31 days in Italy Itinerary

31 days in Italy Itinerary

Created using Inspirock Italy holiday planner
Make it your trip
Fly to Pisa, Ferry to Portoferraio
1
Portoferraio, Elba Island
— 2 nights
Ferry to Porto Biglietterie Sud, Fly to San Teodoro
2
San Teodoro, Sardinia
— 2 nights
Drive
3
Villasimius, Sardinia
— 1 night
Fly
4
Ravello
— 3 nights
Ferry
5
Capri, Island of Capri
— 1 night
Ferry to Naples, Fly to Taormina
6
Taormina, Sicily
— 1 night
Fly
7
Lampedusa
— 1 night
Fly
8
Rome
— 4 nights
Drive
9
Assisi
— 3 nights
Drive
10
Siena
— 3 nights
Drive
11
Florence
— 3 nights
Train
12
Verona
— 3 nights
Drive
13
Venice
— 3 nights
Fly

S M T W T F S
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26
27
28
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30
1
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5
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29

Portoferraio, Elba Island — 2 nights

Portoferraio is a town and comune in the province of Livorno, on the edge of the eponymous harbour of the island of Elba. Kick off your visit on the 24th (Sat): kick back and relax at Spiaggia Di Buzzancone o Cera, enjoy the sand and surf at Spiaggia di Acquarilli, kick back and relax at Spiaggia La Sorgente, stroll through Spiaggia Di Sansone, then stroll through Spiaggia di Capo Bianco, and finally stroll through Spiaggia delle Ghiaie. Keep things going the next day: kick back and relax at Spiaggia Canata, kick back and relax at Spiaggia di Chiessi, tour the pleasant surroundings at Spiaggia Di Seccheto, then enjoy the sand and surf at Spiaggia di Cavoli, and finally enjoy the sand and surf at Spiaggia delle Tombe.

For more things to do, ratings, where to stay, and tourist information, you can read our Portoferraio trip planner.

New York City, USA to Portoferraio is an approximately 15-hour combination of flight and ferry. The time zone difference when traveling from New York City to Portoferraio is 6 hours. When traveling from New York City in September, plan for little chillier days in Portoferraio, with highs around 75°F, while nights are about the same with lows around 62°F. Finish your sightseeing early on the 25th (Sun) to allow enough time to travel to San Teodoro.
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Find places to stay Sep 23 — 25:

San Teodoro, Sardinia — 2 nights

A chance to sip cocktails at swanky beach bars by day and experience the vibrant club scene by night makes San Tedoro vacations extremely popular.
On the 26th (Mon), kick back and relax at Spiaggia Bianca, then stroll through Spiaggia di Porto Ottiolu, then trek along Spiaggia Berchida, and finally kick back and relax at Spiaggia di Capo Comino. On your second day here, enjoy the sand and surf at Porto Istana Beach, kick back and relax at Spiaggia Capo Coda Cavallo, kick back and relax at Cala Brandinchi, stroll through Lu Impostu Beach, then tour the pleasant surroundings at Porto Taverna Beach, and finally tour the pleasant surroundings at Spiaggia La Cinta.

Plan my trip to San Teodoro with suggested itineraries provided by Inspirock.

Traveling by combination of ferry and flight from Portoferraio to San Teodoro takes 4.5 hours. Alternatively, you can do a combination of ferry and bus; or do a combination of ferry, train, and bus. Expect somewhat warmer weather when traveling from Portoferraio in September: highs in San Teodoro hover around 81°F, while lows dip to 62°F. Finish your sightseeing early on the 27th (Tue) so you can drive to Villasimius.
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Find places to stay Sep 25 — 27:

Villasimius, Sardinia — 1 night

Start off your visit on the 28th (Wed): kick back and relax at Cala Pira, learn about winemaking at Colline del Vento, then enjoy the sand and surf at Spiaggia di Punta Molentis, then tour the pleasant surroundings at Simius Beach, and finally enjoy the sand and surf at Porto Giunco.

To find photos, where to stay, reviews, and other tourist information, read Villasimius online journey planner.

