Sicily

Overview

Discover Sicily: Private Tours, Experiences & Custom Travel

Italy’s historic and cultural diversity is perfectly expressed in Sicily, an island rich in history and overflowing with scenic beauty. A visit to Taormina, 200 meters above sea level and looking down onto the Ionian Sea like a terrace, will deliver a calm to the soul, a must see while visiting this island.

From the breathtaking beauty and vantage point of the Greek Roman theater, one can reflect on the power and motionless grace of Mount Etna. A Visit to the Valley of Temples is a must. Along the “Sacred Way” one can visit the Temple of Hercules, the Temple of Concord, and the Temple of Juno. Also, not to be missed is the wonderful Garden of Kolymbetra, an old water reservoir of the Greeks.

Major attractions: Taormina, Mount Etna, Siracuse, the Valley of the Temples, Noto, Piazza Armerina, Segesta, Palermo, Cefalù.

Major theaters and music venues: Teatro Massimo in Palermo, Siracusa's Greek Theater Festival, Taormina Festival.

Plan Your Experience

Explore Sicily

Sicily in pictures

Gallery

A few frames from our own trips. The rest are in the gallery below.

City of Siracusa, Historical Centre, Sicily - Photo by Jesse Andrews

Ragusa Historical Centre, Sicily

Multi-Day Holidays Tours

Whole journeys, planned end to end

Exploring the 1 Euro Houses and Surrounding Areas in Sicily September 10-18, 2022

This unique adventure through Sicily will showcase some of the highlights of this unique island as we meet with local officials and experience towns which are welcoming visitors to restore houses that can be purchased for 1 Euro. We will show you th...

Small Group

8 Days / 7 Nights

Amalfi Coast & Sicily

Embark on a memorable journey with your family through the enchanting Amalfi Coast and captivating Sicily. Discover the beautiful coastal wonders of the Amalfi Coast, from taking scenic boat trips to exploring charming villages. Dive into history at...

Private

9 Days / 8 Nights

Mediterranean Magic: Discover the Islands of Sicily and Malta

This private journey through Sicily and Malta provides an immersive experience of the rich history, culture, and landscapes of these iconic Mediterranean islands. Starting in Palermo, we cover the highlights of Sicily including Agrigento and the Vall...

Private

9 Days / 8 Nights

Harvest Time in Sicily: Experience a Sicilian Wine Journey - 7 Days of Vino, Volcanoes & Villages

Autumn is when Sicily comes alive. The grapes are in, the volcano still breathes, and the villages fill with the smell of pressed fruit and slow cooking. Over seven days you follow the island through its harvest season, from the black slopes of Mount...

Private

7 Days / 6 Nights

Sicilian Secrets & Maltese Discovery

This is a wonderful option for those who want to experience Sicily and Malta in comfort and style. This tour will take you around a number of cities in Sicily that are worth visiting, including the magnificent Malta and it's unforgettable beaches....

Small Group

8 Days / 7 Nights

Private Tour of Sicily's Unesco World Hertiage Sites, Food, Wine and Magnificent Coastal Towns

This is an exclusive tour of Sicily with an expert driver-guide, departing from Catania and including many of Sicily's World Heritage sites like Siracusa, Mt. Etna and her wineries, Taormina and the Greek Amphitheater, Noto, Palermo, Monreale, Erice...

Private

8 Days / 7 Nights

The Kingdom of the Sun - South of Italy - Puglia, Basilicata, Calabria and Sicily - Private Individuals & Small group Tours

Each year we bring people in the travel industry to experience incredible interesting places in Italy and the Mediterranean. This year one of our most thrilling adventures is going to offer a rich and rewarding learning experience through Sicily and...

Private

14 Days / 13 Nights

Kingdom of the Sun Discovery: A private Journey into Italy's Mezzogiorno

Southern Italy reveals itself slowly. In whitewashed towns above the Adriatic, in the ancient cave dwellings of Matera, in long lunches that drift into the afternoon. This private journey through Puglia and Basilicata is made for travelers who want t...

Private

9 Days / 8 Nights

Secrets of Sicily: Unesco Sites, Wineries, Food and Beaches

This is a totally private and exclusive tour of Sicily with an expert driver-guide, which departs from Catania and includes many of Sicily's World Heritage sites like Siracusa, Mt. Etna and her wineries, Taormina and the Greek Amphitheater, Noto, Pal...

