Ride Description:

Italy: where pasta, history, and breathtaking landscapes come together to create a dream cycling destination!

Tuscany is one of Italy’s most beautiful regions, so it’s no surprise that cycling in Tuscany is extremely popular. With its rolling hills, medieval towns, and UNESCO protected countryside, cycling holidays in Tuscany have all the ingredients needed for a unique and unforgettable cycling experience.

Tuscany boasts many fantastic cycling routes. From the rolling hills of Chianti and the Val d’Orcia, to the stunning views from some of the best hill towns in Tuscany, like Siena, Montalcino and San Gimignano, each area has something unique to offer. And that’s before we mention the world famous centre of art, Florence.

Tuscany is steeped in history and culture, and a cycling trip through Tuscany allows you to explore the region’s many historic towns and landmarks, many of which have hardly changed for over 600 years. There are famous historical towns like San Gimignano,  Montalcino, Pienza, Montepulciano and the stunning Piazza Del Campo in Siena, as well as lesser-known towns and villages with many architecturally important and well-preserved buildings and museums provide a rich history to enjoy.It’s also worth noting that in Tuscany the towns and villages are all quite close together, which means there’s lots of potential for coffee and lunch stops!

Another big draw is the food and wine. From fresh pasta dishes to hearty stews and soups, there’s something for everyone to enjoy. And of course, you can’t visit Tuscany without trying some of the local wines, such as Chianti, Vernaccia di San Gimignano and Brunello di Montalcino.

What you soon realise as you travel or cycle within Tuscany, is the food is different in every local province of Tuscany. For example, the pasta dishes (mostly freshly prepared that day) and the sauces vary a lot, from rabbit, to wild boar to venison. 

Tour Fees

The cost of the tour is €3,600/ per person (2 people sharing a room).

Single Supplement  €1,300

Dates and Amounts for Tour Payments

You will be given instructions on how to make payments to Sitnica Travel Agency after you have been selected for the tour.

• A deposit of €1,150 is due by February 2, 2026
• The final payment  of €2,450 is due on May 1, 2026 
• Single Supplement €1,300 is also due on May 1, 2026

About the Tour Company

Alen Augustin, the owner/operator of Sitnica Travel Agency lives in Croatia.  He has provided many tours for CCCTS members in past years including Croatia, Munich to Venice, Portugal, Spain, Slovenia and Central Europe Prague to Budapest.  Alen and his crew have done a fantastic job with every tour they have led for our club and for club members.

Accommodation Reservations:

Accommodation : based on two sharing a Double/Twin room in *** & **** B&Bs, hotels and agriturismos (working farms).  (Rooms with two twin beds are limited).

Riding Conditions:

• Distances are between 35 – 90 km and up to 1100 m of climbing. (See itinerary for detail)  The rides include some longer distances and steep climbs.
• Most rides will be on quiet country roads with busier sections through towns. 
• The majority of the roads are paved and approximately 8% will be on gravel roads. Road bikes with skinny tires are not recommended.
• The average daily high temperature in September is around 25 – 27 C and nightly low is about 15 – 17 C.

Fee Includes:

• Accommodation – 15 nights with breakfast included and 2 people sharing a Double room
• 10 dinners
• Supporting vehicle + luggage transport  (Note that the support van is not available for riders just because they may be tired but only in the case of illness, bike breakdown, emergency)
• Water, fruit, snacks on the van
• English speaking cycling guide and driver 
• Routes on Ride With GPS to be downloaded
• Transfers as mentioned
• SITNICA liability Insurance- though each participant must have their own travel medical insurance
• Limited bicycle technical assistance
• Tour Leader fee
• Tuscan Cooking Class 
• Wine, Olive Oil and Balsamic vinegar tasting

Fee Does Not Include:

• All other meals as stated in proposal
• Lunches ( buy or sit down in a restaurant / cafe /picnic in nature ) 
• Transfers on free days
• Arrival and departure transfers from Florence or any other airport. Participants can arrange their own transportation using local transport companies or taxi cab (recommended).
• Bike rentals or bicycle transfers from/to the arrival airport to/from the Tour start location. More on bike rentals below.
• Health Medical Insurance/Travel or trip cancellation insurance
• City guide Siena ( if desired )
• Additional activities/experiences –  TBD
• Tips for contractor, staff or guides
• Transfers to and from the airport of personal bikes (need to make your  own arrangements.)

