35 days in Italy Itinerary

35 days in Italy Itinerary

Created using Inspirock Italy planner

Plan created by another user. Make it yours
1
Venice
— 3 nights
2
Florence
— 3 nights
3
Cinque Terre
— 1 night
4
Lucca
— 2 nights
5
San Gimignano
— 3 nights
6
Siena
— 2 nights
7
Cortona
— 3 nights
8
Pienza
— 2 nights
9
Montalcino
— 1 night
10
Grosseto
— 1 night
11
Porto Ercole
— 2 nights
12
Capalbio
— 1 night
13
Sovana
— 1 night
14
Pitigliano
— 3 nights
15
Orvieto
— Few hours
16
Assisi
— 1 night
17
Rome
— 3 nights

S M T W T F S
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9
10
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12
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14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
1
2
3
4
5
6
7
8
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10
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14
15
16
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18
19

3
nights
Venice

Venice ©

City of Romance

Virtually unchanged for the last six centuries, Venice is actually a group of islands made famous by a series of canals, bridges, monuments, piazzas, and narrow pedestrian lanes.
Museum-lovers will get to explore Palazzo Mocenigo and Ca' Pesaro Galleria Internazionale d'Arte Moderna. You'll discover tucked-away gems like Passeggiata lungo la restera and Church of Santa Maria e San Donato. There's much more to do: contemplate in the serene atmosphere at Santa Maria dei Miracoli, take in the architecture and atmosphere at Saint Mary of The Rosary, pause for some photo ops at Punta della Dogana, and head off the coast to Giudecca.

To see photos, more things to do, maps, and more tourist information, read Venice trip builder.

Guadalajara, Mexico to Venice is an approximately 20-hour flight. The time zone difference moving from Central Standard Time (CST) to Central European Standard Time (CET) is 7 hours. In September, daily temperatures in Venice can reach 29°C, while at night they dip to 17°C. Wrap up your sightseeing on the 15th (Sun) to allow time to drive to Florence.

Things to do in Venice

Historic Sites · Parks · Museums · Nature

Side Trips

Find places to stay Sep 12 — 15:
Highlights from your plan
Church of Santa Maria e San Donato ©
Church of Santa Maria e San Donato
Passeggiata lungo la restera ©
Passeggiata lungo la restera
Santa Maria dei Miracoli ©
Santa Maria dei Miracoli

3
nights
Florence

Florence ©

Birthplace of the Italian Renaissance

Considered a cultural, artistic, and architectural jewel of Italy, Florence is the birthplace of the Italian Renaissance.
Your inner history buff will appreciate Florence American Cemetery and Memorial and Convento di San Francesco. Your cultural itinerary includes sights like Palazzo Strozzi and Loggia dei Lanzi. Get out of town with these interesting Florence side-trips: Greve in Chianti (Vignamaggio & Enoteca Falorni). And it doesn't end there: get engrossed in the history at Corridoio Vasariano, see the interesting displays at Museo Casa di Dante, explore the world behind art at Museo degli Innocenti, and take in the spiritual surroundings of Sinagoga di Firenze e Museo ebraico.

To see maps, photos, reviews, and tourist information, you can read our Florence road trip tool.

Traveling by car from Venice to Florence takes 3 hours. Alternatively, you can take a train; or fly. In September, plan for daily highs up to 30°C, and evening lows to 17°C. Wrap up your sightseeing on the 18th (Wed) early enough to drive to Cinque Terre.

Things to do in Florence

Museums · Historic Sites · Wineries

Side Trips

Find places to stay Sep 15 — 18:
Highlights from your plan
Museo di Palazzo Davanzati ©
Museo di Palazzo Davanzati
Sinagoga di Firenze e Museo ebraico ©
Sinagoga di Firenze e Museo ebraico
Stibbert Museum ©
Stibbert Museum

1
night
Cinque Terre

Cinque Terre ©

Italian Riviera

Made up of five picturesque towns on the Ligurian coast, Cinque Terre is Italy's answer to the French Riviera.
On the 19th (Thu), pause for some serene contemplation at Santuario di Nostra Signora di Montenero, step into the grandiose world of Castello di Riomaggiore, take in the spiritual surroundings of Oratorio di San Rocco, take in the spiritual surroundings of Oratorio di Santa Maria Assunta, then look for gifts at MG cinque terre, and finally take some stellar pictures from Bar Terza Terra.

