37 days in Sicily Itinerary

37 days in Sicily Itinerary

Created using Inspirock Italy journey planner

Make it your trip
1
Catania
— 4 nights
Drive
2
Palermo
— 5 nights
Drive
3
Cefalu
— 3 nights
Drive
4
San Vito lo Capo
— 2 nights
Drive
5
Calatafimi-Segesta
— 1 night
Drive
6
Trapani
— 4 nights
Ferry
7
Isola di Favignana
— 1 night
Ferry to Marsala, Bus to Agrigento
8
Agrigento
— 2 nights
Drive
9
Enna
— 2 nights
Drive
10
Ragusa
— 2 nights
Drive
11
Noto
— 4 nights
Drive
12
Syracuse
— 3 nights
Drive
13
Taormina
— 3 nights
Drive

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Catania

— 4 nights

Black Pearl of Ionian Sea

The landscape surrounding Catania, a medieval city on Sicily's eastern coast, is dominated by Mount Etna, the tallest active volcano in Europe.
Visiting Trigone Diving School and Borgo di Santa Maria la Scala will get you outdoors. Step off the beaten path and head to Benanti Winery and Basilica Collegiata. Take a break from Catania with a short trip to Etna Discovery in Trecastagni, about 32 minutes away. Next up on the itinerary: take in the architecture and atmosphere at Chiesa di San Giuliano, don't miss a visit to Chiesa della Badia di Sant'Agata, contemplate in the serene atmosphere at Saint Biagio Church - Sant'Agata alla Fornace, and pause for some photo ops at Fontana dell'Elefante.

To see maps, where to stay, reviews, and more tourist information, use the Catania online travel planner.

If you are flying in from United States, the closest major aiports are Catania-Fontanarossa Airport and Comiso Airport. Wrap up your sightseeing on the 30th (Thu) early enough to drive to Palermo.

Things to do in Catania

Outdoors · Tours · Historic Sites · Wineries

Side Trips

Find places to stay Sep 26 — 30:

Palermo

— 5 nights
The capital of Sicily, Palermo was founded by the Phoenicians under the name of Ziz.
Escape the urban bustle at Off-Road Tours and Riserva Naturale Orientata Di Capo Gallo. Step off the beaten path and head to La Bottega nella Roccia and Sicilia Sub Diving Center. You'll find plenty of places to visit near Palermo: Terrasini (Riserva Naturale Orientata - Capo Rama & Museo del Carretto Siciliano), Riserva naturale orientata Bosco della Ficuzza, Rocca Busambra, Bosco del Cappelliere e Gorgo del Drago (in Corleone) and Lido Fondachello (in Santa Flavia). Spend the 1st (Fri) wandering through the wild on a nature and wildlife tour. And it doesn't end there: contemplate the long history of La Magione, admire the landmark architecture of Villa Bonanno, take in the architecture and atmosphere at Santissimo Salvatore, Palermo, and get engrossed in the history at Museo Archeologico Regionale "Antonino Salinas".

For other places to visit, photos, more things to do, and other tourist information, go to the Palermo journey planning website.

Drive from Catania to Palermo in 2.5 hours. Alternatively, you can take a bus; or take a train. Finish your sightseeing early on the 5th (Tue) so you can drive to Cefalu.

Things to do in Palermo

Outdoors · Wildlife · Tours · Parks

Side Trips

Find places to stay Sep 30 — Oct 5:

Cefalu

— 3 nights
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. Take a break from the city and head to Visit Sicily Tours and Spiaggia Torre Conca. You'll discover tucked-away gems like Chiesa del Purgatorio and Chiostro della Cattedrale di Cefalu. Change things up with these side-trips from Cefalu: Castelbuono (Cappella Palatina - Cappella di Sant'Anna & Putia Sicilian Creativity). There's lots more to do: take in the pleasant sights at Lungomare Cristoforo Colombo, don't miss a visit to Corso Ruggero, visit Villaggio di Sant Ambrogio, and admire the striking features of Palazzo Vescovile.

To find ratings, maps, traveler tips, and more tourist information, read our Cefalu route builder.

Traveling by car from Palermo to Cefalu takes an hour. Alternatively, you can take a train; or take a bus. Wrap up your sightseeing on the 8th (Fri) early enough to drive to San Vito lo Capo.

