TASTE Italy Mid:
Adventure Tour of Tuscany and Umbria
September 27-October 3, 2025
Experience the Essence, Italy at its finest!
Destination: Val d’Orcia to Forte dei Marmi
Price: $4.895 per person
Duration: 8 Days/7 Nights
Style/Level: Point to point, Classic, Intermediate
Average Temperature: High: 73F Low: 54F
Experience the beauty of Tuscany as we journey from the Western border of Umbria to the historic west coast of Tuscany Shores. Explore the charming towns of Chianti, Montepulciano, Siena, and Florence before ending the journey at the beautiful Forte dei Marmi. 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-cyclist, a daily itinerary will include options for scenic hikes, historic tours, and/or farm-to-table culinary adventures, customized for the group ensuring an enriching experience 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 ‘Agriturismo’ type accommodation to give us a real taste of local life.
Experience Tuscany when its culinary treasures are ripe for the picking
Harvest olives to be pressed into oil at a local mill.
Enjoy award-winning wine made from native Sangiovese grapes.
Pedal deep into the forests of Mount Amiata, filled with porcini mushrooms and chestnuts.
Cook with our friends enjoying hand-rolled pici pasta
Enjoy the regional agricultural farms growing earthy beans and tender artichokes.
Savor renowned Chianina beef and succulent wild boar, 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
Upon your arrival, our guides will be waiting to greet you at Bologna Airport. Two shuttles will depart at 12:00 PM and 3:30 PM, transporting you to the charming region of Val d’Orcia Italy. After checking into the hotel, each participant will undergo a bike fitting to ensure a comfortable riding experience. 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 also conduct a safety briefing and discuss the details of our week-long tour, including an overview of the plans for Day 2.
Meals: Lunch, Dinner
Destination: Val d’Orcia
Day 2 Sunday September 28. 2025: Warm Up Ride
Cyclist: We begin by pedaling along the scenic Strada del Brunello, winding through rolling hills and vineyards. The golden fields and cypress trees create a breathtaking backdrop as we make our way toward the foothills of Mount Aminata. We will stop at a local trattoria for lunch of pici pasta and glass of Brunello. As we enter the foothills of Mount Amiata start to look for the telltale signs of porcini mushrooms—thick, sturdy stems and a cap that can vary in color. For chestnuts, search for spiky burrs on the ground, which may contain the delicious nuts.
Meals: Breakfast, lunch, dinner
Distances: 35 miles 2500 feet elevation
Day 3 Monday September 29, 2025: D’Orcia to Cortona/ Umbria
Today’s ride takes us to the spectacular hill town of Cortona in the Umbria region looking over the Chiana River valley (“Val di Chiana”) famous for the Chianina steak. As we ride, through Montepulciano to Cortona you will notice the landscape changing; the hills flatten into the expansive plains of Val di Chiana. This area is known for its fertile soil, perfect for agriculture and livestock. Here we will stop at a farm to learn about the Chianina cattle, famous for producing some of the best beef in Italy. We will then stop at an agriturismo for lunch featuring local ingredients to enjoy a leisurely meal with seasonal dishes, and of course, Chianina steak. The town of Cortona is a perfect introduction to Tuscany since its founding as an Etruscan town dates to 600 BC. Today Cortona retains the look and character of a Medieval city. Take time today or tomorrow to see the Etruscan Museum or the Diocesan Museum with its Fra Angelico paintings. For those who want a burn off their lunch can do and extended 10 mile ride to experience, the landscapes of Crete Senes where we will stop for a coffee break before we transport by van to our next hotel
Chestnut and Porcini Mushroom Pasta
Meals: Breakfast, Lunch Dinner
Shorter Route: 34 miles 2600 Feet elevation
Extended Route: 45 miles 3100 Feet elevation
Day 4 Tuesday, September 30, 2025: Explore Chianti/Siena
Today's loop ride takes us 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.
Meals: Breakfast and Dinner. Lunch on your own.
Shorter Route: 27 miles 1500 feet elevation
Extended Route 38 miles 2100 feet elevation
Day 5 Wednesday October 1, 2025: Chianti to San Gimignano
This morning ride from Villa Campomaggio to San Gimignano is a scenic adventure through the heart of Tuscany. The route offers a blend of rolling hills, vineyards, charming villages, and historical landmarks. We will pass villages including Radda, Panzano & Castellina before we reach the final stretch of San Gimignano “Medieval Manhattan”. Here we will park our bikes and explore the UNESCO World Heritage town.
Meals: Breakfast, Dinner
Shorter Route: 25 Miles 1900 feet elevation.
Extended Route:38 miles 3100 Feet
Day 6 Thursday October 2 25, 2025: Siena to Florence
Another picturesque journey through the heart of Tuscany. You’ll ride across rolling hills, passing vineyards, olive groves, and charming medieval towns, with the grand finale being the vibrant city of Florence. We will stop at a small village just outside of Florence San Miniato known for its white truffles for a delicious lunch before returning. Enjoy dinner on your own in Florence before reconnecting for a walking tour as a group.
Meals: Breakfast, Lunch. Dinner on your own
Shorter Route: 28 miles 1800 feet elevation
Extended Route: 36 miles 2900 feet elevation
Day 7 Friday October 3, 2025: to Forte dei Marmi
Cyclist: Enjoy the final ride from Castelfalfi to Forte dei Marmi.
Meals: Breakfast, Lunch & Dinner
Shorter Route: 35 miles 987 feet elevation
Extended Route: 53 miles 1168 feet elevation
Day 8 Saturday, October 4, 2025: Bye-Bye Italy
After breakfast transportation will bring back to the same airport of arrival in Bologna .
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 and tours/excursions designed as daily options for non riders on tour.
· 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. The bikes are lightweight, ensuring an efficient ride, and are designed for all-day comfort on long-distance rides.
E-bikes are also available for an additional charge of $200.00 for those who prefer an assisted ride.
GPS
Complimentary 2025 Taste Series Jersey; T-Shirt, Water bottle
Support:Expert 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