OVERVIEW

Immerse yourself in Tuscan landscapes of olive groves, cypress trees and vineyards on this self-guided walking exploration. Between the artistic opulence of Florence and the Renaissance piazzas of Montepulciano, discover the wine towns of Chianti and follow ancient pilgrim trails through the agricultural riches of Val d’Orcia.

Wander the impressive streets of Florence and visit the Uffizi gallery where the Renaissance masterpieces of Caravaggio, Botticelli and Da Vinci hang. Walk to the Etruscan founded wine towns of Radda and Gaiole in Chianti and explore the medieval majesty of Siena. Venture deep into UNESCO protected land of Val d’Orcia and enjoy the Roman way of life, soaking in the hot springs of Bagno Vignoni. Sample fine Brunello wines in Montalcino and hike up to Pienza, birthplace of Pope Pius II with breathtaking views across Val d’Orcia. Stay in traditional Tuscan family run hotels, relax into the Tuscan pace of life and round off this unforgettable journey in the sleepy piazzas of Montepulciano.

HIGHLIGHTS:

  • Visit Florence, Siena and walk through splendour of Tuscany
  • Explore the Renaissance architecture of Florence
  • Stay in the Chianti wine towns of Radda and Gaiole in Chianti
  • Walk through lyrical landscapes of golden wheat fields, vineyards and chestnut groves
  • Follow ancient pilgrim trails deep into southern Tuscany
  • Soak in the hot springs of Bagno Vignoni
  • Spend each night in historic family run hotels
  • Stroll through the cobbled streets and piazza’s of Montepulciano

WALK OVERVIEW

TYPE OF WALK
SELF GUIDED
TRIP LENGTH
10 DAYS
WALK GRADE
Moderate

Grade 3 – Moderate

Short, steep hill sections. Moderate active lifestyle and some walking experience recommended.

PRICE FROM
$ 3495

per person twin/double share

SINGLE OCCUPANCY
$ 1695

Accommodations charge the same price per room regardless of whether there are one or two people occupying it. To cover the cost of the accommodation when occupied by one person we need to charge the single occupancy fee.

per person

Book now

ITINERARY

  • Day 1
  • Day 2
  • Day 3
  • Day 4
  • Day 5
  • Day 6
  • Day 7
  • Day 8
  • Day 9
  • Day 10

DAY 1
Arrive Florence

Cradle of the Renaissance, Florence is a city of fine art, fashion and exceptional architecture. Many of Florence’s sights need little introduction. Stroll across the medieval Ponte Vecchio bridge and head to the world-famous Uffizi art gallery where the masterpieces of Leonardo da Vinci and Raphael hang. Visit the Galleria dell’Accademia to see Michelangelo’s statue of David and walk through cobbled streets to Piazza del Duomo to marvel at the exquisite designs of Brunelleschi.

Meals included: None
Accommodation: Hotel David
Located on the southern side of the River Arno, the hotel is set in a 19th century building only a couple minutes’ walk from the Arno River. Classically furnished rooms have a free mini-bar and breakfast is well known for its selection of homemade pastries. The historic centre is a 5-minute bus journey, or you can enjoy a 20 minute riverside walk to Ponte Vecchio and cross into the splendour of Florence.

DAY 2
Walk to Radda in Chianti

Transfer deep into the Chianti winelands to begin your walk on a forested trail to the fortified village of Volpaia, home of the revered Volpaia red wine (a must to sample while you are here). Steeped in wine making tradition, the town has been producing wine since the late 12th century. Beyond Volpaia, the trail follows typical ‘white roads’ lined with cypress trees as you ascend to the hilltop church of Santa Maria Novella (which has retained its original Romanesque structure). The trail rolls on through vineyards to the hilltop town of Radda in Chianti, one of the most celebrated wine towns of the Chianti region.

Walk: 13.5km
Ascent: 500m
Descent: 660m
Meals included: Breakfast & Walkers Lunch
Accommodation: Hotel Palazzo San Niccolo
An elegant 4* hotel in Radda’s the Ciacci and Palagi. Within the building is a peaceful courtyard where you can relax with a glass of local Chianti or head into the garden to soak up the Tuscan sun. Rooms have been classically designed, in keeping with the history of the building. Before you leave this hotel, do take time to visit the small sitting room with an incredibly well-preserved fresco that is said to be a symbol of unity between the 2 families.

