Self-Guided Walking Tours & Biking Tours

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Relax in exquisite villas and hilltop villages overlooking olive groves and rolling vineyards


  • Walk the best sections of Tuscany's “Chianti Classico” wine routes
  • Relax in exquisite villas and hilltop villages overlooking olive groves and rolling vineyards
  • Savor bold, fruit-forward Sangiovese during a classic Chianti wine tour and tasting
  • Explore the glorious medieval city of Siena, an UNESCO World Heritage Site
  • Soak up the culture and learn traditional Italian recipes in the ancient kitchen of the Palazzo Leopoldo

Walk through the best and timeless landscapes of Chianti to Siena in-style, featuring authentic cultural experiences and exquisite overnight stays.

Explore the Heart of Tuscany by walking from Radda and Gaiole in Chianti, two of the most beloved towns of the Chianti Classico region. Walk among castles, fortresses, Romanesque Churches, olive groves and row upon row of vines, interspersed with peaceful wooded valleys. Pamper your palate with a wine tour and tasting at the Recine Winery; a winery dedicated to quality and traditional methods of wine making. Eat, cook and learn family recipes at an Italian cooking class and enjoy dinner at the Michelin star restaurant of your elegant villa.

Each evening, roam the piazza of your charming hamlet and take an aperitif at “osterias” overlooking the Tuscan countryside.

Day 1: Arrive Siena & Transfer to Radda in Chianti

Begin your Chianti tour with two nights in the medieval wine town of Radda in Chianti, perched on a hilltop and surrounded by the stunning landscapes of Sangiovese vineyards. Upon arrival to Siena (easily accessible by train from Florence and Pisa), take a private transfer to your overnight accommodation in Radda in Chianti.

Tonight, celebrate your arrival by dining in town at a local “Trattoria,” a rustic family-run restaurant, for homemade pasta and a glass of the world-famous Chianti Classico.

Overnight: Radda in Chianti

Day 2: Radda in Chianti Loop Walk & Cooking Class

From the doorway of your hotel, walk directly out of town and into the enchanting vineyards of Chianti. Walk uphill to Castelvecchi, one of the most important farms and properties of the nobile “De Vecchi” family. Explore the Church of Pieve di Santa Maria Novella before continuing along a small wooded trail with stunning panoramic views to Volpaia. Grab lunch and explore this adorable hamlet boasting wineries, cafés and artisanal delights. Conclude your journey through rows of cypress trees and a final ascent back to your hotel and spa in the hilltop village of Radda.

This evening enjoy a cooking class in the age-old kitchen of your hotel, Palazzo Leopoldo. With the guidance of three Italian sisters (Anita, Valentina and Rosanna), learn how to cook simple, yet delectable, Chiantigiane cuisine for tonight's dinner (included).

Walk: 8.5 miles / 14 km (+1644/-1647ft.)

Dinner & Overnight: Radda in Chianti

Day 3: Walk to Gaiole in Chianti

After breakfast, begin today’s walk through dense vineyards, orchards, terraced slopes and wooded valleys to Vertine.

This delightful and seemingly untouched hamlet is known to have more stones than people dwelling within its medieval walls. Roam the quiet streets admiring the castle, Renaissance frescoes (by the Florentine school), and the Church of San Bartolomeo a Vertine dating back to the 11th century. Visit the Castello Vertine, a rustic winery, for tastings of local vintages before continuing downhill to Gaiole.

Tonight, enjoy the comforts of your lavish hotel and dinner at it’s associate 1* Michelin restaurant.  

Walk: 9 miles / 14.5 km (+1198/-1752ft.)

Dinner & Overnight: Gaiole in Chianti

Day 4: Gaiole in Chianti Loop Walk & Wine Tour and Tasting

Enjoy the vast variety of Chianti’s landscape as you make your way from Gaiole to the nearby Riecine Winery. Riecine, a converted monastery and farm, boasts quality, passion and dedication to traditional methods of winemaking; methods that have been passed down since the Etruscan times.

Continue your Chianti tour as you walk to the village of Montegrossi and to the stunning monastery of Badia a Coltibuono, meaning “Good Harvest.” Taken over by monks in the 12th century, explore the rooms, wine cellar and gardens established by these experts in viticulture.  

Walk: 9.5 miles / 15 km (+1138/-1122ft.)

