21 Day Sicily Adventure

21 Day Sicily Adventure

Sicily is an incredibly beautiful and historically rich region of Italy that offers a unique blend of ancient architecture, stunning coastlines, a vibrant culinary scene, and warm hospitality. Sicily is the largest island in the Mediterranean and has a rich and diverse history that dates back over 2,500 years. The island was once home to Greek colonies, Roman ruins, and Arab and Norman influences. Explore Greek temples and Byzantine cathedrals, enjoy lunch at an olive mill, learn the ancient methods of sea salt production, rediscover the pleasures of marsala, and feast on Sicily’s multicultural cuisine.

In recent years, Sicily has also emerged as a popular wine tourism destination, thanks to its diverse wine culture and tradition. Sicily boasts over 70,000 hectares of vineyards and a long history of winemaking, dating back to the ancient Greeks. The island produces a wide variety of wines, from crisp white wines to full-bodied reds, thanks to its diverse climate and terroir. Paired with its delicious cuisine, renowned for unique flavors and local ingredients, from fresh seafood to flavorful pasta dishes, Sicily offers a distinctive wine tourism experience.

Why Into The Vineyard

Commitment to Service

We believe life is most enriched when time is spent meaningfully, and the people around us are well cared for. We offer tailored travel that is effortless and designed to inspire discovery, foster connections, and build community.

Private & Customizable Journeys

Travel preferences are as unique as an individual’s fingerprint. Our expertise lies in designing bespoke journeys to the wine regions of the world. Using our global networks, we craft your trip to suit your own style.

Regional Expertise

Discover the world alongside passionate locals who bring each destination to life. Garner authentic insights and connection. Our Sales and Planning teams have explored at length the destinations they specialize in. We continuously revisit regions, inspect accommodations, and experience wineries, so we can deliver the quality and service you expect.

Extraordinary Experiences

We design immersive experiences with excellence. Whatever your request - a private Mendoza vineyard lunch, truffle hunting in Piedmont, or a First Growth in Bordeaux - you will enjoy exclusive access to unparalleled encounters.

Trusted Support

Plan and travel at ease with the support of expert travel professionals. Headquartered in Canada and with staff around the world, we ensure you are supported from initial planning discussions to full on-trip coverage.

Responsible Travel

Our aim is to provide travel that inspires both the traveler and the communities we visit. We prioritize privately-operated accommodations, locally-owned restaurants and generational wineries, and encourage low-carbon private transportation where viable.
Day Description Accommodation
Day 1 Arrival into Sicily Villa Igiea Palermo
Day 2 Introduction to Palermo and Monreale Villa Igiea Palermo
Day 3 Palermo Coast by E-Bike Villa Igiea Palermo
Day 4 Cefalù and Castelbuono Exploration Villa Igiea Palermo
Day 5 Palermo to Marsala via Segesta & Erice Baglio Oneto
Day 6 Marsala Wine Taster Baglio Oneto
Day 7 Salt Pans Experience Baglio Oneto
Day 8 Marsala to Agrigento Region via Selinunte ADLER Spa Resort Sicilia
Day 9 Spa Day at ADLER ADLER Spa Resort Sicilia
Day 10 Valley of the Temples with Picnic at Diodoros Garden ADLER Spa Resort Sicilia
Day 11 Village Experience in the Sican Mountains ADLER Spa Resort Sicilia
Day 12 Bike Adventure in Caltabellotta ADLER Spa Resort Sicilia
Day 13 Agrigento to Siracusa Via Piazza Armerina Grand Hotel Des Ètrangers
Day 14 Uncovering Baroque Wonders Grand Hotel Des Ètrangers
Day 15 Noto Visit and Granita Tasting Grand Hotel Des Ètrangers
Day 16 Siracusa in Depth Grand Hotel Des Ètrangers
Day 17 Syracuse to Taormina via Catania Exploration Hotel Villa Carlotta Taormina
Day 18 Taormina Discovery Hotel Villa Carlotta Taormina
Day 19 Mt. Etna Volcano and Winery Experience Hotel Villa Carlotta Taormina
Day 20 Sicilian Cooking Experience Hotel Villa Carlotta Taormina
Day 21 Departure

Day 1: Arrival into Sicily

Arrival into Sicily
Daily Summary

Welcome to Sicily! On arrival in Palermo, you will be met by our representative and transferred to your accommodation to check in.

