The Soul of Sicily: A Journey Through History, Flavor, and Coastal Beauty

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The Soul of Sicily

cities: palermo - trapani - agrigento - ragusa - siracusa - taormina
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Experience the Pageantry, Passion, and Timeless Beauty of Italy’s Island Jewel

Uncover the vibrant soul of Sicily, where every moment is steeped in drama, beauty, and ancient wonder. This nearly two-week journey takes you across the island’s diverse landscapes and deep cultural roots, from grand cities to seaside villages, and everything in between.

Begin in Palermo, Sicily’s energetic capital, then drift into the charming rhythms of Cefalù, a picture-perfect fishing village. Explore the archaeological marvels of Segesta, the baroque elegance of Trapani, and the island’s famed salt pans and olive groves. And that’s just the beginning.

Stand in awe before the Valley of the Temples, savor sweets at a 150-year-old chocolate factory, and take your seat at the world’s largest Greek theater. Hike or gaze upon the majestic power of Mount Etna, Europe’s most active volcano, before setting sail on a private boat tour of Sicily’s coastline—where history, nature, and myth converge.

Whether it’s your first time or your fifth, Sicily never stops revealing herself. With expert local guides, private transportation, and tailored experiences throughout, Your Own Italy delivers a personal and unforgettable encounter with the island’s soul.

Day by day

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palermo

Summary palermo
Day 1
Day 2
Day 1

Welcome to Sicily: Discover Palermo’s Historic Heart

Your Sicilian adventure begins as your private driver greets you at the airport and escorts you to your boutique hotel in Palermo, Sicily’s vibrant and storied capital.

In the afternoon, meet your expert local guide for an introductory walking tour that brings this fascinating city to life. With a history spanning more than 2,700 years, Palermo is a cultural crossroads where Arab, Norman, and Baroque influences blend into a uniquely Sicilian tapestry.

You’ll explore the majestic 12th-century Palermo Cathedral, resting place of kings, and admire the grandeur of the Teatro Massimo, Italy’s largest opera house. Wander through Piazza Bellini, surrounded by Arab-Norman churches, and marvel at the Baroque beauty of Santa Caterina di Alessandria. At the iconic Quattro Canti, or "Four Corners," you’ll witness one of Palermo’s most picturesque intersections, followed by a stop at Piazza Pretoria, with its elegant fountain and statuary.

To conclude your tour, enjoy a refreshing treat at Mercato il Capo, one of Palermo’s liveliest street markets—where a stop for authentic Sicilian lemon ice offers the perfect introduction to the flavors of the island.

With the Your Own Italy Advantage, your welcome to Sicily is as rich and warm as the island itself.

the Palazzo dei Normanni also known as the Royal Palace in Palermo, Italy
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Day 2

Palermo’s Markets, Mosaics & Macabre Wonders

A Journey Through Sicily’s Trading Soul and Hidden Treasures

Begin your day immersed in the vibrant energy of Palermo’s open-air markets, where history, flavor, and daily life converge. Your private guide will meet you at your hotel and lead you through a fascinating walk that traces Palermo’s roots as a bustling Arabic trading hub during the 9th–11th centuries.

Start at Capo Market, once known as Caput Seralcadi, where stalls overflow with fresh seafood, exotic spices, and lively chatter. Along the way, pause to admire the Baroque Church of the Immaculate Conception, an architectural gem tucked among the stalls. Continue along the ancient Cassaro, Palermo’s oldest street, to reach Ballarò Market, the former suq-al-Balari, located beneath the soaring dome of the Carmine Maggiore Church. Your final stop is Vucciria Market, immortalized in Renato Guttuso’s iconic painting, where the soul of old Palermo is still alive in its narrow alleys and colorful chaos.

After a relaxing lunch at a specially selected local trattoria, your exploration of Palermo continues with a visit to its most unique and powerful landmarks.

Step inside the Palazzo dei Normanni, the royal palace that now houses the Sicilian government, and visit the exquisite Cappella Palatina, where Byzantine mosaics shimmer in gold, depicting sacred stories with astonishing detail and artistry. These mosaics are not only the pride of Palermo—they’re among the finest in the world.

