Classic Chianti Short Break5 Days & 4 Nights 4 Read 5 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
Slower Adventures | Where walking and cycling meet easy-going exploring, our Slower Adventures are the perfect combination. Most days are filled with picturesque journeys with some free time to dive into the destination and experience the people, local food and culture as you go.
Inn to Inn Walking | Walk from place-to-place changing accommodations each night. Generally staying in B&B’s, inns, and guesthouses.
This trip is suitable for:
As a guide, we would suggest that the minimum age of traveler this tour would be suitable for is: 12 Years
Ideal if you have an interest in:
- Short Break
Activity Level & Terrain
This trip is graded ‘easy to moderate’ overall. The terrain is undulating with regular ascents and descents, and summer temperatures can be high. 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 minor roads from time to time. It’s best ahead of time to do some practice walks including stairs and ascents and descents like those you will experience on the trip whilst carrying your day bag. The walks are an average of 15-16 kms each day. Should you also 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, except for some sections on dedicated trails. However, we provide the Macs Adventure Smartphone App making it simple to follow the route using a smartphone. Rest assured that by downloading the route maps in our app, that this will continue to work even in areas without any mobile or internet reception. For extra reassurance there are also turn-by-turn route notes within the app too for the walks.
Stay in charming small hotels, guesthouses and agriturismos. We carefully select small and friendly accommodation that offers great value, so you enjoy every minute. All ae located in glorious settings, be it a town, a hamlet, or the wonderful city of Siena.
Many of our walkers choose to add extra nights along the walk to sample more of the wonderful walking and attractions available in Chianti. If time allows, then we would recommend adding an additional night at the end of the tour in Siena to further explore this iconic city.
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.
The delicious Chianti food and wine is undoubtedly a highlight of this holiday.
Breakfast is included each morning and normally consists of a traditional European style continental breakfast or buffet breakfast that often includes coffee, tea, yoghurt, granola, meat, cheese, and baked goods. In some cases, a hot dish (eggs, pancakes, etc.) will be served or offered á la carte.
Lunches and dinners are not included in this trip. We recommend finding cafés or restaurants located in the towns or along the walking route, or to purchase snacks and a picnic lunch to bring along on the walks from local supermarkets and markets. Alternatively, most accommodations will be happy to provide a packed lunch on request and this can be booked on arrival. Dinner is available either at your accommodation or nearby restaurants. Further details can be found within your information pack and the Macs Adventure Smartphone App.
- Accommodation in en suite rooms in charming hotels, guesthouses and agriturismos on a twin share basis
- Daily breakfasts
- Door to door baggage transfers as per your itinerary
- Transfers as per itinerary
- Access to maps, GPX tracks and daily route information with the Macs Adventure smartphone navigation app
- All your trip documents including a detailed information pack provided digitally through your online Macs “My Account”
- Telephone support from our offices in the event of a problem
- Travel insurance (required) and personal equipment
- Travel from the tour finishing point
- Lunches, dinners, drinks, and snacks
- Tourist taxes (charged locally at hotels)
- Any additional transfers or public transport required to shorten the walks or skip a stage
- Additional nights before, during or after the tour
- Private transfer from the end point of the tour to the airport
- Room upgrades
When To Go
This tour is available to start anytime between April and October.
Peak Season Availability
As Tuscany is a very popular destination, we suggest booking as soon as possible to ensure availability for specific dates. Availability in Siena is very difficult around the times of the 'Palio' horse races held annually normally in early July and then again in mid-August.
Time of Year
The springs months of April, May and June offer warm sunshine, fewer crowds, and pleasant walking conditions. May is when most wildflowers are coming into bloom. The autumn months of September and October are also a favourable time of year, boasting cooler weather and a striking landscape made up of autumnal colours. July and August are good months to go but can be very hot for walking and therefore aren’t best suited for everyone. You will have to start early to miss the heat of the day and carry a lot of water (additional weight) with you. Although the towns and villages are buzzing at this time of year which is great to see.
Getting to the Start
On this tour an included transfer will bring you from Siena to Radda-in-Chianti, your starting point.
To reach Siena fly into Pisa or Rome Airports. There is also an airport in Florence, however flights in and out of this airport are limited.
If arriving at Pisa from the airport take the PisaMover to the main train station (takes 5 minutes). Turn left when exiting arrivals and the PisaMover is at the end of the airport. From Pisa Centrale Train Station trains to Siena leave around every 30 mins, with one change and the journey takes approximately 1 hour 45.
Rome has two airports. From Fiumicino Airport take a train to the central station Roma Termini (taking about 30 minutes). From Ciampino Airport there’s a bus to Roma Termini. From Rome centre change trains in Florence to go to Siena. Trains leave approximately every hour and take about 3 hours 30.
If landing at Florence Airport, there’s a shuttlebus into the centre of Florence (taking around 25 minutes). It stops beside the main railway station of Santa Maria Novella. From Florence a train to Siena takes about 1 hour 30. Some trains are direct whereas others go via Empoli.
Please check the Trenitalia website for timetable planning. Please note that not all buses/trains run on a Sunday, or they may have a reduced timetable.
Getting from the End
As the tour finishes in Siena, use the same travel information as shown in ‘Getting to the Start’ to reverse the journey back to the chosen departure point.
One bag of up to 20kg per person will be transferred from each accommodation to the next.
At Macs Adventure, we work in partnership with many luggage transfer providers who set a limit on how many bags/suitcases they will transfer per person, and also the weight of the bag/suitcase. Your booking includes transfer of 1 bag per person. It is very important that you read the luggage information specific to your tour before departure. If you do not adhere to these limits, there is a great possibility that you will be charged locally both for extra bags or if they are too heavy. This limitation can be a challenge, especially as airlines generally have limits that are higher. However, our luggage providers have reasons for these limits (usually due to the Health and Safety of their employees), which we must respect.
Our pre-departure information pack details 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.
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 goes through a range of scenery including 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 is the Church of San Bartolomeo a Vertine, dating back to the 11th century with Renaissance frescoes by the Florentine School inside. Vertine also has a winery, so there’s the opportunity to stop for a tasting.
Walking downhill into Gaiole in Chianti and to your hotel.
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.
There are two potential walks today that you can choose from, the above distances are based on the short option. This involves transferring to Pieve di San Giovanni Battista a Pievasciata to start the walk from here. Alternatively you can transfer to San Sano for the longer walk. Either way you'll then follow the same route as you make your way on foot to Siena. Making the most of your day walking through this pristine and timeless landscape. As you approach Siena you will walk past the Basilicata dell’ Osservanza from where there are fantastic views over this glorious medieval city.
Shorter walk: 15 kms/10 mi Ascent/Descent: 317m/428m
Longer walk: 21 kms/13 mi Ascent/Descent: 484m/540m
Please let us know at the time of booking which option you attend to take, so we can arrange your transfer accordingly.
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.
Siena is easily accessible by train from Pisa, Florence and Rome.
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