Rest of Day at Leisure

Enjoy the remainder of your day at leisure. Relax and unwind at your accommodation or set out for your own discovery of the area.

Day 2: Introduction to Palermo and Monreale

Daily Summary

Introduction to Palermo and Monreale

After breakfast this morning, meet your private guide and set out together to discover the beauty of the Sicilian capital in all its prosperity. Palermo boasts historical and cultural wealth of inestimable value.

You'll begin in downtown Palermo as you wander the Baroque boulevards, stores and markets, the Arab-Norman quarter, the Duomo and the city's Quattro Canti. It was in these very places that some of the most important pages of Italian history were written. Today young artists, musicians and entertainers continue to enliven the city's cultural fibre.

Continue on towards the lively Capo market, one of the oldest in Europe, with a varied cultural history, melding both Romanesque, Norman, and Saracen historical influences. A tribute to Sicily's Arabian past, this narrow, tent lined street, resembles those one might find in North Africa or the Middle East. Walking through this market one is hit with the intoxicating, and exotic aromas of everything from citrus fruits to fresh fish. Here you will be able to try Palermo's famous Street Food, from Mediterranean olives and local cheeses to a traditional Palermitan sandwich with panelle and chickpea fritters.

This afternoon depart the city and enjoy a visit to one of the island's greatest attractions: the Cathedral of Monreale. A UNESCO World Heritage Site since 2014, you cannot help but be enraptured by this stunning architectural works. With Norman and Arab stylistic influences, the Cathedral and its cloister are the perfect conclusion to your day.

Day 3: Palermo Coast by E-Bike

Daily Summary

Palermo Coast by E-Bike

Meet your driver at your hotel and transfer to a central location on the coast. After meeting your guide and adjusting your bikes, begin cycling to discover the natural side of the city. You'll head along the coast to unveil a series of picturesque and evocative landscapes that Palermo has to offer, before delving deep into the Favorita Park where you’ll be immersed in the Mediterranean flora, with its wonderful scents and colors. You will discover the historical, artistic and geological beauties of Palermo, crossing its enchanting coasts on this tour, which puts a spotlight on the Sea and its influence on Palermo History..

Along the coastal route you will pass through the Borgo dell’Arenella (the village of Arenella) – originally born as a fishing village, before it was developed in the nineteenth century around the Tonnara Florio (Florio tuna fishery) with its beautiful Torre dei Quattro Pizzi (Tower of the Four Points). Today it is home to two marinas: Arenella and Aquasanta.

The tour will continue towards Mondello – a quaint seaside village with a charming beach and beautiful Art Nouveau villas. You will keep pedaling through the Royal Favorita Park – a park stretching across 400 hectares and first created in 1799 by Ferdinand III of Bourbon as a private hunting reserve. You'll also stop to see the Chinese Palace, which was once the royal home for the Bourbons.

Enjoy the scenic cycle back to Palermo city center where you'll be transferred back to your hotel as your ride concludes.

Day 4: Cefalù and Castelbuono Exploration

Daily Summary

Cefalù and Castelbuono Exploration

Set out with your local private guide today to explore two of the most distinctive and visited villages on the northern Sicilian coast: Cefalù, famous for its wonderful conformation and scenic views, and Castelbuono, nestled in the Nebrodi Park in a fairy-tale atmosphere. Today is about taking your time to savor every second of calm and beauty!

Begin your day in Cefalù, a small village that stands at the foot of a promontory and overlooks the sea, with vintage vibes and the most authentic Sicilian culture. Cefalù is one of the most beautiful villages in Italy and represents one of the most fashionable seaside hamlets. The Cathedral, like that of Monreale, is a UNESCO World Heritage Site. Its fine mosaics (1148 AD), featuring an image of Christ Pantocrator in the apse, are often celebrated as the purest Byzantine works of art on Sicilian soil. The location, between the mountain and the sea, creates an extraordinary diverse combination - hiking, relaxation, food, and art.

Your guide will be able to suggest a local restaurant serving traditional dishes for lunch today (to be paid directly).

Continue on this afternoon towards Castelbuono. This small medieval village in the Park of Madonie has a delightfully preserved old town that will captivate you from the very first moment! The town centres around the castle of Ventimiglia, near a Byzantine hamlet called Ypsigro. Walking through its narrow streets is like entering another century.

Return to your accommodation as your time in Castelbuono comes to an end.

