Tuscany In Style
- Hike the famous Chianti Classico wine routes and immerse yourself in stunning landscapes
- Enjoy outstanding accommodations in exquisite 4* and 5* hotels, from castles to historic mansions
- Relish authentic Tuscan flavors with dinners at Michelin-starred restaurants and wine tastings at renowned vineyards.
- Enter the glorious medieval city of Siena on foot and explore its Gothic architecture
Gallery
Itinerary
Day 1 Arrive in Siena; transfer to Gaiole in ChiantiWhat better way to begin this trip than staying at a 5-star hotel in a former castle overlooking the Tuscan countryside. Enjoy free time on arrival to settle in and relax by the pool, and perhaps to sample your first glass of the world-famous red wine, Chianti Classico, which the region is famous for.
Siena is easily accessible from Pisa Airport and from here a transfer is included to Gaiole in Chianti, which is around 40 minute drive.
This exquisite 5* hotel is set in an ancient monastery from the 10th century. The large bedrooms have traditional Tuscan décor and panoramic views over the valley or the courtyard. The outdoor pool has a waterfall and a sun terrace. It’s Il Pievano 1* Michelin restaurant is situated in the castle’s historic hall and offers a large wine list. There’s also a gym, tennis courts, heated indoor pool, sauna, tepidarium, Turkish bath, emotional showers, and spa treatments available (additional charges apply and advance booking is recommended).
After breakfast there’s an included transfer to Radda in Chianti. After taking time to explore this medieval wine town, perched on a hilltop, and surrounded by stunning landscapes, start your hike back to Gaiole in Chianti. The trail 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 should you wish.
Thereafter walk downhill into Gaiole in Chianti and back to the hotel. Dine in style with an included dinner tonight in your hotel's Michelin star restaurant.
Ascent/Descent: 359m/527m (1,178ft/1,729ft)
Please note that the Michelin star restaurant closes normally around the Oct. 22, so if you are arriving later than this, the dinner tonight, won't be included.
This exquisite 5* hotel is set in an ancient monastery from the 10th century. The large bedrooms have traditional Tuscan décor and panoramic views over the valley or the courtyard. The outdoor pool has a waterfall and a sun terrace. It’s Il Pievano 1* Michelin restaurant is situated in the castle’s historic hall and offers a large wine list. There’s also a gym, tennis courts, heated indoor pool, sauna, tepidarium, Turkish bath, emotional showers, and spa treatments available (additional charges apply and advance booking is recommended).
This loop hike out of Gaiole in Chianti reveals the variety of Chianti landscapes as it journeys through woods, vineyards, and olive groves. Make a stop at the stunning monastery of Badia a Coltibuono. Monks took over this monastery in the 12th century and established a tradition of expert viticulture. Enjoy spectacular views over the Tuscan countryside from its lofty hillside look-out. On the way to the monastery, the road to Montegrossi passes the Castello di Montegrossi high on the cliffs above the roadside. Wander through the lovely little hamlet of Montegrossi and take the forest tracks skirting the hillside.
Stop at the Riecine Winery where a wine tour and tasting has been arranged (duration approx. 1,5 hours). At this winery, there have been generations of winemakers since Etruscan times and their objective is to create the very best wines from Sangiovese, the indigenous grape of the Chianti Classico region.
After the tasting the hike heads back into the Valley of Gaiole to return to where the hike began at the Church of San Sigismondo.
Ascent/Descent: 330m/328m (1,083ft/1,076ft)
This exquisite 5* hotel is set in an ancient monastery from the 10th century. The large bedrooms have traditional Tuscan décor and panoramic views over the valley or the courtyard. The outdoor pool has a waterfall and a sun terrace. It’s Il Pievano 1* Michelin restaurant is situated in the castle’s historic hall and offers a large wine list. There’s also a gym, tennis courts, heated indoor pool, sauna, tepidarium, Turkish bath, emotional showers, and spa treatments available (additional charges apply and advance booking is recommended).
Two-thirds of Chianti’s 70,000 hectares are still covered in oak woods and are home to wild boar, hares, deer, and pheasants, which there’s the possibility to spot enroute today. The route follows tracks, quiet roads, and paths to wander amongst the famous vineyards of Castello di Meleto before crossing the rolling hills, past villas, and through olive groves.
The destination of Hotel Le Fontanelle can be seen up on a ridge. It is a restored 13th-century mansion and in a very special locale with views all around.
We suggest departing from Gaiole-in Chianti early so that there’s time to make the most of your stay at this idyllic hotel, with its outdoor and indoor swimming pools, botanic garden, sauna, whirlpool, and steam bath. This evening dinner is included at the hotel.