To see more things to do, maps, where to stay, and other tourist information, refer to the Cinque Terre tour itinerary planning tool.

Drive from Florence to Cinque Terre in 2.5 hours. Alternatively, you can take a train. In September in Cinque Terre, expect temperatures between 30°C during the day and 17°C at night. Finish your sightseeing early on the 19th (Thu) so you can drive to Lucca.

Things to do in Cinque Terre

Find places to stay Sep 18 — 19:
Highlights from your plan
Santuario di Nostra Signora di Montenero ©
Santuario di Nostra Signora di Montenero
Castello di Riomaggiore ©
Castello di Riomaggiore
Oratorio di San Rocco ©
Oratorio di San Rocco

2
nights
Lucca

Lucca ©

City of a Hundred Churches

Lucca, famous for its intact Renaissance-era city walls, remained an independent city-state until the end of the 18th century.
Start off your visit on the 20th (Fri): contemplate the long history of Villa Grabau, contemplate the long history of Villa Torrigiani, appreciate the extensive heritage of Santuario di Santa Gemma Galgani, admire the masterpieces at Museo di Arte Contemporanea Lu.C.C.A. - Lucca Center of Contemporary Art, then take in the architecture and atmosphere at Chiesa di San Pietro Somaldi, and finally make a trip to Chiesa di Santa Maria Corteorlandini. Keep things going the next day: take in the architecture and atmosphere at Chiesa e Convento di San Francesco, take a stroll around Via del Fosso di Lucca, take in the architecture and atmosphere at Church of St. Mary of the Rose, then see the interesting displays at Complesso Museale della Cattedrale, then admire the striking features of Porta San Pietro, and finally look for gifts at La Boutique dei Golosi.

For maps, where to stay, ratings, and tourist information, read Lucca trip maker website.

Traveling by car from Cinque Terre to Lucca takes 2 hours. Alternatively, you can take a train; or do a combination of train and bus. In September in Lucca, expect temperatures between 30°C during the day and 17°C at night. Cap off your sightseeing on the 21st (Sat) early enough to go by car to San Gimignano.

Things to do in Lucca

Side Trip

Find places to stay Sep 19 — 21:
Highlights from your plan
Villa Grabau ©
Villa Grabau
Chiesa di Santa Maria Corteorlandini ©
Chiesa di Santa Maria Corteorlandini
Santuario di Santa Gemma Galgani ©
Santuario di Santa Gemma Galgani

3
nights
San Gimignano

San Gimignano ©

Town of Fine Towers

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.
Sacro Monte San Vivaldo and Mura di San Gimignano will appeal to history buffs. You'll explore and learn at Galleria Gagliardi and iSculpture Gallery San Gimignano & Casole d'Elsa. Get out of town with these interesting San Gimignano side-trips: L'Orcio a Ca di Pesa srl (in Panzano in Chianti), Tavarnelle Val di Pesa (Poggio al Bosco & Badia a Passignano) and Fattoria Casa Sola (in Barberino Val d'Elsa). There's lots more to do: take in the exciting artwork at Balducci Ceramica, learn about winemaking at Fattoria San Donato, enjoy breathtaking views from Torre Salvucci Maggiore, and make a trip to Pieve di Cellole.

To find more things to do, reviews, other places to visit, and tourist information, use the San Gimignano road trip planner.

Traveling by car from Lucca to San Gimignano takes 2 hours. Alternatively, you can take a train; or take a bus. In September in San Gimignano, expect temperatures between 30°C during the day and 17°C at night. Finish your sightseeing early on the 24th (Tue) so you can drive to Siena.