Day 5: Palermo to Marsala via Segesta & Erice

Daily Summary
  • Tour: Palermo to Marsala via Segesta & Erice
  • Accommodation: Baglio Oneto
  • Meals: B

Palermo to Marsala via Segesta & Erice

Check out this morning and meet your driver guide who will be waiting to transfer you towards the Marsala Region. Along the way you will have the opportunity to visit Segesta, a combination of Greek architecture, history and nature as well as Erice, a medieval town steeped in mythology and great food!

On arrival, enjoy a guided tour of the Segesta Archaeological Park, an ancient Greek archaeological site famous for its well-preserved Doric temple and amphitheater, which dates back to the 5th century BC. The centerpiece of the park is the Segesta Temple, an impressive structure that was never completed. The temple's columns, frieze, and pediment still stand today, and it is considered one of the finest examples of Greek architecture in Sicily. The park also features a well-preserved amphitheater, which could seat up to 3,000 people and was built in the 3rd century BC. There is a special charm to these places, and only by walking through them can one fully understand it.

You'll then have the opportunity to explore the medieval mountaintop town of Erice, which overlooks the city of Trapani. The town is renowned for its well-preserved historic center, breathtaking views of the surrounding countryside, and traditional Sicilian atmosphere. Erice's narrow, winding streets are lined with beautiful stone houses and adorned with flowers and vines. But that's not all: according to Greek mythology, Erice is the birthplace of Venus. From Greek to Catholic tradition, Erice was known as "the city of a hundred churches". The town's many churches, such as the Chiesa Matrice and the Chiesa di San Giovanni Battista, boast intricate facades and stunning baroque interiors representing important artistic and religious value.

Erice is also known for its delicious pastries and sweets, such as the famous "genovesi," a traditional Sicilian pastry made with ricotta cheese and pastry cream. Enjoy some samples of these treats at Maria Grammatico's bakery, our favorite bakery in town.

Continue on towards Marsala after your visit to check in to your accommodation.

Day 6: Marsala Wine Taster

Marsala Wine Taster
Daily Summary
  • Tour: Marsala Wine Taster
  • Activity: Afternoon at Leisure
  • Accommodation: Baglio Oneto
  • Meals: B, L

Marsala Wine Taster

After breakfast, meet your local driver and set out to discover the fortified wine named after the city of Marsala.

The Marsala region, a place of warm, mineral-rich soil and sea-kissed breezes has been producing this iconic wine for nearly two centuries. Marsala wine is made from a blend of local white grape varieties, such as Grillo, Inzolia, and Catarratto. After the grapes are harvested and crushed, the juice is fermented and fortified with brandy before being aged in oak casks for at least one year, but some can be aged for up to 30 years! There are several different styles of Marsala wine, ranging from dry to sweet, and they are classified according to their color, age, and sweetness level.

You will be welcomed to a producer such as the historic Florio Winery, built in tufo stone by Vincenzo Florio in 1832. A member of the estate will lead you on a tour of the cellars. Following your visit, sit down to a 4 course lunch paired with 4 Marsala wines. The wine has gained international fame as a key ingredient in many traditional Italian dishes, such as veal Marsala and chicken Marsala.

Afternoon at Leisure

Enjoy the remainder of the afternoon at your leisure, relaxing at your accommodation or perhaps heading into Marsala town for your own self-exploration.

Day 7: Salt Pans Experience

Salt Pans Experience
Daily Summary
  • Tour: Salt Pans Experience
  • Activity: Afternoon at Leisure
  • Accommodation: Baglio Oneto
  • Meals: B

Salt Pans Experience

Not all salt is the same; the taste varies and so does its use. Today after meeting your guide, you will be transferred to Ettore Infersa Salt Pans to embark on your private cruise. Crossing The Lagoon of Stagnone you will reach the breathtaking landscapes of the Isola Grande Nature Reserve with its colorful lagoons. The island is characterized by lagoons and marshes with shallow water ranging from 2 to 6 feet in depth. It is the ideal setting for those who want to immerse themselves in the magic world of salt!

The allure of the salt pans has increased thanks to the unusual beauty of these salt reserves. The method is fairly simple and consists of channelling sea water into small ponds using pumps powered by wind mills,. The water is then allowed to evaporate under the sun, leaving the salt which is then left to dry in piles which are covered in terracotta tiles.