 

Bike Rentals

For those who have rented bikes from our Tour Operator (Sitnica) in the past, please note that they will not be providing bike rentals for this tour.  Rather, they have been in contact with a local supplier and those wishing to rent bikes will be required to rent through them.  They are Ciclismoplus in Florence. They offer a selection of many types of bikes including gravel and e-bikes. The form for booking a rental is  Ciclismoplus – Bike Booking Form .  Note as well that they have advised us that the time of year we will be in Tuscany is a busy time of year and that booking should be done EARLY, preferably no later than January 2026 and prior to making your first installment to Sitnica.

Sitnica has advised us that skinny road tires are NOT recommended for this Tour.

If and when you book your rental via the link above, include the following information in your form (suggest you put this in the Message box on their form)…

Tour: Toscana Tour with Sitnica (Alen Augustin)

Start Date: Sept. 7, 2026 in Borgo i Vicelli

Their form includes boxes where you can choose a location for pickup and dropoff.  In our case, you will be requesting that they deliver and pick up the bikes to/from Borgo i Vicelli.

Rental costs will, of course, depend on the type of bike rented. The cost of transporting the bikes is unknown at this time but it is expected that the cost will be equally divided among all renters.

Itinerary:

Note: This map is intended to illustrate the general area of the tour and cities/towns visited.  It is not a cycling route.  More detailed routes will be made available in Ride With GPS.

 

Day 1 :  Mon. Sept. 7 – Arrival In Florence (It: Firenze)

The recommended mode of transportation from Amerigo Vespucci Airport (FLR) to the first night’s accommodation is taxi cab.

Directions to Borgo i Vicelli are available on their website (link below), or by entering the following address into your map app.

The Country Relais Borgo Vicelli

Via Roma, 588, 50012 Bagno a Ripoli FI, Italy

Accommodations: Borgo i Vicelli 

Our first night’s accommodation is a country chic Tuscan “relais” (inn or small hotel in English) nestled in the Chianti hills, just outside Florence. Discover this charming olive oil and wine resort in the heart of Tuscany, with a spa and swimming pool. This is an exclusive retreat embraced by a 7-hectare estate, mainly cultivated with olive trees and bordered by woods.

All around the stone buildings there is a park with an English lawn and majestic trees which act as a theatrical backdrop to the belvedere terrace. On the lush green grass there will be optional yoga and tai-chi lessons dedicated to those seeking a break of meditation and balance. At the edge of the garden lies the estate of the relais resort, with 2500 olive trees, which every year  produce a fine organic extra virgin olive oil (one of the protagonists of the Evo Restaurant menu).

In the afternoon we sort out the bikes , have a glass of Chianti wine at the meeting and finish this 1st day with a Tuscan welcome dinner.

Included : D            

Day 2 :  Tue Sept 8 – Loop Ride Fiesole (approx. 35 km   + 670m)

Accommodations: Borgo i Vicelli

Our 1st riding day brings us close to the centre of Florence. Soon after starting you can visit the museum of Gino Bartali, a legendary Italian cyclist, who won the Tour de France twice and helped save Jews during World War II. After different bends, with views of Florence we finally reach Fiesole. We are in a beautiful town of Etruscan-Roman origins, located 294 meters above sea level. In Fiesole you can stop to learn about events of the past, from the Roman Amphitheater and the archaeological area to the Convent of St. Francis, or enjoy the slow rhythm of the present. The first settlements in the area date back to the Etruscan era. The Etruscans were a mysterious people coming from what is now known as Turkey but it was under the Romans that Fiesole became the most important town in the area, at least until Florence’s ascent. 

