At a Glance
Bike into a 6-day guided cycling tour through the heart of Tuscany, where every pedal stroke reveals a masterpiece of nature and history. Perfectly suited for casual cyclists, this journey unveils the very best of Tuscany in Italy, one pedal stroke at a time. Journey through a landscape dotted with UNESCO World Heritage Sites as you traverse the famed Strade Bianche, cycling from the Renaissance splendour of Florence and the medieval grandeur of Siena to the iconic towers of San Gimignano. This adventure seamlessly combines culture and leisure, taking you through the region's famed Chianti vineyards.
Your adventure begins in the celebrated Chianti Classico region, winding from Greve’s artisan squares and the historic Villa Vignamaggio to the fortress of Castellina. As you ride the iconic Strade Bianche gravel roads near Gaiole, ...
Trip Highlights
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What's Included
- 5 nights' in 4 star accommodation on a twin share basis
- Transfers (from specified airport/train location)
- All breakfasts, 3 dinners
- Water and coffee are complimentary during meals that are included in the package
- Beautifully planned rides
- Experienced team of local professionals
- GPX Routes
- Bike (Gravel bike & E-bike) hire & helmet
- Wine tour and tasting
- Truffle hunting experience
- Van and mechanical support with snacks and water
- Bike cleaning service
- Cycling jersey
- Water bottle
- City taxes
Itinerary
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Approx. 32km (20 miles), 2 hours biking, Elevation gain: 570m (1870ft) Your journey through Tuscany begins! Upon arrival, you’ll meet your guide and head to your hotel. Once you’ve had a chance to settle in, we’ll set you up with a professional bike fitting to ensure everything is perfectly adjusted for your comfort on the rides ahead. With your bike ready to go, we’ll kick things off with a scenic ride toward Greve in Chianti, a charming town known as the gateway to the Chianti wine region. Greve is famous for hosting the Chianti Classico wine festival and is home to Piazza Matteotti, a picturesque square lined with artisan shops, wine bars, and local cafes. Nearby, you’ll find the historic Villa Vignamaggio, a stunning estate that once belonged to the family of Mona Lisa Gherardini, famously painted by Leonardo da Vinci. This introductory ride is more than just a warm-up. It’s your first chance to soak in the breathtaking Tuscan countryside, explore a quintessential Chianti town, and get a taste of the region’s rich history and culture. It’s the perfect way to ease into your Tuscan adventure while beginning to explore what makes this part of Italy so special. |
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Nestled stop a hill overlooking the rolling vineyards of Chianti, you’ll stay at Hotel Villa Le Barone. Unwind by the infinity pool or indulge in rejuvenating wellness treatments. This historic manor, once the home of the Della Robbia family, invites you to experience timeless luxury amidst fragrant rose gardens and panoramic terraces. |
Hotel Villa Le Barone, Panzano
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Approx. 54km (34 miles), 3-4 hours biking, Elevation gain: 870m (2854 ft) Prepare to pedal deep into the heart of the Chianti Classico region, where our route winds through the area's iconic rolling hills. These landscapes are crowned with majestic medieval towns, many still enclosed by stone walls that have stood for over seven centuries. Our destination for the day is the stunning hilltop fortress of Castellina in Chianti. This ancient town, perched strategically between the rival republics of Siena and Florence, offers panoramic views of the surrounding vineyards and olive groves. As you wander through its historic streets, you'll feel the echoes of the historic conflicts that once defined this land, now a place of serene beauty. After exploring the town, the real highlight awaits: a perfect, well-deserved Italian gelato to celebrate the day's climb before we make our way back to the hotel. |
Hotel Villa Le Barone, PanzanoBreakfast |
Approx. 62km (39 miles), 4 hours biking, Elevation gain: 1050m (3445ft) Our journey continues as we descend from the fortified hilltop village of Radda in Chianti, making our way toward the picturesque town of Gaiole. Famed as the birthplace of the L'Eroica cycling event, Gaiole is a gateway to some of Tuscany's most legendary cycling routes. Here, you'll have the chance to ride on the iconic Strade Bianche, the rustic white gravel farm tracks that crisscross the Tuscan landscape, offering a truly authentic cycling experience. Nearby, the magnificent Brolio Castle dominates the skyline. This imposing fortress has stood for centuries as a symbol of the region's enduring history and is home to Italy's oldest winery. As our ride progresses, the distant spires of Siena will emerge on the horizon, heralding our approach to one of Italy's most beautiful and historic cities—a grand finale to an unforgettable day of exploration. |
