Sept 15 to Sept 22, 2025
We’ll cycle quiet back roads through the Tuscan wine country, visit magnificent medieval villages, discover the best gelato and cappuccino stops, and hike along the shimmering Mediterranean Sea. We’ll also enjoy the mindfulness of daily poetry and yoga, savor the freshest local cuisine, learn to prepare authentic dishes from local cooks, taste the finest wines, olive oils, and cheeses together with the families that produce them, and experience true Tuscan hospitality and local color in all aspects of this unique, Co Ed Tuscan retreat. All ability levels welcome.
See Italy in a whole new light on this amazing cycling vacation in Tuscany. From the shimmering Mediterranean Sea to the rolling hills and ancient villages, we’ll absorb the essence of Tuscany and allow our senses to run wild. From the honey-soaked light of the morning glowing over fields of red poppies, to the golden rays shining through the vineyards in the evening, we will discover the blissful rhythm of Tuscany. We’ll bike the most charming roads in the world, and delight your taste buds with spectacular local foods, all while learning about our surroundings: art, architecture, history, and the art of making olive oil, wine, cheese and authentic Tuscan cuisine.
All ability levels are welcome and each bike ride is guided. The high staff-to-participant ratio means you’ll have someone to encourage you, as well as teach you cycling tips, whether you’re a beginner or a veteran. This is the trip you always promised yourself you’d take. Come join us in the sweet life.
Where We’ll Go on La Dolce Vita Co Ed Tuscany Cycling Retreat:
We will split our time between two spectacular regions of Tuscany: the authentic, unspoiled countryside of the Etruscan coast on the Mediterranean Sea, and Val d’Orcia, known as the heart of Tuscany, with gentle, carefully-cultivated hills peppered with picturesque towns and villages
Some of the towns we will be visiting and riding through are: the Etruscan city of Montalcino, Pienza (the jewel of the Renaissance), Monastero di Sant’Anna (where the English patient was filmed), Abbazia di Monte Oliveto Maggiore (if we time it right we can hear the chanting of the monks), Castagneto Carducci, Sassetta, Suvereto, Montescudaio, Bolgheri, Massa, and Populonia. We’ll have a full day to savor the charms of mystical Siena, considered one of the best-preserved medieval towns in Italy. An expert local guide will lead us into the heart of Siena’s history and art.
Our home base for the first portion of the retreat is the lovely Sport Hotel in the Etruscan coast region. Set in a beautiful Mediterranean garden, the hotel is modern but built in charming, traditional Tuscan style.
The beautifully landscaped grounds feature fruit orchards and olive groves, a state-of- the-art Olympic swimming pool, and great views of the village and sunsets. Our meals are specially prepared and served in the hotel’s noted restaurant, L’Olivo, which specializes in homestyle Tuscan cuisine.
We’ll spend three nights here, exploring the Etruscan coast by day — a cyclist’s paradise of rolling hills and quiet roads through some of Italy’s most prized vineyards. Stretching from medieval village to medieval village, our select routes take in glorious views with sublime spots to stop for a cappuccino or a gelato.
For the next portion of our adventure, we’ll head inland to the magnificent region of Val d’Orcia, where we’ll spend two nights at winery accommodation. Set in a spectacular setting of cypress-lined lanes, ancient stone villages, and undulating hills studded with castles, the winery accommodation is a working wine and olive oil producing estate with beautifully renovated farmhouses and a main villa for our lodging. The estate also includes a small chapel, two swimming pools, and a gourmet restaurant preparing our sumptuous Tuscan meals from fresh, local produce.
The proprietor Donatella, is the producer of award-winning Brunello di Montalcino wines. Her signature vintage, Prime Donne, is produced solely by women.
The cycling in the Val d’Orcia region, particularly the Le Crete (pronounced cret-tay) area, is nothing less than breathtaking. The landscape is the quintessential dream of Tuscany, unfolding its splendid and miraculous beauty mile after mile along some of the most idyllic roads in the world. On our daily rides, we will visit Montalcino, the elegant wine town, jewel-like Pienza, considered the most perfect Renaissance town in Italy, Sant’Anna, the graceful monastery where the English Patient was filmed, and the magnificent frescoes in the grand Abbey of Monte Oliveto Maggiore, where it is still possible to hear the monks celebrate mass in Gregorian chant.