DAY 3
Walk to Gaiole in Chianti

A gentle start begins with a descent southwards to your destination today, Gaiole in Chianti. Walk through wooded valleys, vineyards and olive groves. Enjoy rambling through picture postcard Tuscan landscapes, passing through the hamlets of San Giusto in Salcio and Adine. Descend into the sleepy streets of Gaiole in Chianti where you will spend the next two nights and have the opportunity to learn more of the Chianti wine production and signature Tuscan dishes of Gaiole in Chianti.

Walk: 12km
Ascent: 350m
Descent: 500m
Meals included: Breakfast & Walkers Lunch
Accommodation: Cavarchino
A restored farmhouse on the outskirts of Gaiole, Cavarchino is a charming family run bed and breakfast. On arrival, you can relax in the gardens or take a dip in the pool before strolling into Gaiole centre for dinner. Your host, Irene is always happy to help out with any questions or assistance you might need whilst in Gaiole.

DAY 4
Loop Walk Gaiole in Chianti

Walk through the medieval streets of Gaiole and into the rich Tuscan countryside as the route climbs to Castello di San Donato in Perano, a cluster of well-preserved 10th century houses. Continue on through woodland trails which will see you arrive at the hamlet of Badia a Coltibuono. For over 1000 years the Coltibuono farm has been producing wines, olive oils and has been a great spot for lunch before walking to the hilltop village of Montegrossi. A gentle but straightforward ramble descends back to the tranquility of Gaiole and your hotel.

Walk: 19.5km or 15km
Ascent: 660m or 400m
Descent: 600m or 250m
Meals included: Breakfast
Accommodation: Cavarchino

DAY 5
Transfer & Explore Siena

This morning you will be collected from your hotel and transferred to the medieval city of Siena. At its heart is one of Italy’s most recognisable squares, the scallop shaped Piazza del Campo. Once one of the most significant cities of Europe, Siena’s ornate medieval buildings and fine examples of Renaissance art are a delight to explore. The lively streets are bursting with sweet pastry shops and chaotic deli shops which are a great experience to sample locally produced meats, cheeses and oils.

Accommodation: Hotel Chiusarelli
Spend the night in a typical neoclassical villa dating back to the 1870’s. Located in the historical centre, several years ago the hotel was refurbished to a traditional Sienese house, complete with a large, beautiful preserved frescos. A charming and fitting end to your walking trip.

DAY 6
Train to Buonconvento, Walk to Montalcino

Hop on the train and take a short journey to Buonconvento. Wander along its historical centre, Via Soccini. Continue walking through the iconic Sienese landscapes, along trails and the strade bianche (white roads) lined with the towering and elegant cypress trees and through the Brunello vineyards that grow sangiovese grapes for world class wine. The day ends with a climb up to the 14th century hill town of Montalcino, nestled amongst the hills of the Val d’Orcia.

Walk: 18.5km
Ascent: 540m
Descent: 3170m
Meals included: Breakfast & Lunch
Accommodation: Hotel dei Capitani
Dating back to the middle ages, Hotel dei Capitani is believed to have been used as a refuge for Sienese people fleeing the Florentine army. The hotel pool boasts splendid views across Val d’Orcia and Val d’Arbia, which can also be viewed from your room. All rooms have a typical Tuscan decor.

DAY 7
Walk to Castelnuovo dell’Abate, transfer to Bagno Vignoni

South of Montalcino, an easy-going route, rolls through classic Tuscan landscapes. Just before reaching the delightful town of Castelnuovo dell’Abate, take time to visit the Romanesque Abbey of Sant’Antimo, dating back to the 8th century. The monks at the abbey still meet seven times a day, so you may be fortunate to hear the medieval Gregorian chants. Above the abbey, the village of Castelnuovo is a superb stop for lunch. Later in the afternoon, a private transfer will take you on to the Roman spa town of Bagno Vignoni.

Walk: 12km
Ascent: 280m
Descent: 470m
Meals included: Breakfast
Accommodation: La Locanda Loggiato
Sisters Barbara and Sabrina have been welcoming guests to Bagno Vignoni for almost 20 years. Their 14th century property has been lovingly restored with all en-suite rooms featuring terracotta flooring and traditional wooden beams. A place of relaxation, not all bedrooms have wi-fi (but it is available in communal areas). La Locanda is the perfect environment to relax in after a visit to the thermal baths just a few minutes away in the main piazza.

