37 days in Italy Itinerary

37 days in Italy Itinerary

Created using Inspirock Italy attractions planner

Plan created by another user. Make it yours

Route & dates

1
Santa Maria di Leuca
— 2 nights
2
Lecce
— 3 nights
3
Alberobello
— 4 nights
4
Vieste
— 1 night
5
Assisi
— 2 nights
6
Lampedusa
— 3 nights
7
Pantelleria
— 1 night
8
Isola di Favignana
— 2 nights
9
Palermo
— 4 nights
10
Cefalu
— 4 nights
11
Syracuse
— 2 nights
12
Tropea
— 5 nights
13
Lipari
— 3 nights

2
nights
Santa Maria di Leuca

Santa Maria di Leuca ©
Santa Maria di Leuca, often spelled simply Leuca, is a frazione of the comune of Castrignano del Capo, in the province of Lecce (Apulia), southern Italy. Start off your visit on the 21st (Fri): enjoy the sand and surf at Channel Ciolo, thenpause for some serene contemplation at Basilica Santuario di Santa Maria de Finibus Terrae, thensee what you can catch with a fishing tour, and finally Head underground at Grotta del Soffio. Keep things going the next day: explore the fascinating underground world of Grotta Tre Porte, visit a coastal fixture at Faro di Leuca, thengo for a stroll along the water at Piscina Naturale di Marina Serra, and finally admire the striking features of Ville Di Santa Maria Di Leuca.

To find more things to do, maps, where to stay, and tourist information, use the Santa Maria di Leuca itinerary planner.

Beirut, Lebanon to Santa Maria di Leuca is an approximately 11.5-hour combination of flight and car. Due to the time zone difference, you'll gain 1 hour traveling from Beirut to Santa Maria di Leuca. Traveling from Beirut in August, expect nights in Santa Maria di Leuca to be about the same, around °C, while days are slightly colder, around °C. Finish up your sightseeing early on the 22nd (Sat) so you can go by car to Lecce.

Things to do in Santa Maria di Leuca

Parks Outdoors Nature

Side Trips

Piscina Naturale di Marina Serra, Channel Ciolo
Highlights from your plan
Channel Ciolo ©
Channel Ciolo
Grotta del Soffio ©
Grotta del Soffio

3
nights
Lecce

Lecce ©
Known as the Florence of the South, Lecce is distinguished for its elaborate Baroque monuments.
Discover out-of-the-way places like Circolo Ippico Malepezza and Togo Bay Beach. You'll find plenty of places to visit near Lecce: Boat Tours & Water Sports (in Porto Cesareo), Sidereus (in Salve) and Cava di Bauxite (in Otranto). Next up on the itinerary: kick back and relax at Porto Selvaggio, don't miss a visit to Porta Rudiae, and get to know the fascinating history of Piazza del Duomo.

To see more things to do, other places to visit, reviews, and more tourist information, you can read our Lecce trip planner.

You can drive from Santa Maria di Leuca to Lecce in 1.5 hours. Another option is to take a bus. When traveling from Santa Maria di Leuca in August, plan for somewhat warmer days and a bit cooler nights in Lecce: temperatures range from °C by day to °C at night. Cap off your sightseeing on the 25th (Tue) early enough to go by car to Alberobello.

Things to do in Lecce

Outdoors Parks Beaches

Side Trips

Porto Cesareo, Circolo Ippico Malepezza, Sidereus, Cava di Bauxite, Porto Selvaggio
Highlights from your plan
Circolo Ippico Malepezza ©
Circolo Ippico Malepezza
Boat Tours & Water Sports
Togo Bay Beach ©
Togo Bay Beach

4
nights
Alberobello

Alberobello ©
Alberobello is a small town and comune of the Metropolitan City of Bari, Apulia, southern Italy. You'll discover tucked-away gems like Torre Guaceto Marine Protected Area and Parrocchia Sant'Antonio di Padova. Change things up with these side-trips from Alberobello: Centro Storico di Monopoli (in Monopoli), Centro Storico (in Ostuni) and Matera (Museo Laboratorio della Civilta Contadina, Sassi di Matera, &more). There's still lots to do: wander the streets of Centro Storico Locorotondo, examine the collection at Trullo Sovrano, admire the striking features of I Trulli di Alberobello - World Heritage Site, and pause for some serene contemplation at Parrocchia Santuario Basilica S.S. Cosma E Damiano.

To find ratings, maps, traveler tips, and tourist information, use the Alberobello trip itinerary planner.

You can drive from Lecce to Alberobello in 1.5 hours. Alternatively, you can do a combination of train and taxi; or do a combination of train and bus. Expect a daytime high around °C in August, and nighttime lows around °C. Finish your sightseeing early on the 29th (Sat) to allow enough time to drive to Vieste.

Things to do in Alberobello

Historic Sites Wildlife Parks

Side Trips

Matera, Centro Storico di Monopoli, Torre Guaceto Marine Protected Area, Centro Storico, Centro Storico Locorotondo
Highlights from your plan
Sassi di Matera ©
Sassi di Matera
Torre Guaceto Marine Protected Area ©
Torre Guaceto Marine Protected Area
Centro Storico ©
Centro Storico

1
night
Vieste

Vieste ©
Vieste is a town, comune and former Catholic bishopric in the province of Foggia, in the Apulia region of southeast Italy. On the 30th (Sun), don't miss a visit to Arco di San Felice, get to know the fascinating history of Borgo Antico di Vieste, thenHead underground at Motobarca Desiree Grotte Marine di Vieste, and finally don't miss a visit to Trabucco San Lorenzo.

To see ratings, traveler tips, where to stay, and other tourist information, use the Vieste vacation planner.

Traveling by car from Alberobello to Vieste takes 3.5 hours. Alternatively, you can take a bus; or do a combination of bus, train, and ferry. In August, daytime highs in Vieste are °C, while nighttime lows are °C. Finish your sightseeing early on the 30th (Sun) to allow enough time to drive to Assisi.

Things to do in Vieste

Historic Sites Nature Parks
Highlights from your plan
Borgo Antico di Vieste ©
Borgo Antico di Vieste
Arco di San Felice ©
Arco di San Felice

2
nights
Assisi

Assisi ©
Rich in culture and religious tradition, Assisi is known as the birthplace of St.
Kick off your visit on the 31st (Mon): contemplate in the serene atmosphere at Eremo delle Carceri, step into the grandiose world of Rocca Maggiore, pause for some serene contemplation at Basilica Papale e Sacro Convento di San Francesco d'Assisi, thencontemplate in the serene atmosphere at Basilica di Santa Chiara, and finally take in the spiritual surroundings of San Damiano. Get ready for a full day of sightseeing on the 1st (Tue): contemplate the long history of Piazza del Duomo, thentake in the views from Ponte delle Torri, and then take in the spiritual surroundings of Basilica di Santa Maria degli Angeli - Porziuncola.

Plan a Assisi trip in moments using our itinerary builder.

Traveling by car from Vieste to Assisi takes 5.5 hours. Alternatively, you can take a bus. Expect a daytime high around °C in August, and nighttime lows around °C. Wrap up your sightseeing on the 1st (Tue) early enough to travel to Lampedusa.

Things to do in Assisi

Historic Sites

Side Trip

Spoleto
Highlights from your plan
Basilica di Santa Chiara ©
Basilica di Santa Chiara

3
nights
Lampedusa

Italy's southernmost territory, Lampedusa, is known for its turquoise waters, white-sand beaches, and island charm.
You'll discover tucked-away gems like Cala Croce Beach and Cala Uccello. There's much more to do: get a new perspective on things with Boat Tours & Water Sports, make a trip to Cala Calandra, look for all kinds of wild species at Centro Recupero Tartarughe Marine, and head outdoors with Mare Morto.

To find photos, maps, traveler tips, and tourist information, you can read our Lampedusa online itinerary maker.

Traveling by combination of train and flight from Assisi to Lampedusa takes 6.5 hours. Alternatively, you can fly; or do a combination of train, ferry, and bus. Plan for somewhat warmer nights when traveling from Assisi in September since evenings lows in Lampedusa dip to °C. Finish your sightseeing early on the 4th (Fri) to allow enough time to travel to Pantelleria.

Things to do in Lampedusa

Outdoors Parks Beaches

Side Trip

Centro Recupero Tartarughe Marine
Highlights from your plan
Boat Tours & Water Sports
Cala Croce Beach ©
Cala Croce Beach
Spiaggia dei Conigli ©
Spiaggia dei Conigli

1
night
Pantelleria

Pantelleria ©
Pantelleria, the ancient Cossyra, is an Italian island in the Strait of Sicily in the Mediterranean Sea, 100km southwest of Sicily and 60km east of the Tunisian coast. Kick off your visit on the 5th (Sat): stroll through Cala Cottone, learn about winemaking at Azienda Agricola d'Ancona, contemplate the waterfront views at Lago di Venere, thenmake a trip to Cala Cinque Denti, thenget outside with Favare Grande, and finally delve into the distant past at Acropoli di San Marco.

To see photos, ratings, and more tourist information, refer to the Pantelleria road trip planner.

You can fly from Lampedusa to Pantelleria in 4.5 hours. Other options are to do a combination of ferry and bus; or do a combination of ferry, bus, and train. Traveling from Lampedusa in September, you can expect nighttime temperatures to be little chillier in Pantelleria, with lows of °C. Wrap up your sightseeing on the 5th (Sat) to allow time to travel to Isola di Favignana.

Things to do in Pantelleria

Outdoors Parks Wineries
Highlights from your plan
Cala Cottone ©
Cala Cottone
Lago di Venere ©
Lago di Venere
Azienda Agricola d'Ancona ©
Azienda Agricola d'Ancona

2
nights
Isola di Favignana

Once famous for its white tuff shell quarries and tuna can factory--now turned into a museum--Isola di Favignana attracts divers and beachgoers with its jagged coastline rich in coves and caves.
On the 6th (Sun), take a tour by water with Boat Tours & Water Sports, don't miss a visit to Grotte bue marino, thenget outside with Cala Azzurra, and finally make a trip to Cala Rotonda (Arco di Ulisse). On the 7th (Mon), you'll have a packed day of sightseeing: kick back and relax at Spiaggia di Cala Rossa, thendon't miss a visit to Visita alle grotte di Favignana con le barche dei pescatori, and then explore the fascinating underground world of Grotta del Genovese.

For photos, maps, where to stay, and more tourist information, you can read our Isola di Favignana trip itinerary maker tool.

You can ride a ferry from Pantelleria to Isola di Favignana in 5 hours. Another option is to fly. Expect a daytime high around °C in September, and nighttime lows around °C. Finish your sightseeing early on the 7th (Mon) so you can travel to Palermo.

Things to do in Isola di Favignana

Outdoors Parks Nature

Side Trip

Grotta del Genovese
Highlights from your plan
Boat Tours & Water Sports
Grotte bue marino ©
Grotte bue marino
Cala Azzurra ©
Cala Azzurra

4
nights
Palermo

The capital of Sicily, Palermo was founded by the Phoenicians under the name of Ziz.
Discover out-of-the-way places like Scuba & Snorkeling and Ustica. Explore the numerous day-trip ideas around Palermo: San Vito lo Capo (Santuario Di San Vito & Spiaggia di San Vito lo Capo) and Grotta Mangiapane (in Custonaci). There's lots more to do: take in the architecture and atmosphere at Cattedrale di Palermo, don't miss a visit to Palazzo Pretorio, Municipio di Palermo, contemplate the long history of Catacombe dei Cappuccini, and take in the spiritual surroundings of San Giuseppe dei Teatini.

To find maps, photos, ratings, and tourist information, read Palermo trip maker website.

You can do a combination of ferry and bus from Isola di Favignana to Palermo in 4 hours. Wrap up your sightseeing on the 11th (Fri) to allow time to drive to Cefalu.

Things to do in Palermo

Outdoors Parks Historic Sites

Side Trips

San Vito lo Capo, Grotta Mangiapane
Highlights from your plan
Scuba & Snorkeling
Spiaggia di San Vito lo Capo ©
Spiaggia di San Vito lo Capo
Cattedrale di Palermo ©
Cattedrale di Palermo

4
nights
Cefalu

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. Eschew the tourist crowds and head to Cefalu Coast and Rocca di Cefalu. Plan for a day of cool, family-friendly fun on the 14th (Mon) at Acqua Verde. The adventure continues: make a trip to Lavatoio Medievale, contemplate in the serene atmosphere at Santuario Gibilmanna, pause for some serene contemplation at Duomo di Cefalu, and delve into the distant past at Mura Megalitiche.

To find ratings, reviews, traveler tips, and other tourist information, you can read our Cefalu online attractions planner.

Drive from Palermo to Cefalu in an hour. Alternatively, you can take a train; or take a bus. Finish up your sightseeing early on the 15th (Tue) so you can go by car to Syracuse.

Things to do in Cefalu

Theme Parks Historic Sites Outdoors
Highlights from your plan
Acqua Verde ©
Acqua Verde
Cefalu Coast ©
Cefalu Coast
Lavatoio Medievale ©
Lavatoio Medievale

2
nights
Syracuse

Syracuse ©
Philosopher Cicero once described Syracuse as "the greatest Greek city and the most beautiful of them all." A powerful city-state of ancient Greece, Syracuse now is the capital of the eponymous Italian province on the eastern coast of Sicily.
Start off your visit on the 16th (Wed): stroll around Tecnoparco Museo di Archimede, thenpause for some serene contemplation at Duomo di Siracusa, thenadmire the landmark architecture of Palazzo Benevantano del Bosco, and finally step off the mainland to explore Ortigia. On the next day, take in the architecture and atmosphere at Chiesa di San Giovanni Alle Catacombe, tour the pleasant surroundings at Spiaggia Pineta del Gelsomineto, thenlook for all kinds of wild species at Riserva Naturale Orientata Cavagrande del Cassibile, and finally stroll through Lido Sayonara.

To find maps, traveler tips, ratings, and more tourist information, read our Syracuse driving holiday planning app.

Traveling by car from Cefalu to Syracuse takes 3 hours. Alternatively, you can take a train; or take a bus. Wrap up your sightseeing on the 17th (Thu) early enough to travel to Tropea.

Things to do in Syracuse

Parks Nature Outdoors
Highlights from your plan
Ortigia ©
Ortigia
Tecnoparco Museo di Archimede ©
Tecnoparco Museo di Archimede

5
nights
Tropea

Tropea ©
Tropea is a municipality located within the province of Vibo Valentia, in Calabria (southern Italy).The town is a famous bathing place, situated on a reef, in the gulf of St. You'll discover tucked-away gems like The Sanctuary of Santa Maria dell'Isola and Artistic Creations The Lighthouse. Change things up with these side-trips from Tropea: Pizzo (Piazza della Repubblica & I Vicoli di Pizzo). There's still lots to do: kick back and relax at Acquamarina Beach, stroll through Spiaggia l’Occhiale, get engrossed in the history at Museo Diocesano di Tropea, and stop by Enogastronomia Lorenzo.

For more things to do, traveler tips, maps, and other tourist information, go to the Tropea trip maker website.

Traveling by combination of car and ferry from Syracuse to Tropea takes 4.5 hours. Alternatively, you can do a combination of train and ferry; or take a train. In September, daily temperatures in Tropea can reach °C, while at night they dip to °C. Wrap up your sightseeing by early afternoon on the 22nd (Tue) to allow time for travel to Lipari.

Things to do in Tropea

Outdoors Parks Beaches

Side Trips

Pizzo, Praia di Fuoco
Highlights from your plan
Tropea Beach ©
Tropea Beach
The Sanctuary of Santa Maria dell'Isola ©
The Sanctuary of Santa Maria dell'Isola
I Vicoli di Pizzo
I Vicoli di Pizzo

3
nights
Lipari

Lipari ©
Lipari is the largest of the Aeolian Islands in the Tyrrhenian Sea off the northern coast of Sicily, southern Italy; it is also the name of the island's main town and comune, which is administratively part of the Metropolitan City of Messina. Kick off your visit on the 22nd (Tue): take some stellar pictures from Belvedere Quattrocchi. Here are some ideas for day two: head outdoors with Lido Las palmas, thenkick back and relax at Coral Beach, and then get outside with Caicco Servizi Nautici.

To find more things to do, ratings, and tourist information, you can read our Lipari driving holiday planner.

You can do a combination of train and ferry from Tropea to Lipari in 6 hours. Another option is to do a combination of train, bus, and ferry. Expect somewhat warmer evenings in Lipari when traveling from Tropea in September, with lows around °C. Wrap up your sightseeing on the 25th (Fri) to allow time to travel back home.

Things to do in Lipari

Outdoors Historic Sites Wineries
Highlights from your plan
Caicco Servizi Nautici ©
Caicco Servizi Nautici
Chiesa Vecchia di Quattropani ©
Chiesa Vecchia di Quattropani
Nature & Wildlife Tours

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