Overnight: Gaiole in Chianti

Day 5: Walk to Hotel Le Fontanelle

Start today’s walk early for a full afternoon spent at the premier Hotel Le Fontanelle. Soak in the stunning scenery that encompasses today’s entire route, keeping your eyes peeled for cinghiale (wild boar), hares, deer and pheasants that dwell in the 70,000 hectares of covered oak woods.

Upon reaching the final stretch, look up the ridge for spectacular views of Hotel Le Fontanelle, your overnight resort, perched on a hilltop within the affluent estate of Castelnuovo Berardenga. Serving as a restored 13th century property, enjoy the outdoor & indoor pool, sauna, whirlpool, steam bath and botanical gardens of this idyllic hotel.

Walk: 11 miles / 18 km (+1519/-1686ft.)

Dinner & Overnight: Hotel Le Fontanelle

Day 6: Walk to Siena

Leave the lovely Hotel Le Fontanelle on foot, to the medieval city of Siena.  

In Siena, grab an aperitivo or gelato in the Piazza del Campo, the core of Siena and often regarded as Europe’s greatest medieval squares. Soak in the architecture of the Palazzo Pubblico, Torre Mangia and the amazing architecture of this shell-shaped city. Famous for its centuries of Palio horse races and serving as today’s essential public center, Siena remains a city of extraordinary significance and exquisite beauty.

Walk: 9.5 miles / 15 km (+1339/-1404ft.)

Overnight: Siena

Day 7: Onward Travel

Depending on your travel arrangements, join a history tour or roam the city’s boutique leather shops before departure.

If desired, a private transfer from your hotel to Siena Train Station can be included in this tour (additional costs apply). Please contact us here at Macs Adventure if you would like to add this option or if you need any help planning your onward travel.


Included in this trip are six nights in hand-selected premier accommodations. We’ve carefully hand-picked premiere properties that are the best in the region to ensure that you enjoy every minute of your stay while in Chianti.

Single Rooms & Solo Walkers

This trips is based on two people sharing a room. If you’d like separate rooms, a single supplement is required.

If you would like to request a twin room (same room with two separate beds), please notify us at the time of booking so we can request this option.

This trip is also available to solo walkers (a solo supplement is required).


Breakfast is included each morning and consists of a traditional European style breakfast. Most breakfast include coffee, tea, yogurt, granola, seasonal fruit, meat, cheese and baked goods. In most cases, a hot dish (eggs and pancakes) will be served a la cart or can be ordered off a menu.

Three dinners are included in this trip to ensure a special experience and to feature the best of Tuscan cuisine. Included dinners consist of a cooking class at Palazzo Leopoldo (night 2), dinner at a Michelin star restaurant at Castello di Spaltenna (night 3), and dinner at the restaurant of your private retreat in Hotel Fontanelle (night 5). Note - these dinners also include wine.  

Lunch is not included in this trip, so you are free to choose from nearby available options. For lunches, we recommend finding cafés or restaurants located in the towns along the walking route, or you can purchase snacks and a picnic lunch to bring along with you. Further information can be found within your information pack and route notes.

Cooking Class

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.

Additional Nights

You can easily request to add on an extra night at any location during this itinerary.

Please notify us at the time of booking should you wish to add extra nights.



Palazzo Leopoldo - Radda in Chianti

Nestled in the expanses of the vineyards of Chianti, Palazzo Leopoldo is set in an enchanting mansion originally built in the 1300’s. Retaining its original structure both inside and out, enjoy modern furniture complemented by antiques, elegant and spacious bedrooms, a swimming pool, spa and restaurant serving only the most traditional and delicious Italian cuisine.







Castella di Spaltenna - Gaiole in Chianti

This exquisite 5* hotel is set in an ancient monastery dating back from the 10th century. Relish in the large rooms with traditional Tuscan décor and the panoramic views over the valley and courtyard. Take a swim in the outdoor pool or sunbathe near the waterfall and sun terrace for the most rejuvenating experience. Enjoy the extensive wine list and an evening dining in the Il Pievano 1* Michelin restaurant, situated in the castle’s historic hall, and served in the courtyard by candlelight.







Hotel Le Fontanelle - Pianella

Set in the remote and gorgeous Chianti countryside, delight in luxury with a stay at this remote retreat. Once a small rural village, the property now enchants travelers from near and far in search of beauty, comfort, romance and inspiration. The hotel, once a 13th century house, has been lovingly restored to capture the magical essence of Chianti. Enjoy roaming the grounds, relaxing in the spa, and evenings spent “wining and dining” at the Restaurant Colonna, a ristorante of artistic flair and refined taste.