An afternoon jump into the pool before another Tuscan meal might be just the perfect way to close this introduction day .

Included : B , D

Day 3 :  Wed Sept 9 – Bagno a Ripoli / Radda In Chianti  (approx. 46 km   + 975m)

Accommodations: Palazzo Leopoldo

This is our chance to explore enchanting Chianti, the perfect destination for a wine-lover’s Italian bike tour.  The Chianti countryside boasts vibrant vineyards, picturesque villages, and verdant views over emerald green  hills towards Greve, an iconic town in the Chianti countryside characterized by a dedication to wine, culture, and artisan crafts. We’ll have free time here to park our bikes, enjoy the atmosphere, and taste some tantalizing Tuscan delicacies.

Pedaling on to Panzano, we’ll be rewarded with an unparalleled view over the rolling green hills of Chianti Classico. A last effort of the day brings us to Radda in Chianti, our final destination for the day. This is a charming and historic wine town that dates back to the 9th century. We can stroll around its narrow streets and admire its medieval buildings and walls. We can also visit the Casa del Chianti Classico, a former convent that houses a museum and a wine bar where you can learn more about the history and production of Chianti wine.

We will be staying in a  noble palace overlooking the vineyards of Chiantis  The Palazzo Leopoldo is an elegant 4-star hotel, where antique furnishings coexist with contemporary amenities. This is an exquisite experience made special by a captivating SPA and wellness corners, a typical Tuscan restaurant, a private wine bar and a wide range of activities to experience the real Chianti.

Included : B

Day 4 : Thu Sep 10 – Radda In Chianti / Arezzo  (approx. 62 km   +640m)

Accommodations: ASC Hotel

From the Chianti hills down to the  right bank of the Arno, where the territories of Arezzo, Castiglion Fibocchi and Capolona meet and are crossed by the Via Setteponti and the Via dello Spicchio,  we’ll see many tiny villages and ancient parish churches that stand out among skilfully cultivated fields and sinuous hills where time passes slowly.  A rural and bucolic dimension of great charm for all who visit the place. The Ponte Buriano and Penna Nature Reserve is a Tuscan landscape rich in biodiversity and with a great link with history and art .

We will be staying in Arezzo , a city with an ancient history, one of the most important cities of Etruria and a strategic point in Roman times, reaching its maximum splendour between the Middle Ages and the Renaissance. The city still bears witness to this today, with churches, palaces, monuments and museums housing extraordinary works of art.

Included : B 

Day 5 :  Fri Sep 11 – Arezzo / Arezzo Loop ride   (approx. 65 km   +480m)

Accommodations: ASC Hotel

Val di Chiana is one of the four valleys surrounding Arezzo. The valley is formed by a fertile plain, exploited by the Etruscans and Romans, which became progressively marshy in the Middle Ages. For this reason, the surrounding rolling hills welcomed towns and villages, which grew higher for both defensive reasons and to stay away from unhealthy areas. From the XVI century, reclamation works began, returning the land to agriculture. Today those scenic places are a priceless heritage of art, history and beauty. Seen from above, the Val di Chiana looks like a large garden shaped through the centuries by nature and man, who have worked side by side for this territory. The largest part of the valley falls within the territory of Arezzo and includes some of the most beautiful villages in Tuscany which we will cycle through, such as Castiglion Fiorentino, Foiano della Chiana, Monte San Savino and Marciano della Chiana .

Included : B

Day 6 :  Sat Sep 12 – Arezzo / Pienza  (approx.79.6 km    +960m)

Accommodations: Podere Spedalone (approx. 5 km outside town)

Lucignano is located on the top of a hill on the border between the provinces of Arezzo and Siena, at the crossroads of important roads that through the ages connected the Tirrenian and the Adriatic seas, across the Chiana valley.