DAY 8
Walk to Pienza

Begin the day with a rewarding stretch of uphill to Vignoni Alto, complete with its own fortress tower. Onto San Quirico d’Orcia, the route gently descends through rich agricultural lands. Located on the Via Francigena pilgrim route, in medieval times the beautifully preserved San Quirico d’Orcia was of significant strategic importance, linking Europe with Rome. Do make time to explore the town and enjoy lunch in one of the many rustic restaurants. Continuing onto the hilltop town of Pienza be sure to try the local Pecorino cheese made from sheep’s milk.

Walk: 19.5km or 15km
Ascent: 660m or 400m
Descent: 600m or 250m
Meals included: Breakfast
Accommodation: Hotel La Valle
Within a couple of minutes of Pienza’s historic centre, the hotel occupies a typical Tuscany stone building. Complete with a roof garden, panoramic breakfast room, bar and en-suite rooms, you can enjoy breakfast on the terrace with views that stretch out over golden wheat fields and vineyards.

DAY 9
Walk to Montepulciano

Set across a rolling hilltop, the elegant town of Montepulciano boasts one of Tuscany’s oldest wine producers; Vino Nobile. Walk via the hamlet of Monticchiello through a patchwork of rolling fields as the trail climbs up to Montepulciano. Explore the labyrinth of cobbled streets, lined with elegant Renaissance palaces, former homes of nobility and hidden piazzas. At the heart of the town is the Piazza Grande, a wonderful setting to taste the rich variety of Montepulciano wines. In the evening it’s worth strolling out to the edge of the old town to see the sunset over the Val d’Orcia.

Walk: 15km
Ascent: 550m
Descent: 450m
Meals included: Breakfast & Walkers Lunch
Accommodation: Hotel II Rondo
Located outside the lively town centre, the family run Hotel II Rondo is tucked away in a peaceful corner of Montepulciano. After a day of walking and exploring, relax in the impeccably maintained gardens. In keeping with the period of the building, rooms have been decorated to an 18th century style.

DAY 10
Onward Travel

From Montepulciano the nearby train station, Chiusi Chianciano Terme has regular connections through to Florence, Pisa and Siena. You may also have time to further explore the streets of Montepulciano or relax in the garden of your hotel.

Meals included: Breakfast

WHAT’S INCLUDED

  • 9 nights ensuite room accommodation in Guesthouses, 3* & 4* Hotels
  • All luggage transfers
  • All taxi transfers as described in the itinerary
  • Flexibility to add or include days
  • Option to upgrade to a wine resort in Gaiole in Chianti
  • 9 breakfasts, 3  lunches and 1 dinner
  • Maps, daily walk notes and information pack
  • 24/7 telephone support

ACCOMMODATION & DINING

OVERVIEW

During this tour you will spend each night in small family run boutique B&B’s and 3* and 4* hotels. Chosen for their location, facilities and history, each accommodation is used to welcoming walkers. Many of them will be family run so are very knowledgeable about the region and they will always be happy to chat with you about the history, food and wine. Of course, you can always call us too should you need anything during your walk. As many of the overnight stays are in small villages or towns, on occasion we may have to book another similar accommodation of equal standard. We will discuss these options with you during the booking process.

You will be provided with 9 breakfasts, 2 lunches and 1 dinner. If you have any food allergies or intolerances please let us know at the time of booking so we can let your hosts know. Should you have severe food allergies, it’s always worth bringing a few of your own snacks with you.

MAP

DEPARTURE DATES

  • DATES
    AVAILABILITY
    PRICE
    Single Occupancy
    DETAILS
  • 22 Aug 2020 - 20 Oct 2020
    AVAILABLE
    from

    $3495

    SINGLE OCCUPANCY
    $1695

    Not available from 1st July – 22nd August

  • 4 Apr 2021 - 20 Oct 2021
    AVAILABLE
    from

    $3595

    SINGLE OCCUPANCY
    $1755

    Not available from 1st July – 22nd August

FAQS

Q: What happens if I don’t want to walk one of the days?

As some of the walks on this itinerary are loop walks you can relax in the grounds of your accommodation (some of which have a pool) or explore the local town and wineries. On the days where you will be walking to the next town, it might be possible to travel with the taxi service which transports your luggage. You can also use the local bus service between towns. Your accommodation hosts will also have up to date information and advice should you wish to travel to the next destination by local transport. There is always plenty of information about options for the day in your daily walk notes and as always, you can call us at the office for any help during your walk should you need any assistance.

