LUXE VIP ~ Montepulciano (Italy) Guided COACH-CYCLE (All Inclusive)

Arrive in the medieval hilltop town of Montepulciano and settle into your accommodation before meeting your guide and fellow travelers.

This afternoon, enjoy a leisurely guided walking tour through the town’s cobbled streets, discovering historic piazzas, Renaissance architecture and breathtaking views across the Tuscan countryside.

This evening, gather for a welcome dinner featuring traditional Tuscan cuisine paired with locally produced Vino Nobile di Montepulciano, the perfect introduction to the region’s rich food and wine culture.

Today begins your journey into the heart of Tuscany.

Departing Montepulciano, you’ll ride toward the charming hilltop village of Montefollonico, where your first stop awaits at Ficopazzo — a relaxed and welcoming estate perfect for easing into the day.

Continue through rolling countryside to Capitoni Winery, where tradition meets modern winemaking.

From here, the ride opens into the Val d’Orcia landscape, leading to a truly special experience at Agricola Casagori, where you’ll enjoy a biodynamic organic lunch surrounded by nature.

Continue through the rolling hills of the Val d’Orcia to the Renaissance town of Pienza, where you’ll have time to explore its charming streets before riding on to the medieval village of Monticchiello and returning to Montepulciano.

Cycling Distance: ~45 km

Today is dedicated to discovering the flavours and traditions of Tuscany.

Travel to the UNESCO-listed town of Pienza, famous for its Renaissance architecture, artisan boutiques, and world-renowned Pecorino cheese. Enjoy time to explore before joining a local guide for an authentic truffle hunting experience, learning about this prized delicacy while searching the surrounding countryside.

Finish the day with a relaxed lunch featuring seasonal Tuscan specialities before returning to Montepulciano.

Today is all about Tuscany’s most iconic landscapes.

Ride out toward Monticchiello and onto the famous Monticchiello Curves, where winding roads and cypress-lined hills create one of Italy’s most photographed cycling routes.

Continue to San Quirico d’Orcia, then descend into the unique thermal village of Bagno Vignoni, where the central square is a natural hot spring.

Ride onward to Castiglione d’Orcia before looping back through panoramic countryside to Montepulciano.

Return to Montepulciano, enjoying one final stretch of Tuscany’s iconic rolling hills before arriving back in town.

Cycling Distance: ~50 km

Today is all about embracing Tuscany’s rich culinary traditions.

Join a hands-on Tuscan cooking class, where you’ll learn to prepare traditional regional dishes using fresh, local ingredients under the guidance of an experienced chef. After the class, sit down to enjoy the delicious meal you’ve created together.

The afternoon is yours to relax, explore Montepulciano’s charming streets, or enjoy a glass of wine in one of the town’s historic piazzas.

A shorter, indulgent day focused on Tuscany’s world-class wine culture.

Cycle through the vineyards surrounding Montepulciano, beginning with a visit to Salcheto Winery, known for its sustainable and organic wine production.

Enjoy lunch at a carefully selected family-run agriturismo, where seasonal Tuscan produce and warm local hospitality take centre stage.

Return to Montepulciano with a relaxed afternoon to enjoy the town.

Cycling Distance: ~40 km

Enjoy a slower pace today with a relaxing round of golf at one of Tuscany’s scenic golf courses, surrounded by rolling hills and vineyards.

Non-golfers may choose to spend the day exploring Montepulciano, visiting local boutiques, relaxing at a café, or enjoying the peaceful Tuscan atmosphere.

This evening, regroup for dinner and share stories from the day’s adventures.

Today blends cycling with culture and architecture.

Ride out of Montepulciano toward the iconic Temple of San Biagio, one of the finest examples of Renaissance architecture in the region.

From here, take a quieter route through gravel roads and countryside tracks, offering a different perspective of Tuscany — slower, quieter, and deeply authentic.

Designed as a more relaxed riding day, today’s route invites you to slow down, take in the scenery, and experience Tuscany at its own unhurried pace.

Return to Montepulciano for a relaxed evening.

Cycling Distance: ~45 km

Enjoy a leisurely day to soak up the atmosphere of Montepulciano.

Browse artisan shops, explore historic wine cellars, visit local landmarks, or simply relax with a coffee or aperitivo while taking in the town’s timeless charm.

This evening, celebrate your Tuscan adventure with a memorable farewell dinner featuring regional cuisine, exceptional wines, and great company.

Your final ride brings everything together.

Cycle through vineyard landscapes to Canneto Winery, known for producing exceptional Vino Nobile wines.

Enjoy your final tasting before returning toward town.

Return to Montepulciano to celebrate completing more than 200 kilometres of unforgettable cycling through Tuscany’s vineyards, medieval villages and spectacular Val d’Orcia landscapes.

Cycling Distance: ~45–50 km