At a Glance
Bike your way on a quintessential Tuscan experience with a 6-day cycling adventure through Italy's breathtaking landscapes, savouring culinary delights with every pedal. This guided tour takes you from Pienza's Renaissance charm to Siena's medieval beauty and Chianti's rolling vineyards. Ride through UNESCO-listed Val d'Orcia and explore iconic towns like Pienza, Montalcino, Siena, and Radda. With world-class wines and medieval villages as your reward, this tour is perfect for cyclists looking to immerse themselves in Tuscany’s rich culture with options to tackle on invigorating bike challenges.
Your odyssey commences in the historic town of Arezzo, the gateway to Tuscany's heart. From there, pedal into the enchanting Val d'Orcia, a UNESCO World Heritage site, where cypress-lined roads wind through rolling hills. Discover Pienza, a Renaissance "utopian city," before surrendering to the world-renowned ...
Trip Highlights
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What's Included
- All meals as specified in the itinerary
- 5 nights accommodation in hotels on a twin share basis
- All luggage, hotel and shuttle transfers
- Fully equipped titanium bike, with a helmet and accessories
- Professional guiding: two support vans, 6:1 guest-to-leader ratio
- Sightseeing and activities as stated in the itinerary
- Comprehensive travel planner with detailed pre-trip information
- Park and other entry fees
- Expertise and services of our experienced Trip Leaders
- Snacks and beverages between meals
- Van shuttles to support a variety of route options
- All gratuities at hotels and restaurants
Itinerary
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TWO BIKING OPTIONS: At 10:30 a.m., please meet your Trip Leaders at the main entrance of the Arezzo train station, located in Piazza della Repubblica. We ask that you arrive dressed in your biking clothes with your luggage and a daypack containing anything you might need for the day, such as rain gear and layers. Your main luggage will be taken to our first hotel. Benvenuti in Toscana! From Arezzo, we will shuttle to a beautiful lunch spot overlooking the Val d'Orcia, a UNESCO World Heritage landscape, where we'll enjoy our first Tuscan meal together. Afterward, your trip leaders will provide a bike fitting and safety overview before you set off on a warm-up ride. You'll descend into a valley filled with chestnut groves, then pedal deeper into the Val d'Orcia before climbing out of the valley for sweeping views of rolling hills and iconic cypress-lined lanes. Our ride ends in the charming town of Bagno Vignoni, famous for its ancient thermal baths. |
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You’ll be staying at the charming Albergo Le Terme, located right on the main piazza, surrounded by the picturesque landscapes of Bagno Vignoni. Unwind and relax at its natural thermal spa facilities and wellness-focused amenities. This evening, we will gather for a welcome aperitivo, followed by dinner at the hotel. |
Albergo Le Terme, Bagno Vignoni
Lunch, Dinner |
FOUR BIKING OPTIONS: Today's journey begins in Bagno Vignoni, taking us through the idyllic countryside and storybook towns of the Val d'Orcia. Our route then climbs to Pienza, renowned as "the utopian city" for its remarkable Renaissance architecture. Take time to explore the city's heart, Piazza Pio II, and admire masterpieces like the duomo and Palazzo Piccolomini, designed by Florentine architect Bernardo Rossellino. You can linger over a coffee, browse the famed cheese shops, or continue onward for a more challenging ride. For those seeking a greater challenge, three significant climbs lead to the village of Castelmuzio, set against a backdrop of Vino Nobile vineyards. Our path continues to Montepulciano, the highest of Tuscany's hill towns. After lunch, wander through its winding streets and hidden squares. We invite you to visit an enoteca near Piazza Grande to sample the celebrated Vino Nobile di Montepulciano. Just beyond the town walls, the Tempio di San Biagio offers another beautiful stop. The return ride to Bagno Vignoni features more thrilling ascents and descents. You may choose to take a detour through Monticchiello, a medieval village offering sweeping vistas, or tackle the final climb to Campiglia d'Orcia before enjoying the exhilarating descent back to our hotel. This evening, we will relax with a wine tasting and dinner in the heart of the Val d'Orcia. |
Albergo Le Terme, Breakfast, Lunch, Dinner |
FIVE BIKING OPTIONS: Prepare to capture the beauty of southern Tuscany, as today's ride winds through its most picturesque landscapes. Leaving Albergo Le Terme, our journey takes us toward the acclaimed wine village of Montalcino, renowned for its world-famous Brunello di Montalcino vineyards. Here, you are invited to explore the town's quiet streets and admire its architectural treasures, including La Rocca, a restored 14th-century fortress, and the tower of San Martino, which offers expansive views over the Val d'Orcia. Afterward, visit a local enoteca to sample the region's prized Brunello wine. Once back on your bike, you'll descend through a timeless landscape of olive groves and vineyards, passing the town of Buonconvento. A final climb brings you to an inviting agriturismo for a delicious Tuscan lunch. This afternoon, you may choose to shuttle to our next hotel or continue riding through cypress-lined lanes and fields of green and gold. The route offers a mix of challenging climbs and rewarding descents on the way to our home for the night, Borgo Casabianca. |
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You’ll stay at the rustic, Borgo Casabianca, an agricultural estate on a high ridge between the Chiana Valley and the famed Crete Senesi. Settle in and explore the grounds of this ancient village-turned-hotel, enjoy a refreshing swim at the pool, or take a walk to the nearby hamlet of Sinalunga. Tonight, we will gather at the estate to taste its award-winning organic olive oil before enjoying a Tuscan cookout. |
Borgo Casabianca, AscianoBreakfast, Lunch, Dinner |