Things to do in San Gimignano

Wineries · Museums · Shopping · Historic Sites

Side Trips

Find places to stay Sep 21 — 24:
Highlights from your plan
Fattoria Casa Sola ©
Fattoria Casa Sola
Poggio al Bosco ©
Poggio al Bosco
Sacro Monte San Vivaldo ©
Sacro Monte San Vivaldo

2
nights
Siena

Siena ©

Cultural Heart of Tuscany

Siena, a medieval Tuscan city, features numerous attractions, including a historic town center, alleyways, towers, and well-preserved buildings.
Kick off your visit on the 25th (Wed): contemplate the long history of Palazzo Chigi Saracini, steep yourself in history at Palazzo Piccolomini, learn more about the world around you at Museo di Storia Naturale dell'Accademia dei Fisiocritici, then take in the architecture and atmosphere at Basilica di San Clemente in Santa Maria dei Servi, then contemplate in the serene atmosphere at Sinagoga di Siena, and finally contemplate in the serene atmosphere at Cappella di Piazza.

For photos, reviews, where to stay, and other tourist information, read Siena attractions planner.

Traveling by car from San Gimignano to Siena takes an hour. Alternatively, you can take a bus; or take a train. In September in Siena, expect temperatures between 32°C during the day and 19°C at night. Finish up your sightseeing early on the 26th (Thu) so you can go by car to Cortona.

Things to do in Siena

Historic Sites · Childrens Museums · Museums
Find places to stay Sep 24 — 26:
Highlights from your plan
Palazzo Piccolomini ©
Palazzo Piccolomini
Cappella di Piazza ©
Cappella di Piazza
Sinagoga di Siena ©
Sinagoga di Siena

3
nights
Cortona

Cortona ©

City of Art

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.
Your cultural itinerary includes sights like Fortezza di Girifalco and Saint Michele. You'll explore and learn at Museo Tela Umbra and Daniela Piegai Art Gallery. Explore Cortona's surroundings by going to Abbazia di Montecorona (in Umbertide) and Cattedrale dei Santi Florido e Amanzio (in Citta di Castello). Next up on the itinerary: visit Cortona on the Move, delve into the distant past at Mura etrusche, take in the spiritual surroundings of Santa Maria del Calcinaio, and explore the different monuments and memorials at Belvedere di Cortona.

Before you visit Cortona, use our trip planner to discover what you can do and see there.

Drive from Siena to Cortona in 1.5 hours. Alternatively, you can take a train; or do a combination of bus and train. Wrap up your sightseeing by early afternoon on the 29th (Sun) to allow time for the car ride to Pienza.

Things to do in Cortona

Historic Sites · Wineries · Shopping · Museums

Side Trips

Find places to stay Sep 26 — 29:
Highlights from your plan
Santa Maria del Calcinaio ©
Santa Maria del Calcinaio
Fortezza di Girifalco ©
Fortezza di Girifalco
Chiesa San Francesco ©
Chiesa San Francesco

2
nights
Pienza

Pienza ©
Pienza, a town and comune in the province of Siena, in the Val d'Orcia in Tuscany (central Italy), between the towns of Montepulciano and Montalcino, is the "touchstone of Renaissance urbanism."In 1996, UNESCO declared the town a World Heritage Site, and in 2004 the entire valley, the Val d'Orcia, was included on the list of UNESCO's World Cultural Landscapes.HistoryBefore the village was renamed to Pienza its name was Corsignano. Kick off your visit on the 29th (Sun): do a tasting at Enoteca Di Ghino, stop by La Taverna del Pecorino, then ponder the world of politics at Palazzo Comunale di Pienza, then pause for some serene contemplation at Church of San Francesco, and finally shop like a local with Artemisia Gallery. On the 30th (Mon), you'll have a packed day of sightseeing: contemplate in the serene atmosphere at Cathedral, don't miss a visit to The Checche Oak Tree, then appreciate the extensive heritage of Via di Gracciano nel Corso, then make a trip to Pieve di Corsignano, and finally explore the world behind art at Fortress of Tentennano.