Things to do in Cefalu

Outdoors · Parks · Beaches · Wildlife

Side Trips

Find places to stay Oct 5 — 8:

San Vito lo Capo

— 2 nights
A vacation in San Vito lo Capo offers a chance to enjoy a sheltered bay and a town with distinctive Arab-Norman architecture.
Start off your visit on the 8th (Fri): kick back and relax at Cala Tonnarella dell'Uzzo and then tour the pleasant surroundings at Il sentiero di Monte Monaco. Get ready for a full day of sightseeing on the next day: tour the pleasant surroundings at Spiaggia Zero Barriere and then tour the pleasant surroundings at Riserva Naturale Orientata Monte Cofano.

To find more things to do, reviews, and more tourist information, go to the San Vito lo Capo attractions planner.

You can drive from Cefalu to San Vito lo Capo in 2.5 hours. Alternatively, you can do a combination of train and car; or take a bus. In October, plan for daily highs up to 75°F, and evening lows to 64°F. Finish your sightseeing early on the 10th (Sun) to allow enough time to drive to Calatafimi-Segesta.

Things to do in San Vito lo Capo

Parks · Outdoors · Beaches · Wildlife

Side Trip

Find places to stay Oct 8 — 10:

Calatafimi-Segesta

— 1 night
Calatafimi-Segesta is a small town, more popularly known simply as Calatafimi, in the Province of Trapani, in Sicily, southern Italy.The full name of the municipality was created in 1997 and is meant to highlight the presence within its territory of the 5th century B.C. Doric temple of Segesta, widely regarded as one of the most intact of its type. Kick off your visit on the 10th (Sun): relax and rejuvenate at Terme Gorga, delve into the distant past at Parco Archeologico, and then examine the collection at Ossario di Pianto Romano.

To find ratings, more things to do, and other tourist information, you can read our Calatafimi-Segesta road trip site.

Traveling by car from San Vito lo Capo to Calatafimi-Segesta takes 1.5 hours. Alternatively, you can do a combination of bus and taxi. In October in Calatafimi-Segesta, expect temperatures between 77°F during the day and 61°F at night. Wrap up your sightseeing by early afternoon on the 11th (Mon) to allow enough time to drive to Trapani.

Things to do in Calatafimi-Segesta

Historic Sites · Museums · Spas

Side Trip

Find places to stay Oct 10 — 11:

Trapani

— 4 nights

City of Two Seas

Historically known for its importance in salt production, Trapani has gained recognition as an enticing but affordable vacation locale in Sicily.
Discover out-of-the-way places like Giardini del Balio and Enoteca Lo Sbarco. Explore Trapani's surroundings by going to Marsala (Porta Garibaldi, CANTINA MARTINEZ dal 1866, &more). There's still lots to do: take in the spiritual surroundings of Cattedrale di San Lorenzo, don't miss a visit to Bastione Conca Trapani, slough off your stress at Salus - Private Spa & Beauty Salon, and take in the architecture and atmosphere at Chiesa Colleggio e Convento dei Gesuiti.

Inspirock's itinerary builder makes planning a Trapani trip simple and quick.

Getting from Calatafimi-Segesta to Trapani by car takes about an hour. Other options: take a bus. In October, plan for daily highs up to 77°F, and evening lows to 61°F. Finish your sightseeing early on the 15th (Fri) so you can ride a ferry to Isola di Favignana.

Things to do in Trapani

Wineries · Historic Sites · Baths · Parks

Side Trips

Find places to stay Oct 11 — 15:

Isola di Favignana

— 1 night
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.
Kick off your visit on the 15th (Fri): tour the water at your own pace with Giri in Barca con Andrea Catalano, look for gifts at L'Arte del Creare, and then make a trip to Villa Margherita Giardini Ipogei.

To see photos, more things to do, where to stay, and more tourist information, use the Isola di Favignana online day trip planner.

Ride a ferry from Trapani to Isola di Favignana in 1.5 hours. In October, daytime highs in Isola di Favignana are 77°F, while nighttime lows are 61°F. Wrap up your sightseeing on the 16th (Sat) early enough to travel to Agrigento.

