Experience the golden triangle of Tuscany over three days, combining nature, medieval villages, and cities of art. Pedal through rolling hills, vine-covered landscapes, and historic streets while your guide shares local stories and insights. This journey offers an authentic taste of Tuscan culture and scenery, blending cycling, food, and exploration into one seamless adventure.
Day 1 – Arrival in Siena (0 miles)
Participants leave Rome by private shuttle, enjoying a comfortable transfer to Siena. Upon arrival, the group meets the guide to receive a briefing and get acquainted with their electric bikes. Begin exploring Siena’s historic centre, a labyrinth of narrow alleys, artisan workshops, and wine shops. Hidden piazzas provide perfect spots to savour local delicacies and immerse yourself in the city’s medieval atmosphere.
The day focuses on gentle exploration, allowing participants to adjust to the bike and surroundings while absorbing the charm of Siena’s architecture and streets. There is time to pause for photography, shopping, or simply enjoying the ambience of Tuscany before settling into your accommodation for the evening.
Day 2 – Gaiole in Chianti & Wine Tasting (30 miles)
Departing Siena in the morning, ride into the Chianti countryside, where vineyards and olive groves stretch across rolling hills. The route passes through Gaiole in Chianti, an area rich in history and local culture. Participants encounter landmarks such as the Castle of Brolio and the legendary Leccione, experiencing both natural beauty and architectural heritage along the way.
A wine tasting stop allows riders to indulge in the region’s famous Chianti wines and enjoy a light lunch. After the tasting, participants continue cycling through scenic routes before being transported to Florence by private shuttle. The evening concludes with a celebratory dinner, giving the group time to share experiences and relax after a full day of cycling.
Day 3 – Florence Discovery (11 miles)
Start the day cycling through Florence’s historic streets, discovering iconic landmarks such as Piazza della Signoria, the Duomo, and Ponte Vecchio. The guide provides local anecdotes, highlighting the city’s Renaissance heritage and hidden corners. Participants enjoy the mix of vibrant city energy and cultural exploration, stopping to photograph or rest as desired.
The tour concludes with reflection on the journey, having experienced Siena’s medieval charm, the Chianti countryside, and Florence’s artistic heritage. Return to Rome in the afternoon, carrying memories of Tuscany’s landscapes, cuisine, and history.
This tour spans Siena, Chianti, and Florence, covering both countryside trails and historic city streets. Participants cycle through vineyards, olive groves, and rolling hills, encountering small villages and iconic landmarks along the way.
In Siena, riders experience medieval streets and artisan culture, while Chianti offers panoramic landscapes, historic castles, and authentic wine tastings. Florence provides a mix of artistic heritage and lively streets, giving a full view of Tuscany’s diverse attractions and cultural richness.
On this itinerary, your overnight stays are split between Siena and Florence, each in a comfortable double room at a Bike Hotel (B&B or 3*). Breakfast is included, allowing you to start each day with a nutritious meal before cycling. Luggage transfer is included, so you can move freely without carrying heavy bags, and each property is chosen for its convenience near the start points of your rides.
The accommodations provide a mix of traditional Tuscan charm and modern comfort, giving you a relaxing environment after a full day of cycling. Staff are attentive and knowledgeable about local attractions, helping you make the most of your evenings in Siena and Florence. Special requests for meals or room arrangements can be accommodated with prior notice.
Riders must have prior experience with electric or standard bicycles and be prepared to cycle up to 30 miles in a day. Comfort with mixed surfaces, including asphalt and dirt roads, is essential. Children may participate with bike seats or extensions, and the guide will assess suitability before departure. Helmets and safety gear are required, and participants must follow all instructions provided by the guide.
Physical fitness and readiness are important as each day involves multiple hours of cycling combined with sightseeing. Participants should be prepared for mild inclines and continuous pedaling, dressing in layered clothing suitable for weather changes and bringing hydration and personal items for comfort.
The tour is led by local guides with expert knowledge of Tuscany’s history, culture, and natural landscapes, offering stories and insights that enhance every stop. Previous travellers praise the combination of professional organisation, attention to detail, and small-group focus, ensuring personalised support and an immersive experience.
Sustainability is a key focus, with electric bikes reducing environmental impact and carefully planned routes balancing exploration and comfort. Accommodation in selected B&Bs or 3* hotels, combined with private transfers, luggage handling, and guided tastings, creates a seamless and memorable experience for all participants.
About the centre
Lungotevere delle Armi, Roma
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