Small Group

8 Days / 7 Nights

Mediterranean Marvels: A Private Journey from the Amalfi Coast, Sicily & Malta

This is an exclusive and private journey through some of southern Italy's most remarkable coastal regions and islands. Enjoy the spectacular Amalfi Coast, island of Capri, Pompeii and many of Sicily's most captivating destinations including Mt. Etna...

Private

10 Days / 9 Nights

The splendour of Malta and Gozo islands - Private Individuals & Small group Tours

This is a wonderful holiday option in Malta for those who want to experience this Mediterranean paradise. Our experience on the island includes all of the major highlights of the main island and the blue bays of Gozo. Our expert local guides will t...

Private

6 Days / 5 Nights

A Private Journey with Local Hosts through Southern Italy and Malta including the Amalfi Coast, Capri, Pompeii, Sicily and the Island Nation of Malta

Private

14 Days / 13 Nights

Private & Small Group Tours in Sicily

Days out with people who know the way

Sicily: Taormina and Mt. Etna Private Full Day Off-Shore Excursion

This marvelous tour begins with your private chauffeur who will take you to the Crateri Silvestri, a lunar landscape which will take your breathe away from which you will take incredible pictures of the volcano and the coastline. Following this tou...

Private

7 Hours

The Godfather Tour of Sicily with Wine Tastings

Enjoy an introduction to some of the most authentic areas in Sicily, and explore the towns of Savoca and Forza D'Agro with your local driver/guide who so proudly call this area home.

Small Group

4.5 Hours

Taormina Private Half Day Walking Experience

Discover the ancient city of Taormina and the majestic Greco-Roman theatre with our English speaking guide who will show you the best of this incredible Sicilian city.

Private

2.5 Hours

Highlights of Palermo & Monreale from Cruise

This is a privately guided tour, that departs out of Palermo. You tell us where to pick you up! Your cruise ship, hotel or apartment in Palermo... we will come to get you there to begin this tour of Palermo and Monreale where you will discover Paler...

Private

6 Hours

Isola Bella and the Coast of Taormina Morning Tour By Boat

This half day morning tour of Isola Bella is a wonderful opportunity for visitors to experience the magic of Toarmina from the sea. There are numerous Grottoes and beautiful coastal areas both south and north from Toarmina that you will discover tod...

Private

Taormina and the Etna Wineries

Enjoy a wonderful introduction to the highlights of Taormina with your local expert guide. From your port, we will enjoy a leisurely transfer to Taormina which will take us up the hillside. We will visit together the most panoramic square "Belvedere...

Private

7 Hours

Full day exploring Palermo and its area

This is a full day tour of Sicily's capital city - Palermo and the area around the city. It includes visiting the Monreale cathedral and exploring one of Sicily's most fantastic piazzas. Your English speaking driver guide can pick you up to enjoy th...

Small Group

8 Hours

Guided Excursion Through The Sesi Archeological Park on Pantelleria Island

This is a truly fascinating journey back through time that pre-dates the Greeks, Romans and most known civilizations as we explore I Sesi.

Private

3.5 Hours

Palermo and Monreale Full Day Private Tour

Our Privately guided tour of Palermo and Monreale is one of our favorite tours in Sicily and it is definitely one that will be well worth the money because there is so very much history in both locations that you will definitely need a guide to bring...

Private

8 Hours

Mt. Etna Full Day Tour

This is a private tour of Mt. Etna that departs from Taormina or the port at Messina and includes visiting the beautiful valley around Mt. Etna and experiencing the local wines and olive oil that Sicily is famous for. Mt Etna Volcano is one of the w...

Small Group

8 Hours

Catamaran Tour of Castellammare del Golfo & Scopello

Set sail on the "Catamarano Lionel Richie" for a luxurious and unforgettable journey along Sicily's stunning coastline. Departing from Castellammare del Golfo, this spacious 35-passenger catamaran offers shaded seating, a sunbathing solarium, freshwa...

Small Group

Erice and Segesta day trip

On this tour we visit two of the most historic an picturesque cities in Sicily: Erice and Segesta. Our first stop will be at the magnificent Temple of Segesta. It was built by the Elimian, an old population whose origins maybe are Turkish but were la...

Small Group

Sicily: Private Full Day Tour of Erice - Castellammare del Golfo and Lo Zingaro Nature Reserve

The south western cape of Sicily is one of the most beautiful geographical areas in Sicily and Erice is surely one of the most charming towns. This tour allows visitors to the area to experience the best of the area with a local English speaking guid...