Ascent/Descent: 498m/500m (1,634ft/1,640ft)
This beautiful estate is set in the middle of the Chianti, with fantastic views. It is a 13th century house that has been lovingly restored. Relax in the spa which has an indoor swimming pool, sauna, Turkish bath, jacuzzi, sensorial shower, and massage rooms (additional charges apply for treatments and advance booking is recommended). Other on-site activities include a yoga studio, golf driving range, and tennis courts. The restaurant serves cuisine with artistic flair and refined taste. On our ‘Chianti In Style’ trip dinner on both nights is included.
Today is free to relax at this outstanding hotel. Perhaps use the opportunity to book a spa treatment, play a spot of tennis or practice on the golf pitch and putt. The hotel also offers guided tours of Firenze or San Gimignano, cooking classes, or horseback riding excursions, so check out their website to book any of these options. Alternatively, this is an ideal spot to sit by the pool with a glass of wine and a good book.
This beautiful estate is set in the middle of the Chianti, with fantastic views. It is a 13th century house that has been lovingly restored. Relax in the spa which has an indoor swimming pool, sauna, Turkish bath, jacuzzi, sensorial shower, and massage rooms (additional charges apply for treatments and advance booking is recommended). Other on-site activities include a yoga studio, golf driving range, and tennis courts. The restaurant serves cuisine with artistic flair and refined taste. On our ‘Chianti In Style’ trip dinner on both nights is included.
Leave the lovely Hotel Le Fontanelle on foot and make the most of your last day of hiking through these pristine and timeless landscapes. The route approaching Siena goes past the Basilicata dell’ Osservanza where there are fantastic views over this glorious medieval city.
Siena is famous for the Piazza del Campo which is at the very core of the city and shaped like a scallop-shell. It is also the setting for the famous Palio horse race that takes place each summer. We recommend starting the hike early today to give you plenty of time to explore this iconic city. If time allows, why not add an extra night here to fully enjoy the many attractions here.
Ascent/Descent: 397m/417m (1,303ft/1,368ft)
Located within Palazzo Gori Pannilini from around 1501 in the historic centre of Siena. This delightful palace is the perfect embodiment of the finest Renaissance architecture. There are stunning frescoes and rich decorations that have been brought to light. Bedrooms are individually decorated and have enchanting interiors using high quality fabrics and antique furnishings. The large windows frame some of the best views that medieval Siena has to offer.
Right in the heart of Siena, this exceptional and elegant period residence offers a special stay and a very warm welcome. The building also features a large terrace overlooking the Church of San Domenico and the fortress. This is where breakfast is served and it’s possible to have an aperitif and watch the sunset over the city.
Today your dream vacation ends. From Siena, you can easily access Pisa, Florence and Rome by train.
This trip has a carbon score of 6kg per person per night, meaning it’s one of our best trips! For comparison, a carbon count of 6kg is equivalent to 4.5 ham and cheese sandwiches from the store. Here at Macs, we pride ourselves on being a responsible travel company and continue to adopt, develop and innovate ways to positively impact the environment. Find out more information about how we've carbon counted our trips.
Other Information
Is it for me?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. Of course, you should also love hiking, and on this trip, you take ‘easy to moderate’ graded hikes following trails through classic Chianti landscapes where time has stood still. There are numerous ascents/descents on the hikes, due to the nature of the hilly Tuscan scenery. If time allows, we suggest adding an additional day at the end of the trip in historic Siena to soak up the atmosphere and rejuvenate before continuing with onward travel.
In Style | After a day of exciting adventures and soaking up unbeatable scenery, retreat to stylish accommodations and unwind with fine food and wine. This trip type is for those who like sophisticated places to stay and are looking for active routes but still want the holiday to feel special.
Inn to Inn Walking | Walk from place-to-place changing accommodations each night. Generally staying in B&Bs, inns, and guesthouses.
Solo Travellers, Families with Teens
The minimum age for this tour is: 12 Years
This trip is graded ‘easy to moderate’ overall. The terrain is hilly with regular ascents and descents, and summer temperatures can be high. You should therefore be in good physical fitness to fully enjoy the hiking on this tour. Most of the route follows gravel and farm tracks and trails, and minor roads from time to time. It’s best to train ahead of time and do some practice hikes including stairs and ascents and descents like those you will experience on the trip while carrying your day bag. The hikes are an average of 15-16 km (9.3-10mi) each day and a couple of them are optional and could be skipped if an additional rest day is required. However, should you also wish to skip a hike between towns then you will be responsible for taking a taxi or bus (if possible) to the next place.
We have carefully hand-picked 4* and 5* ‘In Style’ hotels that showcase some of the best accommodation and service this region of Tuscany has to offer, while still offering a warm welcome to hikers.
The accommodation we normally use is detailed below. In Siena, if the hotels listed are not available, then we may book you into similar standard properties, as there are several other options in the city. However, since ‘In Style’ accommodation in Gaiole in Chianti and close to the Hotel Le Fontanelle does not exist, if these hotels are unavailable then you will need to be flexible on your tour start date.
You can add on extra nights in any of the overnight locations on this tour. If time allows, we recommend adding an additional night at the end of the tour in Siena to further explore this iconic city.