After leaving the Arezzo area towards the highlight of the day, which stands on a hill overlooking the Val di Chiana and Val d’Orcia, is a town which is rich in history and art and set in the agricultural landscape of Siena. This is  the ideal place to relax and  also to live in contact with nature, surrounded by gentle hills covered with olive groves, vineyards and forests of pine and chestnut trees. Famous for its characteristic urban structure, the famous cultural events  and also the magnificent vineyards that surround it  which yield the excellent Vino Nobile of Montepulciano DOCG (controlled and warranted designation of origin).

Along Pienza to our agriturismo (farmhouse), Podere Spedalone, which is surrounded by large green spaces where we can spend restful and relaxing days. The swimming pool is free for all guests and the restaurant will surprise every day with new dishes cooked with local and meticulously selected ingredients.

Included : B , D

Day 7 :  Sun Sep 13 – Free Day In Pienza

Accommodations: Podere Spedalone  (approx. 5 km outside town)

Tuscan Cooking Class – Lunch to Follow

“Cook. Taste. Experience Tuscany”

Step into the heart of Tuscan tradition with our immersive cooking class in the beautiful countryside of Podere Spedalone. Guided by our chef, you’ll uncover the secrets of authentic Tuscan cuisine using the freshest ingredients from our farm and trusted local producers.

Together, we’ll prepare a delicious seasonal meal entirely from scratch — the perfect blend of tradition, flavor, and fun.

More about Podere Spedalone: Until about 1960, three families, in all about 45 people, lived on the farm — two families lived in the lower wing, and one in the upper wing. They cultivated the land on the farm’s approximately 160 hectares, much of which remained forest. The entire ground floor of the farm building housed the animals, including work oxen, sheep and horses. From 1961 through 1970 Graziano Mesina grazed his flock of 3000 sheep on the farm. From then until now, the farm was used occasionally for social gatherings, but it was never abandoned. From 2005 to 2006 the property was lovingly restored and transformed into a top class farm house resort maintaining the history of the property.

From 2006 to 2012 Podere Spedalone was opened as a premier agriturismo and from  2012 to 2022 Podere Spedalone was rented and managed by Alessandro Capitoni, a local expert in hospitality and farming who successfully continued and grew the farm and hotel building, a strong brand for Podere Spedalone’s unique and delicious Olive Oils, Saffron, Honey, breads and pastas, and meats.  Since 2023 the farm and hotel have been operated by the owners with a new team of talented experts in farming, luxury hospitality, natural foods and wines.

Included : B ,L (cooking class), D

Day 8 :  Mon Sep 14 – Pienza / Pienza Loop Ride  (approx. 47 km   +900m)

Accommodations: Podere Spedalone  (approx. 5 km outside town)

Today we do a loop ride that includes the Orcia Valley and Bagno Vignoni, known for the ancient healing pools that you will have the opportunity to visit after the picnic lunch. The thermal waters are considered healing and have been a major attraction for those making their pilgrimage on the Via Francigena. From here we will cycle on to the charming, medieval village of Monticchiello.

Before returning to our farmhouse for yet another Tuscan treat, we can visit Pienza, the hometown of Spedalone.  Pienza, a pristine jewel of the Renaissance founded in 1458. Pope Pius II chose the famous Florentine architect Rossellino to transform his home village of Corsignano into one of the few surviving examples of 15th century architecture. Take some time to visit the Piazza Pio II where you can see many historic buildings, from the Palazzo Piccolomini to a beautiful lodge and the stunning Duomo.

Included : B , D                  

Day 9 :  Tue Sep 15 – Pienza / Pienza Loop Ride  (approx. 57 km   +1000m)

Accommodations: Podere Spedalone  (approx. 5 km outside town)

Today’s ride brings us to the fields of sangiovese grapes in the heart of Brunello di Montalcino. The route will take us through the landscapes that inspired many Renaissance paintings. Visit the city of Montalcino and explore its medieval history including a towering fortress built by the Sienese in the 14th century to defend itself in battles against the Florentine. A last meal in Spedalone, probably accompanied by some glasses of Brunello, will make this a lasting memory.