Q: Where would you suggest adding an extra night?

Florence. With so much world-famous Renaissance art and delicious food to sample, Florence is worthy of an extra day. From Florence you can also hop on the train to nearby Pisa (1-hour journey) to see the world-famous leaning tower. Radda in Chianti and / or Gaiole in Chianti Historic towns which are best experience by relaxing poolside at your hotel, sampling the locally produced Chianti. In the evening enjoy typical dishes such as pappa al pomodoro, beef ragu pasta and wild boar stew. Siena An incredibly well-preserved city with the show stopping Piazza del Campo at the heart of Sienese life. It is also possible to take a short bus journey to the hilltop towers of San Gimignano (an hour journey, or private transfers can be arranged).

Q: Can you extend our stay in Siena?

Of course, please let us know at the time of booking if you would like to extend your time in Siena. There is so much to see, we’d suggest at least 1 extra night.

Q: Can my children walk with me?

We don't allow under 16's to do this walk. No discounts can be offered for children who do book.

Q: Is this tour OK for solo walkers?

Yes this tour is ok for solo walkers. It is likely that you’ll bump into other walkers along the trails and in many of the places you will stay. You will also pass through villages and towns should you need any assistance. Generally there is always good network coverage for mobile phones, should you worry about walking alone.

Q: We’re travelling as friends, can we get a triple room?

Triple rooms are in limited availability. Some accommodations do not offer triple rooms but we can always provide a twin or double room with a single room.

Q: Can we reduce the days walked?

Easily! This tour has been created with flexibility in mind. You can easily remove the loop walk in Gaiole in Chianti on day 5 and if you already have plans to be in Florence, we can collect you in Florence and take you directly to Greve in Chianti on day 1. We’re always happy to discuss your needs.

Q: Can we extend the days walked?

Of course, you may want to start by looking at our Tuscan Explorer which is 10 days and 9 nights, starting in Florence and ending in southern wine town of Montepulciano.

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Overview

OVERVIEW

Immerse yourself in Tuscan landscapes of olive groves, cypress trees and vineyards on this self-guided walking exploration. Between the artistic opulence of Florence and the Renaissance piazzas of Montepulciano, discover the wine towns of Chianti and follow ancient pilgrim trails through the agricultural riches of Val d’Orcia.

Wander the impressive streets of Florence and visit the Uffizi gallery where the Renaissance masterpieces of Caravaggio, Botticelli and Da Vinci hang. Walk to the Etruscan founded wine towns of Radda and Gaiole in Chianti and explore the medieval majesty of Siena. Venture deep into UNESCO protected land of Val d’Orcia and enjoy the Roman way of life, soaking in the hot springs of Bagno Vignoni. Sample fine Brunello wines in Montalcino and hike up to Pienza, birthplace of Pope Pius II with breathtaking views across Val d’Orcia. Stay in traditional Tuscan family run hotels, relax into the Tuscan pace of life and round off this unforgettable journey in the sleepy piazzas of Montepulciano.

HIGHLIGHTS:

  • Visit Florence, Siena and walk through splendour of Tuscany
  • Explore the Renaissance architecture of Florence
  • Stay in the Chianti wine towns of Radda and Gaiole in Chianti
  • Walk through lyrical landscapes of golden wheat fields, vineyards and chestnut groves
  • Follow ancient pilgrim trails deep into southern Tuscany
  • Soak in the hot springs of Bagno Vignoni
  • Spend each night in historic family run hotels
  • Stroll through the cobbled streets and piazza’s of Montepulciano

WALK OVERVIEW

TYPE OF WALK
SELF GUIDED
TRIP LENGTH
10 DAYS
WALK GRADE
Moderate

Grade 3 – Moderate

Short, steep hill sections. Moderate active lifestyle and some walking experience recommended.