Enjoy a tasting experience that will introduce you to the various types of salt, hand-harvested from salt pans. You will be taken aback by the different flavors and their unique characteristics. Under the expert guidance of a Salt Sommelier or "Selmelier", you will discover the many types of salt during a food-paired tasting including assorted bread, olive oil, tomatoes, cheeses, and seasonal fruit.

Return by boat the the mainland and return to your accommodation.

Afternoon at Leisure

Enjoy the remainder of the afternoon at your leisure, relaxing at your accommodation.

Day 8: Marsala to Agrigento Region via Selinunte

Daily Summary

Marsala to Agrigento Region via Selinunte

After check-out this morning, your private driver will transfer you to the Agrigento area. Along the way, enjoy a stop in Selinunte for a tour of these picturesque ruins.

Myth, legend, history, culture: the Archaeological Park of Selinunte is all this and more. It is simply immense, in fact, it is the largest archaeological park in Europe. A treasure chest thousands of years old and yet still so alive, so immanent. 270 hectares that tells the story of one of the most flourishing classical civilizations in the Mediterranean. A history already so rich and yet still to be discovered, and one that attracts not only tourists and the curious, but researchers and scholars from all over the world.

Some of its temples are in a good state of preservation, and they remain the last bastion of a very ancient city destroyed during the Punic Wars, which has never been rebuilt since. With your guide, enjoy an in depth guided tour of the park.

Afterwards, continue on towards your accommodation in Agrigento to check-in and enjoy the remainder of the day at leisure.

Day 9: Spa Day at ADLER

Daily Summary

Spa Day at ADLER

Enjoy a day at leisure to simply relax and make use of the facilities at your accommodation. We can assist with making a reservation for a spa treatment for a rejuvenating experience.

ADLER Spa Resort SICILIA, in addition to a fascinating world of pools and saunas, offers a very special Spa. In a privileged position, surrounded by greenery and with a wonderful view of the pine forest and the sea, lie the 13 spa cabins, a panoramic area dedicated to relaxation and the spectacular thalasso whirlpool on the hypogean roof of the spa area.

Day 10: Valley of the Temples with Picnic at Diodoros Garden

Daily Summary

Valley of the Temples with Picnic at Diodoros Garden

Set out with your local driver guide today towards Agrigento to visit one of the most beautiful UNESCO sites not only in Sicily but in the world!

Prepare yourself to be amazed by some of the most well-preserved Greek temples in the world. Nowhere else will you find ancient ruins so faithful to the originals, nestled within the famous Valley of the Temples.
The Archaeological Park of Agrigento was included in the UNESCO World Heritage Site list in 1997, and presents within it an inestimable amount of treasures, the apex of which is represented by the three main temples overlooking the Via Sacra: Temple of Juno, Temple of Concordia, Temple of Hercules. Anyone passing through there, seeing the magnificence of the temples that have been rising from the heights for 2,500 years, cannot help but experience a sense of wonder that transcends history, the ages and the immense legacy of ancient cultures made immortal by time.

After your time at the Valley of the Temples, you will have the chance to enjoy an exclusive picnic inside the park at the Diodoros Garden. Typical, zero-mile, organic food will be served for you following delicious "grandmother's recipes". The location for your picnic, a citrus grove nestled in the sovereign nature of the Valley of the Temples, dates back to 1740, and it is mentioned in ancient maps that the Cistercian Monks wanted to plant the most colorful and productive trees on the island here!

After a post-lunch stretch of the legs to see any remaining sites of interest, return to your accommodation and enjoy the remainder of your day at leisure.

Day 11: Village Experience in the Sican Mountains

Daily Summary

Village Experience in the Sican Mountains

After breakfast, meet your guide at your hotel and head to one of the most typical village of the Agrigento Province, in the ancient heart of Sicily.

Today you will visit a gem nestled inthe Sican Mountains, rich in both charm and history, with a splendid view over a large part of southern Sicily. Here everything moves slowly and along the road you will see panoramic views of valleys, hills, peaks, mountains one after another. The river itself flows slowly, as do the flocks of sheep, and the people walking the streets or playing cards at the bar.

Allow yourself to enjoy the unique way of life of this little village. Over the course of several hours you will go on a relaxing walk through village streets, with tastings of typical local specialties and genuine encounters with authentic people. Make a stop to taste local cheeses, along with the local specialty of "pani cunzatu", a local bread made entirely from local ingredients. You will also taste local almond cookies and honey, local wines, olive oil, and other seasonal artesenal products from the region.