Included : B , D

Day 10 :  Wed Sep 16 – Pienza / Siena  (approx. 52 km   +820m)

Accommodations: Hotel Italia

We’ll pass through Asciano and Le Crete, home to intriguing rock formations and a lone farmhouse flanked by twin cypress trees – a traditional Tuscan scene. We’ll pedal through picturesque vineyards and forests and arrive in Siena, a medieval city with beautifully preserved Gothic architecture. The entire city of Siena was built around the Piazza del Campo, where you can visit the shell-shaped square where the Palio horse race is run and enjoy lunch on your own.

Included : B

Day 11 :  Thu Sep 17 – Free Day In Siena

Accommodations: Hotel Italia

Siena, a gem in the heart of Tuscany, offers a rich tapestry of experiences for visitors. Renowned for its stunning medieval architecture, the city’s focal point is the Piazza del Campo, where the famous Palio di Siena horse race takes place twice a year. Art lovers can explore the Siena Cathedral, a Gothic masterpiece, and the Museo dell’Opera del Duomo, home to exceptional artworks. Food enthusiasts can indulge in local treats like pici pasta and Ricciarelli biscuits, while Siena’s charming streets invite leisurely strolls, revealing hidden treasures.

Probably one day will not be enough but go for it, try to absorb as much of this beauty as possible .

Included : B

Day 12 : Fri Sep 18 – Siena / San Gimignano  (approx. 60 km   +860m)

Accommodations: Poderi Arcangelo (approx. 10 km outside town)

The “Manhattan of the middle ages”, San Gimignano is one of the most fantastic spots to stop at on our Tuscany tour. The region may be famous for its vineyards and wine, which you’ll of course get to try in a tasting session at the end of the day, but you would be amiss not to visit some of the area’s pervasively beautiful architecture and history.  Amongst the rolling Tuscan hills and verdant olive groves lie a trove of Medieval buildings in this 14 towered town. Don’t miss the chance to take some photos in this UNESCO world heritage site!

Poderi Arcangelo will host us for the next 3 nights. Poderi Arcangelo is much more than a winery and agritourism, it is the fruit of generations of passion, hard work and love for the land. The deep roots of the Mora family, proud farmers of the Marche, a rugged land where working the fields was synonymous with toil and sacrifice, are firmly anchored in fertile Tuscany, fulfilling the dream of owning a piece of land to call their own. There, with tenacity and sacrifice, they have transformed small plots into an oasis of high-quality production.

Included : B . D

Day 13 :  Sat Sep 19 – San Gimignano / San Gimignano Loop Ride (approx. 50 km   +800m)

Accommodations: Poderi Arcangelo (approx. 10 km outside town) 

This area is full of small villages away from mass tourism, enchanted corners and unexplored wonders! Some examples: the beautiful village of Certaldo Alto a few steps from Poderi Arcangelo, the views of the small Barberino Val d’Elsa, the Jerusalem of Tuscany in Montaione, the uninhabited Petrognano Semifonte, the dome of Semifonte etc …

Included : B , D

Day 14 : Sun Sep 20 – Free Day In San Gimignano

Accommodations: Poderi Arcangelo (approx. 10 km outside town)

