Cycling Tuscany: Chianti & Siena

This cycling tour is suitable for relatively fit regular cyclists seeking an active holiday. You'll spend much of the day in the saddle experiencing a region and discovering its variety.

This tour is graded moderate, based on the shorter route options available each day, with the longer and steeper alternatives taking it up to moderate to strenuous. The grading reflects the tour as a whole, so individual days may feel a bit tougher or easier depending on which route you choose.

Accommodation is a mix of charming hotels, a countryside agriturismo and a B&B, each chosen for its great location, character, warm welcome to cyclists and lovely views. Some properties also have swimming pools. We'll always try to keep you at the accommodation shown in your itinerary, but we may occasionally need to use an alternative of equal or higher standard.

Yes, solo travelers are very welcome. There will be a supplement because some costs, like transfers, aren't shared. Or if you'd like to book a single room, just ask. These are available for a supplement.

Breakfast is included every morning. Lunch and dinner aren't included, so you're free to choose where you'd like to eat, whether that's a local trattoria, a village cafe or a picnic spot along the way.

You can start this tour on any day of the week from March to the end of October. Spring, early summer and autumn offer the most comfortable temperatures for cycling, with April, May and June especially lovely, and September and October bringing a gold-and-red landscape. If you travel during the hotter summer months, it's worth setting off earlier in the day to beat the heat, or choosing dates outside peak summer if you'd rather avoid it altogether, although the towns and villages are at their liveliest during this time.

Your bags will be collected from your accommodation each day and moved onto your overnight accommodation. We ask you to limit your luggage to one bag of up to 20kg/44lbs per person.

Navigation is straightforward using our app which has maps, tracks and daily route info. Simply download the information and tracks for offline use and follow the route on your phone. Once on the trail you do not need signal for the app to work and follow your progress.

Getting to the start: fly into Pisa Airport. By train, you can travel from Florence or Pisa to Poggibonsi, the start of the tour, taking around 1 hour or 1 hour 16 minutes respectively - check Tren Italia for timetables. On arrival at Poggibonsi train station, you'll be met and transferred to your accommodation.

Getting from the end: at the end of your tour, a transfer is included to Chiusi train station. By air, from Chiusi you can take a train to Florence (1 hour 26 minutes) and then a bus or taxi to Florence Airport. If flying from Pisa, take a train from Chiusi (2 hours 40 minutes, changing in Florence).

You'll need your standard cycling gear. Bike hire comes with a pannier rack and bag, a pump, lock, a basic repair kit, and handlebar phone. On booking, our Tour Info will give you a complete packing list.

Since you'll have your bike with you, shortening or skipping sections may not be easy. For the best local advice on transport options for cyclists, please consult your accommodation provider or reach out to our local bike partner, where applicable. Local taxis or public transport may be an option in some areas if you need to reach your next stop, so it's worth asking locally.

We hire bikes suited to the terrain, including e-bikes for a bit of extra assist, in a range of sizes - just let us know your height when booking so we can get your frame right. If you would like to bring your own bike then, in the majority of cases, this is not a problem, please contact us to talk it through. We encourage all cyclists to wear a helmet, and it is law in many countries across Europe. We recommend bringing your own helmet for hygiene and safety reasons, however on most tours you can hire one.

The following bikes are available for hire:

Hybrid bike: Cube Touring ONE, a lightweight aluminium trekking bike with an adjustable stem, 8-speed Shimano derailleur, hydraulic disc brakes, Trelock lights and a comfort saddle.
E-bike (touring, step-through): Winora Sinus 9, with a Bosch Performance Line motor and Bosch PowerTube battery.
Road bike: Wilier Triestina GTR, Shimano Ultegra groupset, carbon frame.
E-bike (road): Wilier Centro1 Hybrid, carbon frame with intelligent servo assistance.

Tandem bikes aren't available on this tour, and brand and model may vary depending on availability. The minimum age for e-bike hire is 16.

Please let us know your height for bike sizing, and your head circumference if you'd like to hire a helmet.

Bike hire includes a spare inner tube, a helmet (though we recommend bringing your own), a repair kit and pump, a pannier bag, one lock and a water bottle holder, plus a battery charger for e-bikes.

Many people choose an e-bike for the extra assistance on hillier days, though do note e-bikes are heavier than standard bicycles. Gravel and road bikes are only recommended for experienced cyclists comfortable with the riding position and the fitness this style of biking demands.

We highly recommend that you have travel insurance when you book with Macs Adventure. Your policy should cover medical treatment (including repatriation and emergency evacuation by air ambulance or helicopter), injury, death, third-party liability, and trip cancellation