PRICE FROM
$ 3495

per person twin/double share

SINGLE OCCUPANCY
$ 1695

Accommodations charge the same price per room regardless of whether there are one or two people occupying it. To cover the cost of the accommodation when occupied by one person we need to charge the single occupancy fee.

per person

Book now
Itinerary

ITINERARY

  • Day 1
  • Day 2
  • Day 3
  • Day 4
  • Day 5
  • Day 6
  • Day 7
  • Day 8
  • Day 9
  • Day 10

DAY 1
Arrive Florence

Cradle of the Renaissance, Florence is a city of fine art, fashion and exceptional architecture. Many of Florence’s sights need little introduction. Stroll across the medieval Ponte Vecchio bridge and head to the world-famous Uffizi art gallery where the masterpieces of Leonardo da Vinci and Raphael hang. Visit the Galleria dell’Accademia to see Michelangelo’s statue of David and walk through cobbled streets to Piazza del Duomo to marvel at the exquisite designs of Brunelleschi.

Meals included: None
Accommodation: Hotel David
Located on the southern side of the River Arno, the hotel is set in a 19th century building only a couple minutes’ walk from the Arno River. Classically furnished rooms have a free mini-bar and breakfast is well known for its selection of homemade pastries. The historic centre is a 5-minute bus journey, or you can enjoy a 20 minute riverside walk to Ponte Vecchio and cross into the splendour of Florence.

DAY 2
Walk to Radda in Chianti

Transfer deep into the Chianti winelands to begin your walk on a forested trail to the fortified village of Volpaia, home of the revered Volpaia red wine (a must to sample while you are here). Steeped in wine making tradition, the town has been producing wine since the late 12th century. Beyond Volpaia, the trail follows typical ‘white roads’ lined with cypress trees as you ascend to the hilltop church of Santa Maria Novella (which has retained its original Romanesque structure). The trail rolls on through vineyards to the hilltop town of Radda in Chianti, one of the most celebrated wine towns of the Chianti region.

Walk: 13.5km
Ascent: 500m
Descent: 660m
Meals included: Breakfast & Walkers Lunch
Accommodation: Hotel Palazzo San Niccolo
An elegant 4* hotel in Radda’s the Ciacci and Palagi. Within the building is a peaceful courtyard where you can relax with a glass of local Chianti or head into the garden to soak up the Tuscan sun. Rooms have been classically designed, in keeping with the history of the building. Before you leave this hotel, do take time to visit the small sitting room with an incredibly well-preserved fresco that is said to be a symbol of unity between the 2 families.

DAY 3
Walk to Gaiole in Chianti

A gentle start begins with a descent southwards to your destination today, Gaiole in Chianti. Walk through wooded valleys, vineyards and olive groves. Enjoy rambling through picture postcard Tuscan landscapes, passing through the hamlets of San Giusto in Salcio and Adine. Descend into the sleepy streets of Gaiole in Chianti where you will spend the next two nights and have the opportunity to learn more of the Chianti wine production and signature Tuscan dishes of Gaiole in Chianti.

Walk: 12km
Ascent: 350m
Descent: 500m
Meals included: Breakfast & Walkers Lunch
Accommodation: Cavarchino
A restored farmhouse on the outskirts of Gaiole, Cavarchino is a charming family run bed and breakfast. On arrival, you can relax in the gardens or take a dip in the pool before strolling into Gaiole centre for dinner. Your host, Irene is always happy to help out with any questions or assistance you might need whilst in Gaiole.

DAY 4
Loop Walk Gaiole in Chianti

Walk through the medieval streets of Gaiole and into the rich Tuscan countryside as the route climbs to Castello di San Donato in Perano, a cluster of well-preserved 10th century houses. Continue on through woodland trails which will see you arrive at the hamlet of Badia a Coltibuono. For over 1000 years the Coltibuono farm has been producing wines, olive oils and has been a great spot for lunch before walking to the hilltop village of Montegrossi. A gentle but straightforward ramble descends back to the tranquility of Gaiole and your hotel.

Walk: 19.5km or 15km
Ascent: 660m or 400m
Descent: 600m or 250m
Meals included: Breakfast
Accommodation: Cavarchino

DAY 5
Transfer & Explore Siena

This morning you will be collected from your hotel and transferred to the medieval city of Siena. At its heart is one of Italy’s most recognisable squares, the scallop shaped Piazza del Campo. Once one of the most significant cities of Europe, Siena’s ornate medieval buildings and fine examples of Renaissance art are a delight to explore. The lively streets are bursting with sweet pastry shops and chaotic deli shops which are a great experience to sample locally produced meats, cheeses and oils.