The arrival of Giuseppe Mora and young Bruno in San Gimignano is a story of hope and determination. With only the power of their savings and a vision of a future project, they bought a small piece of land and a modest farmhouse, planting the first vines with the same care with which they cultivated dreams.
The story of Bruno and his double toil, between railway work and tending the fields, is the emblem of a family that does not give up in the face of difficulties and a tribute to resilience and the desire to build something big starting from a small place. The transformation of the farmhouse into a winery and the gradual expansion of the company are testimony to the constant commitment and confidence in the future .The decision to embrace organic farming is a tangible sign of love for the land and respect for the environment.
Bruno’s passing in 2006 was a hard blow for the family, but Sandra has shown extraordinary strength in carrying on the legacy left by her father. With the precious support of experts in the sector, she has continued to cultivate the passion and love that have always characterized the lands of Poderi Arcangelo.Today, with the involvement of her son, the company looks to the future with confidence and determination. The vineyards on the company tell a story of innovation and tradition, where mechanization marries respect for nature. Podere Arcangelo is not just a company, but a symbol of love, dedication and quality that continues to shine in the heart of Tuscany.

Included will be wine and olive oil tasting followed by lunch.

Included : B,L, D

Day 15 :  Mon Sep 21 – San Gimignano / Florence  (approx. 55 km   +1100m)

Accommodations: Borgo i Vicelli

How can we say goodbye to Tuscany before having a last glimpse of the Chianti area. Chianti, the area of rolling hills stretching between Florence and Siena, Arezzo and the hills of Pisa, has long been considered the “heart of Tuscany”. Its splendid landscape is dotted with dense vineyards, chestnut forests, oaks and maples, attractive medieval villages, romantic castles and charming colonial farmhouses. It is also the birthplace of one of the world’s most famous red wines: Chianti.

We return to where we started, Borgo i Vicelli, a country chic Tuscan relais nestled in the Chianti hills near Florence. There, we will be hosted to a farewell meal and a warm goodbye .

Included : B , D

Day 16 : Tue Sep 22 – Departure

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Registration and Participant Selection:

As has always been the case, members will NOT be able to register for the lottery unless their membership status is CURRENT.  Since registration opens in 2025 but the Tour is in 2026, participants must renew their membership for 2026.  Failure to renew before December 31, 2025 will result in the members' status moving to GRACE.  If an accepted rider’s membership status turns to GRACE, they will be notified and will be required to immediately renew or be removed from the accepted list.

If you intend to register for this Tour, you should renew your membership for 2026 before you register.

The Registration Lottery will be on the CCCTS website during the dates and times shown.  A computerized lottery system and waitlist will be utilized if the ride is over-subscribed. A $100 CDN payment is required at the time of registration. The lottery signup will run for eight days, after which the Ride Leader will review the results.

The selection process will consider the following criteria in evaluating candidates:

• membership has been renewed for 2026
• fitness and riding ability and experience required for the tour
• a history of demonstrating safe riding practices
• acceptable social behavior.

The Tour Coordinator may interview riders or others who know them to verify their suitability for the tour. The Tour Coordinator also has the option to prioritize 30% of the tour applicants up to a maximum of 5 people.

• The Tour Coordinator will notify registrants of their selection status. If the ride is not filled to capacity, registration will continue until the closing date shown.
• Tour member selection is done primarily by lottery results, but the Tour Coordinator will have the final decision on who is accepted or not for the tour

 

Tour Operator’s Cancellation Policy

Cancellations must be made in writing to Sitnica: info@sitnica.tcloud.hr  and Tour Leader rhondasmithryan@gmail.com and the following charges apply:

• 90 – 76 days before departure 10%  ( 10/06 – 24/06 )
• 75 – 59 days before departure 30%  ( 25/06 – 11/07 )
• 58 – 45 days before departure 40%  ( 12/07 – 25/07 )
• 44 – 15 days before departure 80%  ( 26/07 – 23/08 )
• less than 15 days before departure 100%   ( 24/08 – arrival )

 

Communicable Illness Policy

The CCCTS Communicable Illnesses Policy takes into consideration regulations and recommendations from the Public Health Agency of Canada, BC Centre for Disease Control and Public Health Ontario. Refer to the CCCTS Communicable Illnesses Policy and Procedures on the club website for full details and what you need to know before participating in this trip.