Classic Chianti

8 Days & 7 Nights 4 Read 2 reviews
  • Walk the best sections of Tuscany's “Chianti Classico” wine routes
  • Relax in exquisite villas and hilltop villages overlooking olive groves and rolling vineyards
  • Savor bold, fruit-forward Sangiovese during a classic Chianti wine tour and tasting
  • Explore the glorious medieval city of Siena, an UNESCO World Heritage Site
  • Soak up the culture and learn traditional Italian recipes in the ancient kitchen of the Palazzo Leopoldo
Walk through the best and timeless landscapes of Chianti to Siena in-style, featuring authentic cultural experiences and exquisite overnight stays. Explore the Heart of Tuscany by walking from Radda and Gaiole in Chianti, two of the most beloved towns of the Chianti Classico region. Walk among castles, fortresses, Romanesque Churches, olive groves and row upon row of vines, interspersed with peaceful wooded valleys. Pamper your palate with a wine tour and tasting at the Recine Winery; a winery dedicated to quality and traditional methods of wine making. Eat, cook and learn family recipes at an Italian cooking class and enjoy dinner at the Michelin star restaurant of your elegant villa. Each evening, roam the piazza of your charming hamlet and take an aperitif at “osterias” overlooking the Tuscan countryside.

What To Expect

This tour is a perfect mix of culture, walking, and enjoying “the finer things in life.” Learn to cook traditional Italian cuisine, savor rich red wines, and stay in elegant hotels that are the best this area has to offer. Daily walks are graded moderate and average 8-11 miles along rolling terrain. Enjoy following dirt trails and “Strada Bianca’s” (gravel paths) through the classic Chianti landscapes of olive groves, lush vineyards and charming romantic villages; where time continues to stand still.

Tour Style:

Self Guided | Go at your own pace on an independent active trip.


Multi Center Walking | You will spend multiple nights in one or more of the locations on this walking tour

This trip is suitable for:


Ideal if you have an interest in:

  • Foodie Adventures
  • Wine, Whiskey & More...
  • Wellness & Spa

Activity Level & Terrain

Grade & Terrain

We have created this “best of” itinerary to showcase the best walks and to create the perfect balance of walking, sightseeing and culture.

This itinerary is graded moderate, with five days of walking and a maximum distance of 11 miles. Daily walks average around 9 miles (4-6 hours) along rolling terrain as you walk to-and-from hilltop villages. Note - two of the days have “loop walks” that are optional.

On most days you will be walking on routes following gravel, farm tracks and dirt trails, while on some days you will be following backcountry roads.

You should be in decent physical shape and comfortable walking everyday to fully enjoy the walking on this tour.



While the route is not waymarked (with the exception of some sections where you will be walking dedicated trails), navigating is easy using the Macs Adventure Navigation App.

Your daily walks will be mapped in the app with GPX tracks, including route notes and turn-by-turn directions. All of these resources are available to download for offline use. More information is outlined within your detailed information pack, in addition to 24/7 telephone support from Macs Adventure should you require assistance.



Included in this trip are six nights in hand-selected premier accommodations. We’ve carefully hand-picked premiere properties that are the best in the region to ensure that you enjoy every minute of your stay while in Chianti.

Single Rooms & Solo Walkers

This trips is based on two people sharing a room. If you’d like separate rooms, a single supplement is required.

If you would like to request a twin room (same room with two separate beds), please notify us at the time of booking so we can request this option.

This trip is also available to solo walkers (a solo supplement is required).


Breakfast is included each morning and consists of a traditional European style breakfast. Most breakfast include coffee, tea, yogurt, granola, seasonal fruit, meat, cheese and baked goods. In most cases, a hot dish (eggs and pancakes) will be served a la cart or can be ordered off a menu.

Three dinners are included in this trip to ensure a special experience and to feature the best of Tuscan cuisine. Included dinners consist of a cooking class at Palazzo Leopoldo (night 2), dinner at a Michelin star restaurant at Castello di Spaltenna (night 3), and dinner at the restaurant of your private retreat in Hotel Fontanelle (night 5). Note - these dinners also include wine.  

Lunch is not included in this trip, so you are free to choose from nearby available options. For lunches, we recommend finding cafés or restaurants located in the towns along the walking route, or you can purchase snacks and a picnic lunch to bring along with you. Further information can be found within your information pack and route notes.