Stop for lunch at the home of a local family, with dishes and products prepared traditionally.

Throughout the day you will be shown a lesser known Sicily, directly through it's people. this is a truly authentic experience far from the well worn tourist destinations.

Day 12: Bike Adventure in Caltabellotta

Daily Summary

Bike Adventure in Caltabellotta

Taking a bike tour is in itself one of the moments that best connects body and soul. Doing it in the Agrigento countryside is even more so! The extraordinary landscapes this area offers is completely unique in the Sicilian landscape: green and fertile areas, endless countryside, history, wildlife and practically pure air!

Setting out with your private bike guide and personal E-bikes, immerse yourself in an atmosphere of peace, nature and physical activity in the Caltabellotta region. The region is characterized by its rugged terrain, dotted with vineyards, olive groves, and citrus orchards. The town of the same name sits on a hilltop overlooking the surrounding countryside and is steeped in history and culture, with numerous ancient ruins and historic landmarks that date back to the Greek and Roman eras. One of the most notable landmarks in Caltabellotta is the Castello di Caltabellotta, a medieval castle that sits atop the hill overlooking the town.

During the day stop for a traditional lunch at one of the towns you pass through.

Day 13: Agrigento to Siracusa Via Piazza Armerina

Agrigento to Siracusa Via Piazza Armerina
Daily Summary

After breakfast at the estate, check out of your accommodation and meet your private driver for a day of exploration on your way to Siracusa.

You will be transferred to Piazza Armerina to visit the mosaics of the Roman Villa del Casale, named after an agricultural settlement known as “Casale”, or farmhouse, that flourished there in the 15th century. With your experienced local guide, you will visit this beautiful Roman Villa that consists of 3,500 square meters of mosaic pavement, still perfectly intact. It may have also been a hunting lodge and a location to entertain important guests. The mosaics include a 60-meter-long hunting scene, in which groups of men struggle and sweat as they capture ferocious animals in India and North Africa before transporting them to Rome for gladiator games.

After the visit, enjoy a coffee or lunch at leisure nearby. You'll then be transferred to your next accommodation to enjoy the remainder of your day settling in to your new surrounds.

Day 14: Uncovering Baroque Wonders

Daily Summary

Uncovering Baroque Wonders

After breakfast, meet your private driver for a day of exploration of the Val di Noto, famous for its late Baroque towns, whose historic centers have been included in the UNESCO World Heritage List. The influence of the late Baroque in these towns is such that there is no other place in the world with the same characteristics. Rebuilt in 1693 following a violent earthquake, they thus present a very regular layout and urban innovations, embellished with the decorations typical of this artistic movement. Visit Ragusa and then Modica for a unique look at the qualities that define Baroque style: structural strength, compositional majesty, all executed in a theatrically dramatic style.

Ragusa is also known as the "city of bridges" for the presence of three very picturesque and historically valuable structures. In 1693, a devastating earthquake caused the almost total destruction of the entire city, claiming more than five thousand victims. The architectural masterpieces built after the earthquake, along with all those in the Val di Noto, were declared a UNESCO World Heritage Site in 2002. Ragusa is one of the most important places for the presence of Baroque art treasures, such as its churches and 18th-century palaces, and makes for a visual treat of a first stop for the day.

Modica represents, in addition to its distinctly baroque component, an extraordinary phenomenon of geographical anthropization: many dwellings in the old part of the city, leaning on each other, are often the extension of ancient caves populated since prehistoric times. Modica is also well-known for its chocolate-based sweets, whose routes can be traced back to Aztec traditions brought to Sicily via the Spaniards. Enjoy a visit to one of the oldest confectionary shops in Sicily for a sweet taste of history.

You'll be delivered back to your hotel after the tour for dinner and an evening at your leisure.

Day 15: Noto Visit and Granita Tasting

Daily Summary

Noto Visit and Granita Tasting

After a morning at leisure, your private driver will lead you to Noto this afternoon, a short 45 minute journey from Siracusa.

It has been said that Noto is one of Europe's most beautifully built cities: this remote little place emerges in memory as one of the finest achievements of the age that produced Mozart and Tiepolo. Today you will find yourself facing one of the highest points of Sicilian and Italian urban art and architecture. Called the "capital of Baroque", the historic center of Noto has been declared a UNESCO World Heritage Site. Noto has been the set of several films, some made by the greatest masters of world cinema.

