards, olive groves, and charming medieval villages. Those wanting a day off will have opportunities to tour the historic city of Siena, famous for its medieval architecture and the Piazza del Campo
Hotel: Borgo San Felice
Meals: Breakfast, Lunch Dinner
Day 5 Wednesday October 1, 2025: chianti descovered
Today we pedal through Tuscany’s Chianti region, where vineyard-lined hills, olive groves, and medieval towns set the stage. Our route follows the legendary Strade Bianche—the iconic white gravel roads that deliver grit, charm, and pure cycling joy. Along the way, we’ll pause in hilltop hamlets and pass rows of Sangiovese vines. But don’t get too comfortable just yet... Because this ride ends with a crushing finale—you'll be leaving your mark on the vintage in the best way possible. This is more than a ride—it’s a full-bodied adventure with a finish you’ll never forget.
Hotel: Borgo San Felice
Meals: Breakfast, Lunch. Dinner on your own
Day 6 Thursday October 2, 2025: san gimignano
This morning we change it up with a special visit to Alessandro and his dog, the hunt for Tuscany’s elusive black gold. The morning ends with a rustic lunch featuring the very flavors we foraged—fueling up before we hop on our bikes through another scenic adventure through the heart of Tuscany. We will pass villages including Radda, Panzano & Castellina before we reach the final stretch to the “Medieval Manhattan”. Our journey concludes in this UNESCO World Heritage town of San Gimignano, where you’ll have time to explore at your own pace, savor a local dinner, and perhaps walk in the footsteps of ancient pilgrims along the historic Via Francigena.
Hotel: Pedere Bellavista, San Gimignano
Meals: Breakfast, Lunch. Dinner on your own
Day 7 Friday October 3, 2025: florence
Today we’ll take our final journey to the grand finale in Florence, a city bursting with art, culture, and vibrant energy—the perfect destination to celebrate our unforgettable adventure.
Hotel: Albani, Florence
Meals: Breakfast & Farewell Dinner, Lunch on your own in Florence
Day 8 Saturday, October 4, 2025: Bye-Bye Italy
After breakfast transportation will bring back participants with 2 designated shuttle times to the same airport of arrival in Florence (FLR) .
Inclusions and Details
Accommodations/Meals
· Thoughtfully selected accommodations that reveal the character of the region
· Airport and Luggage transfers on first day and last day of tour
· Luggage transfer between hotels
· Meals: Daily breakfast, snacks at all stops, with lunches and dinners included except on designated "on-your-own" days as listed.
· Wine is included during the welcome and farewell dinner events. However, all other alcoholic and specialty beverages are not covered.
Activities
· All activities listed in the tour itinerary for cyclists with daily tours/excursions designed for non-riders.
· Entrance fees to historic sites, parks, and exclusive events related to the tour.
· Gratuities for baggage handling, porters, and hotel services
Bike and Gear
The bikes included with the price of the tour will be high-performance carbon road bikes equipped with electronic shifters and hydraulic disc brakes. They feature 30-inch tires, ideal for both comfort and performance on various terrains. .
E-bikes are also available for an additional charge of $200.00 for those who prefer an assisted ride.
GPS
2025 Taste Series Bike Jersey; T-Shirt, Water bottle, Tote Bag
SupportExpert bilingual guides with extensive local knowledge. Support vehicle that follows the day’s route, distributes refreshments, and offers lifts.
Pick-up and drop-off before and after your tour from predetermined meeting points for non-riders
Daily bike maintenance to ensure optimal performance.
NOT Included
Airfare
Few Lunches and Dinners listed as “on your own” days
Travel Protection
Gratuities for Guides