Accommodation: Hotel Chiusarelli
Spend the night in a typical neoclassical villa dating back to the 1870’s. Located in the historical centre, several years ago the hotel was refurbished to a traditional Sienese house, complete with a large, beautiful preserved frescos. A charming and fitting end to your walking trip.

DAY 6
Train to Buonconvento, Walk to Montalcino

Hop on the train and take a short journey to Buonconvento. Wander along its historical centre, Via Soccini. Continue walking through the iconic Sienese landscapes, along trails and the strade bianche (white roads) lined with the towering and elegant cypress trees and through the Brunello vineyards that grow sangiovese grapes for world class wine. The day ends with a climb up to the 14th century hill town of Montalcino, nestled amongst the hills of the Val d’Orcia.

Walk: 18.5km
Ascent: 540m
Descent: 3170m
Meals included: Breakfast & Lunch
Accommodation: Hotel dei Capitani
Dating back to the middle ages, Hotel dei Capitani is believed to have been used as a refuge for Sienese people fleeing the Florentine army. The hotel pool boasts splendid views across Val d’Orcia and Val d’Arbia, which can also be viewed from your room. All rooms have a typical Tuscan decor.

DAY 7
Walk to Castelnuovo dell’Abate, transfer to Bagno Vignoni

South of Montalcino, an easy-going route, rolls through classic Tuscan landscapes. Just before reaching the delightful town of Castelnuovo dell’Abate, take time to visit the Romanesque Abbey of Sant’Antimo, dating back to the 8th century. The monks at the abbey still meet seven times a day, so you may be fortunate to hear the medieval Gregorian chants. Above the abbey, the village of Castelnuovo is a superb stop for lunch. Later in the afternoon, a private transfer will take you on to the Roman spa town of Bagno Vignoni.

Walk: 12km
Ascent: 280m
Descent: 470m
Meals included: Breakfast
Accommodation: La Locanda Loggiato
Sisters Barbara and Sabrina have been welcoming guests to Bagno Vignoni for almost 20 years. Their 14th century property has been lovingly restored with all en-suite rooms featuring terracotta flooring and traditional wooden beams. A place of relaxation, not all bedrooms have wi-fi (but it is available in communal areas). La Locanda is the perfect environment to relax in after a visit to the thermal baths just a few minutes away in the main piazza.

DAY 8
Walk to Pienza

Begin the day with a rewarding stretch of uphill to Vignoni Alto, complete with its own fortress tower. Onto San Quirico d’Orcia, the route gently descends through rich agricultural lands. Located on the Via Francigena pilgrim route, in medieval times the beautifully preserved San Quirico d’Orcia was of significant strategic importance, linking Europe with Rome. Do make time to explore the town and enjoy lunch in one of the many rustic restaurants. Continuing onto the hilltop town of Pienza be sure to try the local Pecorino cheese made from sheep’s milk.

Walk: 19.5km or 15km
Ascent: 660m or 400m
Descent: 600m or 250m
Meals included: Breakfast
Accommodation: Hotel La Valle
Within a couple of minutes of Pienza’s historic centre, the hotel occupies a typical Tuscany stone building. Complete with a roof garden, panoramic breakfast room, bar and en-suite rooms, you can enjoy breakfast on the terrace with views that stretch out over golden wheat fields and vineyards.

DAY 9
Walk to Montepulciano

Set across a rolling hilltop, the elegant town of Montepulciano boasts one of Tuscany’s oldest wine producers; Vino Nobile. Walk via the hamlet of Monticchiello through a patchwork of rolling fields as the trail climbs up to Montepulciano. Explore the labyrinth of cobbled streets, lined with elegant Renaissance palaces, former homes of nobility and hidden piazzas. At the heart of the town is the Piazza Grande, a wonderful setting to taste the rich variety of Montepulciano wines. In the evening it’s worth strolling out to the edge of the old town to see the sunset over the Val d’Orcia.

Walk: 15km
Ascent: 550m
Descent: 450m
Meals included: Breakfast & Walkers Lunch
Accommodation: Hotel II Rondo
Located outside the lively town centre, the family run Hotel II Rondo is tucked away in a peaceful corner of Montepulciano. After a day of walking and exploring, relax in the impeccably maintained gardens. In keeping with the period of the building, rooms have been decorated to an 18th century style.