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Nestled just outside Siena, you’ll stay at La Torre alle Tolfe, a historic estate and organic farm where the rolling Tuscan hills serve as your breathtaking backdrop. Here, you can immerse yourself in tranquillity with a dip in the saltwater pool, find rejuvenation in the yoga and wellness classes, or indulge in authentic Tuscan cuisine crafted from the estate's own organic produce. |
Hotel La Torre alle Tolfe, SienaBreakfast, Dinner |
Approx. 47km (29 miles), 3-4 hours biking, Elevation gain: 680m (2230ft) Prepare for an incredible day of cycling as we journey through history, past majestic castles, and toward medieval towers that pierce the sky. After a hearty breakfast, our ride first leads us to the remarkable castle of Monteriggioni. This perfectly preserved fortified town, famously featured in the film Gladiator, is encircled by a complete crown of imposing medieval walls. As you approach, the sight of its turreted fortifications rising from the Tuscan landscape is a truly breathtaking spectacle that offers a vivid glimpse into the past. From there, we continue to San Gimignano, a magnificent UNESCO World Heritage Site. Often called the "Medieval Manhattan," this hilltop town is renowned for its forest of ancient towers. During the 13th century, the town's noble families engaged in a fierce competition to construct the tallest tower as a symbol of their wealth and power, resulting in 72 towers at its peak. Today, fourteen of these magnificent structures still stand, creating an unforgettable skyline that dominates the surrounding countryside. |
Hotel La Torre alle Tolfe, SienaBreakfast |
Approx. 55km (34 miles), 3 hours biking, Elevation gain: 970m (3182ft) Get ready for a one-of-a-kind cycling adventure through the Crete Senesi, a striking region known as the "clays of Siena." This area was once an ancient ocean seabed over two million years ago, and its unique grey-blue clay, chalk, and rock salt formations now create a landscape unlike anywhere else on Earth. During the ride, you'll visit historic villages that highlight the rich culture of the region. Asciano, a former Sienese stronghold from the 13th century, features medieval architecture and a charming atmosphere. You'll also stop in Buonconvento, a picturesque village known for its well-preserved walls and its connection to Sienese landscape painters, offering a glimpse into the area's artistic history. The day ends in the hilltop town of Montalcino, famous for its stunning views and renowned wine. Here, you'll enjoy a traditional Tuscan dinner paired with Brunello di Montalcino, one of Italy’s most celebrated wines. It's the perfect way to wrap up a day of exploring this unforgettable part of Tuscany. Step into the heart of the Val d'Orcia at Chiostro di Pienza, a restored 15th-century convent, your home for the night. Unwind with panoramic views from the rooftop terrace, indulge in exquisite Tuscan cuisine at the gourmet restaurant, and let the tranquil wellness centre soothe your senses after a day of exploration. |
Chiostro di Pienza, Val d'OrciaBreakfast, Dinner |
Approx. 30km (19 miles), 2 hours biking, Elevation gain: 540m (1772ft) We begin the day early with a trip to Montepulciano, one of Tuscany’s renowned hilltop towns known for its rich history, stunning architecture, and world-famous wines. The ride takes us through classic Tuscan landscapes of rolling hills, vineyards, and olive groves. Upon reaching Montepulciano, there’s time to explore the village, admire its charming streets and historic squares, and enjoy a coffee at a local café. After taking in the beautiful views and relaxed atmosphere of the town, we head back to the hotel to check out. With our bags packed, it’s time to bid farewell to Tuscany and wrap up an incredible cycling journey through this picturesque region. NOTE: This itinerary is provided as an example only – prevailing conditions and local arrangements may cause variation. |
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Please contact us for group bookings and private departures. Single Supplement is available on request.
More Info
- The departure is Florence. The tour begins at Florence Train Station (Santa Maria Novella) at 2.00 pm.
- The finish point is Val d’Orcia, Pienza. Your tour ends with a transfer back to Florence Train Station (Santa Maria Novella) leaving the hotel at 10.30 am.