Things to do in Isola di Favignana

Shopping · Outdoors · Tours · Transportation
Find places to stay Oct 14 — 16:

Agrigento

— 2 nights

Valley of the Temples

Historically one of ancient Greece's leading cities, Sicily's Agrigento is home to the seven monumental temples that make up the well-preserved Valley of the Temples.
On the 16th (Sat), stop by Panificio Dalli Cardillo, then soak in style at Grotta delle Muse - Centro Benessere & Spa, and then take an in-depth tour of Collezione La Gaipa. On your second day here, explore the world behind art at Mudia_Museo Diocesan Agrigento, then contemplate in the serene atmosphere at Santuario di San Calogero, then take in the spiritual surroundings of Chiesa San Nicola, and finally see the interesting displays at Fabbriche Chiaramontane.

To find reviews, maps, other places to visit, and tourist information, read our Agrigento trip app.

Traveling by combination of ferry and bus from Isola di Favignana to Agrigento takes 5 hours. Alternatively, you can do a combination of ferry and bus. Traveling from Isola di Favignana in October, Agrigento is somewhat warmer at night with lows of 67°F. Finish up your sightseeing early on the 18th (Mon) so you can go by car to Enna.

Things to do in Agrigento

Museums · Baths · Spas · Historic Sites
Find places to stay Oct 16 — 18:

Enna

— 2 nights
Enna is a city and comune located roughly at the center of Sicily, southern Italy, in the province of Enna, towering above the surrounding countryside. Start off your visit on the 18th (Mon): ponder the design of Fontana del Ratto di Proserpina, take some stellar pictures from Belvedere, then contemplate the long history of Chiesa di Santa Chiara, then get outside with Lago Pergusa, and finally relax and rejuvenate at Energika Centro fitness & chinesiologia. Keep things going the next day: appreciate the views at Rocca di Cerere, contemplate the waterfront views at Lago Nicoletti, then take in the architecture and atmosphere at Santuario del SS. Crocifisso di Papardura, and finally enjoy breathtaking views from Torre di Federico II.

For photos, where to stay, other places to visit, and other tourist information, use the Enna trip itinerary maker website.

Traveling by car from Agrigento to Enna takes 1.5 hours. Wrap up your sightseeing on the 20th (Wed) to allow time to drive to Ragusa.

Things to do in Enna

Nature · Parks · Historic Sites · Outdoors

Side Trip

Find places to stay Oct 18 — 20:

Ragusa

— 2 nights

Town of Bridges

Once a flourishing ancient city, Ragusa was rebuilt after a devastating earthquake in 1693.
On the 20th (Wed), contemplate in the serene atmosphere at Chiesa di Santa Maria delle Scale, admire the landmark architecture of Circolo di Conversazione, don't miss a visit to Palazzo Arezzo Di Trifiletti, then don't miss a visit to Teatro Donnafugata, then take in the architecture and atmosphere at Chiesa di San Nicolo Inferiore, and finally surround yourself with nature on Zuleima. Get ready for a full day of sightseeing on the 21st (Thu): examine the collection at Vescovado, then see the interesting displays at Museo dei Presepi Tradizionali, then stop by Maioliche Artistiche Giorgio & Ivano Alemanna, and finally contemplate in the serene atmosphere at Cattedrale di San Giuliano.

To find photos, more things to do, maps, and tourist information, read Ragusa itinerary planner.

You can drive from Enna to Ragusa in 2 hours. Expect a daytime high around 77°F in October, and nighttime lows around 59°F. Finish up your sightseeing early on the 22nd (Fri) so you can go by car to Noto.

Things to do in Ragusa

Historic Sites · Museums · Shopping · Outdoors

Side Trips

Find places to stay Oct 20 — 22:

Noto

— 4 nights
Noto is a city and comune in the Province of Syracuse, Sicily, Italy. Visiting Spiaggia di Santa Maria del Focallo and Abbronzatissima Beach Club will get you outdoors. Eschew the tourist crowds and head to Spiaggia di Gallina and Chiesa San Domenico. Change things up with these side-trips from Noto: Basilica di San Sebastiano (in Palazzolo Acreide), Adelfio - Marzamemi (in Marzamemi) and Parrocchia Ss Annunziata (in Ispica). The adventure continues: explore the historical opulence of Palazzo Castelluccio, take in the architecture and atmosphere at Chiesa di San Carlo Borromeo, get to know the fascinating history of Via Corrado Nicolaci, and take in the spiritual surroundings of Convento San Francesco d'Assisi all'Immacolata.