Private

Mt. Etna and the Etna Wineries with Tastings and Full Lunch at Cantina Patria

If and when you decide to come to Sicily, this is an experience you do not want to miss.

Private

8 Hours

Hotels

Rooms we would happily sleep in again

Italy,Sicily

Hotel

Agriturismo Vecchia Masseria

★ ★ ★ ★

A beautifully renovated traditional farm estate set in the midst of fields and forest with swimming...

Lobby Bar +3 more

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Italy,Sicily,Siracusa

Hotel

Albergo Domus Mariae

★ ★ ★ ★

A former 14th-century aristocratic property, the elegant Domus Mariae Benessere has been recently re...

Buffet Breakfast +8 more

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Italy,Sicily,Siracusa

Hotel

AlgilÃ Ortigia Charme Hotel

★ ★ ★ ★

Set within two beautifully restored Baroque palaces in the heart of Ortigia, Algilà Ortigia Charme H...

Bar +10 more

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Italy,Sicily,Castellammare del Golfo

Hotel

Costamante Suites

★ ★ ★ ★

An intimate 4-star retreat in the historic heart of Castellammare del Golfo, Costamante Suites & SPA...

Breakfast +5 more

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Italy,Sicily,Taormina

Hotel

Grand Hotel Miramare

★ ★ ★ ★

Overlooking the Mediterranean Sea, this upscale hotel is an 11-minute walk from Palazzo Corvaia and...

Air-conditioning +9 more

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Italy,Sicily,Ragusa

Hotel

La Dimora Di Spartivento

★ ★ ★

A restored country retreat in Sicily's Val di Noto, La Dimora Di Spartivento pairs quiet Baroque-cou...

Air-conditioning +9 more

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Italy,Sicily,Trapani

Hotel

Mangia's Resort Favignana

★ ★ ★ ★

Mangiaâ€™s Favignana Resort, an exclusive retreat nestled on one of the most breathtaking stretches...

24h reception +31 more

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Italy,Sicily

Hotel

Planeta Estate La Foresteria

★ ★ ★ ★

The La Foresteria**** resort is the hallmark of the hospitality of the Planeta family (www.planeta.i...

Buffet Breakfast +6 more

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Italy,Sicily

Hotel

Relais Santa Anastasia

★ ★ ★ ★

Offering a garden with pool, Relais Santa Anastasia is set in a former abbey in the hills surroundin...

Buffet Breakfast +8 more

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Italy,Sicily,Taormina

Hotel

San Domenico Palace Hotel Taormina

★ ★ ★ ★ ★

On the east coast of Sicily lies a luxury 5-star hotel The San Domenico Palace Hotel offers its gu...

24h reception +15 more

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Italy,Sicily,Mondello

Hotel

Villa Esperia Mondello

★ ★ ★

Just steps from Mondello's golden beach near Palermo, Hotel Villa Esperia is a relaxed seaside retre...