You can drive from San Teodoro to Villasimius in 3.5 hours. Other options are to take a bus; or do a combination of bus and train. In September, daytime highs in Villasimius are 85°F, while nighttime lows are 63°F. Cap off your sightseeing on the 28th (Wed) early enough to catch the flight to Ravello.
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Find places to stay Sep 27 — 28:

Ravello — 3 nights

Best known for its celebrated terraced gardens, Ravello is a hidden gem of Italy's Amalfi Coast.
Visit Fornillo and Lido Capo di Conca for some beach relaxation. You'll explore the less-touristy side of things at Duomo di Sant'Andrea and Boat Tours & Water Sports. Venture out of the city with trips to Societa Agricola Tenuta San Francesco - S.R.L. (in Tramonti) and Positano (Il Sentiero Degli Dei & Food Tours). There's still lots to do: admire the natural beauty at Villa Cimbrone Gardens, head outdoors with Amalfi Coast, contemplate the long history of Villa Rufolo, and contemplate in the serene atmosphere at Duomo di Ravello.

For reviews, photos, where to stay, and more tourist information, read our Ravello tour planner.

You can fly from Villasimius to Ravello in 3 hours. Other options are to do a combination of bus, ferry, train, and taxi; or do a combination of bus and ferry. Traveling from Villasimius in September, expect nights in Ravello to be somewhat warmer, around 70°F, while days are little chillier, around 79°F. Finish up your sightseeing early on the 1st (Sat) so you can catch the ferry to Capri.
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Find places to stay Sep 28 — Oct 1:

Capri, Island of Capri — 1 night

The island of Capri encompasses all the magical allure of the Mediterranean--dramatic blue waters, lush mountainous landscape, and picturesque island villages.
On the 2nd (Sun), stroll through Fortini Coastal Walk, stroll through Monte Solaro, get engrossed in the history at Villa San Michele, then take some stellar pictures from Belvedere Cannone, then stroll through I Faraglioni, and finally take in nature's colorful creations at Giardini di Augusto.

To see other places to visit, more things to do, reviews, and other tourist information, go to the Capri trip itinerary site.

You can ride a ferry from Ravello to Capri in 1.5 hours. Other options are to do a combination of taxi and ferry; or do a combination of bus and ferry. Expect a daytime high around 72°F in October, and nighttime lows around 63°F. Wrap up your sightseeing on the 2nd (Sun) to allow time to travel to Taormina.
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Parks · Nature · Trails · Outdoors
Side Trip
Find places to stay Oct 1 — 2:

Taormina, Sicily — 1 night

With its warm island weather and cliffside location overlooking the Ionion Sea, Taormina has been one of Sicily's most popular getaway destinations since the early 19th century.
Kick off your visit on the 3rd (Mon): stop by Sicilian Store, don't miss a visit to Corso Umberto, take in the pleasant sights at Piazza IX Aprile, don't miss a visit to Ancient Theatre of Taormina, then stroll around Villa Comunale, and finally pause for some serene contemplation at Duomo di Taormina.

To find ratings, maps, reviews, and other tourist information, refer to the Taormina trip planner.

Traveling by combination of ferry and flight from Capri to Taormina takes 4.5 hours. Alternatively, you can do a combination of ferry and train; or do a combination of ferry and bus. In October, plan for daily highs up to 76°F, and evening lows to 64°F. Wrap up your sightseeing on the 3rd (Mon) early enough to fly to Lampedusa.
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Find places to stay Oct 2 — 3:

Lampedusa — 1 night

Italy's southernmost territory, Lampedusa, is known for its turquoise waters, white-sand beaches, and island charm.
On the 4th (Tue), tour the pleasant surroundings at La Tabaccara, tour the pleasant surroundings at Cala Pulcino, then tour the pleasant surroundings at Spiaggia dei Conigli, then enjoy the sand and surf at Cala Croce Beach, and finally identify plant and animal life at Centro di Recupero Tartarughe e Fauna Selvatica WWF.