What to Expect at the La Dolce Vita Co Ed Tuscany Cycling Tour:
Most mornings we will begin with yoga to awaken our senses and limber our bodies before enjoying a buffet breakfast with foamy cappuccinos. Then we’ll pedal our E-Bikes (or road bikes) on the Tuscan roads, famous for their cypress trees, lack of traffic, and friendly drivers. Our afternoons will be spent exploring villages, swimming in the calm sea or our 25 meter pool which is right out our door, and rekindling the spark for life.
Throughout the retreat, you will have personal and individualized professional instruction and guidance during all activities. Our staff consists of world-class athletes and coaches, who will offer you heartfelt support and instruction. We’ll create small riding groups to ensure everyone rides with others at a similar ability level. Riding options are provided for beginners to accomplished riders. And, all rides are fully supported with a bike mechanic and a sag wagon (full of fruit, water, cookies and, of course, chocolate). PLUS we have E-Bikes!!!
We provide enriching and rejuvenating adventure retreats to renew the spirit and strengthen the body. A unique and powerful approach to creating vibrant health and personal empowerment deals for women of any age, background, or athletic ability. Programs targeting the mind, body, and spirit have been developed and refined over 16 years by world champion triathlete Colleen.
Yes! Beginning, elite and everyone in between riders will love the Tuscan countryside for bike riding at its best. A variety of options are available for our rides depending on each person's comfort level. We also have e bikes for those who would like a gentle helping hand. If you can, we suggest you start a training or workout program at least 3 months beforehand so you can get the most out of the week. It does not need to be a hard-core program, just get out, play and be active a few days a week. If you just can't find the time, don't worry, there will always be others in the same situation and the supportive staff will help you along. On this trip you can rent an E-bike which is the great equalizer and you won’t need to worry about getting ready for the trip.
Exquisitely beautiful, quiet little roads wander everywhere through this ancient land, winding past views of the shining Mediterranean Sea, up to scenic hilltop towns, past ancient olive groves, and alongside prize-winning vineyards. Italy is the center of the world for road cycling, so immerse yourself in the cycling culture and discover an intimate view of Tuscany at your own pace. A fully-equipped support van will accompany each ride, providing water, snacks, and mechanical assistance—and serving as a sag wagon if you desire. We have two different bikes to rent: If you are an avid cyclist, you are welcome to ride a road bike, or you can also rent an E-bike.
Great road bikes and E-bikes are available for rent. Last year the whole group was on E-bikes and it was a blast! But for die-hards the rental road bikes tend to be all carbon bikes from BMC, Colnago, Bianchi and other top manufacturers. The bikes are so good the guides coming over from the US never bring their bikes and opt save the travel hassle and damage risk and ride the rentals. Bike rental is usually 400 to 450 Euro per week which is paid in cash in Italy. There are ATMs in just about every town we’ll visit so getting euro is easy. Just make sure you have a 4 digit pin. The bikes rentals come with helmets but you are welcome to bring your own if you’d like.
Set in ancient olive groves near the Mediterranean coast, our first hotel is the ideal base from which to explore the beautiful hilltop villages, prize-winning vineyards, and rolling landscape of this rich area of Tuscany known as the Etruscan Coast. We will discover the labyrinths of stone-cobbled streets in numerous medieval villages which may include Castagneto Carducci, our home village, with its tiny shops, ancient churches, magnificent hilltop views, and delicious ice creams. On our cycling routes, we will visit many medieval villages which may include the wine-making fortress-village of Bolgheri. We will travel to Siena, one of Italy's great cities, and have a cultural tour of the monuments and art treasures—with shopping time to browse the wealth of gorgeous boutiques and shops in this jewel-like town. We learn to cook delicious Tuscan dishes at a local farmhouse, then dine under the fig trees and dance under the stars. In the village of Monteverdi we will visit our dear friend Rolando Stefanacci for an amazing lunch with afternoon talk. We will enjoy a wine tasting and lunch at a beautiful family owned winery that has produced a 100 point Super Tuscan wine. In the Val d'Orcia we will stay in a similarly idyllic setting and visit many beautiful towns and sights which may include Montalcino, the elegant wine town and jewel-like Pienza, considered the most perfect Renaissance village in Italy.
The part of the Mediterranean Sea near our home village is referred to as the Tyrrhenian Sea. It is warm, clear, and generally tranquil, providing excellent salt-water swimming. Bring your goggles, sunscreen, swimsuit, and love of the sea! Also, both of the hotels at which we will be staying have wonderful lap pools.
If you've never been to Europe, relax! You will love it. If you've been many times- you'll be surprised, refreshed, and delighted by our intimate version of the European experience. We will pick you up and always be available for any questions and with a helping hand. You'll feel like part of an extended Italian family at this retreat.