39 days in Italy Itinerary

39 days in Italy Itinerary

Created using Inspirock Italy trip planner

Make it your trip
Fly to Verona Villafranca Airport, Drive to Trento
1
Trento
— 3 nights
Drive
2
Venice
— 3 nights
Drive
3
Bologna
— 4 nights
Train
4
Florence
— 3 nights
Drive
5
Assisi
— 4 nights
Drive
6
Orvieto
— 2 nights
Drive
7
Rome
— 4 nights
Train
8
Naples
— 4 nights
Fly
9
Taormina, Sicily
— 2 nights
Fly
10
Bari
— 4 nights
Fly
11
Turin
— 4 nights
Fly

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Trento

— 3 nights

Painted City

Tyrol's capital and one of the nation's wealthiest cities, Trento serves as the commercial and cultural center of the region.
Visit Arco Castle and Santuario di San Romedio for their historical value. Get a sense of the local culture at Castel Thun and Castello del Buonconsiglio Monumenti e Collezioni Provinciali. Explore the numerous day-trip ideas around Trento: South Tyrol Museum of Archaeology (in Bolzano), Borghetto sul Mincio (in Valeggio Sul Mincio) and Malcesine (Mountbaldo & Scaliger Castle in Malcesine). The adventure continues: appreciate the extensive heritage of Piazza Duomo and see the interesting displays at MUSE - Science Museum.

To find traveler tips, where to stay, and more tourist information, use the Trento tour itinerary planning website.

Jacksonville, USA to Trento is an approximately 18-hour combination of flight and car. Due to the time zone difference, you'll lose 6 hours traveling from Jacksonville to Trento. Plan for little chillier temperatures traveling from Jacksonville in September, with highs in Trento at 77°F and lows at 55°F. Finish your sightseeing early on the 15th (Tue) so you can drive to Venice.

Things to do in Trento

Historic Sites · Museums · Childrens Museums · Parks

Side Trips

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.
Get a sense of the local culture at Basilica Palladiana and Scala Contarini del Bovolo. Padua Botanical Garden - World Heritage Site and Basilica di Santa Maria Gloriosa dei Frari will appeal to history buffs. Explore the numerous day-trip ideas around Venice: Verona (Piazza Bra, Museo di Castelvecchio, &more) and Padua (Basilica of St. Anthony, Scrovegni Chapel, &more). And it doesn't end there: pause for some serene contemplation at Scuola Grande di San Rocco, take in the views from Ponte dei Sospiri, and take a stroll through Cannaregio.

For photos, maps, reviews, and other tourist information, use the Venice tour itinerary planner.

You can drive from Trento to Venice in 2.5 hours. Another option is to take a train. In September, daily temperatures in Venice can reach 77°F, while at night they dip to 59°F. Finish your sightseeing early on the 18th (Fri) so you can drive to Bologna.

Things to do in Venice

Historic Sites · Parks · Neighborhoods

Side Trips

Bologna

— 4 nights

Heart of Italian Cuisine

A city famous for its cuisine, Bologna is the seat of the oldest university in the world, founded in 1088.
Visit Basilica di Sant'Apollinare in Classe and Castello Scaligero for their historical value. You'll discover tucked-away gems like Chiesa di Santa Maria della Vita and Basilica di San Domenico. Explore Bologna's surroundings by going to Castello di Gradara (in Gradara), Arco d'Augusto (in Rimini) and Playa del Sol (in Riccione). There's much more to do: explore the ancient world of Grotte di Catullo, steep yourself in history at Basilica di San Petronio, pause for some serene contemplation at Santuario di Madonna di San Luca, and take in the spiritual surroundings of Basilica San Vitale.

To find reviews, more things to do, where to stay, and more tourist information, you can read our Bologna road trip planner.

Traveling by car from Venice to Bologna takes 2 hours. Alternatively, you can take a train. In September, daytime highs in Bologna are 78°F, while nighttime lows are 59°F. Cap off your sightseeing on the 22nd (Tue) early enough to catch the train to Florence.