Your day concludes with a descent into the Capuchin Catacombs, one of Sicily’s most haunting and unforgettable sites. In this underground monastery crypt, perfectly preserved mummified remains line the walls, silently narrating centuries of history and tradition. While not for the faint of heart, this powerful space offers a rare glimpse into Sicilian beliefs about death, legacy, and the afterlife.

This tour weaves together the flavors, colors, and mysteries of Palermo in a way that only Your Own Italy can deliver—immersive, enlightening, and entirely unforgettable.

street food at the ballaro and capo markets with fish meat typical of palermo in the center of sicilian cuisine during a summer day in 2024
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trapani

Summary trapani
Day 3
Day 3

Segesta, Erice & Trapani

A Day of Ancient Temples, Hilltop Villages, and Coastal Charm

Your day begins as your private driver meets you at your hotel and whisks you westward toward the archaeological site of Segesta, one of the most awe-inspiring destinations in all of Sicily. Nestled atop a hill surrounded by open countryside, you’ll explore the world’s best-preserved Greek temple—a majestic, unfinished Doric structure that stands in serene isolation. With panoramic views and echoes of antiquity, this stop offers a striking window into Sicily’s classical past.

From Segesta, continue to the enchanting medieval town of Erice, perched high above the sea. You’ll stroll cobbled streets lined with craft shops, turreted castles, and panoramic terraces that offer breathtaking views of the Mediterranean. A highlight of your visit is the renowned pasticceria of Maria Grammatico, where the air is filled with the scent of freshly baked almond pastries, Sicilian cassate, and cannoli. Whether you indulge in a sweet treat or simply take in the ambiance, this is a quintessential Erice experience.

In the afternoon, your driver will escort you to Trapani, where you’ll check into your boutique hotel and have free time to explore this historic port city at your leisure. Discover the Torre di Ligny, a 17th-century watchtower at the westernmost tip of town, now home to the Museum of Prehistory and the Sea. Don’t miss the Chiesa del Purgatorio, which houses the intricately carved wooden sculptures used in the famed Easter Processione dei Misteri.

With The Your Own Italy Advantage, this journey blends history, beauty, and local flavor into an unforgettable day of exploration in western Sicily.

Ruins of a Greek Temple in the ancient city of Segesta
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agrigento

Summary agrigento
Day 4
Day 4

Wine, Temples & Timeless Beauty in Agrigento

A Day of Flavor, History, and Evening Elegance Among Ancient Ruins

Set out in comfort as your private driver picks you up from your hotel for the scenic journey to Agrigento, one of Sicily’s most storied destinations. Along the way, you’ll stop at the Planeta Estate in Ulmo Sambuca, a renowned winery that blends tradition with innovation. Surrounded by rolling vineyards and olive groves, enjoy a leisurely lunch and curated wine tasting, featuring bold Sicilian reds and crisp whites paired with regional cuisine that reflects the rich flavors of the island.

Upon arrival in Agrigento and check-in at your boutique hotel, your experience continues with a private evening tour of the Valley of the Temples—one of the largest and most majestic archaeological sites in the world. With the crowds gone and the summer heat subsiding, you'll stroll the ancient roads in tranquil evening light, as the illuminated Greek temples glow softly against the night sky.

Your expert guide will bring to life the stories of these monumental structures—testaments to the grandeur of Magna Graecia and the timeless allure of Sicily’s classical past. Whether you’re savoring wine on the estate or standing in awe beneath the Temple of Concordia, this day is a seamless blend of sensory pleasure, cultural depth, and unhurried discovery—an experience only Your Own Italy can deliver.

a line of wine glasses partially filled with different varietals for a wine tasting
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ragusa

Summary ragusa
Day 5
Day 6
Day 5

Mosaics & the Baroque South

Villa Romana del Casale and the Journey to Ragusa

Begin your day with a scenic drive as your private driver escorts you from Agrigento to Ragusa, one of Sicily’s most captivating Baroque towns. En route, you’ll stop in Piazza Armerina for a privately guided tour of the Villa Romana del Casale, a UNESCO World Heritage Site renowned for its extraordinary collection of Roman mosaics.