For maps, traveler tips, other places to visit, and other tourist information, read our Pienza trip tool.

Traveling by car from Cortona to Pienza takes an hour. Alternatively, you can take a bus; or do a combination of train and bus. In September in Pienza, expect temperatures between 32°C during the day and 19°C at night. Cap off your sightseeing on the 1st (Tue) early enough to go by car to Montalcino.

Things to do in Pienza

Historic Sites · Museums · Neighborhoods · Shopping

Side Trips

Find places to stay Sep 29 — Oct 1:
Highlights from your plan
Church of San Francesco ©
Church of San Francesco
Palazzo Piccolomini ©
Palazzo Piccolomini
Cathedral ©
Cathedral

1
night
Montalcino

Montalcino ©

City of Honey

In the heart of wine country, the hill town of Montalcino offers a glimpse of untouched medieval-era Tuscany.
Start off your visit on the 2nd (Wed): take in the spiritual surroundings of Pieve di Santa Innocenza a Piana, appreciate the extensive heritage of Borgo Medievale Cinto da Mura, then step into the grandiose world of Castello Tricerchi, then learn about winemaking at Fattoria La Magia, and finally do a tasting at Piombaia wine cellar.

To see photos, traveler tips, where to stay, and more tourist information, go to the Montalcino road trip planning site.

Montalcino is just a short distance from Pienza. October in Montalcino sees daily highs of 26°C and lows of 15°C at night. Finish your sightseeing early on the 2nd (Wed) to allow enough time to drive to Grosseto.

Things to do in Montalcino

Wineries · Historic Sites

Side Trip

Find places to stay Oct 1 — 2:
Highlights from your plan
Castello Tricerchi ©
Castello Tricerchi
Fattoria La Magia ©
Fattoria La Magia
Piombaia wine cellar ©
Piombaia wine cellar

1
night
Grosseto

Grosseto
Grosseto is a city and comune in the central Italian region of Tuscany, the capital of the Province of Grosseto. For traveler tips, more things to do, maps, and other tourist information, go to the Grosseto journey planner.

Drive from Montalcino to Grosseto in an hour. October in Grosseto sees daily highs of 26°C and lows of 15°C at night. You will leave for Porto Ercole on the 3rd (Thu).

Things to do in Grosseto

Outdoors · Tours · Historic Sites · Parks
Find places to stay Oct 2 — 3:

2
nights
Porto Ercole

Porto Ercole ©
Porto Ercole is an Italian town located in the municipality of Monte Argentario, in the Province of Grosseto, Tuscany. Start off your visit on the 3rd (Thu): explore the historical opulence of Forte Filippo, contemplate the long history of Rocca Spagnola, then see the interesting displays at Forte Stella, then kick back and relax at La Formica, and finally examine the collection at Fortezza Spagnola. On your second day here, enjoy the sand and surf at Cala Grande, appreciate the extensive heritage of Centro Storico di Porto Ercole, and then kick back and relax at Campeggio Feniglia.

For maps, photos, traveler tips, and other tourist information, use the Porto Ercole trip itinerary tool.

Traveling by car from Grosseto to Porto Ercole takes an hour. In October, plan for daily highs up to 26°C, and evening lows to 15°C. Finish up your sightseeing early on the 5th (Sat) so you can go by car to Capalbio.