- Major commercial flights provide convenient access to Florence. The closest airport to Florence, Italy, is Florence Airport, Peretola (FLR), located just 4.4 km from the city centre. Other nearby airports include Pisa International Airport (PSA), approximately 68.8 km away, and Bologna Airport (BLQ), about 83.5 km away.
April to October offers ideal temperatures for cycling and savouring Tuscany. Tuscany's climate offers a pleasant experience year-round, with distinct seasonal changes. In spring, temperatures are mild, typically ranging from 15-20°C (60-68°F), ideal for enjoying the blooming landscapes. Summer brings warmer weather, with average daily temperatures reaching the low thirties (around 30-33°C or 86-91°F), perfect for sunny days and warm evenings. Autumn sees a comfortable cooling, with temperatures settling between the high teens and low twenties (approximately 18-23°C or 64-73°F). Winters are generally mild, with daytime temperatures that usually remain above freezing, creating a cool but pleasant environment for visiting the region's attractions.
Level: Perfect for casual cyclists and e-bike enthusiasts looking to enjoy a leisurely ride while savoring the "bella vita".
Total Kilometres: Approximately 250 km (155 miles) of scenic, moderate rides through Chianti vineyards, medieval hill towns, and UNESCO landscapes.
Day 1: Approx. 32km (20 miles), 2 hours biking, Elevation gain: 570m (1870ft)
Day 2: Approx. 54km (34 miles), 3-4 hours biking, Elevation gain: 870m (2854ft)
Day 3: Approx. 62km (39 miles), 4 hours biking, Elevation gain: 1050m (3445ft)
Day 4: Approx. 47km (29 miles), 3-4 hours biking, Elevation gain: 680m (2230ft)
Day 5: Approx. 55km (34 miles), 3 hours biking, Elevation gain: 970m (3182ft)
Day 6: Approx. 30km (19 miles), 2 hours biking, Elevation gain: 540m (1772ft)
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Ridley ASTR GRX600: Included in trip price. Explore epic landscapes! Lightweight, responsive, and adventure-ready. Perfect for gravel, touring, and thrill seekers. |
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Ridley Kalazy: Included in trip price. Cruise in comfort with flat handlebars, smooth ride, and stylish design. Ideal for relaxed, scenic holiday cycling. |
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Ridley Urbx Mixte E-Bike: Included in trip price. Glide through your holiday with ease. Upright comfort, smooth handling, and stylish design making every ride relaxing, scenic, and unforgettable. |
Where to Meet: Please plan to meet us at Florence Train Station (Santa Maria Novella) at 2pm. Your guides will contact you via WhatsApp 24 hours in advance to confirm the name of the staff member meeting you.
Drop off Location: Following the conclusion of the tour, we will assist you with planning and booking of onward travel. We will run one transfer to Florence Train Station (Santa Maria Novella) leaving the hotel at 10.30 am. For alternative destinations or departure times, please contact us.
Transfer Time: Please consider eating lunch before we collect you from Florence. The transfer time from Florence to the first hotel is approximately 1 hour. Transfer back to Florence train station on the last day takes around 2 hours.
Riding in Tuscany: The general road conditions in Tuscany are good, and most roads are quiet with light traffic. The majority of the roads are tarmac, but we will also be riding on some gravel roads - these are well maintained and enjoyable whether you’re on a road, gravel, or E-bike.
Cuisine: The food in Tuscany is exceptional, with a variety of local specialties to enjoy. Restaurants now cater for both vegan and vegetarian diets. Homemade local red wines like Brunello and Chianti are a must-try!
Onlyluxe Travel acts as travel agency and work with different tour operators.
Payment Detail
All pricing is in Australian dollars and are quoted on a per person twin share basis. A supplementary price is available (see below). Bookings are not confirmed until full payment and the signed Booking Form has been received by Onlyluxe Travel.
A non-refundable 30% deposit is payable within 7 days of your booking, with the final balance due 120 days prior to departure. If a booking is made 120 days or less before departure, the full payment is payable immediately. Last minute bookings are payable before arrival. Failure to pay on time may result in automatic cancellation of a booking with cancellation penalties payable to Onlyluxe Travel. If you pay by credit card or PayPal a surcharge will be added to the total price.
Single Supplement
All accommodation is twin share. Single guests will share with someone of the same gender. If a single room is demanded, a supplementary price of will apply. The supplementary price refers to our quotation and needs to be stipulated at the time of booking.