FOUR BIKING OPTIONS: Today's ride takes you into the Crete Senesi, a unique clay landscape known for its chalky, rolling hills—the biancane—which have been a source of inspiration for Florentine and Sienese artists since the 14th century. Your day begins with a gentle ride toward the quiet town of Asciano, passing pastures where sheep graze among historic stone farmhouses. From there, a steady climb leads you to the high point of the Crete Senesi, where you can pause to admire the view of Siena in the distance. The route continues over a series of rolling hills to the southern edge of the Chianti region. Here, we'll stop at a favourite agriturismo near Castelnuovo Berardenga for a hearty Tuscan lunch. |
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After lunch, we'll continue to our home for the next two nights, the Villa Curina Resort, a 16th-century villa nestled in Chianti's wooded hills with sweeping views of the countryside. Unwind at the serene Italian-style garden, a small church with frescoes by Arcangelo Salimbeni, or rejuvenate with a dip in the pool. This evening, we will shuttle to Siena, a city celebrated for its medieval beauty and the historic Palio horse race. You will have the evening to explore and dine on your own in Siena; your leaders will be happy to recommend their favourite restaurants. |
Villa Curina Resort, CurinaBreakfast, Lunch |
FOUR BIKING OPTIONS: Today’s ride takes you through classic Tuscan scenery: vineyards, olive groves, oak forests, and rolling hills. Feeling up for a challenge? Try the Monteluco climb, a favourite among local cyclists. Prefer an easier pace? Follow the gentler route and stop at Ceramiche Rampini, a family-run ceramics workshop known for hand-painted Renaissance-style pieces—perfect for browsing or finding a unique souvenir. The ride continues into the Chianti region, stopping in Radda, a charming town known for its role as the capital of the Chianti League in the 1400s and its production of Chianti Classico wine. Here, you’ll have time to explore, enjoy lunch on your own, and shop for keepsakes like a cycling jersey featuring the famous Gallo Nero (Black Rooster) logo. After Radda, you can either take a shuttle back to the hotel for a relaxing afternoon or keep cycling for one last big ride. The route includes a downhill stretch through Sangiovese vineyards, traditional Tuscan buildings, and a final climb through the Chianti forest before returning to Villa Curina Resort. Tonight, we’ll wrap up with a sunset aperitivo at the hotel and then head to a local restaurant for our farewell dinner. |
Villa Curina Resort, CurinaBreakfast, Dinner |
Level 2, Approx. 21km (13 miles), 2-4 hours biking, Elevation gain: 365m (1200 ft) Spend a final, tranquil morning at the hotel, or if you prefer one last adventure, join a final ride through the medieval village of San Gusmè to Castelnuovo Berardenga. Here, you can pause at a local bar for a traditional cappuccino or a caffè corretto—a shot of espresso with a splash of grappa. After bidding your leaders arrivederci, you'll travel by private coach to Florence, where your journey concludes. NOTE: This itinerary is provided as an example only – prevailing conditions and local arrangements may cause variation.. |
NoneBreakfastDates & Prices
Please contact us for private departures and group bookings. Single Supplement is available on request.
More Info
- The departure point is Arezzo. Meet trip leaders at 1030 a.m. at the main entrance on the city center side of the Arezzo train station,located in Piazza della Repubblica (Arezzo, Italy).
- The finish point is Florence. Your trip ends at 1p.m. at Florence Peretola Airport (also known as Amerigo Vespucci) in Florence, Italy.
- Major commercial flights provide convenient access to Florence. The closest airport to Florence is Florence Airport, Peretola (Aeroporto di Firenze-Peretola), also known as Amerigo Vespucci Airport. It is located approximately 4 kilometers (2.5 miles) northwest of Florence's city center, making it very convenient for travelers heading to or from the city.
Please note that trip start and end locations are subject to change and can vary by departure. Do not schedule your flights until your reservation is confirmed.
Summertime in Tuscany is typically hot. Temperatures are generally a bit cooler in early May and late October. On most days you'll be comfortable biking in a short sleeved jersey or synthetic T-shirt, although when you head out in the morning, you might want to wear a lightweight jacket or vest, arm warmers and knee/legwarmers. Rain is possible year-round—don't forget to bring waterproof breathable rain gear.
The routes on this trip are rated Levels 2-5.
Level 1, 2-3 hours, 13-35km (8-22 miles), Maximum Elevation Gain 305m (1000 ft)
Level 2, 2-4 hours, 29-51km (18-32 miles), Maximum Elevation Gain 671m (2200 ft)
Level 3, 3-5 hours, 42-68km (26-42 miles), Maximum Elevation Gain 1036m (3400 ft)
Level 4, 4-6 hours, 58-87km(36-54 miles), Maximum Elevation Gain 1341m (4400 ft)
Level 5, 5-7+ hours, 77-113+ km (48-70+ miles), Maximum Elevation Gain 1341m+ (4400+ ft)
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Performance Bike: (Included in trip price) Ideal for avid cyclists. Redesigned for 2024. Next gen titanium frame with carbon wheels. Responsive, efficient and comfortable. Drop handlebars only |
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Hybrid E-Bike: (Included in your trip price) Lightweight titanium frame. Lower top tubes for easier mounting and dismounting. Upright handlebars only. Limited availability on Unplugged Bike Tours. Mininum age to ride e-bike: 16+ |
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Performance E-Bike: (Additional fee) Fully internal battery with quick-swap capability for extended range Industry-leading Bosch drive unit with electronic shifting Featherweight titanium chassis Carbon wheels and hydraulic disc brakes Drop handlebars only. Minimum age to ride e-bike: 16+ |
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Tandem Bike: (Additional fee) Hand-built frame features Co-Motion's custom-designed Cro-Moly steel tubeset, powerful Avid disc brakes, Shimano Ultegra drive train. Custom upgraded wheelset. Best for riders with some tandem experience. |
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.