With your private guide, stroll through the city: grandiose flights of steps lead worshippers and tourists alike up to the ornately carved entrance doors of the churches, the roads open out in to sweeping piazzas lined by palaces built in a stone of soft pink and golden yellow hues. A tour of Noto might start from the main square with a visit to a few of the stunning Palazzos, the Church of San Domenico and, of course, the town's magnificent Cathedral to name but a few of the many buildings worth visiting in Noto.

At the end of the tour you will taste the best Sicilian Granita with fresh brioches from a nearby café - an extraordinary conclusion to a tour of one of Europe's most scenic towns.

Day 16: Siracusa in Depth

Daily Summary

Siracusa in Depth

Meet your private driver at your hotel lobby for a full day of exploration of Siracusa. Is it the most beautiful city in Sicily? Hard to say. What is certain is that it is impossible remaining indifferent to the expressive, historical, human and cultural power of Siracusa (or Syracuse in English). Siracusa has a millennial history: counted among the largest metropolises of the classical age, it excelled in power and wealth with Athens, which tried in vain to subjugate it. It was the home of the mathematician Archimedes, who placed himself at the head of its defense during the siege of the Romans in 212 BC.

The ancient heart of Siracusa is the island of Ortigia: stroll through this cross-section of enchanting poetry, where myth comes to life in the Fountain of Arethusa, a mirror of fresh water located in Ortigia and coming into contact with the salt water of the sea, in which the legend of Arethusa and Alphaeus, one of Siracusa's most fascinating and poignant myths, is set. The panoramic beauty of Ortigia is well known, thanks to a location that makes it unique in the Sicilian landscape. The human setting that surrounds it only adds to its charm, its narrow alleys are full of life, crowded with typical markets selling local products, delicious seafood restaurants, and cheese, fruit and vegetable stores. Its charm lies in the myriad of temples, castles and churches hidden in its every corner, such as the majestic Cathedral, built on top of an ancient Greek temple.

Day 17: Syracuse to Taormina via Catania Exploration

Syracuse to Taormina via Catania Exploration
Daily Summary

After breakfast, check out from your hotel and meet your guide for a private transfer to Taormina by way of one of the island's most contrasting cities: Catania.

Just under an hour away, you'll reach Catania. One of the most interesting aspects about the Catania fish market is not just the activity of the pescheria itself, but the crowd that it attracts - the hustle and bustle of locals perusing the vibrant seafood on offer and deciding whether or not to make a purchase. Decidedly more low-key, there are butchers, cheesemongers and fruit and vegetable sellers to round out the offerings, but the star of the show remains the Catania fish market.

The beauty of Sicilian markets is all in their authenticity, the varied colors, the identity-mixing of environment, food and humans in its most traditional form.

After a couple hours of exploration, continue on your way to Taormina to check into your accommodation.

Additional Options for Day 17

Grand Hotel Timeo - Deluxe Sea View Junior Suite with Balcony or Terrace

Grand Hotel Timeo - Deluxe Sea View Junior Suite with Balcony or Terrace

A breezy haven of history-flecked, carefree glamour.  Here, old-world grandeur is punctuated with a cosmopolitan spirit. Long evenings on the panoramic terrace sparkle with cultured conversation, and the lure of the sea is never far away. Authentic Sicilian warmth fills the walls and spills out to the stunning gardens, while signature cocktails and Michelin-starred dining satiate the tastebuds. Grand Hotel Timeo was the first hotel to be built in Taormina, harnessing the history and mystique of nearby Mount Etna and Greek theatre. This is a place where the old world and new harmonize.

Day 18: Taormina Discovery

Daily Summary

Taormina Discovery

After breakfast at your hotel, meet your guide for a private discovery of Taormina, founded by the Greeks in 358 B.C. and occupied by the Romans and Byzantin. This quaint town is located on the East coast of Sicily, overlooking the Ionian Sea. Taormina is called the “Pearl of the Mediterranean” as it is nestled on Mount Tauro and offers the beauty of Mediterranean architecture all while being surrounded by endless magnificent views of both sea and mountain. Thanks to its hilltop presence, Taormina offers visitors a breathtaking panorama. From its Greek theatre, you can admire the bay of Giardini Naxos and Mount Etna, the highest active volcano in Europe, while on the other side you can gaze out over the coastline toward Messina and view the proximity of the Calabrian coast.

