Classic Chianti

This tour is perfect for anyone who walks regularly, has a decent level of fitness and wants to explore at their own pace.

The terrain is undulating with regular ascents and descents. Most of the route follows gravel and farm tracks and trails, and minor roads from time to time.

This route is graded easy to moderate overall. Within the tour, individual days may vary in difficulty, with some sections a bit tougher or easier than the overall rating suggests.

Accommodation on this route is a mix of small, family-run hotels, guesthouses and agriturismos set in villages, hamlets and the city of Siena, chosen for their character and warm welcome. On our premium tour option, you can upgrade to 4-star and 5-star properties for a more luxurious stay. Because some of the higher-standard properties are limited in number, you may need to be flexible with your start date to secure them, and during busier periods you might be booked into an alternative of the same or better standard. We recommend adding an extra night in Siena at the end of your tour to explore this historic city further.

Solo travelers are welcome on the Classic Chianti and Chianti Short Break tours, with a supplement to cover costs that aren't shared, and a single room is available on request for the same supplement. If you choose the Chianti In Style tour, please note it isn't available to solo travelers, as the costs of its included taxi transfers and single luxury-hotel rooms make the solo supplement prohibitive.

Breakfast is included every day on all tour options, typically a continental or buffet spread with coffee, tea, yogurt, granola, meats, cheeses and baked goods, with a hot dish sometimes on request. If you choose the Tuscany In Style tour, three dinners are also included: the first at the Castello di Spaltenna, where the restaurant has a Michelin-starred chef, and the other two during your two-night stay at the Hotel Le Fontanelle, each a genuine culinary highlight. On the Classic Chianti and Chianti Short Break tours, lunch and dinner are at your own expense, leaving you free to explore - pick up a packed lunch from your accommodation or a local market, or stop at a cafe along the way, and dine at your accommodation or a nearby restaurant in the evening.

This route is available to start any time between April and October. As Tuscany is a popular destination, we recommend booking as early as possible, especially around the dates of the 'Palio' horse races held in Siena in early July and mid-August each year, when availability is particularly tight.

Spring offers warm sunshine, fewer crowds and pleasant walking conditions, with wildflowers blooming in May. September and October are also a great time to go, with cooler weather and autumn colors. July and August can be very hot for walking, so you'll want to start early in the day and carry plenty of water. The towns and villages have a lively atmosphere throughout the year, while the trails themselves stay relatively quiet and peaceful.

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.

It's vital that you adhere to these limits. Heavier bags, or additional items might not be transferred, and you may be charged locally. Airlines may have different allowances, but our luggage handlers do not have the same capacity or equipment, and their health and safety is our priority.

The route is not way-marked for the most part, although some sections run along dedicated, marked trails.

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.

Pisa, Florence and Rome are the most convenient airports for this tour, all well connected to Siena and the wider region by train. From Pisa Airport, take the PisaMover shuttle to Pisa Centrale station, then a train to Siena (around 1 hour 45 minutes with one change). From Rome, take a train from Fiumicino Airport to Roma Termini (around 30 minutes) or a bus from Ciampino Airport to Termini, then change trains in Florence for Siena (around 3 hours 30 minutes in total). From Florence Airport, a shuttle bus runs to Florence's Santa Maria Novella station (around 25 minutes), from where trains run to Siena (around 1 hour 30 minutes, some direct and some via Empoli). Check Trenitalia for timetables, as not all services run on Sundays or may run a reduced schedule.

If you choose a tour that starts in Radda-in-Chianti or Gaiole-in-Chianti, an included transfer will take you from Siena to your starting point.

If you choose the Florence to Siena tour, you'll make your own way to Florence first using the airport connections above, before beginning your walk.

The tour finishes in Siena, from where you can use the same travel information in reverse for your onward journey. A private transfer from the end point of the tour to the airport can be arranged as an optional extra.

You'll need good hiking shoes or boots, comfortable hiking clothes, waterproofs, a daypack, and we recommend hiking poles. A portable charger for your cell phone is essential. On booking, our Tour Info will give you a complete packing list.

On certain days you can shorten the route or skip it entirely by using a taxi or public transport.

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