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Classic Chianti Short Break

5 Days & 4 Nights 4 Read 2 reviews
  • A short break in Tuscany walking classic Chianti wine routes
  • Row upon row of vineyards, olive groves and cypresses
  • Sample the rich velvety red and world-class wines of Chianti
  • Hike into the glorious medieval city of Siena, a Gothic open-air museum
  • Hand-picked very comfortable accommodations in remarkable locations
On this short break walking adventure in Tuscany discover the unforgettable and classic landscapes of the Chianti wine region. Known as Tuscany’s “third” city, after Florence and Siena, Chianti is formed of castles, fortresses, Romanesque Churches, olive groves and row upon row of vines, interspersed with pretty wooded valleys. You will walk from village to village, finishing in Siena, whose ancient centre, is a UNESCO World Heritage Site. This alluring region has been producing world-famous velvety red wines since the 13th century and there will be plenty of opportunities during your walks to visit local vineyards and to enjoy some wine-tasting.

What To Expect

On this short break you will take moderate walks through the classic wine region of Chianti. Everywhere you walk you will enjoy fantastic views and great local hospitality from the hand-picked accommodations.

Tour Style:

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

Activity:

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

This trip is suitable for:

Multi-Generational

Ideal if you have an interest in:

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

Activity Level & 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.

Navigation

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.

Accommodations

Stay in good quality B&B’s, 3* and 4* hotels, all located in glorious settings, be it a town, a hamlet or the wonderful city of Siena.

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

Solo Walkers & Single Rooms

This trip is available to solo walkers, although there is a supplement due to the fact that some of the costs (such as transfers) are not shared. Single rooms are available on request and a supplement is payable.

Meals

A breakfast will be provided by your accommodation every morning. Usually they are buffet-style or continental breakfasts. Dinners are not included, however there are options to dine out in any of the towns, villages and many, many options in Siena.

Lunches are also not included, but you can find small stores in which to purchase items for a picnic lunch, or your accommodation can possibly make a picnic lunch if you ask in advance. In your route notes we give advice on where you can eat/pick up lunch.

Included
  • 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
Excluded
  • Travel insurance (required)
  • Travel to starting point/from finish point
  • Lunches & dinners
  • Drinks and snacks
  • Personal equipment
Extras
  • Additional nights before, during or after the trip

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.

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.

Equipment

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 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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Itinerary

Day 1 Arrive in Radda in Chianti and overnight Day 2 Walk to Gaiole in Chianti via Vertine 9 miles / 14 km Day 3 Walk to Lecchi-in-Chianti 6 miles / 10 km Day 4 Transfer to San Sano, walk to Siena 12 miles / 20 km Day 5 Onward Travel

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