  • Overnights in hand-picked accommodations
  • Breakfast included
  • Baggage transfers
  • Transfers as per itinerary
  • Route notes, maps and detailed information pack
  • Access to the Macs Smartphone App
  • 24-7 Emergency telephone support
  • Travel insurance (required)
  • Travel to starting point/from finish point
  • Lunches & selected dinners
  • Lunches & 3 Dinners
  • Drinks and snacks
  • Personal equipment
  • Additional nights before, during or after the trip

When To Go


This tour is available to start anytime between April and October. 

As availability in Siena is very difficult around the times of the 'Palio' horse races, held each year on the 2nd of July and the 16th of August, we suggest you book as soon as your plans are finalized to ensure available for specific dates.

Please note that the wine tour and tasting is not available before Easter or on a Sunday, so please keep this in mind when booking and try to avoid beginning your tour on a Thursday, if possible.

When to Go?

The best time to visit Chianti is during the early spring and late fall.

July and August are also great months to go but can be very hot for walking. If booked during these months, we therefore advise you to begin walks very early in the morning to avoid the midday heat. 

Getting to the Start

Getting to Radda in Chianti

Included in this trip is a private transfer from Siena to Radda in Chianti (Day 1).

Getting to Siena

Air & Train

To get to Siena, Pisa and Florence both have airports with flights from international and national destinations.

We recommend flying into Florence and taking a taxi from the airport to the Florence Train Station. Trains to Siena from Florence depart several times per day (approx. 2 hours total, note—some trains are direct while others have a change over in Empoli).

If flying into Pisa, take the tram from the airport to the Pisa Centrale Train Station. Trains to Siena leave from Pisa Centrale Train Station every 30 minutes (approx. 2 hours total, including one change over along the route).

Getting from the End

Getting from Siena

By Train:

Trains to Florence, Pisa and Rome depart everyday directly from Siena Train Station. Trains, ticketing and more information can be found within your pre-departure information pack. For additional information, please check the Trenitalia website for updated timetables.

Luggage Transfer

Luggage Transfer

Your bags will be transferred from your accommodation as per your itinerary and moved onto your next overnight accommodation. We ask you to limit your luggage to one bag of up to 50 lbs. per person.

General Information

Cooking Class

The cooking lesson on the second day of this trip takes place in Palazzo Leopoldo’s original ancient kitchen, for a truly authentic Tuscan experience. The cooking lesson begins around 5:00 PM and lasts for about 4-5 hours, ending with dinner derived from the meals made during the course. The meal prepared consists of a 4-course menu, using traditional recipe's and seasonal ingredients. Please let us know at the time of booking if you have any particular preferences, intolerances or food allergies so that we may personalize the menu for you in advance.

Wine Tour & Tasting

The wine tour and tasting on the fourth day of this trip takes place at the Riecine Winery (about 1.5 miles from Gaiole). The tour and tasting begins at 10:30 AM at the entrance to the winery, where your friendly hosts will greet you and take you on a tour of the winery and vineyards (approx. 1 hour). Enjoy learning all about the history, grapes and methods, followed by a tasting, before continuing on with your day’s walk.  For more information about the winery check the Riecine Winery website.

Please note that tours are only offered after Easter and are closed on Sundays. Please check your dates before booking to avoid any conflicts with this tour.



Our pre-departure information pack has  detailed advice and a packing list on what to bring. This includes warm and cold walking gear, hiking boots, rain gear, day pack and other specifics.

Travel Insurance

Travel Insurance

Travel insurance helps protect your travel investment, your belongings and most importantly you, from unforeseen circumstances that may arise before or during your trip. For more information, please visit our travel insurance page.

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Day 1 Arrive in Radda in Chianti and overnight Day 2 Radda in Chianti Loop Walk via Castelvecchi and Volpaia Vineyards 8 miles / 13 km Day 3 Walk to Gaiole in Chianti via Vertine 9 miles / 14 km Day 4 Gaiole in Chianti Loop Walk via Badia a Coltibuono Monastery 9 miles / 15 km Day 5 Walk to Lecchi in Chianti 6 miles / 10 km Day 6 Transfer to San Sano, walk to Siena 12 miles / 20 km Day 7 Free Day in Siena Day 8 Onward Travel

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