Step into a world frozen in time as you explore this vast Roman villa, where intact floor mosaics cover room after room—each more mesmerizing than the last. From intricate geometric designs to sweeping scenes of myth, nature, and Roman daily life, these vivid artworks are considered the finest of their kind in the world. Your expert guide will illuminate their meaning and craftsmanship, offering a rare glimpse into aristocratic life during the late Roman Empire.

Following your visit, your driver will continue the journey to Ragusa, where you’ll settle into your charming hotel in the heart of the historic center. With The Your Own Italy Advantage, your day unfolds effortlessly—blending cultural wonder with comfort and personalized attention every step of the way.

detail of mosaic in the Romana del Casale in Sicily, Italy
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Day 6

Baroque Splendor & Timeless Charm

A Walking Tour of Ragusa Ibla and Modica

Set out from your accommodations with your private driver, who will escort you to the heart of Ragusa Ibla, the enchanting historic center of Ragusa. Rebuilt in splendid Baroque style after the devastating earthquake of 1693, Ragusa Ibla is a feast for the eyes, with its elegant palazzi, ornate churches, and intricately sculpted balconies that adorn narrow stone alleys.

Your private guide will lead you through the winding streets of this UNESCO-listed town, pausing at architectural masterpieces like the Duomo di San Giorgio, a commanding cathedral perched at the head of a graceful piazza. You'll continue your stroll through the atmospheric lanes, discovering quiet courtyards, breathtaking views of the steep surrounding valleys, and the rhythmic charm of Sicilian life.

The tour concludes with a visit to the Giardino Ibleo, a tranquil public garden beloved by locals. With its palm-lined walkways, shaded benches, and panoramic vistas, it's the perfect spot to soak in the beauty and serenity of southern Sicily.

As always, The Your Own Italy Advantage ensures every step is rich in history, elegantly paced, and seamlessly arranged to give you an authentic connection with Italy’s most captivating corners.

narrow street between baroque buildings in Ragusa, Italy
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Modica: Baroque Beauty & the Art of Chocolate

An Introductory Tour of One of Sicily’s Sweetest Cities

After your time in Ragusa, your private driver will accompany you to the nearby town of Modica, another gem in Sicily’s baroque crown and a proud UNESCO World Heritage Site. Like Ragusa, Modica rose from the ruins of the 1693 earthquake with elegance and ambition, blending late-Baroque splendor with traces of its medieval past.

Your tour begins at the magnificent Cathedral of San Giorgio, perched high above the town. From its grand staircase and strategic hilltop setting, you’ll enjoy panoramic views across Modica’s rooftops and valleys—a photographer’s dream. As you enter the cathedral, marvel at its ornate façade and beautifully restored interior, a shining example of Sicilian Baroque artistry.

Next, stroll through Modica’s charming streets to the Church of San Giovanni Evangelista, crowned by a monumental staircase flanked by trees and baroque balconies. The journey here is as memorable as the destination, offering a deeper glimpse into the town’s graceful design.

No visit to Modica is complete without tasting what it's most famous for—chocolate. You’ll visit the Chocolate Museum, where the town’s rich confectionary history comes alive. Learn how Modica’s chocolate-making tradition, inspired by ancient Aztec methods, has made it one of Italy’s culinary treasures. End your tour with a tasting of traditionally ground chocolate in unique flavors like pistachio, lemon, raspberry, and pomegranate.

With The Your Own Italy Advantage, you don’t just visit Modica—you savor its culture, architecture, and sweet spirit in every step.

The San Giovanni Evangelista church in Modica, Italy
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siracusa

Summary siracusa
Day 7
Day 8
Day 7

Scenic Transfer to Syracuse with a Stop in Noto

Explore the Heart of Sicilian Baroque Along the Way

Your private driver will pick you up at your hotel for a seamless transfer to your accommodations in Syracuse. Along the way, you’ll enjoy a stop in the charming town of Noto, a true architectural jewel and one of the crown treasures of Sicily’s Baroque heritage.

