14 days in Tuscany Itinerary

14 days in Tuscany Itinerary

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Route & dates

14 days in Tuscany Itinerary

Start: Cape Town
Fly:  17​h 15​min
1
Florence
— 2 nights
bus:  1​h
2
Radda in Chianti
— Few hours
bus:  1​h
3
Florence
— 1 night
Drive:  1​h 15​min
4
San Gimignano
— 1 day
Drive:  45​min
5
Volterra
— 1 night
Drive:  1​h 30​min
6
Lucca
— 2 nights
Drive:  1​h
7
Capezzano Pianore
— Few hours
Drive:  1​h
8
Lucca
— Few hours
Drive:  1​h 30​min
9
Certaldo
— 1 night
train:  30​min
10
Monteriggioni
— Few hours
Drive:  30​min
11
Siena
— 1 night
Drive:  1​h
12
Montalcino
— Few hours
Drive:  1​h 30​min
13
Pitigliano
— 2 nights
Drive:  1​h
14
Arcidosso
— Few hours
Drive:  1​h 15​min
15
Montepulciano
— Few hours
Drive:  45​min
16
Cortona
— 1 night
Drive:  1​h
17
Arezzo
— 1 night
Drive:  1​h 15​min
18
Greve in Chianti
— Few hours
bus:  45​min
19
Florence
— Few hours
Fly:  17​h 15​min
End: Cape Town


Learn more about your trip

2
nights
Florence

Florence ©
Considered a cultural, artistic, and architectural jewel of Italy, Florence is the birthplace of the Italian Renaissance.
Start off your visit on the 3rd (Sat): examine the collection at Academy Of Florence Art Gallery, stop by Officina Profumo-Farmaceutica di Santa Maria Novella, get great views at Piazzale Michelangelo, take in the architecture and atmosphere at Cathedral of Santa Maria del Fiore, then get great views at Basilica San Miniato al Monte, and finally admire the masterpieces at Uffizi Galleries.

You can plan Florence trip in no time by asking Inspirock to help create your itinerary.

Cape Town, South Africa to Florence is an approximately 17.5-hour flight. You can also do a combination of flight and train. Traveling from Cape Town to Florence, you'll gain 1 hour due to the time zone difference. Expect warmer weather when traveling from Cape Town in August: highs in Florence hover around 35°C, while lows dip to 20°C. Finish your sightseeing early on the 4th (Sun) to allow enough time to take a bus to Radda in Chianti.

Things to do in Florence

Historic Sites Museums Shopping
Find places to stay Aug 2 — 4:
Highlights from your plan
Academy Of Florence Art Gallery ©
Academy Of Florence Art Gallery
Gallerie Degli Uffizi ©
Gallerie Degli Uffizi
Cathedral of Santa Maria del Fiore ©

few
hours
Radda in Chianti

Radda in Chianti ©
Kick off your visit on the 4th (Sun): explore the historical opulence of Castello di Vertine, do a tasting at Fattoria Vignavecchia, and then get great views at Volpaia.

For traveler tips, photos, more things to do, and tourist information, refer to the Radda in Chianti route app .

You can take a bus from Florence to Radda in Chianti in an hour. Alternatively, you can drive; or do a combination of train and taxi. In August, plan for daily highs up to 38°C, and evening lows to 21°C. Finish up your sightseeing early on the 4th (Sun) so you can catcht the bus to Florence.

Things to do in Radda in Chianti

Historic Sites Wineries

Side Trip

Castello di Vertine
Find places to stay Aug 4 — 5:
Highlights from your plan
Castello di Vertine ©
Castello di Vertine
Volpaia ©
Volpaia

1
night
Florence

Florence ©
Start off your visit on the 17th (Sat): see the interesting displays at Convento di San Francesco, then take an in-depth tour of Basilica di Santa Croce, then see the interesting displays at Pitti Palace, and finally take in the views from Ponte Vecchio.

