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Palermo - Agrigento - Syracuse - Taormina
9 Customer Feedbacks
9 to 13+ Nigths from $2,100*
This sample price: priced within the past 7 days for arrival on 9/24/2025, departure from Chicago CHI (All Airports)(IL), US. Choose your own departure city, cabin type and dates.
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This is a suggested independent itinerary that you customize. Please select the best flights, hotels, trains, activities, transportation and number of nights in each destination to fit your needs.
Picture it: Sicily - right now! Your perfect escape is found on this idyllic island, with a rich and unique culture, especially in regard to art, music, literature, cuisine, and architecture. Sicily has plenty to see and do and this flexible vacation package highlights Palermo (notorious for its mafia glamour, but that aside, uncover forgotten treasures in its museums and wander through its packed outdoor markets), Agrigento (home to the Valley of the Temples with the best preserved Greek ruins outside Greece), Syracuse (Siracusa) (a former stronghold of the Greek empire; full of medieval and Baroque buildings), and finally Taormina (perched on the edge of a cliff overlooking the Ionian Sea this dreamy city has drawn artists, writers, and intellectuals for decades). Admire various other points of interest with stops at the Norman Castello di Caccamo, the historical Piazza Armerina, and the haunting Necropolis of Pantalica! This is a flexible vacation package. Select your number of nights in each city, desired hotel and activities.
This 9 night sample itinerary includes:
  • Flight into Palermo and out of Catania
  • Hotel for 2 nights in Palermo
  • Transfer from Hotel in Palermo to Hotel in Agrigento via Castello di Caccamo
  • Hotel for 2 nights in Agrigento
  • Transfer from Hotel in Agrigento to Hotel in Syracuse via Piazza Armerina
  • Hotel for 2 nights in Syracuse
  • Transfer from Hotel in Syracuse to Hotel in Taormina via Necropolis of Pantalica
  • Hotel for 2 nights in Taormina
  • Transfer from Hotel in Taormina to Catania Airport
Price history for this itinerary (past 7 days):
From Boston BOS (MA), US for 10 nights
3030.24 * incl.tax
From Chicago CHI (All Airports)(IL), US for 9 nights
2099.95 * incl.tax
From Los Angeles LAX (CA), US for 11 nights
2220.77 * incl.tax
Related Itineraries:
Related Cities:
Palermo (Sicily) (12)     Catania (Sicily) (9)     Taormina (Sicily) (8)     Agrigento (Sicily) (6)     Syracuse (Sicily) (3)    
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With Int'l Flight     Without Int'l Flight
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Arrival date
Stay
1. Palermo (Sicily)
  118 hotels
2. Agrigento (Sicily)
   (47 hotels)
3. Syracuse (Sicily)
   (80 hotels)
4. Taormina (Sicily)
   (93 hotels)
Guest:
Please contact us for any special arrangements such as more than three rooms and partial stays.
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Trip Summary
2 nights in Palermo (Sicily)

Known as a bridge between the East and West, thanks to its geographic location on the northwestern shore of Sicily, this Italian city is the island's center of tourism. Travelers will discover plenty of historic and cultural attractions in Palermo - the result of a long and dramatic history of conquest. Years of transitioning between Phoenician, Arab, Byzantine, and Roman rule can be seen today in a city full of souk-like bazaars, diverse architectural styles, and a large variety of cuisine.

Discover The Cathedral, The Three Markets (Ballarò, Vucciria, Capo), Pizza at Pollicino, Mondello, Teatro Massimo, Castello Utveggio on the top of Mt. Pellegrino, Chiesa della Martorana - a Byzantine Church, Teatro Massimo (3rd largest theatre in Erope), Quattro Canti (represents the four primary districts) and Piazza Pretoria, and so much more.



