27 days in Italy Itinerary

27 days in Italy Itinerary

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Route & dates

27 days in Italy Itinerary

Start: Malaga
Fly + bus:  8​h 30​min
1
Trapani, Sicily
— 3 nights
Drive:  4​h 30​min
2
Ragusa, Sicily
— 3 nights
Drive:  2​h 15​min
3
Taormina, Sicily
— 2 nights
+4
train + foot + bus + Fly + train:  6​h 30​min
4
Lecce
— 3 nights
Drive + ferry:  5​h 45​min
5
Forio, Isola d'Ischia
— 1 day
ferry + Drive:  4​h 15​min
6
Orvieto
— 3 nights
Drive:  1​h 30​min
7
Assisi
— 4 nights
Drive:  1​h 45​min
8
Siena
— 4 nights
Drive:  3​h 30​min
9
Venice
— 2 nights
Fly:  5​h 45​min
End: Malaga

3
nights
Trapani, Sicily

Trapani ©
Historically known for its importance in salt production, Trapani has gained recognition as an enticing but affordable vacation locale in Sicily.
Your inner history buff will appreciate Tempio di Segesta and Ex Stabilimento Florio delle Tonnare di Favignana e Formica. Explore hidden gems such as Spiaggia di Macari and IL Duomo. When in Trapani, make a side trip to see Cala Rossa in Isola di Favignana, approximately 1h 30 min away. Next up on the itinerary: stop by La Pasticceria Maria Grammatico and examine the collection at Museo del sale.

For ratings, photos, traveler tips, and other tourist information, go to the Trapani route maker tool .

Malaga, Spain to Trapani is an approximately 8.5-hour combination of flight and train. You can also fly; or do a combination of bus, flight, and train. Expect a daytime high around 35°C in July, and nighttime lows around 23°C. Wrap up your sightseeing on the 8th (Mon) early enough to drive to Ragusa.

Things to do in Trapani

Historic Sites Outdoors Beaches

Side Trips

Erice, Isola di Favignana, Tempio di Segesta, Spiaggia di Macari
Highlights from your plan
Spiaggia di Macari ©
Spiaggia di Macari
La Pasticceria Maria Grammatico ©
La Pasticceria Maria Grammatico

3
nights
Ragusa, Sicily

Ragusa ©
Once a flourishing ancient city, Ragusa was rebuilt after a devastating earthquake in 1693.
Your inner history buff will appreciate Duomo San Giorgio and Scicli. Step out of the city life by going to Cavagrande del Cassibile and Ear of Dionysius (Orecchio di Dionisio). Get out of town with these interesting Ragusa side-trips: Noto (St. Nicholas Cathedral & Centro Storico) and Syracuse (Syracuse Cathedral & Greek Theater). And it doesn't end there: take in the architecture and atmosphere at Cathedral of St. George, get to know the fascinating history of Ragusa Ibla, and take in the spiritual surroundings of Chiesa del Carmine.

To find more things to do, reviews, where to stay, and other tourist information, refer to the Ragusa travel planner.

Getting from Trapani to Ragusa by car takes about 4.5 hours. Other options: do a combination of train and bus; or take a bus. In July, daytime highs in Ragusa are 37°C, while nighttime lows are 26°C. Wrap up your sightseeing on the 11th (Thu) to allow time to drive to Taormina.

Things to do in Ragusa

Historic Sites Parks Nature

Side Trips

Syracuse, Noto, Modica, Scicli, Cavagrande del Cassibile
Highlights from your plan
St. Nicholas Cathedral ©
St. Nicholas Cathedral
Cathedral of St. George ©
Cathedral of St. George
Duomo San Giorgio ©
Duomo San Giorgio

2
nights
Taormina, Sicily

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.
On the 12th (Fri), enjoy breathtaking views from Porta Catania di Taormina, head off the coast to Isola Bella, admire the local landmark of Quattro Fontane di Taormina, then stroll through Villa Comunale, then don't miss a visit to Corso Umberto, and finally don't miss a visit to Piazza IX Aprile. Keep things going the next day: don't miss a visit to Bell Tower and Astronomical Clock (Orologio Astronomico), take in the architecture and atmosphere at Duomo di Messina, and then see some colorful creatures with a scuba or snorkeling tour.

For where to stay, ratings, and tourist information, you can read our Taormina holiday site .

Drive from Ragusa to Taormina in 2.5 hours. Alternatively, you can do a combination of bus and train; or take a bus. In July, plan for daily highs up to 36°C, and evening lows to 27°C. Finish your sightseeing early on the 13th (Sat) to allow enough time to travel to Lecce.

Things to do in Taormina

Outdoors Wildlife Parks

Side Trips

Messina, Scuba & Snorkeling
Highlights from your plan
Scuba & Snorkeling
Quattro Fontane di Taormina ©
Quattro Fontane di Taormina
Porta Catania di Taormina ©
Porta Catania di Taormina

3
nights
Lecce

Lecce ©
Known as the Florence of the South, Lecce is distinguished for its elaborate Baroque monuments.
Do some cultural sightseeing at Basilica di Santa Caterina d'Alessandria and Cattedrale Di Otranto. Take a break from the city and head to Fishing Charters & Tours and Grotta della Poesia. Change things up with these side-trips from Lecce: Centro Storico Otranto (in Otranto), Togo Bay Beach (in Porto Cesareo) and Centro Storico di Gallipoli (in Gallipoli). There's still lots to do: contemplate in the serene atmosphere at Basilica di Santa Croce and kick back and relax at Channel Ciolo.

To find ratings, maps, traveler tips, and other tourist information, go to the Lecce online day trip planner .

You can do a combination of train and flight from Taormina to Lecce in 6.5 hours. Alternatively, you can do a combination of ferry and car; or do a combination of train and flight. Expect a bit cooler evenings in Lecce when traveling from Taormina in July, with lows around 22°C. Finish your sightseeing early on the 17th (Wed) so you can travel to Forio.

Things to do in Lecce

Historic Sites Parks Outdoors

Side Trips

Otranto, Centro Storico di Gallipoli, Channel Ciolo, Togo Bay Beach, Grotta della Poesia
Highlights from your plan
Channel Ciolo ©
Channel Ciolo
Cattedrale Di Otranto ©
Cattedrale Di Otranto

1
day
Forio, Isola d'Ischia

Forio ©
Kick off your visit on the 18th (Thu): step into the grandiose world of Castello Aragonese d'Ischia, take in nature's colorful creations at Giardini La Mortella, then steep yourself in history at Sant'Angelo (Serrara Fontana), and finally pause for some serene contemplation at Chiesa del Soccorso.

To see more things to do, ratings, where to stay, and other tourist information, you can read our Forio trip builder app .

Getting from Lecce to Forio by combination of car and ferry takes about 6 hours. Other options: do a combination of train and ferry; or do a combination of bus and ferry. In July, daily temperatures in Forio can reach 36°C, while at night they dip to 26°C. Wrap up your sightseeing on the 18th (Thu) early enough to travel to Orvieto.

Things to do in Forio

Historic Sites Museums Nightlife

Side Trips

Sant'Angelo (Serrara Fontana), Castello Aragonese d'Ischia
Highlights from your plan
Castello Aragonese d'Ischia ©
Castello Aragonese d'Ischia
Sant'Angelo (Serrara Fontana) ©
Sant'Angelo (Serrara Fontana)
Chiesa del Soccorso ©
Chiesa del Soccorso

3
nights
Orvieto

Orvieto ©
The striking town of Orvieto, perched on a volcanic cliff overlooking the Umbrian countryside, is known as the Green Heart of Italy.
Discover out-of-the-way places like Fosso Bianco - Bagni San Filippo and Pitigliano Centro Storico. Get outdoors at Cascate del Mulino and Cascata delle Marmore. Change things up with these side-trips from Orvieto: Giardino dei Tarocchi (in Pescia Fiorentina), Civita di Bagnoregio (in Civita di Bagnoregio) and La Scarzuola (in Montegabbione). Next up on the itinerary: don't miss a visit to Pozzo di San Patrizio and contemplate the long history of Duomo di Orvieto.

To see reviews, where to stay, other places to visit, and other tourist information, you can read our Orvieto trip 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. Traveling from Forio in July, Orvieto is a bit cooler at night with lows of 21°C. Wrap up your sightseeing on the 21st (Sun) early enough to drive to Assisi.