Rebuilt in the late 1700s after a devastating earthquake, Noto stands as a model of urban planning and baroque design. As you stroll through its golden-hued streets, you’ll admire the stunning façades of churches, palaces, and civic buildings, all crafted in the distinctive honey-colored limestone that glows in the Sicilian sun. Noto, along with Ragusa and Modica, forms the trio known as the “Three Baroque Gems”—each a unique expression of beauty, culture, and history.

This perfectly timed stop gives you a taste of the Val di Noto, an area rich in artistic legacy and one of UNESCO’s prized World Heritage Sites. With Your Own Italy, even a transfer becomes an experience to remember.

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Day 8

Discover Syracuse: Ortigia by Golf Cart & Immersive Archeological Tour

Morning: Explore the Charm of Ortigia
Your private guide will meet you at your hotel and escort you to your waiting golf cart for a leisurely ride through the enchanting, narrow streets of Ortigia, the historic heart of Syracuse. As you glide past elegant Baroque facades and lively piazzas, your guide will point out hidden gems and historical landmarks that bring this storied island to life. Along the way, pause to enjoy a classic Sicilian arancino, the perfect mid-morning treat, before heading to lunch at a selected local restaurant known for its authentic regional cuisine.

Afternoon: Step Back in Time at the Paolo Orsi Museum & Archeological Park
After lunch, you’ll meet your guide at the entrance to the renowned Paolo Orsi Archeological Museum, one of the most important in all of Europe. Here, you’ll journey through Sicily’s ancient past as you explore an extraordinary collection of artifacts—from prehistoric tools and Greek statues to Roman mosaics and Byzantine relics—displayed across four curated sectors.

Your experience continues with a visit to the adjacent Archeological Park, where you’ll marvel at the world’s largest Greek theater, a testament to Syracuse’s ancient prominence. You’ll also explore the Roman amphitheater, a striking symbol of the city’s layered cultural legacy.

From the charming alleys of Ortigia to the timeless grandeur of antiquity, this day offers a captivating look at Syracuse—thoughtfully curated with comfort, insight, and ease by Your Own Italy.

a narrow, winding street on the Island of Ortigia in Syracuse
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taormina

Summary taormina
Day 9
Day 10
Day 11
Day 9

Journey to Taormina with Mt. Etna Adventure and Winery Lunch

Begin your day with a scenic transfer to Taormina, accompanied by your private driver. Along the way, you’ll stop for an unforgettable visit to Mt. Etna, Europe’s highest and most active volcano. Upon arrival, you’ll meet your expert guide, who will lead you on a journey across this dramatic landscape shaped by centuries of eruptions. You’ll take in breathtaking views of craters, lava fields, and the Ionian coast, with opportunities to explore the unique terrain and learn about the mountain’s powerful natural history.

After descending from the heights of Etna, you’ll head to the nearby Gambino Winery, nestled along the volcano’s fertile slopes. Here, you’ll enjoy a gourmet lunch and wine tasting experience, sampling varietals cultivated in the mineral-rich soil and paired with local specialties. It’s the perfect blend of nature, flavor, and Sicilian hospitality.

Following lunch, you’ll continue on to Taormina, where your driver will deliver you to your hotel in this elegant hilltop town overlooking the sea—relaxed, inspired, and ready to explore more of Sicily’s treasures.

The Isola Bella in Taormina, Italy.
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Day 10

Discover the Charm of Taormina: A Private Guided Walking Tour

Your private guide will meet you at your accommodations and lead you on a journey through the elegant hilltop town of Taormina, one of Sicily’s most enchanting destinations. Beginning at Porta Messina, the historic gateway to the city, you’ll stroll along the vibrant Corso Umberto I, lined with chic boutiques, artisan shops, and charming cafés.

As you make your way through town, your guide will highlight Taormina’s architectural and cultural gems, including the Palazzo Corvaja, a medieval palace with a rich history; the Roman Odeon, a small but fascinating theater; and the Piazza IX Aprile, a panoramic terrace offering breathtaking views of the Ionian Sea and Mt. Etna.