For maps, more things to do, and more tourist information, use the Noto trip maker site.

Traveling by car from Ragusa to Noto takes 1.5 hours. Alternatively, you can take a train; or take a bus. Wrap up your sightseeing on the 26th (Tue) early enough to drive to Syracuse.

Things to do in Noto

Outdoors · Historic Sites · Parks · Beaches

Side Trips

Find places to stay Oct 22 — 26:

Syracuse

— 3 nights

Pearl of the Mediterranean

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.
Discover out-of-the-way places like Azienda Agricola Pupillo and Ceramiche Artigianali Dolu. And it doesn't end there: surround yourself with nature on Ortigia Island Excursion, indulge your thirst for a good beer at Civico Maltato - Beer Shop, see the interesting displays at Museo dei Pupi - Siracusa, and hunt for treasures at Il Mercato di Ortigia.

To see maps, more things to do, reviews, and tourist information, refer to the Syracuse journey planning website.

You can drive from Noto to Syracuse in an hour. Other options are to take a train; or take a bus. You will leave for Taormina on the 29th (Fri).

Things to do in Syracuse

Historic Sites · Museums · Shopping · Wineries
Find places to stay Oct 26 — 29:

Taormina

— 3 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.
Step out of the city life by going to Antonio - Escursioni in Barca and Lido la Pigna. You'll explore the less-touristy side of things at Wine Tours & Tastings and Castillo de Castelmola. When in Taormina, make a side trip to see Azienda Vinicola Barone di Villagrande in Milo, approximately Milo away. And it doesn't end there: admire the local landmark of Quattro Fontane di Taormina, admire the striking features of Porta Catania di Taormina, make a trip to Via Teatro Greco, and take in the architecture and atmosphere at Duomo di Taormina.

To see where to stay, more things to do, ratings, and tourist information, use the Taormina attractions planner.

Traveling by car from Syracuse to Taormina takes 1.5 hours. Alternatively, you can take a train; or take a bus. In October, daytime highs in Taormina are 76°F, while nighttime lows are 64°F. Finish your sightseeing early on the 1st (Mon) to allow enough time to drive back home.

Things to do in Taormina

Wineries · Tours · Historic Sites · Outdoors

Side Trips

Find places to stay Oct 29 — Nov 1:

Sicily travel guide

4.5
The largest island in the Mediterranean Sea, Sicily is a ruggedly attractive land. The island has a long history of foreign domination and has been controlled by the Greeks, Romans, Arabs, and Normans. The result is a distinct culture blending elements from all of those areas and featuring an intriguing dialect. This is a huge island with plenty of small villages to tour, each with its own treasures. Beyond the popular coastal areas, Sicily's inland attractions include an unspoiled landscape of mountains, hills, and villages that sometimes seem frozen in time. While the natural environment is its biggest draw, Sicily's greatest asset may be its people. They are proud of their traditions and incredibly hospitable to visitors.

Province of Messina travel guide

4
Ruins · Landmarks · Islands
Messina is the capital of the Italian Metropolitan City of Messina. It is the third-largest city on the island of Sicily, and the 13th-largest city in Italy, with a population of more than 238,000 inhabitants in the city proper and about 650,000 in the Metropolitan City. It is located near the northeast corner of Sicily, at the Strait of Messina, opposite Villa San Giovanni on the mainland, and has close ties with Reggio Calabria. According to Eurostat the FUA of the metropolitan area of Messina has, in 2014, 277,584 inhabitants.The city's main resources are its seaports (commercial and military shipyards), cruise tourism, commerce, and agriculture (wine production and cultivating lemons, oranges, mandarin oranges, and olives). The city has been a Roman Catholic Archdiocese and Archimandrite seat since 1548 and is home to a locally important international fair. The city has the University of Messina, founded in 1548 by Ignatius of Loyola.Messina has a light rail system, Tranvia di Messina, that was opened on 3 April 2003. This line is and links the city's central railway station with the city centre and harbour.

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