Things to do in Porto Ercole

Beaches · Outdoors · Parks · Historic Sites

Side Trip

Find places to stay Oct 3 — 5:
Highlights from your plan
Forte Filippo ©
Forte Filippo
Fortezza Spagnola ©
Fortezza Spagnola
Forte Stella ©
Forte Stella

1
night
Capalbio

Capalbio ©
Capalbio is a comune (municipality) in the Province of Grosseto in the Italian region Tuscany, located about 150km south of Florence and about 45km southeast of Grosseto.Capalbio borders the following municipalities: Manciano, Montalto di Castro, Orbetello.HistoryThe name derives probably from the Latin Caput Album or Campus Albus (White Cape or Field, respectively), due to the white alabaster stone dug in the area.Capalbio is known for the first time in 805 CE, when it was donated to the Abbey of the Tre Fontane, near Rome, by Charlemagne. Start off your visit on the 5th (Sat): enjoy the sand and surf at Spiaggia di Torba, do a tasting at Jacobelli Liquori, then take in the architecture and atmosphere at Pieve di San Nicola, and finally learn about winemaking at Tenuta Montauto.

To see other places to visit, more things to do, ratings, and other tourist information, you can read our Capalbio online trip itinerary builder.

Traveling by car from Porto Ercole to Capalbio takes an hour. When traveling from Porto Ercole in October, plan for little chillier days in Capalbio, with highs around 22°C, while nights are about the same with lows around 15°C. Wrap up your sightseeing on the 6th (Sun) to allow time to travel to Sovana.

Things to do in Capalbio

Beaches · Outdoors · Parks · Wineries

Side Trip

Find places to stay Oct 4 — 6:
Highlights from your plan
Jacobelli Liquori ©
Jacobelli Liquori
Pieve di San Nicola ©
Pieve di San Nicola
Tenuta Montauto ©
Tenuta Montauto

1
night
Sovana

Sovana ©
Sovana is a small town in southern Tuscany, Italy, a frazione of Sorano, a comune in the province of Grosseto.HistoryEtruscan by origin, Sovana became a Roman municipium, and, from the 5th century, an episcopal see. Start off your visit on the 6th (Sun): examine the collection at Parco minerario naturalistico di Gavorrano, then get to know the fascinating history of Il ghetto degli ebrei, then learn about winemaking at La Biagiola Winery, and finally get to know the fascinating history of Centro storico. Keep things going the next day: see the interesting displays at Parco Nazionale Museo delle Miniere dell'Amiata, then enjoy breathtaking views from Rocca degli Aldobrandeschi, then learn about winemaking at Villa Acquaviva - La Fattoria, and finally learn about winemaking at Sassotondo Azienda Agricola Carla Benini.

To find other places to visit, reviews, traveler tips, and tourist information, you can read our Sovana holiday maker app.

Getting from Capalbio to Sovana by car takes about an hour. In October, daily temperatures in Sovana can reach 24°C, while at night they dip to 13°C. Finish your sightseeing early on the 7th (Mon) to allow enough time to travel to Pitigliano.

Things to do in Sovana

Wineries · Historic Sites · Museums

Side Trips

Find places to stay Oct 6 — 7:
Highlights from your plan
Villa Acquaviva - La Fattoria ©
Villa Acquaviva - La Fattoria
Parco minerario naturalistico di Gavorrano ©

3
nights
Pitigliano

Pitigliano ©
Pitigliano is a town in the province of Grosseto, located about 80km south-east of the city of Grosseto, in Italy. Kick off your visit on the 8th (Tue): contemplate in the serene atmosphere at Basilica Santuario di Maria SS. del Suffragio, examine the collection at Museo della Preistoria della Tuscia e della Rocca Farnese, then contemplate in the serene atmosphere at Romitori di Ischia di Castro, and finally pause for some serene contemplation at Chiesa di Santa Maria e San Rocco. Keep things going the next day: see the interesting displays at Museo Civico Archeologico della Civilta Etrusca, contemplate the long history of Insediamento rupestre di Vitozza, and then enjoy the sand and surf at Spiaggia di Capodimonte.

To see ratings, photos, more things to do, and other tourist information, use the Pitigliano road trip planner.

Pitigliano is very close to Sovana. In October in Pitigliano, expect temperatures between 24°C during the day and 13°C at night. On the 10th (Thu), wrap the sightseeing up by early afternoon so you can drive to Orvieto.

