7 Days & 6 Nights

4.8

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

Our Tuscany in Style tour is perfect for those who want to savor every moment of their travel experience. Imagine hiking through the timeless Tuscan landscapes of Chianti & Siena, sampling gourmet cuisine and dining at a Michelin star restaurant, sipping world-class wine, and staying in premium hotels. Chianti, with its castles, olive groves, and row upon row of vines, is famously known for producing rich, velvety red wines since the 13th century and offers an intoxicating mix of exceptional experiences. Sound like a dream? Experience the charm of Tuscany ‘In Style’ with Macs Adventure.

From $3,995.00

Select Date Inquire Tour Brochure

Gallery

All Photos (10)

Itinerary

Expand all

Day 1 Arrive in Siena; transfer to Gaiole in Chianti

Siena is easily accessible from Pisa Airport by train. From Siena a transfer is included to Gaiole in Chianti, which is around 40 minutes’ drive.

What better way to begin this trip than staying at a 5-star hotel in a former castle overlooking the Tuscan countryside. Free time on arrival to relax by the pool and settle in, and perhaps to sample your first glass of the world-famous red wine, Chianti Classico, which the region is famous for.

Overnight Gaiole in Chianti

Accommodations

A sample of our typical carefully chosen accommodation in this location. Where you stay will vary depending on availability, but will be a similar standard.

Castello di Spaltenna | 5 Star | Hotel

This exquisite 5* hotel is set in a 10th century monastery. 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).

Day 2 Transfer to Radda; hike back to Gaiole in Chianti via Vertine 9 miles / 14 km

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 the stunning landscapes. Commence the walk back to Gaiole in Chianti 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 back to the hotel. Sample an included dinner tonight in its 1* Michelin restaurant.

Ascent/Descent: 359m/527m

Please note that the Michelin star restaurant closes normally around the 22-Oct, so if you are arriving later than this, the dinner tonight, won't be included.

Overnight Gaiole in Chianti

Accommodations

A sample of our typical carefully chosen accommodation in this location. Where you stay will vary depending on availability, but will be a similar standard.

Castello di Spaltenna | 5 Star | Hotel

Day 3: Gaiole in Chianti loop walk via Badia a Coltibuono Monastery & Riecine Winery 9 miles / 15 km

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. It offers 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.

Perhaps stop at the Riecine Winery where it’s possible to arrange a wine tasting in the afternoon (please note they are not open on Sundays and only offer tours after Easter so please check your dates before confirming your booking). 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.

The hike heads back into Gaiole to return to where it begins at the Church of San Sigismondo.

Ascent/Descent: 335m/335m (1,099ft/1,099ft)

Overnight Gaiole in Chianti

Accommodations

A sample of our typical carefully chosen accommodation in this location. Where you stay will vary depending on availability, but will be a similar standard.

Castello di Spaltenna | 5 Star | Hotel

Day 4 Hike to Hotel Le Fontanelle, near Pianella 11 miles / 18 km

Two-thirds of Chianti’s 70,000 hectares are still covered in oak woods where wild boar, hares, deer, and pheasants still reside, which there’s the possibility to spot en route today. The route follows tracks, quiet roads, and paths to wander amongst the famous vineyards of Castello di Meleto. Before crossing the rolling hills, pass 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 the 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

Overnight Hotel le Fontanelle

Accommodations

A sample of our typical carefully chosen accommodation in this location. Where you stay will vary depending on availability, but will be a similar standard.

Hotel le Fontanelle | 5 Star | Hotel

This 13th century estate is set in the middle of the Chianti and 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.

Day 5 Free day at Hotel Le Fontanelle

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 horse 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.

Overnight Hotel le Fontanelle

Accommodations

A sample of our typical carefully chosen accommodation in this location. Where you stay will vary depending on availability, but will be a similar standard.

Hotel le Fontanelle | 5 Star | Hotel

Day 6 Hike to Siena 9 miles / 115 km

Leave the lovely Hotel Le Fontanelle on foot and make the most of the last day of walking through these pristine and timeless landscapes. The route approaching Siena goes past the Basilicata dell’ Osservanza from 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 walk early today to give 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: 410m/430m

Overnight Siena

Accommodations

A sample of our typical carefully chosen accommodation in this location. Where you stay will vary depending on availability, but will be a similar standard.

Relais Degli Angeli | 4 Star | Hotel

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.

Grand Continental Siena | 5 Star | Hotel

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.

Day 7: Onward travel from Siena

THIS TRIP'S CARBON SCORE

This trip has a carbon score of 14kg per person per night, meaning it’s one of our best trips! For comparison, a carbon count of 14kg is equivalent to 7 bottles of champagne. That’s a lot of bubbles!. 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.

Reviews

Expand all

Other Information

Expand all

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.

Tour Type:

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.

Activity:

Inn to Inn Walking | Walk from place-to-place changing accommodations each night. Generally staying in B&Bs, inns, and guesthouses.

This trip is suitable for:

Families with Teens

The minimum age for this tour is: 12 Years

Ideal if you have an interest in:

Foodie

Wine

Activity Level & Terrain

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.

Accommodation & Meals Navigation What's Included

Included

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
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 (Days 2, 4, 5)
Wine tour and tasting
Transfers as per your itinerary (including on Day 1 from Siena Train Station to Gaiole-in-Chianti
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”

Excluded

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
Travel insurance (required) and personal equipment

Extras

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 Travel & Transfers

Getting to the Start

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.

Getting from the End

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.

Luggage Transfer

One main bag of up to 20kg/44lbs per person will be transferred from each accommodation to the next.

Info & FAQ

General Information

How far in advance do I need to book? What personal equipment do I need? Which is the best airport? How does the luggage transfers work?

Tuscany In Style

Walk Tuscan wine trails through the timeless landscapes of Chianti to Siena, staying in ‘In Style’ accommodation. This very special tour combines walking with opportunities to eat authentic Tuscan cuisine at a Michelin star restaurant, tour a vineyard and of course sample the world-renowned wines, and stay in the outstanding hotels. An intoxicating mix of exceptional experiences.