If you're feeling up for a small hike, join the guide on the trail to Castelmola for a huge visual reward. This is a stunning scenic walk that heads up many steps and zig zagging paths to the iconic village of Castelmola, the village is perched on top of a hill well above Taormina, the views overlooking Isola Bella and the Ionian Sea are well worth the effort of the climb, there are many points of historical interest on route.

Return to your hotel on foot for an afternoon at leisure to enjoy Taormina and relax.

Day 19: Mt. Etna Volcano and Winery Experience

Daily Summary

Mt. Etna Volcano and Winery Experience

Be whisked away in a Jeep for a day of nature and wine in a fascinating day at UNESCO World Heritage site, Mt. Etna, the highest active volcano on the Eurasian tectonic plate at 3,357 meters high. With your nature guide, take in breathtaking scenery, postcard views, a mix of colors, unspoiled sounds and far from the madding crowds, more than 400 craters and fairy tale trails: an adventure to be experienced in a blend of mind-body harmony, immersing you in one of the most intense environments nature has to offer.

At the end of the tour, it's off to one of the best Etna DOC Winery for another special experience! Visit Cottanera winery for a private tour and lunch. With its pioneer viticulture, It is today one of the most extraordinary companies in Italian and international enology. The vineyards grow over lava stone, 700 meters above sea level on the northern slope of the volcano. It showcases the particularities of a unique and precious territory. You will be guided through a story telling of Cottanera history with a description of the local territory, followed by a tour of the wine cellar, and walk through the vineyards. The wine tasting will be accompanied by a lunch with recipes selected from the Cottanera's family cookbook.

After this incredible day, the Jeep will take you back to your accommodation for some rest and relaxation.

Day 20: Sicilian Cooking Experience

Daily Summary

Sicilian Cooking Experience

Meet your guide after breakfast for a fun morning immersing yourselves in traditional Sicilian cuisine. Today, visit a small commune nearby to the Sicilian city of Messina for a unique experience at a local Sicilian home with the 'Mothers of the Village' as they are affectionately known. Work together with a local 'mama' to make a typical Sicilian pasta, 'maccaruni' from scratch before enjoying the fruits of your labor for lunch. You will enjoy the characteristic atmosphere of the Sicilian families, in one of the most out-of-the-box experiences, where what counts is genuineness, the culture of flavor and taste, the storytelling and warmth of the most traditional Sicily! After lunch, a stop is due to Savoca, where you will enjoy a walking tour of the town, admiring “The Godfather” set with the typical streets and the famous Bar Vitelli. You will take a walk on the panoramic promenade to the famous church of San Nicolò or better called Santa Lucia which was used in the Godfather movie for the marriage of Michael Corleone and Apollonia Vitelli. A taste of lemon granita is a must whilst wandering the promenade!

You'll then be delivered back to your hotel for a relaxing afternoon at leisure.

Day 21: Departure

Daily Summary
  • Transfer: Hotel to Airport
  • Meals: B

After checking out of your accommodation say a fond farewell to Sicily. Meet your private driver at your hotel who will transfer you to Catania airport for your departing flight.

Arrivederci Sicilia!

Villa Igiea Palermo

Villa Igiea Palermo

Discover history, majesty and serenity at Villa Igiea: a turn-of-the-century palazzo at the perimeter of vivid Palermo, the foot of Mount Pellegrino and the Gulf of Palermo. A long-loved seaside-meets-city sanctuary for royalty, dignitaries and Hollywood luminaries, trace their paths through tiered villa gardens that sweep down to the port and out to the Tyrrhenian Sea. The villa offers rooms and suites designed by Olga Polizzi, two restaurants which showcase Sicily's rich cuisine, a spa and a pool. Here is where impeccable hospitality and Belle Époque-era luxury combining to form the high-watermark of a visit to this sun-drenched Italian island.

Baglio Oneto

Baglio Oneto

At the end of the 18th century, as Marsala wine became renowned around the world, the Baglio was built to lord over this agricultural area. Coming from the Latin "balarm" meaning fortified house, this type of fortified residence, characterized by high walls, a tower, and defensive elements can be found all around Sicily. The  Baglio offers elegant rooms and suites, with the utmost comfort being guaranteed and showcasing the colors of the true Sicilian tradition — coloured ceramics, hand-crafted wrought iron, the discreet elegance of solid wood and flooring with floral motifs. In your room, you will find a balcony or terrace so you may delight in the views of the surrounding landscape, savour the beauty of the Marsala countryside or the spectacle of the sunset over the sea.

