Classic Chianti Short Break5 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
What To Expect
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
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.
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.
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.
- 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 & dinners
- Drinks and snacks
- Personal equipment
- 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.
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.
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.
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 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.
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 20kg. per person.
ItineraryDay 1 Arrive in Radda in Chianti and overnight
What better way to begin your Classic Chianti tour than staying in the Medieval wine town of Radda in Chianti, perched on a hilltop and surrounded by the stunning landscapes of the region. Siena is easily accessible from Pisa Airport (1H45) and from here a transfer to Radda is included.
Tonight celebrate the beginning of your tour by selecting a delightful restaurant in which to eat some homemade pasta and enjoy a glass of the world-famous red wine, Chianti Classico.
As you have an included transfer from Siena to Radda in Chianti you will not need to locate your hotel on your day of arrival. However it is located in the old part of the town and on the pedestrianised street of Via Roma.
A beautifully renovated manor house dating from the 1700s, Relais Vignale is the perfect place to relax after a long day in the saddle. The hotel has a lounge with fireplace, garden, outdoor heated swimming pool, enoteca, and restaurant with panoramic terrace.
Set off on today’s walk which will take you through a dense concentration of vineyards, olive groves, orchards, terraced slopes and wooded valleys.
Reach Vertine a hamlet with a castle and medieval walls. Inside these walls see the Church of San Bartolomeo a Vertine, dating back to the 11th century. Inside you can admire part of the Renaissance frescoes by the Florentine school. Vertine also has a winery if you care to stop for some wine tasting. Walk downhill into Gaiole in Chianti and to your delightful B&B.
This adorable B&B on the outskirts of Gaiole in Chianti has great views. It is located within a restored stone farmhouse and at the end of your walk you can relax by the outdoor pool. It is a 5-10 minute walk fom the centre of town.
Two-thirds of Chianti’s 70,000 hectares are still covered in oak woods and boar, hares, deer and pheasants still live in these locales. You may be lucky enough to spot one of these wild animals en route.
Pass through Lecchi in Chianti, a quaint, stone village that has origins dating back to the medieval age. Several characteristics from this period, such as its narrow alleyways, can be seen and this offers a lovely and ancient atmosphere.
Located in a very quiet environment in the heart of Chianti region, Hotel Le Pozze di Lecchi offers two outdoor pools with panoramic views over the Tuscan hills and vineyards. The rooms are fully equipped with air conditioning, satellite LCD TV and minibar. The restaurant Monna Ginevra serves traditional and regional cuisine prepared in a style lounge. On sunny days, guests can enjoy meals on the outdoor terraces.
Transfer to the delightful hamlet of San Sano and then make your way on foot to Siena. Make the most of your last day of walking through these pristine and timeless landscapes. As you approach Siena you will walk past the Basilicata dell’ Osservanza from where there are fantastic views over this glorious Medieval city.
Located inside Siena's historic walls, Hotel Athena offers an elegant Italian restaurant and a furnished terrace with views of the town and the surrounding valley. Internet is free.With air conditioning, rooms are spacious and elegantly furnished with warm colour schemes and tiled floors. Rooms on the upper floors offer beautiful views.
Hotel Alma Domus enjoys the privilege of being in the heart of Siena’s historic city centre. Many of the rooms have balconies over looking city views and they are all stylishly decorated.
The Hotel Duomo is located in an antique mansion, whose history can be traced to the 12th century and it was originally the home of the noble family Loli. It was restored on the old foundations in 1726 with the façade in the Renaissance style. The furniture of the hotel is modern, with some traces of the past still visible in the wood beams and the brickwork in the breakfast room. On the terrace, above the sienese roofs, you can sun yourself in total relaxation, immersed in the romantic atmosphere of the mediaeval town, in one of the most beautiful regions of Italy, Tuscany.
Take your onward journeys by train to Pisa (1H45), Florence (1H30) or Rome (3H30).
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