2 nights in Agrigento (Sicily)

Agrigento was built in the hilly countryside just off the southern coast of Sicily, on top of the ancient Greek colong town of Akragas. It is known for impressive Greek temples. Located just outside of the city, the Valley of the Temples (Parco Archeologico Valle dei Templi) is the site of the best-preserved Doric temples outside Greece. It's been a UNESCO World Heritage site since 1997. The Greek poet Pindar once called it `the most beautiful city of those inhabited by mortals.

Visit and explore The Valley of the Temples; The Cathedral; The Old Town; Scala Dei Turchi (Stairs of the Turks); The Regional Archaeological Museum; San Lorenzo; Monastero di Santo Spirito; Agigento`s beaches and so much more.



2 nights in Syracuse (Sicily)

Syracuse (Siracusa, in Italian), is part of the UNESCO World Heritage List, and was once considered one of the most impressive cities in the Greek World, competing for supremacy with Athens and even taking on the rising powers of Rome and Carthage. Located on the southeastern coast of the Italian island of Sicily, Syracuse is the capital of the province of Syracuse and offers a myriad of ancient attractions including the Greek Theatre, the Temple of Apollo, and the Castello Maniance.

Visit and explore the great Greek Theater, Latomia del Paradiso (Quarries) and the Ear of Dionysius, Santa Maria delle Colonne (Cathedral), San Giovanni Crypt and Catacombs, Latomia dei Cappuccini (Quarries), Santa Lucia, Temple of Apollo, Roman Amphitheater and Altar of Hiero II, Foro Italico and Fonte Arethusa, Eurialo Castle, and so much more.



2 nights in Taormina (Sicily)

Taormina is perched on a series of high terraces overhung with tropical gardens overlooking a breath taking coastline and views of Mount Etna. It oozes elegance, style and glamour which has been created by a rich history full of romantic myths, legends and love stories. The town is full of beautiful flower draped villas and palazzos amongst candlelit narrow alleys with boutiques, cafes and restaurants on the pedestrianised Corso Umberto.

Visit and explore the great Piazza IX Aprile and San Giuseppe; Cattedrale di San Nicola; Via Circonvallazione, Latomia dei Cappuccini (Quarries); Isola Bella (Beautiful Island); Porta Catania and Palazzo Duca di Santo Stéfano; Palazzo Corvaia; Villa Comunale; Sant'Agostino, and so much more.



Book This Package
Flexible Itinerary
Palermo (Sicily)
Day 1
Arrive to Palermo (Sicily)
Overnight in Palermo (Sicily)   118 hotels offered
Optional   89 Things to do
Day 2
Overnight in Palermo (Sicily)   118 hotels offered
Optional   89 Things to do
Day 3
Departing from Palermo (Sicily)
Transportation to next city by: Regional Air
Agrigento (Sicily)
Day 3
Arrive to Agrigento (Sicily)
Overnight in Agrigento (Sicily)   47 hotels offered
Optional   4 Things to do
Day 4
Overnight in Agrigento (Sicily)   47 hotels offered
Optional   4 Things to do
Day 5
Departing from Agrigento (Sicily)
Transportation to next city by: Regional Air
Syracuse (Sicily)
Day 5
Arrive to Syracuse (Sicily)
Overnight in Syracuse (Sicily)   80 hotels offered
Optional   30 Things to do
Day 6
Overnight in Syracuse (Sicily)   80 hotels offered
Optional   30 Things to do
Day 7
Departing from Syracuse (Sicily)
Transportation to next city by: Regional Air
Taormina (Sicily)
Day 7
Arrive to Taormina (Sicily)
Overnight in Taormina (Sicily)   93 hotels offered
Optional   82 Things to do
Day 8
Overnight in Taormina (Sicily)   93 hotels offered
Optional   82 Things to do
Day 9
Departing from Taormina (Sicily)
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Palermo (Sicily) Hotels (118 total)
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Agrigento (Sicily) Hotels (47 total)
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Syracuse (Sicily) Hotels (80 total)
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Taormina (Sicily) Hotels (93 total)
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Tours in Palermo (Sicily) (89 total)
›
Tours in Agrigento (Sicily) (4 total)
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Tours in Syracuse (Sicily) (30 total)
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Tours in Taormina (Sicily) (82 total)
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Italy

