We noticed that you are based in the United States - click here to visit our USA website. US 
Peace of Mind Booking Guarantee 

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.

Trip Style:

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


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

This trip is suitable for:

Ideal if you have an interest in:

  • Foodie Adventures
  • Wine, Whisky & More...
  • Luxury & Unique Stays


  • Classic

Grade & Terrain

This trip is graded ‘moderate’ overall, as the terrain is somewhat hilly. You should therefore be in good physical fitness to fully enjoy the walking on this tour. Most of the route follows gravel and farm tracks and trails, and you will also be following minor roads from time to time. You’ll be walking an average of 14-15 km each day and any loop walks on our longer itineraries are optional. Should you wish to skip a walk between towns then you will be responsible for taking a taxi or bus (if possible) to the next place.


The route is not waymarked (with the exception of some sections where you will be walking dedicated trails). Detailed routes note and GPS data will be provided for you via the Macs Adventure App. Further information will be provided upon receipt of your booking.

Accommodation Information

6 Nights luxury accommodation is included in your trip. We carefully hand-picked 4* and 5* properties and they are the best that this region of Tuscany has to offer.

The accommodation we normally use is detailed below. In Radda in Chianti and Siena, if the hotels listed are not available, then we may book you into similar standard properties. However since luxury accommodation in Gaiole in Chianti and close to the Hotel Le Fontanelle does not exist you may need to be flexible on your tour start date.

You can add on extra nights in any of the overnight locations on this tour.

Single Rooms & Solo Walkers

This trip is not available to solo walkers due to the very high price involved, as some of the costs (such as transfers) are not shared. Single rooms are available on request and a supplement is payable.


3 Dinners are included as part of your tour. The first will be part of the cooking class at Palazzo Leopoldo on Night 2. Another dinner will be included on Night 3 at the Castello di Spaltenna where the restaurant has a 1* Michelin chef. The 3rd will be at the Hotel Le Fontanelle. All of the dinners will include wine. These included dinners will be special experiences and will feature the best of Tuscan cuisine.

The price of your tour also includes breakfast each morning.  Lunch is  not included so you are free to choose from the available options. In your route notes we give advice on where you can eat/pick up lunch.

  • 6 Nights in 4* and 5* luxury hotels
  • Breakfast included
  • Baggage transfers
  • Transfers as per itinerary
  • Breakfasts
  • 3 Dinners (including 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 walk

When To Go

You can start this walking tour anytime between April and October. Please bear in mind that July and August can be very hot for walking. We advise that if you choose to walk during these months that you begin the walks very early in the morning, so as to avoid the midday heat. Availability in Siena is very difficult around the times of the 'Palio' horse races held each year.

Getting to the Start

On this tour an included transfer will bring you from Siena to Radda-in-Chianti, your starting point. 

In order to reach Siena you can fly into Pisa or Rome Airports. There is also an airport in Florence, however flights in and out of this airport are limited.

From Pisa you can take a special “people mover” from the airport to the Pisa Centrale Train Station and then a train to Siena. They leave every 30 mins, with one change and the journey takes approximately 1H45. From Rome you can take a Leonardo Express Train into Rome centre and then a train to Siena (however you have to go to Florence, then change). The trains leave approximately every hour and the journey will take approximately 3H30. From Florence you can take a train to Siena. The journey time is about 1H30. Some trains are direct whereas on others you will have to change in Empoli.

Please check the Trenitalia website for timetable planning.

Getting from the End

As the tour finishes in Siena, you can use the same travel information as in Getting to the Start.

Baggage Transfer

Your bags will be transferred from your accommodation as per your itinerary and moved onto your next overnight stay. We ask you to limit your luggage to one bag of up to 20kg per person.

General Information


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. 

How fit do I need to be?
How far in advance do I need to book?
What personal equipment do I need?
When is the best time of year?
Which is the best airport?
How does the luggage transfers work?


Day 1 Arrive in Radda in Chianti and overnight Day 2 Radda in Chianti Loop Walk via Castelvecchi & 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 Riecine Winery & Badia a Coltibuono Monastery 9 miles / 15 km Day 5 Walk to Hotel Le Fontanelle 11 miles / 17 km Day 6 Walk to Siena 9 miles / 15 km Day 7 Onward Travel

The Macs Adventure Way

  • Tried & Tested Adventures Tried & Tested Adventures
  • Freedom Freedom
  • Book With Confidence Book With Confidence
  • Expertise Expertise
  • Positive Impact Positive Impact
Built with our knowledge and expertise, to suit you.
  • Knowledgeable and helpful friendly specialist adventure planners
  • Wide variety of trips to suit all interests and experience levels
  • Start on any date that suits you
  • Choose your ideal trip length and difficulty
  • Range of accommodation options
  • Choice of trip styles
Authentic adventure travel experiences on your own terms.
  • Choose your own travel companions
  • Walk, cycle and explore at your own pace
  • Make your own decisions
  • Choose your own path
  • Indulge your passions
Feel secure in making the right choice for your precious adventure time.
  • 15,000+ unbiased trip & service reviews
  • Feefo Platinum Award 2022
  • As featured in the Guardian, National Geographic Traveller, and more
  • Founder owned & operated since 2003
  • Passionate team members based in the US, the UK & Europe
  • 100% Financial Protection
  • "Peace of Mind Guarantee" means no worries if you need to change your plans
You can be confident that every detail of your holiday has been expertly planned.
  • Meticulously planned adventures
  • Quality, hand-picked accommodation
  • Seamless and reliable arrangements
  • Comprehensive trip information & insider tips
  • Detailed maps, route notes and mobile GPS app
  • Helpful 24/7 support should you need it
Travel the right way, and make a positive impact.
  • Travel responsibly
  • Explore off the beaten track
  • Support locally owned businesses
  • Engage with local communities
  • Minimise your impact
  • Maximise the benefit of your travel
  • Challenge yourself & grow
£ - GBP - Pound
Country/Region name: