22 days in Italy Itinerary

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 2nd (Wed): head off the coast to Isola Bella, admire the local landmark of Quattro Fontane di Taormina, tour the pleasant surroundings at Villa Comunale, then don't miss a visit to Corso Umberto, and finally don't miss a visit to Piazza IX Aprile. On the 3rd (Thu), you'll have a packed day of sightseeing: see some colorful creatures with a scuba or snorkeling tour and then pause for some serene contemplation at Duomo di Messina.

To see photos, other places to visit, ratings, and more tourist information, use the Taormina online trip itinerary planner .

Reykjavik, Iceland to Taormina is an approximately 11.5-hour combination of flight and train. You'll lose 1 hour traveling from Reykjavik to Taormina due to the time zone difference. Plan for much hotter temperatures traveling from Reykjavik in October, with highs in Taormina at 28°C and lows at 20°C. Finish your sightseeing early on the 3rd (Thu) to allow enough time to drive to Cefalu.

Cefalù is a city and comune in the Province of Palermo, located on the northern coast of Sicily, Italy on the Tyrrhenian Sea about 70km east of the provincial capital and 185km west of Messina. Kick off your visit on the 4th (Fri): steep yourself in history at Piazza del Duomo, pause for some serene contemplation at Duomo di Cefalu, take a stroll through Cefalu Coast, then explore the ancient world of La Rocca, and finally don't miss a visit to Lavatoio Medievale.

To find other places to visit, photos, ratings, and tourist information, read Cefalu online route builder .

Drive from Taormina to Cefalu in 2.5 hours. Alternatively, you can take a train; or take a bus. Finish your sightseeing early on the 4th (Fri) so you can travel to Forio.

On the 5th (Sat), don't miss a visit to Castello Aragonese d'Ischia, then take in nature's colorful creations at Giardini La Mortella, and then pause for some serene contemplation at Chiesa del Soccorso.

To find more things to do, maps, where to stay, and tourist information, refer to the Forio road trip planning app .

You can do a combination of train, flight, and ferry from Cefalu to Forio in 7.5 hours. Alternatively, you can do a combination of train and ferry; or ride a ferry. October in Forio sees daily highs of 26°C and lows of 20°C at night. Finish your sightseeing early on the 5th (Sat) to allow enough time to travel to Orvieto.

The striking town of Orvieto, perched on a volcanic cliff overlooking the Umbrian countryside, is known as the Green Heart of Italy.

Get a sense of the local culture at Pitigliano Centro Storico and Castello di Montorio. Get some historical perspective at Piazza della Repubblica and Necropoli di Tarquinia. Explore the numerous day-trip ideas around Orvieto: Santuario della Madonna delle Grazie (in Pitigliano), Cascata delle Marmore (in Marmore) and Civita di Bagnoregio (in Civita di Bagnoregio). There's still lots to do: kick back and relax at La Feniglia, admire the sheer force of Cascate del Mulino, contemplate the long history of Pozzo di San Patrizio, and take in nature's colorful creations at Giardino dei Tarocchi.

For ratings, maps, traveler tips, and tourist information, go to the Orvieto visit planner.

Getting from Forio to Orvieto by combination of ferry and car takes about 4.5 hours. Other options: do a combination of ferry and train; or do a combination of ferry, flight, and train. Plan for a bit cooler nights when traveling from Forio in October since evenings lows in Orvieto dip to 13°C. Wrap up your sightseeing on the 9th (Wed) early enough to drive to Assisi.

Rich in culture and religious tradition, Assisi is known as the birthplace of St.

Do some cultural sightseeing at San Damiano and Rocca Paolina. Visiting Riviera del Conero e Colli dell'Infinito and Grotte di Frasassi will get you outdoors. You'll find plenty of places to visit near Assisi: Santuario Della Santa Casa (in Loreto), Cattedrale di Santa Maria Assunta Spoleto (in Spoleto) and Palazzo Ducale di Urbino (in Urbino). Next up on the itinerary: take in the spiritual surroundings of Basilica di Santa Chiara, contemplate the long history of Eremo delle Carceri, take in the architecture and atmosphere at Basilica di San Francesco, and examine the collection at Museo della Porziuncola.

For more things to do, traveler tips, other places to visit, and other tourist information, read our Assisi holiday planner.

Traveling by car from Orvieto to Assisi takes 1.5 hours. Alternatively, you can take a train; or take a bus. October in Assisi sees daily highs of 24°C and lows of 12°C at night. Finish your sightseeing early on the 13th (Sun) so you can drive to Siena.

Siena, a medieval Tuscan city, features numerous attractions, including a historic town center, alleyways, towers, and well-preserved buildings.

Do some cultural sightseeing at Abbazia di Sant'Antimo and Camposanto. Deepen your sense of the past at sights like San Gimignano 1300 and Historic Centre of San Gimignano. Get out of town with these interesting Siena side-trips: Abbazia di San Galgano (in Chiusdino), Pisa (Duomo di Pisa & Battistero) and Piazza della Cisterna (in San Gimignano). Dedicate the 17th (Thu) to wine at some of the top wineries in the area. And it doesn't end there: step into the grandiose world of Castello di Monteriggioni, enjoy breathtaking views from Torre del Mangia, get lost in a book at Biblioteca Piccolomini, and make a trip to Centro Storico di Siena.

To see more things to do, traveler tips, other places to visit, and tourist information, refer to the Siena trip planner .

Traveling by car from Assisi to Siena takes 2 hours. Alternatively, you can take a bus; or take a train. In October, plan for daily highs up to 26°C, and evening lows to 15°C. Finish your sightseeing early on the 18th (Fri) so you can drive to Venice.

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.

Your cultural itinerary includes sights like Campo del Ghetto and Cannaregio. Scuola Grande di San Rocco and Basilica Santa Maria Gloriosa dei Frari will appeal to history buffs. Change things up with these side-trips from Venice: Castello Estense (in Ferrara) and Padua (Basilica di Sant’Antonio & Scrovegni Chapel). Next up on the itinerary: indulge in some culinary diversions at a local gastronomic tour, take a stroll through Dorsoduro, contemplate the long history of Ponte dei Sospiri, and take in the architecture and atmosphere at San Giorgio Maggiore.

For other places to visit, traveler tips, reviews, and more tourist information, read Venice trip planner.

Getting from Siena to Venice by car takes about 3.5 hours. Other options: take a train; or take a bus. Traveling from Siena in October, expect Venice to be little chillier, temps between 22°C and 12°C. Wrap up your sightseeing on the 22nd (Tue) early enough to travel back home.