ADLER Spa Resort Sicilia

ADLER Spa Resort Sicilia

Sitting inconspicuously on a hill overlooking the golden beach and azure sea of the Agrigento coast, ADLER Spa Resort SICILIA blends Sicily’s mesmerizing natural world with the finest experience sustainable travel can offer. Bordering the Torre Salsa Nature Reserve in the south-west of Sicily, an area rich in historical and natural beauty, the Resort is a jewel that fits perfectly into the surrounding natural environment. The dedication to Wellness & Spa make it the perfect refuge for relaxing, regenerating the body and restoring the spirit. Lose yourself among the colors, scents and flavors of the Mediterranean, and discover a new place your heart can call home. 

Grand Hotel Des Ètrangers

Grand Hotel Des Ètrangers

Set in heart of Ortigia, Grand Hotel Des Étrangers is an art deco icon and byword for understated elegance. The Des Étrangers story began in 1906, when a historic mansion in Siracusa was transformed into an acclaimed restaurant and hotel. Each room and suite is a unique combination of beautiful design, comfort and glamour. The hotel offers an impeccable service in a historic building that has been carefully restored and designed to offer an authentic luxury experience.

Hotel Villa Carlotta Taormina

Hotel Villa Carlotta Taormina

An elegant boutique hotel in Taormina with panoramic views across the Ionian Sea. Hotel Villa Carlotta is an independent hotel owned and run by the Quartucci family who have been making guests feel at home since they opened their first boutique hotel, Hotel Villa Ducale, in Taormina in 1993. This enchanting hotel in Taormina is in a unique historic setting overlooking the Ionian Sea. The rooms and interiors at Hotel Villa Carlotta have recently been renovated to create an intimate oasis of elegance and calm with service provided by an exceptional team of staff. We see Carlotta more like a sophisticated home than a hotel.

Optional Accommodations

Grand Hotel Timeo

Grand Hotel Timeo

A breezy haven of history-flecked, carefree glamour.  Here, old-world grandeur is punctuated with a cosmopolitan spirit. Long evenings on the panoramic terrace sparkle with cultured conversation, and the lure of the sea is never far away. Authentic Sicilian warmth fills the walls and spills out to the stunning gardens, while signature cocktails and Michelin-starred dining satiate the tastebuds. Grand Hotel Timeo was the first hotel to be built in Taormina, harnessing the history and mystique of nearby Mount Etna and Greek theatre. This is a place where the old world and new harmonize.

Price Includes

Bespoke organization of the trip

Bilingual guide with expert regional knowledge

Regional restaurant recommendations

Accommodation as per the daily summary

Meals as per the daily summary

All transfers on private basis as per the daily summary

All tours on private basis as per the daily summary (unless otherwise stated)

Wine tasting fees

Price Excludes

International and domestic airfares

Any entrance tickets not mentioned in the itinerary

All meals and beverages not included in the daily summary

Dinner restaurant reservations (available for a supplement)

Gratuity (at your discretion)

Travel insurance

Items of a personal nature

Rental vehicle hire (if applicable)



Paolo is the founder and director of Into the Vineyard, and has dedicated himself to create unforgettable wine-focused experiences. He is passionate about understanding the traveler's needs and building upon them to create personalized trips.

He has a deep connection to his Italian heritage, stemming from his parents' immigrations and numerous trips to Italy. Paolo has over 15 years of experience as a destination travel guide, leading cycling and walking trips in 18 countries around the world. He is fluent in five languages, a testament to his dedication to traveling and understanding different cultures.

Paolo's love for sports, including sailing, water polo, and cycling keep him youthful along with spending time with his family of four.

Jason Greenwood

Project Manager

Jason set out to discover the world over a decade ago and has developed a knack for organising trips to unique and remote destinations. Originally from Australia, his love of adventure and photography has taken him across the globe, from the dense jungles of Borneo to the northern reaches of Scandinavia.

Drawing on his personal experience in the Middle East, Africa, and Europe and knowledge designing trips for clients travelling to Australia, New Zealand, and Asia, Jason joins the team to ensure adventures run smoothly and safely.