Things to do in Bologna

Historic Sites · Parks · Beaches · Outdoors

Side Trips

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.
Deepen your sense of the past at sights like Duomo di San Gimignano and Camposanto. Satisfy your inner culture vulture at Loggia dei Lanzi and Duomo di Pisa. Explore Florence's surroundings by going to Historic Centre of San Gimignano (in San Gimignano), Battistero di San Giovanni (in Pisa) and Abbazia di San Galgano (in Chiusdino). And it doesn't end there: appreciate the extensive heritage of Centro Storico, contemplate in the serene atmosphere at Basilica San Miniato al Monte, take in the architecture and atmosphere at Basilica of Santa Maria Novella, and take an in-depth tour of Museum of Opera of Saint Maria of Fiore.

To find other places to visit, ratings, more things to do, and tourist information, use the Florence holiday maker tool.

Getting from Bologna to Florence by train takes about 1.5 hours. Other options: drive; or take a bus. September in Florence sees daily highs of 78°F and lows of 59°F at night. Finish your sightseeing early on the 25th (Fri) so you can drive to Assisi.

Things to do in Florence

Historic Sites · Museums

Side Trips

Assisi

— 4 nights

City of Peace

Rich in culture and religious tradition, Assisi is known as the birthplace of St.
Satisfy your inner culture vulture at City Centre and San Damiano. Eremo Le Celle and San Quirico d'Orcia will appeal to history buffs. Explore the numerous day-trip ideas around Assisi: Chiesa di San Francesco (in San Quirico d'Orcia), Abbazia di Sant'Antimo (in Castelnuovo dell'Abate) and Fortezza di Montalcino (in Montalcino). Next up on the itinerary: pause for some serene contemplation at Cattedrale di San Rufino, make a trip to Eremo delle Carceri, contemplate the long history of Piazza del Duomo, and contemplate in the serene atmosphere at Basilica di Santa Chiara.

To see ratings, reviews, where to stay, and tourist information, go to the Assisi trip itinerary planner.

Getting from Florence to Assisi by car takes about 2.5 hours. Other options: take a train. In September in Assisi, expect temperatures between 78°F during the day and 57°F at night. Wrap up your sightseeing on the 29th (Tue) to allow time to drive to Orvieto.

Things to do in Assisi

Historic Sites · Parks · Neighborhoods · Nature

Side Trips

Orvieto

— 2 nights

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 30th (Wed): admire the landmark architecture of Duomo di Orvieto, then explore the fascinating underground world of Orvieto Underground, then go for a walk through Civita di Bagnoregio, and finally take in the architecture and atmosphere at Chiesa di Sant'Agostino. Keep things going the next day: make a trip to Pozzo di San Patrizio, appreciate the extensive heritage of Piazza della Repubblica, then take in nature's colorful creations at Villa Lante, and finally admire the striking features of Palazzo dei Papi.

To find other places to visit, traveler tips, and more tourist information, refer to the Orvieto day trip website.

You can drive from Assisi to Orvieto in 1.5 hours. Alternatively, you can take a train; or take a bus. In September, daily temperatures in Orvieto can reach 78°F, while at night they dip to 59°F. Cap off your sightseeing on the 1st (Thu) early enough to go by car to Rome.

Things to do in Orvieto

Historic Sites · Parks · Nature

Side Trips

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 Necropoli di Tarquinia and Centro Storico Associazione Centro Storico for their historical value. Your cultural itinerary includes sights like Giardino dei Tarocchi and Abbey of St. Paul Outside the Walls. Get out of town with these interesting Rome side-trips: Villa d'Este (in Tivoli) and Parco Archeologico di Ostia Antica (in Ostia Antica). And it doesn't end there: make a trip to Santa Maria Sopra Minerva, take in the architecture and atmosphere at Arcibasilica di San Giovanni in Laterano, steep yourself in history at St. Peter's Square, and take an in-depth tour of Le Domus Romane di Palazzo Valentini.

To find reviews, more things to do, traveler tips, and tourist information, use the Rome trip website.

Drive from Orvieto to Rome in 2 hours. Alternatively, you can take a train; or take a bus. In October, daily temperatures in Rome can reach 73°F, while at night they dip to 55°F. Finish your sightseeing early on the 5th (Mon) to allow enough time to take a train to Naples.

Things to do in Rome

Historic Sites · Parks · Museums

Side Trips

Naples

— 4 nights
Naples is the capital of the Italian region Campania and the third-largest municipality in Italy after Rome and Milan. Get a sense of the local culture at Villa dei Misteri and Villa San Michele. Visit Chiesa di Santa Maria di Costantinopoli and Castello Aragonese d'Ischia for their historical value. Get out of town with these interesting Naples side-trips: Paestum Ruins (in Paestum) and Capri (Giardini di Augusto & I Faraglioni). There's lots more to do: get engrossed in the history at Museo del Tesoro di San Gennaro, get to know the fascinating history of Underground Naples, explore the ancient world of Parco Acheologico di Ercolano, and steep yourself in history at Castel dell'Ovo.