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

Traveling by flight from Taormina to Lampedusa takes 3 hours. Alternatively, you can do a combination of car and ferry; or do a combination of bus and ferry. Traveling from Taormina in October, expect somewhat warmer with lows of 71°F in Lampedusa. Cap off your sightseeing on the 4th (Tue) early enough to catch the flight to Rome.
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Find places to stay Oct 3 — 4:

Rome — 4 nights

Eternal City

Aptly nicknamed the Eternal City, Rome is the birthplace of the Roman Empire, one of the world's greatest civilizations ever.
Visit Colosseum and Vatican Museums for their historical value. Satisfy your inner culture vulture at Pantheon and St. Peter's Basilica. Go for a jaunt from Rome to Ostia Antica to see Parco Archeologico di Ostia Antica about 42 minutes away. And it doesn't end there: don't miss a visit to Centro Storico Associazione Centro Storico, explore the different monuments and memorials at Catacombs of Saint Callixtus, admire the striking features of Villa Borghese, and contemplate in the serene atmosphere at Cupola di San Pietro.

For where to stay, ratings, other places to visit, and tourist information, read Rome trip itinerary planner.

Fly from Lampedusa to Rome in 3 hours. Alternatively, you can do a combination of ferry and bus; or do a combination of ferry, bus, and train. Expect slightly colder evenings in Rome when traveling from Lampedusa in October, with lows around 55°F. Finish up your sightseeing early on the 8th (Sat) so you can go by car to Assisi.
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Side Trips
Find places to stay Oct 4 — 8:

Assisi — 3 nights

City of Peace

Rich in culture and religious tradition, Assisi is known as the birthplace of St.
Get some historical perspective at Duomo di Orvieto and Pozzo di San Patrizio. Discover out-of-the-way places like Basilica di Santa Maria degli Angeli - Porziuncola and Eremo delle Carceri. Explore Assisi's surroundings by going to Cattedrale di Santa Maria Assunta Spoleto (in Spoleto) and Castello Monte Vibiano Vecchio (in Mercatello). The adventure continues: contemplate in the serene atmosphere at Basilica di Santa Chiara, delve into the distant past at Roman Forum and Archaeological Museum, appreciate the extensive heritage of Centro Storico di Assisi, and take in the architecture and atmosphere at San Damiano.

For maps, reviews, traveler tips, and tourist information, read Assisi holiday maker tool.

Drive from Rome to Assisi in 2.5 hours. Alternatively, you can take a train; or take a bus. October in Assisi sees daily highs of 70°F and lows of 51°F at night. Finish your sightseeing early on the 11th (Tue) to allow enough time to drive to Siena.
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Side Trips
Find places to stay Oct 8 — 11:

Siena — 3 nights

Cultural Heart of Tuscany

Siena, a medieval Tuscan city, features numerous attractions, including a historic town center, alleyways, towers, and well-preserved buildings.
Get a sense of the local culture at Historic Centre of San Gimignano and Abbazia di San Galgano. Explore hidden gems such as Centro Storico di Siena and Tenuta Torciano. You'll find plenty of places to visit near Siena: San Quirico d'Orcia (in San Quirico d'Orcia), San Gimignano (Guardastelle Vineyard, San Gimignano Bell Tower, &more) and Abbazia di Sant'Antimo (in Castelnuovo dell'Abate). And it doesn't end there: savor the flavors at Food & Drink, take in the spiritual surroundings of San Francesco, contemplate the long history of Battistero di San Giovanni, and pause for some serene contemplation at Duomo di Siena.

For other places to visit, photos, and other tourist information, read Siena road trip planning site.