Things to do in Pitigliano

Historic Sites · Parks · Beaches · Outdoors

Side Trips

Find places to stay Oct 7 — 10:
Highlights from your plan
Basilica Santuario di Maria SS. del Suffragio ©
Romitori di Ischia di Castro ©
Romitori di Ischia di Castro
Chiesa di Santa Maria e San Rocco ©
Chiesa di Santa Maria e San Rocco

few
hours
Orvieto

Orvieto ©

Green Heart of Italy

The striking town of Orvieto, perched on a volcanic cliff overlooking the Umbrian countryside, is known as the Green Heart of Italy.
Start off your visit on the 10th (Thu): steep yourself in history at Palazzo dei Sette, then examine the collection at Etruscan Museum "Claudio Faina", then contemplate in the serene atmosphere at Sant'Andrea, Orvieto, and finally get to know the fascinating history of Piazza della Repubblica.

To see traveler tips, where to stay, other places to visit, and more tourist information, you can read our Orvieto route planning tool.

You can drive from Pitigliano to Orvieto in an hour. In October, plan for daily highs up to 24°C, and evening lows to 13°C. Wrap up your sightseeing on the 10th (Thu) to allow time to drive to Assisi.

Things to do in Orvieto

Historic Sites · Museums
Find places to stay Oct 10 — 11:
Highlights from your plan
Sant'Andrea, Orvieto ©
Sant'Andrea, Orvieto
Etruscan Museum ©
Etruscan Museum "Claudio Faina"

1
night
Assisi

Assisi ©

City of Peace

Rich in culture and religious tradition, Assisi is known as the birthplace of St.
Start off your visit on the 11th (Fri): explore the ancient world of Anfiteatro Romano, take in the spiritual surroundings of Museo Diocesano e Cripta di San Rufino, don't miss a visit to Oratorio S. Francesco Piccolino, appreciate the extensive heritage of Centro Storico di Assisi, then contemplate the long history of Casa del Maestri Comacini, and finally contemplate the long history of Arco del Seminario.

For where to stay, photos, and tourist information, go to the Assisi road trip planning tool.

You can drive from Orvieto to Assisi in 1.5 hours. Alternatively, you can take a train; or take a bus. In October, daily temperatures in Assisi can reach 24°C, while at night they dip to 12°C. Cap off your sightseeing on the 11th (Fri) early enough to go by car to Rome.

Things to do in Assisi

Find places to stay Oct 10 — 11:
Highlights from your plan
Museo Diocesano e Cripta di San Rufino ©
Museo Diocesano e Cripta di San Rufino
Centro Storico di Assisi ©
Centro Storico di Assisi
Casa del Maestri Comacini ©
Casa del Maestri Comacini

3
nights
Rome

Rome ©

Eternal City

Aptly nicknamed the Eternal City, Rome is the birthplace of the Roman Empire, one of the world's greatest civilizations ever.
Deepen your sense of the past at sights like Domus Aurea and Basilica di Santa Prassede. Eschew the tourist crowds and head to Quirinale Palace (Palazzo del Quirinale) and Complesso del Vittoriano. Go for a jaunt from Rome to Fara in Sabina to see Abbazia di Farfa about 58 minutes away. There's still lots to do: don't miss a visit to Vatican Necropolis, appreciate the history behind Trajan's Column, ponder the design of Fontana del Tritone, and explore the ancient world of Mercati di Traiano - Museo dei Fori Imperiali.

To find photos, ratings, and more tourist information, you can read our Rome online route planner.

Drive from Assisi to Rome in 2.5 hours. Alternatively, you can take a train; or take a bus. October in Rome sees daily highs of 26°C and lows of 15°C at night. Finish your sightseeing early on the 14th (Mon) to allow enough time to travel back home.

Things to do in Rome

Historic Sites · Museums · Parks

Side Trips

Find places to stay Oct 11 — 14:
Highlights from your plan
Foro di Cesare ©
Foro di Cesare
Vatican Necropolis ©
Vatican Necropolis
Mercati di Traiano - Museo dei Fori Imperiali ©

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