From Chianti to the coast
DAY 01 RADDA IN CHIANTI
Basic Option: Radda to Lucarelli Loop
Approximately 17 miles with 1,200 feet of climbing
Avid Option: Radda to La Piazza to Lucarelli Loop
Approximately 27 miles with 1,600 feet of climbing
After your arrival at the airport, a personal driver will take you to your hotel in the Chianti area. Your Trek Travel guides will meet you at the Hotel at 11:00 am. After a 1 hour of drive , you will arrive in Radda in Chianti, one of the region’s historic gems. After enjoying a simple lunch of tasty Tuscan specialties at local trattoria. Enjoy outstanding views today across the tranquil countryside, covered with vines heavy with sangiovese grapes as you traverse a ridge on the way toward Castellina, another famed Chianti town. Later a rewarding descent will take you into a lush green valley and through Lucarelli before beginning your final climb back into Radda. This evening you’ll gather with your guides and fellow guests for drinks on the hotel’s terrace overlooking the surrounding rolling hills before enjoying a Tuscan feast together.
DAY 02 MONTELUCO / CASTELNUOVO BERARDEGNA
Basic Option: Chianti Loop
Approximately 53 miles with 4,900 feet of climbing
Avid Option: Chianti Loop with San Martino
Approximately 70 miles with 6,000 feet of climbing
Short Option: Radda to Castelnuovo B
Approximately 53 miles with 4,900 feet of climbing
Your ride today will take you above the vineyards to Monteluco, the highest point in Chianti, before enjoying a well-deserved descent offering unparalleled views of the Tuscan countryside. Then pedal to Felsina Winery in Castelnuovo Berardenga for a tour of the cellars before settling in for a signature picnic prepared by your Trek Travel guides, replete with tastes of Fèlsina’s famed wines. Later it’s back into the saddle to ride through the small towns on the southernmost border of the Chianti Classico region, through enchanting villages before climbing to the tiny village of Lecchi, to mingle with the locals over a mid-afternoon espresso. Alternatively you can also continue directly through town to pedal up the hills, or collines, surrounded by vineyards. This evening, Radda in Chianti is yours to explore to discover your own classic dishes.
DAY 03 CASOLE D’ELSA / SAN GIMIGNANO / SIENA
Basic Option: Radda to Casole d’Elsa
Approximately 52 miles with 3,000 feet of climbing
Avid Option: Radda to Casole d’Elsa to Sovicille
Approximately 65 miles with 4,000 feet of climbing
The heart of central Tuscany awaits today, as you ride south along quiet ribbons of road past silver green olive groves and gently undulating vineyards. Relax and immerse yourself in the beauty of this region as you glide past myriad blooming wildflowers, ancient stone walls and lush shady forest. Stop at Casole d’Elsa for lunch - where you can explore the local bistros of this Etruscan settlement featuring ancient brick buildings and panoramic views of the surrounding farmland. Later enjoy the expansive views of rolling hills toward San Gimignano and Siena before dropping down into the valley that leads to Borgo Pretale. This evening a private shuttle will take you to Siena where you will meet Andrea, our knowledgeable tour guide who will lead you and your fellow guests on a tour of discovery through Italy’s best preserved medieval city.
DAY 04 VAL D’ELSA / ROCCATEDERIGHI
Basic Option: Borgo Pretale to Roccatederighi to Scarlino Approximately 60 miles with 3,300 feet of climbing
Avid Option: Borgo Pretale to Scarlino via Roccastrada Loop Approximately 77 miles with 5,000 feet of climbing
Short Option: Borgo Pretale to Roccatederighi Approximately 40 miles with 2,800 feet of climbing
Your ride today traverses Colline Metallifere: the “Metal Hills” a densely wooded area, punctuated by small fortified medieval villages, named for its mineral resources. Enjoy quiet roads and peaceful riding as you climb from the Val d’Elsa into the forested hills, on a route offering views largely unchanged for hundreds of years. Leaving the forest behind, the route heads to the town of Roccatederighi, where the remains of its fortress walls enclose the jewel-like central square. After enjoying a lunch of seasonal specialties, begin your descent into the plains of the Maremma, a region where Etruscan and medieval villages, vineyards and woods, sand beaches and blue sea characterize the landscape - long considered the wildest area of Tuscany. A final climb will lead you to your home for the next two nights, La Cianella. Tonight you’ll dine at the luxurious Relais, with a view of the magnificent sunset over the sea that stretches from nearby Elba to Corsica.
DAY 05 CASTIGLIONE DELLA PESCAIA
Basic Option: Scarlino to Castiglione della Pescaia Loop
Approximately 60 miles with 4,200 feet of climbing
Avid Option: Scarlino to Castiglione della Pescaia Loop with Guernica Option
Approximately 65 miles with 5,200 feet of climbing
Short Option: Scarlino to Castiglione della Pescaia
Approximately 36 miles with 2,500 feet of climbing
Today’s ride encompasses the rich vineyards, forested hills, and dense olive groves of this region before descending toward the sea. With plenty of time to explore the hilltop villages and centuries-old buildings that line the route, it’s a day to explore and ride at your own pace. You’ll ride to the crystalline waters of the Mediterranean town of Castiglione della Pescaia. Find a café or trattoria right on the beach to refuel and relax with a Tuscan lunch and perhaps a dip in the Tyrrhenian Sea. Later it’s back onto two wheels to explore the valley between the mountains and the sea, where the roads meander back to the hotel. Pick up some last minute necessities, like well-aged balsamic vinegar, or your favorite bottle of Tuscan wine or return to the hotel to enjoy a final luxurious afternoon by the pool. This evening join your traveling companions and guides for a farewell social hour on the terrace, before ending the day with glasses raised to toast a fantastic week and newfound friends before tucking into a magnificent feast at the hotel.
DAY 06 SCARLINO / FOLLONICA
Basic Option: Scarlino to Follonica Loop
Approximately 18 miles with 1,500 feet of climbing
If you have the energy, return to your bicycle and relish one last ride in Tuscany. This last challenge takes you high up to the castle of Scarlino before again heading down to the sea. If you’d rather, linger over a hot cappuccino and enjoy a leisurely day.
DAY 07 DEPARTURE
Private transfer to the airport for your flight home.