For photos, ratings, where to stay, and other tourist information, you can read our Florence sightseeing planner .

Traveling by bus from Greve in Chianti to Florence takes an hour. Alternatively, you can drive. Wrap up your sightseeing on the 17th (Sat) to allow time to travel back home.
Find places to stay Aug 4 — 5:
Highlights from your plan
Ponte Vecchio ©
Ponte Vecchio

1
day
San Gimignano

San Gimignano ©
A historical gem in the heart of Tuscany, San Gimignano is known as the Town of Fine Towers for its jutting skyline of high city walls.
Kick off your visit on the 5th (Mon): admire the landmark architecture of Mura di San Gimignano, appreciate the extensive heritage of San Gimignano 1300, view the masterpieces at Galleria Gagliardi, then shop like a local with iSculpture Gallery San Gimignano, and finally learn about winemaking at Fattoria Il Piano - Vineyard.

To see reviews, where to stay, photos, and more tourist information, refer to the San Gimignano road trip site .

Traveling by car from Florence to San Gimignano takes 1.5 hours. Alternatively, you can take a bus; or take a train. In August, daytime highs in San Gimignano are 35°C, while nighttime lows are 20°C. Finish your sightseeing early on the 5th (Mon) so you can drive to Volterra.

Things to do in San Gimignano

Museums Wineries Shopping
Find places to stay Aug 5 — 6:
Highlights from your plan
San Gimignano 1300 ©
San Gimignano 1300
Fattoria Il Piano ©
Fattoria Il Piano
Mura di San Gimignano ©
Mura di San Gimignano

1
night
Volterra

Volterra ©
Volterra is a walled mountaintop town in the Tuscany region of Italy of which its history dates to before the 7th century BC and has substantial structures from the Etruscan, Roman, and Medieval periods.HistoryVolterra, known to the ancient Etruscans as Velathri or Vlathri and to the Romans as Volaterrae, is a town and comune in the Tuscany region of Italy. On the 6th (Tue), see the interesting displays at Museo Etrusco Guarnacci, delve into the distant past at Roman Theatre, take in the architecture and atmosphere at Chiesa di San Lino, then take in the exciting artwork at Societa Cooperativa Artieri Alabastro, then explore the historical opulence of Palazzo dei Priori, and finally stop by Boutique del Tartufo.

To find reviews, other places to visit, photos, and other tourist information, go to the Volterra trip itinerary planner.

You can drive from San Gimignano to Volterra in an hour. Another option is to take a bus. August in Volterra sees daily highs of 35°C and lows of 20°C at night. Cap off your sightseeing on the 6th (Tue) early enough to go by car to Lucca.

Things to do in Volterra

Museums Historic Sites Shopping
Find places to stay Aug 5 — 6:
Highlights from your plan
Palazzo dei Priori ©
Palazzo dei Priori
Roman Theatre ©
Roman Theatre
Museo Etrusco Guarnacci ©
Museo Etrusco Guarnacci

2
nights
Lucca

Lucca ©
Lucca, famous for its intact Renaissance-era city walls, remained an independent city-state until the end of the 18th century.
On the 7th (Wed), admire the striking features of St Martin Cathedral, pause for some serene contemplation at Basilica of San Frediano, admire the natural beauty at Palazzo Pfanner, then take in the architecture and atmosphere at Chiesa di Sant'Agostino, then admire the striking features of Acquedotto del Nottolini, and finally don't miss a visit to Torre delle Ore.

For photos, other places to visit, ratings, and more tourist information, go to the Lucca holiday builder site .

Getting from Volterra to Lucca by car takes about 1.5 hours. Other options: take a bus; or do a combination of bus and train. In August, daytime highs in Lucca are 35°C, while nighttime lows are 20°C. Wrap up your sightseeing on the 8th (Thu) early enough to travel to Capezzano Pianore.