You’ll continue past the Cathedral of San Nicola, a fortress-like church blending Norman and Gothic elements, and the Roman Naumachia, an ancient structure believed to have served as a water reservoir or stage for mock naval battles.

Your tour will culminate at the magnificent Ancient Greco-Roman Theater, still in use today for concerts and cultural events. With its dramatic backdrop of sea and volcano, this amphitheater is one of the most iconic and breathtaking sites in all of Italy. Let Taormina’s timeless beauty captivate you at every turn.

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Day 11

Departure – Arrivederci!

As you bid farewell to Italy, you carry with you not just memories of breathtaking landscapes, exquisite cuisine, and timeless history, but also the warmth of newfound friendships. Your driver will ensure a smooth journey to the airport, giving you plenty of time to make your flight. Though your adventure may be coming to an end, Italy salutes you with a heartfelt “Arrivederci!”—until we meet again.

Now that you’ve traveled with Your Own Italy, you’ll always have friends eager to welcome you back whenever you long for the beauty, flavors, and magic of this incredible land once more.

an aerial view of Isola Bella in Taormina, Italy
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What’s Included

Charming Accommodations

Palermo – 2 nights in a boutique hotel or historic apartment.
Trapani - 1 nights in a boutique hotel or historic apartment.
Agrigento – 1 nights in a boutique hotel or historic apartment.
Ragusa – 2 nights in a boutique hotel or historic apartment.
Syracuse – 2 nights with boutique hotel or historic apartment.
Taormina – 2 nights in a boutique hotel or historic apartment.

Expert Guides and Skip-the-Line Access

Enjoy the expertise of English-speaking local guides who bring Italy’s history, art, and culture to life. With skip-the-line tickets, you’ll spend less time waiting and more time exploring.

Immersive Private Tours and Exclusive Excursions

Palermo:

  • Discover Palermo’s Historic Heart - Private Walking Tour.
  • Palermo’s Markets, Mosaics & Macabre Wonders

Trapani :

  • Segesta, Erice & Trapani

Agrigento:

  • Wine, Temples & Timeless Beauty in Agrigento

Ragusa:

  • Villa Romana del Casale and the Journey to Ragusa
  • A Walking Tour of Ragusa Ibla and Modica

Syracuse:

  • Scenic Transfer to Syracuse with a Stop in Noto
  • Ortigia by Golf Cart & Immersive Archeological Tour

Taormina:

  • Journey to Taormina with Mt. Etna Adventure and Winery Lunch
  • Discover the Charm of Taormina: A Private Guided Walking Tour
palermo
2 nights
trapani
1 nights
agrigento
1 nights
ragusa
2 nights
siracusa
2 nights
taormina
2 nights
Package Pricing
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Pricing (per person)
Rates depend on group size**
2-3 travelers: $10,300 per person
4-5 travelers: $9,650 per person
6 or more travelers: $8,300 per person
**prices subject to hotel availability
Vacation Airfare
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To book your international flights at preferred rates, contact an UP AND AWAY TRAVEL International Specialist:
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+1 (800) 275 8001
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kyle@upandaway.com
Vacation Insurance
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We highly recommend purchasing travel insurance at the time of booking to protect against potential fund forfeiture due to cancellation or unexpected incidents such as injury or loss. We offer travel insurance through our partner, Allianz.
Awards
Tripadvisor Award
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Schedule 30 minutes call with Carmen
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Best trip ever!
We would like to sincerely thank Carmen and her team for the wonderful two week itinerary planned for us in Italy as well as your dedication and constant communication in keeping us always informed with our tour guides and drivers.
Being that this was our first time traveling to Italy, Your Own Italy made our hotel (beautiful hotels) , transportation, and tour reservations for us which made our trip stress free where we could relax and enjoy our time. All the private drivers and AP Tour Guides were wonderful, gracious, very knowledgeable and informative. We really enjoyed them and learned a lot from them.
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