DAY 10
Onward Travel

From Montepulciano the nearby train station, Chiusi Chianciano Terme has regular connections through to Florence, Pisa and Siena. You may also have time to further explore the streets of Montepulciano or relax in the garden of your hotel.

Meals included: Breakfast

What’s Included

WHAT’S INCLUDED

  • 9 nights ensuite room accommodation in Guesthouses, 3* & 4* Hotels
  • All luggage transfers
  • All taxi transfers as described in the itinerary
  • Flexibility to add or include days
  • Option to upgrade to a wine resort in Gaiole in Chianti
  • 9 breakfasts, 3  lunches and 1 dinner
  • Maps, daily walk notes and information pack
  • 24/7 telephone support
Accommodation & Dining

ACCOMMODATION & DINING

OVERVIEW

During this tour you will spend each night in small family run boutique B&B’s and 3* and 4* hotels. Chosen for their location, facilities and history, each accommodation is used to welcoming walkers. Many of them will be family run so are very knowledgeable about the region and they will always be happy to chat with you about the history, food and wine. Of course, you can always call us too should you need anything during your walk. As many of the overnight stays are in small villages or towns, on occasion we may have to book another similar accommodation of equal standard. We will discuss these options with you during the booking process.

You will be provided with 9 breakfasts, 2 lunches and 1 dinner. If you have any food allergies or intolerances please let us know at the time of booking so we can let your hosts know. Should you have severe food allergies, it’s always worth bringing a few of your own snacks with you.

Map

MAP

Departure Dates

DEPARTURE DATES

  • DATES
    AVAILABILITY
    PRICE
    Single Occupancy
    DETAILS
  • 22 Aug 2020 - 20 Oct 2020
    AVAILABLE
    Details
    from

    $3495

    SINGLE OCCUPANCY
    $1695
  • 4 Apr 2021 - 20 Oct 2021
    AVAILABLE
    Details
    from

    $3595

    SINGLE OCCUPANCY
    $1755
Faqs

FAQS

Q: What happens if I don’t want to walk one of the days?

As some of the walks on this itinerary are loop walks you can relax in the grounds of your accommodation (some of which have a pool) or explore the local town and wineries. On the days where you will be walking to the next town, it might be possible to travel with the taxi service which transports your luggage. You can also use the local bus service between towns. Your accommodation hosts will also have up to date information and advice should you wish to travel to the next destination by local transport. There is always plenty of information about options for the day in your daily walk notes and as always, you can call us at the office for any help during your walk should you need any assistance.

Q: Where would you suggest adding an extra night?

Florence. With so much world-famous Renaissance art and delicious food to sample, Florence is worthy of an extra day. From Florence you can also hop on the train to nearby Pisa (1-hour journey) to see the world-famous leaning tower. Radda in Chianti and / or Gaiole in Chianti Historic towns which are best experience by relaxing poolside at your hotel, sampling the locally produced Chianti. In the evening enjoy typical dishes such as pappa al pomodoro, beef ragu pasta and wild boar stew. Siena An incredibly well-preserved city with the show stopping Piazza del Campo at the heart of Sienese life. It is also possible to take a short bus journey to the hilltop towers of San Gimignano (an hour journey, or private transfers can be arranged).

Q: Can you extend our stay in Siena?

Of course, please let us know at the time of booking if you would like to extend your time in Siena. There is so much to see, we’d suggest at least 1 extra night.

Q: Can my children walk with me?

We don't allow under 16's to do this walk. No discounts can be offered for children who do book.

Q: Is this tour OK for solo walkers?

Yes this tour is ok for solo walkers. It is likely that you’ll bump into other walkers along the trails and in many of the places you will stay. You will also pass through villages and towns should you need any assistance. Generally there is always good network coverage for mobile phones, should you worry about walking alone.

Q: We’re travelling as friends, can we get a triple room?

Triple rooms are in limited availability. Some accommodations do not offer triple rooms but we can always provide a twin or double room with a single room.

Q: Can we reduce the days walked?

Easily! This tour has been created with flexibility in mind. You can easily remove the loop walk in Gaiole in Chianti on day 5 and if you already have plans to be in Florence, we can collect you in Florence and take you directly to Greve in Chianti on day 1. We’re always happy to discuss your needs.

Q: Can we extend the days walked?

Of course, you may want to start by looking at our Tuscan Explorer which is 10 days and 9 nights, starting in Florence and ending in southern wine town of Montepulciano.

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