Things to do in Lucca

Historic Sites Parks
Find places to stay Aug 6 — 8:
Highlights from your plan
Basilica of San Frediano ©
Basilica of San Frediano
Palazzo Pfanner ©
Palazzo Pfanner
St Martin Cathedral ©
St Martin Cathedral

few
hours
Capezzano Pianore

Capezzano Pianore ©
Start off your visit on the 8th (Thu): look for all kinds of wild species at Candalla Waterfalls, take in the architecture and atmosphere at Collegiata di Santa Maria Assunta, and then examine the collection at Museo d'Arte Sacra di Camaiore.

To find maps, where to stay, and other tourist information, use the Capezzano Pianore trip itinerary builder .

Traveling by car from Lucca to Capezzano Pianore takes an hour. In August, daytime highs in Capezzano Pianore are 33°C, while nighttime lows are 22°C. Wrap up your sightseeing by early afternoon on the 8th (Thu) to allow enough time to travel to Lucca.

Things to do in Capezzano Pianore

Wildlife Parks Nature

Side Trip

Camaiore
Find places to stay Aug 8 — 9:
Highlights from your plan
Candalla Waterfalls ©
Candalla Waterfalls
Museo d'Arte Sacra di Camaiore ©
Museo d'Arte Sacra di Camaiore

few
hours
Lucca

Lucca ©
Start off your visit on the 8th (Thu): contemplate the long history of Villa Torrigiani.

To find traveler tips, reviews, more things to do, and more tourist information, refer to the Lucca tour planner.

You can drive from Capezzano Pianore to Lucca in an hour. Finish your sightseeing early on the 8th (Thu) so you can drive to Certaldo.

Things to do in Lucca

Historic Sites

Side Trip

Villa Torrigiani
Find places to stay Aug 8 — 9:
Highlights from your plan
Villa Torrigiani ©
Villa Torrigiani

1
night
Certaldo

Certaldo
Certaldo is a town and comune of Tuscany, Italy, in the Metropolitan City of Florence, in the middle of Valdelsa. To see more things to do, other places to visit, ratings, and tourist information, use the Certaldo trip planning tool .

You can drive from Lucca to Certaldo in 1.5 hours. Other options are to take a train; or take a bus. In August, daytime highs in Certaldo are 35°C, while nighttime lows are 20°C. On the 9th (Fri), you're off toMonteriggioni.

Things to do in Certaldo

Tours Outdoors Wineries
Find places to stay Aug 8 — 9:

few
hours
Monteriggioni

Monteriggioni ©
Monteriggioni is a comune in the province of Siena in the Italian region Tuscany. Start off your visit on the 9th (Fri): examine the collection at Monteriggioni prima del Castello, step into the grandiose world of Castello di Monteriggioni, and then look for gifts at Fattoria Castello di Monteriggioni.

To see where to stay, more things to do, traveler tips, and tourist information, use the Monteriggioni online journey builder .

Monteriggioni is just a stone's throw from Certaldo. In August, daytime highs in Monteriggioni are 37°C, while nighttime lows are 22°C. Wrap up your sightseeing by early afternoon on the 9th (Fri) to allow time for the train ride to Siena.

Things to do in Monteriggioni

Shopping Museums Wineries
Find places to stay Aug 9 — 10:
Highlights from your plan
Fattoria Castello di Monteriggioni ©
Castello di Monteriggioni ©
Castello di Monteriggioni
Monteriggioni prima del Castello ©

1
night
Siena

Siena ©
Siena, a medieval Tuscan city, features numerous attractions, including a historic town center, alleyways, towers, and well-preserved buildings.
Start off your visit on the 9th (Fri): pause for some serene contemplation at Siena Cathedral and then steep yourself in history at Palazzo Chigi Saracini.

To find reviews, photos, and other tourist information, go to the Siena journey planning website .

Siena is just a short distance from Monteriggioni. August in Siena sees daily highs of 37°C and lows of 22°C at night. On the 10th (Sat), wrap the sightseeing up by early afternoon so you can drive to Montalcino.

