Super Tuscany bike tour:
A Luxurious Journey Across Italy’s Finest Landscapes
Immerse yourself in the luxury of Tuscany’s renowned wine country on our exclusive Super Tuscan Bike Tour.
Inspired by the prestigious “Super Tuscan” wines, which epitomize excellence and innovation in winemaking, this journey combines the thrill of cycling with unparalleled elegance.
Ride high-end bikes through picturesque vineyards and historic towns, indulging in exquisite wines and gourmet meals.
Stay at two carefully selected wine Relais, where you’ll be pampered amidst the stunning landscapes of Chianti and Brunello. Experience the best of Tuscany in an unforgettable way, blending adventure with ultimate comfort.
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wow moment
Exclusive Wine Relais Experiences – Indulge in the elegance of Borgo San Felice and Mastrojanni, where world-class hospitality meets the finest Tuscan wines
Ride Through Iconic Tuscan Hilltowns – Cycle the rolling landscapes of Chianti Classico and Montalcino, weaving through vineyards, medieval villages, and breathtaking Renaissance towns
Pedal Through Cinematic Beauty – Explore the UNESCO-listed Val d’Orcia, where golden wheat fields and cypress-lined roads set the stage for unforgettable rides—including the landscapes made famous in Gladiator
Savor the True Flavors of Tuscany – Delight in hand-rolled pici pasta, local pecorino cheese, fresh-pressed olive oil, truffles, and seasonal delicacies like fava beans, artichokes, chestnuts, porcini mushrooms, Chianina beef, and wild boar cinghiale
Taste Italy’s Most Celebrated Wines – Sip Brunello di Montalcino, Chianti Classico, and Vino Nobile, all crafted from native Sangiovese grapes, alongside the bold, international blends of Super Tuscans—always paired with the perfect espresso or cappuccino.
DAY 1
Arrive at Borgo San Felice from Florence and immerse yourself in this charming historic hamlet and winery. Discover the piazza, chapel, and old lanes. After a bike fitting you have time for a test ride to nearby Castelli, visit Castelnuovo Berardenga with its medieval charm and Villa Chigi Saracini. Ride through the vineyards of Chianti Classico, enjoying the picturesque landscapes.
DISTANCE 36.1 km
+637 m / -632 m
DAY 2
Embark on a scenic loop through Radda, Badia Coltibuono, and Gaiole. Enjoy a coffee break in the hilltop town of Radda in Chianti, where history and modern life blend seamlessly. Take a wine tour and lunch at the historic Badia a Coltibuono winery, surrounded by vineyards planted by monks over a millennium ago. Visit Gaiole, renowned for the “L’Eroica” vintage bike event, and soak in the local culture.
DISTANCE 52.4 km
+1160 m / -1159 m
DAY 3
Cycle through the picturesque landscapes of Monteaperti, Le Crete, Asciano, and San Giovanni d’Asso. Pause in Asciano for a perfect coffee break amidst the stunning Crete Senesi. Reach Montalcino, famed for its Brunello wine, and explore the town’s Etruscan and Roman roots. Visit the Abbey of Sant’Antimo, a masterpiece of Romanesque architecture with a serene atmosphere. End the day at Relais Mastrojanni, enjoying the tranquility of the countryside.
DISTANCE 76.9 km
+1373 m / -1418 m
DAY 4
Ride to the UNESCO World Heritage Site of Val d’Orcia, with stops in Bagno Vignoni and Pienza. Enjoy a coffee break in the thermal village of Bagno Vignoni, where history and relaxation meet. Discover Pienza, a Renaissance jewel designed by Pope Pius II, and stroll through its charming streets. Visit the iconic Vitaleta Chapel before heading back, capturing the essence of Tuscany.
DISTANCE 59.7 km
+1361 m / -1181 m
DAY 5
Ride towards Poggio alle Mura, home to the impressive Castello Banfi, where history and viticulture intertwine. Explore the medieval castle and its extensive wine estate, learning about the art of winemaking. Stop at Solaria winery for a delightful wine tour experiencing the hospitality of the Cencioni family. Cycle through lush vineyards and rolling hills, soaking in the Tuscan sun. we suggest a farewell dinner at Mastrojanni winery, toasting to an unforgettable journey.
DISTANCE 49.0 km
+1034 m / -1037 m
DAY 6
Say goodbye to Tuscany any way you see fit. Sleep in, stroll around the grounds, or opt for a final early morning short loop ride.
DAY 7
Pedal through the stunning landscapes of Castiglion del Bosco and Murlo, marveling at the panoramic views. Experience the gravel paths of L’Eroica, feeling the thrill of Tuscany’s most celebrated cycling routes, the ride end in Siena outskirt.
Arrive Siena, the medieval masterpiece, and take time to explore its rich history and vibrant culture. Visit Piazza del Campo, Torre del Mangia, and the majestic Duomo, each telling a story of its own
DISTANCE 48.0 km
+928 m / -991 m
INFO TOUR
best period from April to End of October
DIFFICULTY Moderate to Challenge
TOTAL DISTANCE 272 km / 170 miles in 5 stages
TOUR REVIEWS
Price & Inclusions
Price
from € 2950 per person in double occupancy – hotel are luxury and price can vary depending period and type of room
single room supplement € 1490
Extra day stage to Siena from € 370 per person
Inclusions
five nights in luxury hotels with private bath and breakfast
Five breakfast & one Brunello wine tour
Bike Delivery to the first hotel in Borgo San Felice, professional bike fitting
RideWithGPS App: tracks, route notes, off-line navigation
Trip notes: Sightseeing & meals suggestions
All Baggage transfers
Drop Off bikes and gear in Montalcino
Keepsake Cicloposse water bottle
All tax & service charge
Not Included
Bike Rental per entire tour:
Gravel, road bike, E-bike € 260 | Trekking € 190 | E- road or E-gravel € 350
City Tax Each village charges a tax per each day between euro 0,70 to euro 3,00
Optional
Cooking lesson & Wine tasting
Escape to Borgo San Felice, a Tuscan dream nestled in the heart of Chianti Classico!
This isn’t just a resort; it’s a beautifully restored medieval borgo where history meets luxury. Imagine wandering through ancient streets, savoring Tuscan gourmet dishes, and indulging in spa treatments—all while surrounded by breathtaking vineyards and olive groves.
Close to Siena, but a world away from ordinary, Borgo San Felice is where unforgettable memories are made. Your Tuscan fairy tale awaits
Discover Mastrojanni Relais, an exquisite wine resort nestled in the scenic hills of Montalcino!
Imagine waking up to breathtaking views of Tuscan vineyards, as this hotel is located on the highest and most panoramic point of the estate.
Mastrojanni Relais offers a blend of Tuscan style and modern comfort, providing unforgettable moments. Just a short distance from Sant’Antimo Abbeys, immerse yourself in the heart of val d’Orcia.
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