Classic Chianti Short Break5 Days & 4 Nights 4.3 Read 3 reviews
- A short break in Tuscany walking classic Chianti wine routes
- ow 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
- and-picked very comfortable accommodations in remarkable locations
What To Expect
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...
- Wellness & Spa
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.
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 walk
When To GoYou 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 stay. We ask you to limit your luggage to one bag of up to 20 kg per person.
The distances and ascent/descents are approximations of the recommended routes. Please be prepared by packing all necessary items, for example, proper rain gear (jacket and pants), sun hat, sunscreen. Your information pack has a detailed equipment list which includes standard walking gear such as good walking boots or shoes, warm and waterproof clothes for the cooler months and lightweight clothing for summer, and a day pack.
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.
It is a requirement of booking this tour with Macs Adventure that you have suitable travel insurance which covers you for the activity and emergency evacuation and hospital care.
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.
We suggest you book as soon as your plans are finalised as the region is extremely popular. 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.
You will need good walking shoes/boots (ideally waterproof), comfortable walking clothes, and dependent on when you are travelling; waterproof jacket and trousers, a daypack and hats/gloves etc. Our info packs have a list of all equipment to bring on your walk.
If you prefer to walk in cooler months then May, June and September/October will be perfect for you. The autumnal colours are spectacular in Tuscany. The summer months (July, August) can be very hot. We advise that if you want to travel during these months that you start out on your walks early, so avoiding the midday heat.
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.
Centrally set in Gaiole in Chianti. All rooms are equipped with heating, Air-conditioning, kettle and cups, USB charge points, wifi, and TV receiving international channels. In addition, all the bedrooms and bathrooms are acoustically insulated for maximum privacy.
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.
La Chicca B&B is run by the Garavini family. The accommodation is situated in an old villa in the San Prospero area, just outside of the historic Siena’s walls. It’s just a 5 mins walk from the Piazza Campo. The B&B has 6 spacious double rooms (3 are ensuite, 2 have an external shared bathroom) with fans and central heating.
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.
Take your onward journeys by train to Pisa (1H45), Florence (1H30) or Rome (3H30).
The Macs Adventure Way
- Tried & Tested Adventures
- Book With Confidence
- Positive Impact
- 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
- Choose your own travel companions
- Walk, cycle and explore at your own pace
- Make your own decisions
- Choose your own path
- Indulge your passions
- 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
- 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 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
Getting to the Alta Via- An Adventure in itself!The Dolomites is not the easiest European mountain range to reach-unl ...
What to pack for the Alta Via 1I recently undertook the challenging Alta Via 1 trek through the stun ...
Adventure Of The Week: The Alta Via 1In Italy’s Dolomites range, soaring limestone towers reflect the gold ...
Adventure Of The Week: Classic Walks Of Gran ParadisoAlpine mountain trails arguably provide the greatest scenery. With th ...