Self-Guided Walking Tours & Biking Tours

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Walk Chianti’s enchanting Tuscan countryside from Radda in Chianti to Siena


  • Walk Chianti’s enchanting Tuscan countryside from Radda in Chianti to Siena
  • Enjoy a Florence city tour, for Italian Renaissance culture, art and architecture
  • Taste bold “Chianti Classico” vintages and hearty homemade pastas in family-run trattorias
  • Wander beside towering cypress trees, rolling vineyards and endless rows of olive groves
  • Sip an aperitivio in the bustling piazza of Siena, a UNESCO World Heritage Site

A classic and full discovery of Tuscany's Chianti wine region from Florence to Siena. Discover Florence, the heart of the Italian Renaissance, and walk the beloved and poetic landscapes of Chianti on foot from Radda in Chianti to Siena, for an unforgettable getaway under the Tuscan sun.

Follow Tuscan trails as you walk from village to village from Radda in Chianti to Siena. Wander through hilltop fortresses, olive groves, rustic farmhouses and row upon row of manicured vines interspersed with peaceful wooded valleys. Discover Romanesque Florence, the medieval city of Siena, and the stunning “Chianti Classico” region between, with ample time to experience local wineries and your delightful hamlets.

Spoil your senses with a nine day retreat relishing in the intoxicating mix of serene scenery, rich ragus and a glass of savory Sangiovese that is quintessential Tuscany.

Day 1: Arrive Florence 

Welcome to the heart of the Italian Renaissance where beauty, art, history and culture is the essence of everyday life. Wander the old streets of Florence where magnificent Baroque and Gothic churches, fortresses and cathedrals pose in every direction. Explore 13th century Basilicas, the Ponte Vecchio “The Old Bridge,” the Uffizi Gallery and the Pitti Palace, where the House of Medici shaped Florence into a helm of arts and humanities.

Finish your day with a “passeggiate” (evening walk), an Italian social ritual within the Piazza della Repubblica for fantastic people watching and osterias boasting gourmet Italian cuisine.

Overnight: Florence

Day 2: Florence City Tour & Transfer to Radda in Chianti

This morning, join a local guide for a fascinating morning tour exploring world-famous artwork and Florence’s top attractions. Discover Palazzo Vecchio, the infamous fortress and town hall of Florence, rub il Porcellino’s nose for luck, navigate Accademia Galleria for Michelangelo’s “David,” and be awed by the exterior of Florence’s Cathedral “Duomo.”  

After lunch, take a private transfer to Radda in Chianti (approx.1.5 hours). For two nights, stay in this spectacular Medieval town, perched high upon a hilltop and surrounded by the stunning landscapes of Sangiovese vineyards. 

Overnight: Radda in Chianti

Day 3: Radda in Chianti Loop Walk

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 the hilltop village of Radda.

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

Overnight: Radda in Chianti

Day 4: Walk to Gaiole in Chianti

After breakfast, depart for 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 in town, for tastings of local vintages before continuing downhill to Gaiole.

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

Overnight: Gaiole in Chianti

Day 5: Gaiole in Chianti Loop Walk

Enjoy the vast variety of Chianti’s landscape as you loop around Gaiole’s countryside. Stop over at the nearby Riecine Winery, a converted monastery and farm, for wines boasting quality, passion and dedication to traditional methods of winemaking.

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 6: Walk to Lecchi in Chianti

Today, make your way to Lecchi in Chianti, a quaint, stone village with origins dating back to the late 13th century. Once a great estate linked to the Ricasoli family, enjoy the rolling vineyard trails winding around Lecchi and the surrounding valley. Soak in views of the castle ruins of Monteluco in Lecchi, located on the hill overlooking the village, and the ancient characteristics, narrow alleyways and distinctive limestone houses of this lovely hamlet.

In Lecchi, choose from various local “Trattorias,” rustic family-run restaurants, for homemade pastas and a glass of the world-famous Chianti Classico.

Walk: 6.5 miles / 10 km (+994/-778ft.)

Overnight: Lecchi in Chianti

Day 7: Transfer to San Sano & Walk to Siena

Take a private transfer to the delightful village of San Sano and make your way on foot to Siena. Soak in the pristine and natural beauty of this day of walking through Chianti’s timeless landscape.

Walk past the Basilica dell’Osservanza, rebuilt and restored twice since its construction in 1451, for fantastic views over the glorious Medieval city of Siena. Siena, famous for its centuries of Palio horse races and serving as todays essential public center, remains a city of extraordinary significance and exquisite beauty. Grab a gelato or aperitif in the Piazza del Campo in celebration of this final stretch.

Walk: 13 miles / 20 km (+1631/-1795ft.)

Overnight: Siena

Day 8: Discover Siena (Free Day)

Today is yours to explore the grandeur and the amazing architecture of this ancient, shell-shaped city. Join a walking tour or set out on your own to explore the Cathedral of Sata Maria Assunta, the Crypt and the Piccolomini Library of the Piazza del Duomo. Climb to the top of the striped Tower of Mangia or visit the Santa Maria della Scala where pilgrims and abandoned children once sought refuge. 

Overnight: Siena

Day 9: Onward Travel

Depending on your travel arrangements, roam the city’s boutique leather shops before a private transfer from your hotel to Siena Train Station.

