Chianti in Luxury

7 Days & 6 Nights 4.7 Read 3 reviews
  • Walk in style on Tuscany's Chianti Classico wine routes
  • Outstanding 4* & 5* hotels in exquisite locations
  • Chianti wine tour & tasting
  • Hike into the glorious medieval city of Siena, a Gothic open-air museum
  • A traditional cooking class in the ancient kitchen of the Palazzo Leopoldo
Walk Tuscan wine trails through the timeless landscapes of Chianti to Siena, staying in luxury accommodations. This very special tour combines perfect walking and opportunities to eat and learn to cook authentic Tuscan food with touring a vineyard and stays in the finest premium hotels. An intoxicating mix of exceptional experiences. This alluring region has been producing world-famous velvety red wines since the 13th century. Situated between Florence and Siena, Chianti, known as Tuscany’s “third city”, is formed of castles, fortresses, Romanesque Churches, olive groves and row upon row of vines, interspersed with pretty wooded valleys.

What To Expect

This tour is geared towards those who like “the finer things in life”; traditional gourmet cuisine, some of the best red wine in the world and outstanding hotels that are the best this area has to offer. Of course you should also love walking and on this tour you take moderate hikes following trails through classic Chianti landscapes where time has stood 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...
  • Elegance & Unique Stays


  • Classic

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.

  • 6 Nights in 4* and 5* luxury hotels
  • Breakfast included
  • Baggage transfers
  • Transfers as per itinerary
  • Breakfasts
  • 3 Dinners (wine included and one in a 1* Michelin restaurant)
  • Cooking Class (4-5H)
  • Wine Tour & Tasting
  • Route notes, maps and detailed information pack
  • Information pack * 24-7 Emergency telephone support
  • Travel insurance (required)
  • Travel to starting point/from finish point
  • Lunches & selected 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 in Palazzo Leopoldo takes place in the original ancient kitchen of the hotel. You will prepare a 4-course menu and the traditional food that will be cooked will depend on the season, in order to offer the most fresh ingredients. Moreover, at the time of booking you can let us know what is to your particular taste so that you may have a personalized menu. They also accommodate vegetarians and people with food intolerances or allergies. The cooking lesson begins at 5:00 pm, lasts for 4-5H and ends with dinner (eating the dishes that you made during the course) and a good Chianti Classico wine.

Wine Tour & Tasting

This will be organised on Day 4. You walk past the Riecine Winery about 1.5-2km from Gaiole. The tour and tasting is booked for 10:30am. Your friendly wine hosts will take you on a tour of the vineyard, which will take about 1 hour You will then continue on with today’s walk. For more information about the winery check the Riecine Winery website.

Please note that the winery is closed on Sunday’s. Therefore if your tour begins on a Thursday you will be unable to have the tour. Also they only offer tours after Easter so please check your dates before booking.



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 & Volpaia Vineyards 9 miles / 14 km Day 3 Walk to Gaiole in Chianti via Vertine 9 miles / 15 km Day 4 Gaiole in Chianti Loop Walk via Riecine Winery & Badia a Coltibuono Monastery 10 miles / 15 km Day 5 Walk to Hotel Le Fontanelle 11 miles / 18 km Day 6 Walk to Siena 10 miles / 15 km Day 7 Onward Travel

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