General Cancellation Policies
- Outside of 120 days monies will be refunded less 30% of full fee
- Within 120 days prior to arrival all monies will be forfeited
- No refunds will be given in the event of non-arrival, any unused services or unused nights due to flight or weather disruption
- We strongly recommend guests protect themselves with travel insurance and medical insurance
Please Note: Cancellations must be advised in email and will take effect from the date they are received.
Liability
The participant agrees to indemnify Onlyluxe Travel, and its servant, tour operator and agents, in relation to any liability, loss and damage which the tour operator, or its servants and/or agents may incur as a result of the participants, negligence or misconduct during the tour.
Smoking is not permitted on the bus, or in tents or in other accommodation being used by tour operator at the time that a trip is being conducted.
Child Policy
Please consult travel consultant on age limit.
Changes to Itineraries
Local conditions may necessitate changes to sightseeing, walking and driving routes, camping and accommodation locations. While every effort will be made to provide the services and experiences as offered in our brochure, on our website, and in our trip letters, we reserve the right to vary your itinerary. In the event that we are forced to change your arrangements, substitute arrangements of a similar standard will be provided. The tour operator will not be liable where interruptions to itineraries are caused by weather conditions, technical problems to transport used by the tour operator, industrial action, political or civil commotion or other circumstances beyond our control. We refer you to the conditions regarding travel insurance.
Changes in Prices
While we will do its utmost to honour its pricing unforeseen circumstances may mean that prices may be subject to change without notice.
Pre-Existing Medical Conditions and Age Limits
You need to advise Onlyluxe travel and the tour operator on any pre-existing medical condition, mobility impairment and/or disability that might reasonably be expected to increase the risk of your requiring medical attention, or that might affect the normal conduct of a trip and the enjoyment of other trip members. Onlyluxe Travel and the tour operator may require an assessment of your medical condition from a qualified medical practitioner. If you fail to adequately notify the tour operator of any pre-existing medical conditions and/or disability, the tour operator reserves the right, at its reasonable discretion, to cancel your participation in a trip at any time, including after the commencement of your trip, with no right of refund if your medical condition, mobility impairment and/or disability could be reasonably expected to affect the normal conduct of the trip and the enjoyment of other trip members.
Cancellation by The Tour Operator
The tour operator is at the mercy of nature in all her beauty and all her fury. The tour operator will under no circumstance knowingly place at risk the health and well-being of our guests and guides. In the case of natural threats, acts of God and the like (e.g. bushfires, impassable snow, etc) the tour operator may need to cancel a tour with very little notice. In some cases, this can occur after the tour has commenced. The tour operator reserves the right to cancel any tour up to 60 days prior to departure if the minimum number requirement is unable to meet for a tour. If the tour operator needs to cancel for any reason, the cost of the tour or any other costs associated with travel to the designated pick up point, overnight accommodation, meals, etc will not be covered by the Onlyluxe Travel and therefore we strongly recommend travel insurance be taken out prior to travel.
Force Majeure
'Force Majeure' means (without restriction) any event which Onlyluxe Travel or its third party providers could not, even with due care, foresee or avoid. Force Majeure covers events such as, but not limited to, adverse weather conditions, fire and all similar events beyond our control. In the case of Force Majeure Onlyluxe Travel will not accept liability, and reserves the right to change and cancel trips.
Evacuations
In rare circumstances, due to injury or unforeseen illness, the tour operator may need to evacuate you from a remote part of the walk. Helicopter evacuations are expensive and in most cases will be at a cost to the customer.
For Australian residents, under the Australian Government Medicare Act, it is prohibited for any domestic travel insurance product to provide any financial reimbursement with regard to ambulance or air ambulance services. We therefore strongly advise our customers to take specific ambulance cover through their health insurance provider. Evacuation cost will not be covered by the Onlyluxe Travel and therefore it is also strongly recommended that our customers take out travel insurance to cover (amongst other things) the costs associated with evacuation.
Travel Insurance
In view of the heavy cancellation penalties applied to cancelled reservations in certain circumstances, we strongly recommends suitable travel insurance be purchased at the time the holding deposit is paid. We recommend insurance cover that covers any loss which may be suffered due to cancellation. We also strongly recommend comprehensive travel insurance against loss of baggage and medical expenses.