Things to do in Siena

Historic Sites Shopping
Find places to stay Aug 9 — 10:
Highlights from your plan
Duomo di Siena ©
Duomo di Siena
Cappella di Piazza ©
Cappella di Piazza
Siena Tartufi (truffle hunting) ©
Siena Tartufi (truffle hunting)

few
hours
Montalcino

Montalcino ©
In the heart of wine country, the hill town of Montalcino offers a glimpse of untouched medieval-era Tuscany.
On the 10th (Sat), do a tasting at Azienda Agricola Patrizia Cencioni Solaria and then take a stroll around San Quirico d'Orcia.

For other places to visit, where to stay, more things to do, and other tourist information, read our Montalcino planner .

Traveling by car from Siena to Montalcino takes an hour. Alternatively, you can do a combination of train and bus; or take a bus. Expect a daytime high around 37°C in August, and nighttime lows around 22°C. Wrap up your sightseeing on the 10th (Sat) early enough to drive to Pitigliano.

Things to do in Montalcino

Shopping Historic Sites Wineries

Side Trip

San Quirico d'Orcia
Find places to stay Aug 10 — 11:
Highlights from your plan
San Quirico d'Orcia ©
San Quirico d'Orcia

2
nights
Pitigliano

Pitigliano ©
Pitigliano is a town in the province of Grosseto, located about 80km south-east of the city of Grosseto, in Italy. Start off your visit on the 11th (Sun): contemplate in the serene atmosphere at Antico Ghetto e Sinagoga Pitigliano, see the interesting displays at Museo Civico Archeologico della Civilta Etrusca, admire the masterpieces at Museo di Palazzo Orsini, then take in the architecture and atmosphere at Santuario della Madonna delle Grazie, then take in the architecture and atmosphere at Chiesa di Santa Maria e San Rocco, and finally appreciate the extensive heritage of Pitigliano Centro Storico.

To find ratings, maps, more things to do, and tourist information, refer to the Pitigliano online route planner .

You can drive from Montalcino to Pitigliano in 1.5 hours. Alternatively, you can take a bus. In August, daytime highs in Pitigliano are 36°C, while nighttime lows are 21°C. Cap off your sightseeing on the 12th (Mon) early enough to travel to Arcidosso.

Things to do in Pitigliano

Historic Sites Museums
Find places to stay Aug 10 — 12:
Highlights from your plan
Pitigliano Centro Storico ©
Pitigliano Centro Storico
Antico Ghetto e Sinagoga Pitigliano ©
Museo di Palazzo Orsini ©
Museo di Palazzo Orsini

few
hours
Arcidosso

Arcidosso ©
Arcidosso is a comune (municipality) in the Province of Grosseto in the Italian region Tuscany, located about 100km south of Florence and about 35km northeast of Grosseto and near the town of Montalcino.HistoryThe first certain documentation of the existence of the settlement of Arcidosso is from the year 860, when it is said to belong to the Abbey of San Salvatore. Start off your visit on the 12th (Mon): take in the architecture and atmosphere at Chiesa di Santa Maria dell'Ermeta and then do a tasting at Basile Azienda Agricola Biologica.

To find ratings, photos, reviews, and other tourist information, refer to the Arcidosso trip itinerary app .

Drive from Pitigliano to Arcidosso in an hour. In August, plan for daily highs up to 37°C, and evening lows to 22°C. On the 12th (Mon), wrap the sightseeing up by early afternoon so you can drive to Montepulciano.

Things to do in Arcidosso

Wineries Historic Sites

Side Trips

Basile Azienda Agricola Biologica, Chiesa di Santa Maria dell'Ermeta
Find places to stay Aug 12 — 13:
Highlights from your plan
Basile Azienda Agricola Biologica ©
Basile Azienda Agricola Biologica

few
hours
Montepulciano

Montepulciano
Perched on a limestone ridge in the heart of Tuscany, Montepulciano is known worldwide for its production of red wine, the Vino Noble.
Kick off your visit on the 12th (Mon): learn about winemaking at De' Ricci.