If you need help planning your onward travel, please contact us at our office here at Macs Adventure, and we would be more than happy to help.



Included in this trip are eight nights in hand-selected accommodations. We’ve carefully chosen properties that offer comfort and are located in beautiful settings to ensure that you enjoy every minute of your stay while in Chianti.

We regularly use the following properties but may accommodate you elsewhere if these are unavailable. 

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 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.

Lunches and dinners are not included in this trip, so you are free to choose from nearby available options. Part of the fun is finding local cafés or restaurants (osterias, trattorias or ristorantes), located in the towns and along the walking route for gourmet Italian cuisine. For lunches, you can purchase snacks, or even pack a picnic lunch, to bring along with you. Further information can be found within your information pack and route notes.

Florence City Tour

Included in this itinerary, on the second day of this trip, is a morning Florence City Tour. Enjoy a three-hour, small group tour (25 people max), with an expert local guide to experience world-famous artwork and this Renaissance city’s top attractions. Tours are chosen for optimal experience and headphones are given so you can better hear the guide, with English translation. Please note that the tour, time and itinerary booked is dependent on capacity and can vary. More information can be found at the time of booking and within your trip summary document.

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.




Florence - Hotel Davanzati

Hotel Davanzati is a family-run hotel owned and operated by the Fuzier Cayla family. Enjoy staying in this traditional hotel with original Tuscan furnishing, refurbished comforts, Italian hospitality and proximity to Florence's top attractions.




Radda in Chianti - Palazzo San Niccolo

Located in an ancient and beautiful building in the old center of Radda in Chianti, enjoy charming rooms, modern comforts and panoramas of Chianti's stunning landscape.




Gaiole in Chianti - Cavarchino B&B - Gaiole in Chianti

This beloved family-run B&B is conveniently located on the outskirts of Gaiole in Chianti for a perfectly peaceful getaway in the Chianti countryside. End your day of walking by relaxing at this restored stone farmhouse, outdoor pool and lush gardens.







Lecchi in Chianti - Le Pozzi di Lecchi

Located deep within the quiet farmland of the Chianti region, Hotel Le Pozze di Lecchi offers two outdoor pool, delicious cuisine, comfortable rooms and patio terraces boasting panoramic views over the Tuscan hills and vineyards.







Siena - Hotel Alma Domus

Enjoy the privilege and exclusivity of being in the heart of Siena’s historic city center. Take comfort in your stylish room and upon the balconies overlooking the city's dramatic skyline.








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.

When To Go?

The best time to visit Tuscany’s Chianti region 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 always 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

This itinerary is graded moderate, with five days of walking and a maximum distance of 13 miles in one day. 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 Florence

By Air:

We recommend flying into Florence Airport, which has flights from international and national destinations.

Upon arrival to Florence Airport (FLR), take a taxi from the airport to your overnight accommodation. Taxis are lined up outside the arrivals exit gate for a transfer, at your convenience, to your overnight hotel.  

If desired, a private transfer from Florence Airport to your overnight hotel in Florence can be arranged for you instead (additional costs apply). Please let us know at the time of booking if you prefer this option.

Getting from Siena

By Train:

Included in this trip is a private transfer from your hotel to the Siena Train Station on the final day. Trains to Florence, Pisa and Rome depart everyday directly from Siena Train Station. Please inform us at the time of booking if you require a morning or afternoon transfer.

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.


  • 8 Nights in hand-selected B&Bs and boutique hotels
  • 8 Breakfasts
  • Florence City Tour
  • Transfer from Florence to Radda in Chianti (Day 2)
  • Transfer to San Sano (Day 7)
  • Transfer to Siena Train Station (onward travel)
  • Baggage transfers
  • Turn-by-turn route notes
  • Detailed information pack
  • Macs Adventure Navigation App
  • 24/7 Emergency telephone support


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


  • Additional nights before, during or after the trip
  • Single room supplement (if required)
  • Solo supplement (if required)

We are often asked the following questions and we hope that you will find the answers useful. Please do not hesitate to contact us if you have any other questions (or for more advice), from our team here at Macs Adventure.

How fit do I need to be?

This walking trip is graded moderate and involves 4-6 hours of walking each day, and a maximum distance of 13 miles in one day, so you should enjoy an active lifestyle to get the most from your time in Tuscany. 

How far in advance do I need to book?

As Tuscany is a very popular destination, we suggest you book as soon as your plans are finalized to ensure availability for specific dates.

How does the luggage transfers work?

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.

Which is the best airport?

Florence, Pisa or Rome are convenient airports to fly into both nationally and internationally. Most destinations within Italy have a central train station in which to arrive and depart. 

What happens if I become ill or can’t walk a stage?

If you are not up for walking the entire route, you can stop at any town along the way and call a taxi, or one of our local representatives, from the contact information found within your pre-departure information pack. If you become ill or want to avoid walking an entire day, that's Ok. Due to being a high tourist destination, local taxis and car services are available to call from your hotel, or you can catch a ride with the morning luggage transfer (when applicable). Specifics and contacts numbers can be found within your pre-departure information pack, or you can ask the host of your overnight hotel for assistance. If you need medical services, please seek immediate assistance at your hotel or nearby hospital.

As always, 24/7 support from Macs Adventure is only a phone call away.


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Macs Adventure - US Office: 3200 Carbon Place Suite 102, Boulder, CO 80301