Things to do in Orvieto

Parks Historic Sites Nature

Side Trips

Civita di Bagnoregio, La Scarzuola, Cascata delle Marmore, Fosso Bianco - Bagni San Filippo, Giardino dei Tarocchi
Highlights from your plan
Cascata delle Marmore ©
Cascata delle Marmore
La Scarzuola ©
La Scarzuola
Fosso Bianco - Bagni San Filippo ©
Fosso Bianco - Bagni San Filippo

4
nights
Assisi

Assisi ©
Rich in culture and religious tradition, Assisi is known as the birthplace of St.
Museum-lovers will appreciate Museo della Porziuncola and Palazzo Ducale di Urbino. Escape the urban bustle at Riviera del Conero e Colli dell'Infinito and Piana di Castelluccio di Norcia. Get out of town with these interesting Assisi side-trips: Grotte di Frasassi (in Genga), Cattedrale di Santa Maria Assunta Spoleto (in Spoleto) and Santuario Della Santa Casa (in Loreto). Next up on the itinerary: pause for some serene contemplation at Basilica di Santa Chiara, contemplate in the serene atmosphere at Eremo delle Carceri, and step into the grandiose world of Rocca Paolina.

Plan trip to Assisi with our itinerary maker to find out where to go and what to do.

You can drive from Orvieto to Assisi in 1.5 hours. Other options are to take a train; or take a bus. In July, daily temperatures in Assisi can reach 37°C, while at night they dip to 20°C. Wrap up your sightseeing on the 25th (Thu) early enough to drive to Siena.

Things to do in Assisi

Historic Sites Parks Nature

Side Trips

San Francesco, Arezzo, Cattedrale di Santa Maria Assunta Spoleto, Grotte di Frasassi, Santuario Della Santa Casa, Riviera del Conero e Colli dell'Infinito
Highlights from your plan
Piana di Castelluccio di Norcia ©
Piana di Castelluccio di Norcia
Santuario Della Santa Casa ©
Santuario Della Santa Casa

4
nights
Siena

Siena ©
Siena, a medieval Tuscan city, features numerous attractions, including a historic town center, alleyways, towers, and well-preserved buildings.
Abbazia di Sant'Antimo and Abbazia di San Galgano will appeal to history buffs. Discover out-of-the-way places like Dog Beach and San Gimignano 1300. Change things up with these side-trips from Siena: Fortezza di Montalcino (in Montalcino), Pisa (Duomo di Pisa & Battistero) and San Gimignano (Historic Centre of San Gimignano & San Gimignano Bell Tower). There's much more to do: make a trip to Centro Storico di Siena, browse the collection at Biblioteca Piccolomini, and enjoy breathtaking views from Torre del Mangia.

For ratings, reviews, traveler tips, and other tourist information, you can read our Siena trip builder website .

You can drive from Assisi to Siena in 2 hours. Alternatively, you can take a bus; or take a train. In July, daytime highs in Siena are 37°C, while nighttime lows are 22°C. Wrap up your sightseeing on the 29th (Mon) early enough to drive to Venice.

Things to do in Siena

Historic Sites Outdoors Beaches

Side Trips

San Gimignano, Pisa, Montalcino, Abbazia di San Galgano, Dog Beach
Highlights from your plan
San Gimignano 1300 ©
San Gimignano 1300
Fortezza di Montalcino ©
Fortezza di Montalcino
Abbazia di Sant'Antimo ©
Abbazia di Sant'Antimo

2
nights
Venice

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.
Start off your visit on the 30th (Tue): pause for some serene contemplation at Basilica di Sant’Antonio, contemplate in the serene atmosphere at Scrovegni Chapel, then take in the views from Ponte dei Sospiri, then contemplate in the serene atmosphere at Scuola Grande di San Rocco, and finally take in the architecture and atmosphere at San Giorgio Maggiore. Here are some ideas for day two: take in the spiritual surroundings of Basilica Santa Maria Gloriosa dei Frari, take a stroll through Cannaregio, then get to know the fascinating history of Campo del Ghetto, and finally make a trip to Dorsoduro.

To see where to stay, other places to visit, and more tourist information, refer to the Venice online trip itinerary maker .

Traveling by car from Siena to Venice takes 3.5 hours. Alternatively, you can take a train; or take a bus. In July in Venice, expect temperatures between 36°C during the day and 22°C at night. Wrap up your sightseeing on the 31st (Wed) to allow time to travel back home.

Things to do in Venice

Historic Sites Neighborhoods

Side Trip

Padua
Highlights from your plan
Campo del Ghetto ©
Campo del Ghetto
Scuola Grande di San Rocco ©
Scuola Grande di San Rocco

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