To see other places to visit, ratings, and other tourist information, read Montepulciano journey planner.

Drive from Arcidosso to Montepulciano in 1.5 hours. August in Montepulciano sees daily highs of 37°C and lows of 22°C at night. Finish your sightseeing early on the 12th (Mon) to allow enough time to drive to Cortona.

Things to do in Montepulciano

Wineries
Find places to stay Aug 12 — 13:

1
night
Cortona

Cortona
The hilltop town of Cortona gained international attention as the subject of the 2003 film "Under the Tuscan Sun." With the Chiana Valley and Lake Trasimeno as its backdrop, Cortona is one of Tuscany's hotspots for art and culture.
On the 13th (Tue), see the interesting displays at Museo Civico Archeologico and then shop like a local with Daniela Piegai Art Gallery.

For traveler tips, other places to visit, maps, and other tourist information, go to the Cortona day trip planning website .

Traveling by car from Montepulciano to Cortona takes an hour. Alternatively, you can take a bus; or do a combination of bus and train. Wrap up your sightseeing by early afternoon on the 13th (Tue) to allow enough time to take a train to Arezzo.

Things to do in Cortona

Museums Shopping

Side Trip

Museo Civico Archeologico
Find places to stay Aug 12 — 13:

1
night
Arezzo

Arezzo ©
Arezzo is a city of art with colorful frescoes and abundance of goldsmiths and antique jewelers.
Start off your visit on the 13th (Tue): contemplate in the serene atmosphere at Badia delle Sante Flora e Lucilla, get engrossed in the history at Munacs, and then take in the architecture and atmosphere at Chiesa di Santa Maria delle Grazie.

For reviews, ratings, where to stay, and other tourist information, read Arezzo itinerary planner .

Arezzo is just a short distance from Cortona. Finish up your sightseeing early on the 14th (Wed) so you can go by car to Greve in Chianti.

Things to do in Arezzo

Historic Sites Museums
Find places to stay Aug 13 — 14:
Highlights from your plan
Badia delle Sante Flora e Lucilla ©
Badia delle Sante Flora e Lucilla
Chiesa di Santa Maria delle Grazie ©

few
hours
Greve in Chianti

Greve in Chianti ©
On the 14th (Wed), pause for some serene contemplation at Abbazia di San Michele Arcangelo a Passignano, take in the spiritual surroundings of Chiesa Di Santo Stefano A Montefioralle, and then step into the grandiose world of Castello di Montefioralle.

For traveler tips, where to stay, and other tourist information, refer to the Greve in Chianti vacation site .

Traveling by car from Arezzo to Greve in Chianti takes 1.5 hours. Alternatively, you can do a combination of train and bus; or take a bus. In August in Greve in Chianti, expect temperatures between 35°C during the day and 20°C at night. Wrap up your sightseeing by early afternoon on the 14th (Wed) to allow time for the bus ride to Florence.

Things to do in Greve in Chianti

Historic Sites

Side Trip

Abbazia di San Michele Arcangelo a Passignano
Find places to stay Aug 14 — 15:
Highlights from your plan
Castello di Montefioralle ©
Castello di Montefioralle
Chiesa Di Santo Stefano A Montefioralle ©

few
hours
Florence

Florence ©
On the 14th (Wed), contemplate in the serene atmosphere at The Baptistery of St. John and then make a trip to Piazza della Signoria.

For other places to visit, reviews, maps, and other tourist information, go to the Florence trip itinerary app .

Traveling by bus from Greve in Chianti to Florence takes an hour. Alternatively, you can drive. Finish up your sightseeing early on the 14th (Wed) so you can travel back home.

Things to do in Florence

Historic Sites
Find places to stay Aug 14 — 15:
Highlights from your plan
The Baptistery of St. John ©
The Baptistery of St. John
Piazza della Signoria ©
Piazza della Signoria

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