Traveling by car from Assisi to Siena takes 2 hours. Alternatively, you can take a bus; or take a train. In October, daytime highs in Siena are 73°F, while nighttime lows are 56°F. Wrap up your sightseeing on the 14th (Fri) to allow time to drive to Florence.
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Find places to stay Oct 11 — 14:

Florence — 3 nights

Birthplace of the Italian Renaissance

Considered a cultural, artistic, and architectural jewel of Italy, Florence is the birthplace of the Italian Renaissance.
Satisfy your inner culture vulture at Piazzale Michelangelo and Florence Academy of Fine Arts. You'll explore the less-touristy side of things at Duomo di Pisa and Battistero di San Giovanni. Change things up with these side-trips from Florence: Pisa (Camposanto & Leaning Tower of Pisa), Torre Guinigi (in Lucca) and Montecatini Alto (in Montecatini Alto). Next up on the itinerary: get great views at Basilica San Miniato al Monte, contemplate in the serene atmosphere at The Baptistery of St. John, contemplate the long history of Museo Nazionale del Bargello, and admire the landmark architecture of Cappelle Medicee.

To find ratings, photos, where to stay, and more tourist information, you can read our Florence road trip planner.

Traveling by car from Siena to Florence takes 1.5 hours. Alternatively, you can take a bus; or take a train. In October, daytime highs in Florence are 71°F, while nighttime lows are 54°F. Finish your sightseeing early on the 17th (Mon) to allow enough time to take a train to Verona.
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Find places to stay Oct 14 — 17:

Verona — 3 nights

City of Romeo and Juliet

The famous setting for Shakespeare's star-crossed lovers, Romeo and Juliet, Verona is one of northern Italy's main tourist destinations, largely owing to its incredibly rich artistic heritage.
Get some historical perspective at Castello Scaligero and Basilica di San Zeno Maggiore. Your cultural itinerary includes sights like Borghetto sul Mincio and Scaliger Castle in Malcesine. You'll find plenty of places to visit near Verona: Palazzo Te (in Mantua), Mountbaldo (in Malcesine) and Road of 52 Tunnels (in Valli del Pasubio). Next up on the itinerary: explore the ancient world of Grotte di Catullo, make a trip to Piazza Bra, kick back and relax at Jamaica Beach, and catch a live performance at Arena di Verona.

To find other places to visit, more things to do, traveler tips, and other tourist information, go to the Verona trip builder app.

Take a train from Florence to Verona in 2.5 hours. Alternatively, you can drive. Expect little chillier weather when traveling from Florence in October: highs in Verona hover around 66°F, while lows dip to 50°F. Finish your sightseeing early on the 20th (Thu) so you can drive to Venice.
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Find places to stay Oct 17 — 20:

Venice — 3 nights

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.
Eschew the tourist crowds and head to Centro Storico di Venezia and San Giorgio Maggiore. Deepen your sense of the past at sights like Piazza San Marco and Scrovegni Chapel. Venture out of the city with trips to Padua (Padua Botanical Garden - World Heritage Site & Basilica of St. Anthony). Next up on the itinerary: wander the streets of Dorsoduro, visit Cannaregio, explore the world behind art at Peggy Guggenheim Collection, and admire the striking features of Basilica di San Marco.

To see more things to do, where to stay, other places to visit, and other tourist information, use the Venice planner.

Traveling by car from Verona to Venice takes 1.5 hours. Alternatively, you can take a shuttle; or take a train. In October, daily temperatures in Venice can reach 66°F, while at night they dip to 51°F. Cap off your sightseeing on the 23rd (Sun) early enough to catch the flight back home.
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Side Trip
Find places to stay Oct 20 — 23:

Italy travel guide

4.6
Landmarks · Ruins · Beaches
Italy is a land of high fashion, fine art, exquisite architecture, luxury sports cars, outstanding cuisine--and an insatiable taste for "la dolce vita." It's also home to the greatest number of World Heritage Sites in the world, making it an ideal place for your next holiday. The country boasts a varied landscape of mountain ranges, alpine lakes, and coastal towns, so it's no wonder travelers often refer to it as the bel paese (beautiful country). With so many places to visit, visitors often have a difficult time planning their itinerary. The smaller villages each feature a distinct character and a blend of architecture, art, and cuisine. In the country, you'll find countless archeological sites dating back to Roman times and beyond. The country's cities and seaside resorts are cosmopolitan powerhouses with museums, galleries, restaurants, shops, open-air markets, and pedestrian-friendly historic areas.
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