Single Rooms & Solo Hikers
This trip is not available to solo hikers 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.
Meals
Daily breakfast and three dinners are included on this tour. The first will be at the Castello di Spaltenna where the restaurant has a 1* Michelin chef and the others during the two-night stay at the Hotel Le Fontanelle. These included dinners will be special experiences and will feature the best of Tuscan cuisine.
Lunch is not included so you are free to choose from the available options. The Macs Adventure Smartphone App gives advice on where to eat/pick up lunch on each hike.
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.
- Accommodation in en suite rooms in 4* and 5* hotels on a double share basis
- Daily breakfasts
- Three dinners including one in a 1* Michelin restaurant with wine
- Wine tour and tasting
- Transfers as per your itinerary
- Door to door baggage transfers as per your itinerary
- All your trip documents including a detailed information pack provided digitally through your online Macs “My Account”
- Access to maps, GPX tracks and daily route information with the Macs Adventure smartphone navigation app
- Telephone support from our offices in the event of a problem
- Travel insurance (required) and personal equipment
- Lunches, other dinners, drinks, and snacks
- Tourist taxes (charged locally at hotels)
- Travel to and from Siena
- 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
This trip 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 challenging around the times of the 'Palio' horse races, which are held annually in early July and then again in mid-August over the course of 4 days each month.
Time of Year
The Spring months offer warm sunshine, fewer crowds, and pleasant hiking conditions. May is when most wildflowers are coming into bloom. The autumn months of September and October are also a favorable time of year, boasting cooler weather and a striking landscape made up of fall colors. July and August are good months to go but can be very hot for hiking 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. The towns and villages are very vibrant at any time of year, which makes for a great atmosphere, yet as soon as you get on the hikes its relatively quiet and peaceful.
This trip starts in Gaiole in Chianti and includes a transfer to your hotel from Siena (takes approx. 40min).
To reach Siena, we recommend flying into Pisa Airport (PSA) or Rome Airports (FCO or CIA). There is also an airport in Florence (FLR), however flights in and out of this airport are limited.
If arriving in Pisa: From the airport take the PisaMover that departs approx. every 10min to the Pisa Centrale Train Station (takes 5 minutes). After exiting Arrivals, follow the signs for the PisaMover, turning left and walking along the passageway to the little Pisamover station at the end of this passageway. You can either take the stairs up or go up to the platform with the elevator. Once upstairs you can buy a ticket from the machine. From Pisa Centrale Train Station, trains to Siena leave around every 30 mins, with one change and the journey takes approx. 1H45.
If arriving in Rome (note Rome has two airports): From Rome Fiumicino Airport (FCO), take the Leonardo Express Train that’s located inside the airport and departs every 15min to the central train station Roma Termini (takes about 32min). From Ciampino Airport (CIA), there’s a bus to Roma Termini (takes about 40min). From Rome’s Roma Termini Train Station, trains to Siena leave around every hour and the journey takes approx. 3H30.
If arriving in Florence: There’s a tram that departs approx. every 10min that will take you to Florence’s main railway station – the Santa Maria Novella (takes 20min). From there a train to Siena takes about 1H30. Some trains are direct 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.
If you’d prefer to avoid public transport from the airport, a private transfer can be requested. Please let us know at the time of booking if you would like to add this option (additional costs apply). Once your trip is confirmed please share your flight information with us, including your arrival time, as soon as you have booked your flights, so that we have those details well in advance and we can arrange the transfer for you ahead of time.
It's easy to travel from Siena by train to the major airports of Florence, Pisa, and Rome.
The Siena Train Station and Bus Station are located in the valley below the city center. (about a 2km/1.25mi walk from the majority of accommodations we use). To make your way to the station you have a few options (each payable locally): 1) take the escalators 2) take a bus or 3) take a taxi.
Approx. total journey times from Siena are:
To Florence 2H15 – 3H15
- The train to Florence Santa Maria Novella station is usually a direct train that goes via Empoli and takes around 1H30. Some trains are direct whereas others go via Empoli.
To Rome 2H15 – 3H20
- To Roma Termini Train Station it’s normally necessary to change trains in Florence or Chiusi-Chianciano Terme and takes around 3H30.
To Pisa 2H00 – 3H15
- To Pisa’s Train Station there is usually a train that departs approx. every 30min that goes via Empoli and takes around 1H45.
Once again it will be necessary to travel from the central train stations in these cities back to the airports (see ‘Getting to the Start’ for further information about this).
Alternatively, we can arrange a taxi from Siena to your departure city or airport. Please let us know in advance if you wish to include this option for an additional fee.
Please check the Trenitalia website for timetable planning. There are also local buses that you can take for your onward travel and you can find the information here. Please note that not all buses/trains run on a Sunday, or they may have a reduced timetable.
One main bag of up to 20kg/44lbs per person will be transferred from each accommodation to the next.
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