Italy – Tuscany Biking – Deluxe
“Birthplace of the Renaissance, land of Dante’s poetry and Chianti wine, muse to Michelangelo.”
Tuscany is rightly world-renowned for offering all the ingredients of a truly enriching travel experience. Travelling by bicycle allows you to discover the quieter, more authentic side of this region—away from the well-trodden tourist routes and into the very soul of Italy.
Is it one of the most beautiful regions on earth? We certainly think so.
On our Classic trip, we stay in a carefully curated mix of distinctive hotels, charming agriturismi, and comfortable inns. With the exception of Siena, all feature fabulous swimming pools—and every host will welcome you with open arms.
Enjoy!
Small groups with personalized attention
- A ride you’ll never forget: from Asciano to Pienza, with a picnic en route at a secret spot boasting breathtaking views.
- Carefully selected hotels
- A meal to remember: lunch at Tre Porte in the picture-perfect village of Monticchiello.
- Dine à la carte at hidden local restaurants off the tourist trail
Italy – Tuscany Biking – Deluxe
Arrive in Siena and join your group for a walking tour led by our favorite local guide, bringing the city’s vibrant history to life. In the evening, enjoy a welcome reception followed by dinner at a traditional trattoria.
Hotel Santa Caterina, Siena
Ride north through the rolling fields and vineyards of Chianti. Enjoy lunch in a small village before continuing through Radda on the way to Castellina. In the evening, savor exclusive wine tastings and a delicious dinner at a local trattoria.
The following day offers a scenic loop ride, including a stop at the Castle of Meleto, an iconic site tied to one of Chianti’s most important noble families. Rest comfortably at your elegant hotel—once a noble palace—in the heart of Castellina.
Day 2 Distance: 46 km, 900 m gain or 75 km, 1,335 m gain
Day 3 Distance: 49 km, 860 m gain or 63 km, 1,050 m gain
Palazzo Squarcialupi, Castellina in Chianti
Begin with a thrilling descent from Castellina to the southern valley. Stop to explore the medieval village of Monteriggioni, renowned for its intact city walls and cobbled streets. After a countryside lunch, continue through quiet landscapes to your hotel, surrounded by vineyards and complete with a relaxing pool.
Distance: 56 km, 700 m gain; optional add-on: 39 km, 600 m gain
Relais Borgo di Toiano, Sovicille
Ride westward through gentle descents and rolling terrain toward Monteroni d’Arbia for lunch. Then continue to Casabianca, a countryside agriturismo owned by a mother and daughter who share a passion for wine. On the way, you may visit Monte Oliveto Maggiore, a Benedictine monastery with stunning Renaissance frescoes painted by Signorelli and Sodoma.
Distance: 55 km, 930 m gain or 78 km, 1,370 m gain
Hotel Borgo Casa Bianca, Asciano
he final leg of your journey offers the most iconic landscapes of Tuscany. Cycle past Petroio and Castelmuzio toward Pienza, a Renaissance jewel nestled among rolling hills. On the second day, ride through postcard-perfect scenery to Montepulciano and Monticchiello, two of Tuscany’s most beloved villages.
Your hotel, located just steps from Pienza’s central plaza, offers spacious rooms and an inviting atmosphere. Cap off your week with a celebratory dinner and local wines shared with new friends.
Day 6 Distance: 30 km, 650 m gain or 46 km, 990 m gain
Day 7 Distance: 37 km, 735 m gain or 81 km, 1,535 m gain
Hotel Il Chiostro, Pienza
After breakfast, we transfer you to Chiusi train station for onward travel.
Cost Includes
Cost Includes
- Land Cost US $3,950 Includes 7B/2L/6D
- Single Room Supplement US $990
- Bike Rentals US $325
- E-bikes* (on request): US $560
Cost Excludes
- Bicycle hire
- Insurance
FAQs
Only if you prefer to! Our Great Explorations fleet includes high-performance hybrid and road bikes, fully equipped for your adventure. Each bike comes with a custom fitting and setup, hand pump, spare inner tube, repair kit, multi-tool, tire levers, seat bag, lock, map case, and water bottle. Hybrid bikes also include a handlebar bag.
If you’d rather bring your own bike, that’s absolutely fine too.
We do recommend bringing your own helmet for hygiene and safety reasons. However, if you’d prefer to borrow one of ours, just let us know in advance.
Our trips cater to a wide range of fitness levels. That said, the fitter you are, the more you’ll enjoy the experience. For cycling tours, some pre-trip riding is helpful—we’ll even send you optional training tips. Not sure what’s best for you? Our Travel Advisors can help you select a trip that matches your fitness and goals.
A simple self-check: Can you ride 45 km (30 miles) in a morning or afternoon? Or take a brisk two-hour walk?
If you’re joining a cycling tour, the best prep is to get out and ride. For hiking trips, walking or light hiking beforehand is ideal. Build up gradually—both in distance and intensity—until you’re comfortable with the kind of activity planned for your tour.
Focus on two key areas:
Endurance: so you’re comfortable with multiple days of activity
Intensity: to handle any tougher sections, like hills
We’ll send you detailed training suggestions once your trip is confirmed.
I’m already pretty fit—will I find this tour challenging enough?
Definitely. For avid cyclists or hikers, we offer optional extensions with extra distance and elevation. Your guide will outline the available options each evening so you can choose the level of challenge that suits you for the next day. We can also help you pick a tour that leans more towards a higher level of activity, with longer daily distances or more elevation gain.
Each day, you’ll have route options of varying difficulty. Your guide will explain the choices, and you can decide based on how you feel—perhaps tackling a longer route one day and taking a more relaxed option the next.
Some travelers go at their own pace while others team up. Either way, everyone enjoys the flexibility. A support van follows the route, ready to provide assistance, snacks, or a lift if needed.
Our trips naturally attract travelers with a mix of fitness levels, so whether you prefer a steady pace or a faster one, you’ll likely find others to match. This also works well for friends or couples who may have different energy levels but want to enjoy the experience together.
No problem. If you’re unable to cycle or hike on a particular day, your guide will arrange a comfortable transfer for you—and your luggage—to the next stop.
No. Our support van transports your luggage between accommodations. Hybrid bikes include a handlebar bag for personal items, and you’re also welcome to leave a small day bag in the van. Road cyclists typically carry essentials like phones or light jackets in their jersey pockets.
All accommodations
Daily breakfasts, most lunches (including our famous picnics), and most dinners
Support and guidance from one or more experienced Dropin Bike leaders
Snacks and drinks throughout the day
Van support for different route options
A detailed Trip Planner with all pre-trip information
Private guided visits to museums, historic sites, wineries, and other highlights noted in your itinerary
All hotel and restaurant gratuities
Park and entry fees
Luggage transfers and porter service
Dropin Bike water bottle
Complimentary Dropin Bike t-shirt (on your first trip) or cycling jersey (on your second trip)
Welcome and farewell wine receptions
Please refer to your specific tour page for the exact list of what’s included.
Some tours offer pre- and post-trip extensions. Check your tour’s page on our website or contact us for advice.
While Great Explorations doesn’t book flights, trains, or car rentals directly, we’re happy to recommend trusted travel agents who have helped many of our guests with excellent service.
Please wait for your tour confirmation before booking any non-refundable airline tickets.
You’ll receive a trip confirmation package with detailed logistics, including where the tour begins and ends, nearby airports, and suggested transport options. All tours start and finish in or near towns accessible by train, bus, or taxi.
If you’re planning to drive to the starting point, contact one of our Travel Advisors for information on parking.