For more things to do, ratings, and more tourist information, go to the Naples holiday planner.

Traveling by train from Rome to Naples takes 2 hours. Alternatively, you can drive; or fly. October in Naples sees daily highs of 74°F and lows of 58°F at night. Finish up your sightseeing early on the 9th (Fri) so you can catch the flight to Taormina.

Things to do in Naples

Historic Sites · Museums · Parks · Nature

Side Trips

Taormina, Sicily

— 2 nights
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 10th (Sat): go for a walk through Piazza IX Aprile, don't miss a visit to Corso Umberto, get to know the fascinating history of Piazza Duomo, admire the local landmark of Quattro Fontane di Taormina, then stroll through Isola Bella, and finally do a tasting at Gambino Vini. Here are some ideas for day two: don't miss a visit to Bell Tower and Astronomical Clock (Orologio Astronomico), take in the architecture and atmosphere at Duomo di Messina, steep yourself in history at Le Quattro Fontane, then appreciate the extensive heritage of Palazzo Ciampoli di Taormina, and finally walk around Villa Comunale.

For more things to do, other places to visit, reviews, and tourist information, go to the Taormina day trip planning app.

Getting from Naples to Taormina by flight takes about 2.5 hours. Other options: do a combination of car and ferry; or do a combination of train and ferry. Traveling from Naples in October, you can expect nighttime temperatures to be somewhat warmer in Taormina, with lows of 64°F. Finish up your sightseeing early on the 11th (Sun) so you can catch the flight to Bari.

Things to do in Taormina

Historic Sites · Parks · Wineries · Nature

Side Trips

Bari

— 4 nights

Gateway to Apulia

Puglia's capital city, Bari, is a growing metropolis of industry and one of the country's most important commercial ports.
Get a sense of the local culture at Piazza del Duomo and Museo Nazionale Archeologico. Step off the beaten path and head to Cripta del Peccato Originale and Piazza Vittorio Emanuele II (Largo Catuma). Explore the numerous day-trip ideas around Bari: Cattedrale di Trani (in Trani), Casa Grotta di Vico Solitario (in Matera) and Castel del Monte (in Andria). And it doesn't end there: take in the spiritual surroundings of Basilica di Santa Croce, take in the architecture and atmosphere at Basilica San Nicola, and don't miss a visit to Centro Storico, Lecce.

To see photos, reviews, more things to do, and more tourist information, read Bari online trip itinerary builder.

You can fly from Taormina to Bari in 3 hours. Alternatively, you can do a combination of car and ferry; or take a bus. Expect a bit cooler evenings in Bari when traveling from Taormina in October, with lows around 56°F. Finish your sightseeing early on the 15th (Thu) so you can fly to Turin.

Things to do in Bari

Historic Sites · Museums · Parks · Nature

Side Trips

Turin

— 4 nights

City of Magic

A city of technology and industry, Turin is in northwestern Italy, a one-hour drive from the French border and slightly more than that from the Mediterranean Sea.
Visit Castello di Fenis and Cattedrale di San Lorenzo - Duomo di Genova for their historical value. Satisfy your inner culture vulture at Teatro Romano and Via Giuseppe Garibaldi. Explore the numerous day-trip ideas around Turin: Galata Museo del Mare (in Genoa), Forte di Bard (in Bard) and Porta Pretoria (in Aosta). Next up on the itinerary: admire the landmark architecture of Palazzo Reale, examine the collection at Museo Nazionale dell'Automobile, make a trip to Piazza San Carlo, and take some stellar pictures from Basilica of Superga.

To see maps, other places to visit, photos, and other tourist information, use the Turin travel route planner.

Getting from Bari to Turin by flight takes about 3.5 hours. Other options: take a train; or drive. Expect a bit cooler temperatures when traveling from Bari in October; daily highs in Turin reach 58°F and lows reach 51°F. You'll have a few hours on the 19th (Mon) to wrap things up before traveling home.

Things to do in Turin

Historic Sites · Museums · Parks

Side Trips

Italy travel guide

4.6
Landmarks · Ruins · Sacred & Religious Sites
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.