Relais degli Angeli - Siena

Situated in the heart of Siena, this exceptional and elegant residence offers a special stay and warm welcome. Delight in spacious rooms full of luxurious light, frescoed ceilings, marble bathrooms and refined style. In the mornings and evenings, enjoy breakfast and an aperitif overlooking the Church of San Domenico and the fortress upon the beautiful large terrace.








This tour is available to start anytime between April and October. 

As 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, we suggest you book as soon as your plans are finalized to ensure available for specific dates.

Please note that the wine tour and tasting is not available before Easter or on a Sunday, so please keep this in mind when booking and try to avoid beginning your tour on a Thursday, if possible.

When to Go?

The best time to visit Chianti is during the early spring and late fall.

July and August are also great months to go but can be very hot for walking. If booked during these months, we therefore advise you to begin walks very early in the morning to avoid the midday heat. 


While the route is not waymarked (with the exception of some sections where you will be walking dedicated trails), navigating is easy using the Macs Adventure Navigation App.

Your daily walks will be mapped in the app with GPX tracks, including route notes and turn-by-turn directions. All of these resources are available to download for offline use. More information is outlined within your detailed information pack, in addition to 24/7 telephone support from Macs Adventure should you require assistance.

Grade & Terrain

We have created this “best of” itinerary to showcase the best walks and to create the perfect balance of walking, sightseeing and culture.

This itinerary is graded moderate, with five days of walking and a maximum distance of 11 miles. Daily walks average around 9 miles (4-6 hours) along rolling terrain as you walk to-and-from hilltop villages. Note - two of the days have “loop walks” that are optional.

On most days you will be walking on routes following gravel, farm tracks and dirt trails, while on some days you will be following backcountry roads.

You should be in decent physical shape and comfortable walking everyday to fully enjoy the walking on 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.

Luggage Transfer

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.

Travel Insurance

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 by clicking this link.

Getting to Radda in Chianti

Included in this trip is a private transfer from Siena to Radda in Chianti (Day 1).

Getting to Siena

Air & Train

To get to Siena, Pisa and Florence both have airports with flights from international and national destinations.

We recommend flying into Florence and taking a taxi from the airport to the Florence Train Station. Trains to Siena from Florence depart several times per day (approx. 2 hours total, note—some trains are direct while others have a change over in Empoli).

If flying into Pisa, take the tram from the airport to the Pisa Centrale Train Station. Trains to Siena leave from Pisa Centrale Train Station every 30 minutes (approx. 2 hours total, including one change over along the route).

Getting from Siena

By Train:

Trains to Florence, Pisa and Rome depart everyday directly from Siena Train Station. Trains, ticketing and more information can be found within your pre-departure information pack. For additional information, please check the Trenitalia website for updated timetables.



  • 6 Nights in premier hotels
  • 6 Breakfasts
  • 3 Dinners (wine included one dinner at a Michelin star restaurant)
  • Luggage transfers
  • Private transfer from Siena to Radda in Chianti (arrival)
  • Cooking Class
  • Wine Tour & Tasting
  • Turn-by-turn route notes
  • Detailed information pack
  • Macs Adventure Navigation App
  • 24/7 Telephone support


  • Travel insurance
  • Flights
  • Travel to-and-from Siena
  • Lunches & 3 Dinners
  • Drinks and snacks
  • Personal equipment


  • Private transfer from Florence to Radda in Chianti (arrival)
  • Private transfer to Siena Train Station (onward travel)
  • Additional nights before, during or after the trip
  • Single room supplement (if required)
  • Solo supplement (if required)

How fit do I need to be?

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.

How far in advance do I need to book?

We suggest you book as soon as your plans are finalized 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.

Please note that the wine tour and tasting is only offered after Easter and is closed on Sundays. Please try to avoid beginning your tour on a Thursday if possible, and check your date before booking to avoid any conflicts with this tour.

What personal equipment do I need?

You will need to bring good walking shoes/boots (ideally waterproof), comfortable walking clothes, layers, waterproof jacket and pants, a daypack and hats/gloves etc. Our pre-departure information pack has a suggested list of all equipment to bring on your walk.

When is the best time of year?

If you prefer to walk in cooler weather, May, June and September/October will be perfect for you. The autumn colors are especially spectacular in Tuscany.  The summer months of July and August can be very hot, but are also very popular times to visit the region. We suggest starting your walks early in the day during these months to avoid walking in the heat of the day. 

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