For centuries <b>Italy</b> has drawn foreign visitors - mostly for its architectural, artistic, and scenic splendors. Italy can truly be all things to all people. From the passion and excitement of noisy urban crowds to the quiet, rural idyll where the traditional life can be experienced, Italy's great cities are replete with rich attractions and culture alongside some of the most pristine beaches and spectacular mountains in the world.
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Price Guidance

The package rates displayed are your total price per person based on Double Occupancy and your Arrival Date and Number of Nights selected. You can change details after selecting your travel date.

Price history for this itinerary (past 7 days):

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Palermo - Agrigento - Syracuse - Taormina
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Palermo (Sicily)
Known as a bridge between the East and West, thanks to its geographic location on the northwestern shore of Sicily, this Italian city is the island's center of tourism. Travelers will discover plenty of historic and cultural attractions in Palermo - the result of a long and dramatic history of conquest. Years of transitioning between Phoenician, Arab, Byzantine, and Roman rule can be seen today in a city full of souk-like bazaars, diverse architectural styles, and a large variety of cuisine.

Discover The Cathedral, The Three Markets (Ballarò, Vucciria, Capo), Pizza at Pollicino, Mondello, Teatro Massimo, Castello Utveggio on the top of Mt. Pellegrino, Chiesa della Martorana - a Byzantine Church, Teatro Massimo (3rd largest theatre in Erope), Quattro Canti (represents the four primary districts) and Piazza Pretoria, and so much more.
Agrigento (Sicily)
Agrigento was built in the hilly countryside just off the southern coast of Sicily, on top of the ancient Greek colong town of Akragas. It is known for impressive Greek temples. Located just outside of the city, the Valley of the Temples (Parco Archeologico Valle dei Templi) is the site of the best-preserved Doric temples outside Greece. It's been a UNESCO World Heritage site since 1997. The Greek poet Pindar once called it `the most beautiful city of those inhabited by mortals.

Visit and explore The Valley of the Temples; The Cathedral; The Old Town; Scala Dei Turchi (Stairs of the Turks); The Regional Archaeological Museum; San Lorenzo; Monastero di Santo Spirito; Agigento`s beaches and so much more.
Syracuse (Sicily)
Syracuse (Siracusa, in Italian), is part of the UNESCO World Heritage List, and was once considered one of the most impressive cities in the Greek World, competing for supremacy with Athens and even taking on the rising powers of Rome and Carthage. Located on the southeastern coast of the Italian island of Sicily, Syracuse is the capital of the province of Syracuse and offers a myriad of ancient attractions including the Greek Theatre, the Temple of Apollo, and the Castello Maniance.

Visit and explore the great Greek Theater, Latomia del Paradiso (Quarries) and the Ear of Dionysius, Santa Maria delle Colonne (Cathedral), San Giovanni Crypt and Catacombs, Latomia dei Cappuccini (Quarries), Santa Lucia, Temple of Apollo, Roman Amphitheater and Altar of Hiero II, Foro Italico and Fonte Arethusa, Eurialo Castle, and so much more.
Taormina (Sicily)
Taormina is perched on a series of high terraces overhung with tropical gardens overlooking a breath taking coastline and views of Mount Etna. It oozes elegance, style and glamour which has been created by a rich history full of romantic myths, legends and love stories. The town is full of beautiful flower draped villas and palazzos amongst candlelit narrow alleys with boutiques, cafes and restaurants on the pedestrianised Corso Umberto.

Visit and explore the great Piazza IX Aprile and San Giuseppe; Cattedrale di San Nicola; Via Circonvallazione, Latomia dei Cappuccini (Quarries); Isola Bella (Beautiful Island); Porta Catania and Palazzo Duca di Santo Stéfano; Palazzo Corvaia; Villa Comunale; Sant'Agostino, and so much more.

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