Air-conditioning +4 more

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Villas

Private homes with stories of their own

Italy,Sicily

Villa

Villa Avvenente

4 Beds 4 Baths 8

Air Conditioning +14 more

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Italy,Sicily

Villa

Villa Calmo

3 Beds 2 Baths 6

Air Conditioning +12 more

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Italy,Sicily,Trapani

Villa

Villa del Bastione

3/4 Beds 2 Baths 6/10

Air Conditioning +15 more

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Italy,Sicily

Villa

Villa Della Pace

4 Beds 4 Baths 8+2

Air Conditioning +13 more

From €12,640 / night

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Italy,Sicily

Villa

Villa Eccezionale

7 Beds 6 Baths 17

Air Conditioning +14 more

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Italy,Sicily,Mondello

Villa

Villa Mondello

6 Beds 6 Baths 15

Balcony +10 more

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Italy,Sicily

Villa

Villa Recupero

5 Beds 5 Baths 9

Air Conditioning +14 more

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Italy,Sicily,Marsala

Villa

Villa Sole di Marsala

7 Beds 6 Baths 14

Air Conditioning +16 more

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Italy,Sicily

Villa

Villa Sontuoso

5/6 Beds 6/7 Baths 11/14

Air Conditioning +13 more

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Italy,Sicily,Palermo

Villa

Villa Sussurro delle Onde

5/6 Beds 6/7 Baths 10/13

Air Conditioning +14 more

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Photo Gallery

Cefalu, Eastern Coast of Sicily near Palermo

Aeolian Islands

Agrigento

Castellammare del Golfo

Taormina

Termini Imerese

Tindari

Trapani

Aeolian Islands

Agrigento

Castellammare del Golfo

Catania

Cefalu

Enna

Erice

Forza D'Agro

Giardini Naxos

Island of Favignana

Island of Ustica

Marsala

Messina

Modica

Mondello

Monreale

Noto

Palermo

Pantelleria Island

Piazza Armerina

Porticello

Ragusa

San Vito Lo Capo

Savoca

Scala dei Turchi

Sciacca

Scopello

Segesta

Selinunte

Siracusa

Taormina

Termini Imerese

Tindari

Trapani

Our Featured Properties

Stays we picked one by one

Italy,Sicily

Villa

Villa Recupero

5 Beds 5 Baths 9

Air Conditioning +14 more

View Details

Italy,Sicily,Marsala

Villa

Villa Sole di Marsala

7 Beds 6 Baths 14

Air Conditioning +16 more

View Details

Italy,Sicily,Mondello

Villa

Villa Mondello

6 Beds 6 Baths 15

Balcony +10 more

View Details

Italy,Sicily,Trapani

Villa

Villa del Bastione

3/4 Beds 2 Baths 6/10

Air Conditioning +15 more

View Details

Italy,Sicily

Villa

Villa Della Pace

4 Beds 4 Baths 8+2

Air Conditioning +13 more

From €12,640 / night

View Details

Italy,Sicily

Villa

Villa Sontuoso

5/6 Beds 6/7 Baths 11/14

Air Conditioning +13 more

View Details

Italy,Sicily,Palermo

Villa

Villa Sussurro delle Onde

5/6 Beds 6/7 Baths 10/13

Air Conditioning +14 more

View Details

Italy,Sicily

Villa

Villa Eccezionale

7 Beds 6 Baths 17

Air Conditioning +14 more

View Details

Italy,Sicily

Villa

Villa Calmo

3 Beds 2 Baths 6

Air Conditioning +12 more

View Details

Italy,Sicily

Villa

Villa Avvenente

4 Beds 4 Baths 8

Air Conditioning +14 more

View Details

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Popular Transfer Routes in Sicily

The rides our guests ask for most, with a driver who knows the way.

Italy Vacation Specialists provides licensed private transfer services throughout Italy, including Sicily and surrounding areas. With over 20 years of experience, our professional English-speaking drivers offer both Business Class and Luxury Class vehicles for airport transfers, city-to-city rides, and full-day chauffeur services. All vehicles are fully insured, well-maintained, and operated by vetted local drivers who know the roads, traffic patterns, and best routes across the region.

Catania Taormina

Private Transfer

Palermo Catania

Private Transfer

Catania Syracuse

Private Transfer

Palermo Agrigento

Private Transfer

Palermo Trapani

Private Transfer

Catania Piazza Armerina

Private Transfer

Palermo Cefalù

Private Transfer

Taormina Syracuse

Private Transfer

Catania Ragusa

Private Transfer

Palermo Taormina

Private Transfer

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In their words

Stories That Stay With You

Here's what our guests share about their unforgettable journeys

“My husband and I just took a two week trip to Italy that was planned for us by Eleanor Kinchin-Smith. It was a fantastic trip and we could not have been more thrilled. We worked together with Ele to let her know about our interests and our style of travel. She…”
Emily and David Davison Read their story

“Jesse & Giuseppe, Sandy and I have been looking through my slides of our trip to Southern Italy. We had such a good time with you and Giuseppe that we wanted to let you know again. You were the best guides ever”
Bob & Sandy Read their story

“As a travel agent, but also a traveler to Italy, thee is no other company I would recommend than the Italy Vacation Specialists. Not only do they really care about what they are doing, they also really know Italy and try to educate many people about ways they…”
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“In August 2018, my family of four and myself travelled from Vancouver, BC to Rome Italy and spent 3 weeks touring Italy with IVS. This company had come highly recommended by many friends and associates of ours who had used them before and indeed to say they do…”
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“In September of 2018 I brought a group of 12 from Venice to Sicily and organized all of my services with the Italy Vacation Specialists. Being a travel agent and in the business, I know how complicated organizing travel arrangements can be in Italy and the IVS…”
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“I have traveled to Italy 2x with the IVS for my own pleasure trips and 2x for business with IVS. These guys really pay attention and make your trip go like clockwork. Italy is nuts, just saying! There are so many rules and restrictions now, so we did not want…”
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