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14-Day Sicily In-Depth Tour Leisurely Pace

The 14-Day Sicily in-depth tour is a splendid trip through Sicily’s sightseeing highlights. And it includes trips to Sicily’s famous volcanic islands.

The tour itinerary includes 2 nights in Palermo and 3 nights in Taormina. Along the way the tour provides plenty of time to relax and enjoy Sicily. The leisurely paced Sicily tour itinerary provides time to stroll around independently between scheduled tours and excursions.

The leisurely paced Sicily tour highlights include excursions to visit local farms and dinners in authentic local restaurants. The expert Sicily tour guides will introduce you to the island’s rich history.

The Sicily in-depth tour itinerary visits Aeolian Islands, Agrigento, Monreale, Palermo, Ragusa, Salina, Taormina, and Traponi. Along the way, you’ll discover the blending of cultures that makes Sicily a living testament of the Mediterranean’s history and various cultures.

Families, friends, groups, and singles will all enjoy history’s great civilizations coming to life on this two week Sicily in-depth tour. Submit the form or call 800.227.1577 for the price of this leisurely-paced Sicily escorted tour with airfare from your preferred departure city and for more tour information.


Leisurely Pace Sicily In-depth Tour Sightseeing Highlights

  • Spend 2 nights in Sicily’s vibrant city Palermo.
  • Spend 3 nights in Taormina, the gorgeous resort town and jewel of Sicily
  • Spend 1 night in Agrigento the ancient Greek archaeological site in Sicily
  • Visit UNESCO World Heritage sites: Palermo, Agrigento, and Ragusa
  • Visit the stunning 12th-century Norman cathedral in Monreale
  • Be amazed by the Greek Theatre and the Duomo in Taormina
  • Explore the ancient Greeks in Agrigento and Taormina
  • Agrigento: Join a local expert who will guide you through the Temples of Juno, Concorde and Hercules, some of the best preserved Greek temples in the world
  • See the world’s finest Byzantine mosaics in Monreale
  • Visit the Greek and Roman Gods in Agrigento’s Valley of the Temples.
  • Palermo: Local guide escorts you to sightseeing highlights
  • Taormina: Visit the Greek Theater and stroll Corso Umberto

Leisurely Sicily In-depth Tour Includes

  • 12 nights in Sicily highlights Palermo, Trapani, Agrigento, Ragusa, Salina, and Taormina
  • Meals: Breakfast daily, 6 dinners, 1 lunch
  • Inclusive Sicily tour includes airport transfers, tours, entrance fees, and meals per itinerary
  • Small group up to 26 guests
  • Personal radio headsets give you the freedom to wander during visits to famous highlights without missing any of your local expert’s fascinating insights and commentaries
  • Baggage handling everywhere, with seamless and prompt delivery to your door at every hotel
  • Hotel and restaurant tips included – you’ll never have to worry about how much to give, nor search for foreign currency. Plus, all taxes and porterage charges at hotels included

Click here to review the day-by-day Sicily escorted tour itinerary.


Leisurely Sicily In-depth Tour Accommodations

  • Palermo 2 Nights – Hotel Porta Felice
  • Trapani 2 Nights – I Mulini Resort
  • Agrigento 1 Night – Baia Di Ulisse
  • Ragusa 2 Nights – Poggio Del Sole Hotel
  • Salina 2 Nights – Hotel La Salina Borgo Di Mare
  • Taormina 3 Nights – NH Collection Taormina

Optional Tours

Leisurely Sicily In-Depth Optional Tours

Bitter Almonds: Erice village & Sicilian pastry baking lesson and tasting

Sicily’s Baroque Valley: Scicli & Modica with lunch

Stromboli Sunset Cruise with pasta dinner on board

14-Day Sicily In-depth Tour

Submit form for the price of the leisurely paced Sicily in-depth tour with airfare from your home airport.

  • Check date for Sicily trip you are interested and submit form.

Sicily In-depth Tour Day-by-Day Itinerary

Travel through Mediterranean history meeting the ancient Greeks, ancient Romans, Byzantines, Normans, Carthaginians, crusaders, Bourbons, and Ottomans on this leisurely trip through Sicily’s sightseeing highlights. e Sicily escorted tour. This Sicily in-depth tour provides authentic Sicilian experiences including visiting a local countess, businessmen, and meals in restaurants. The day-by-day itinerary provides time for your expert Sicily tour guide to bring you through its rich history and culture.

Day 1 – Overnight Flight

You’re on your way to Sicily – an island paradise nestled amongst the deep blue waves of the Mediterranean. Look past the Italy you think you know and see how this coastal farmland balances ancient traditions and modern comforts.

Day 2 – Palermo, Italy – Tour Begins

Start your journey in Palermo (UNESCO), Sicily’s welcoming capital city. Uncover the island’s deeply rooted heritage, teeming with Arab-Norman architectural masterpieces and delicate Classical designs. Come to know your fellow travelers over a welcome dinner.

Meals: Dinner

Day 3 – Palermo

Decide how you explore because it’s your choice! Tour Palermo and head to Monreale Cathedral, ascending on foot to see the gold Byzantine mosaics -OR- descend into a WWII air raid shelter before exploring the historic city center with a guide. No matter how you spend your morning, you’ll spend your afternoon tasting your way through Ballarò Market’s olives, spices, and other local produce. End your day at a medieval palace, where a countess guides you through her family’s home, joining you for an aperitif and hors d’oeuvres.

Meals: Breakfast

Day 4 – Palermo – Impact Moment – Trapani

Experience an impact moment with Addiopizzo, an anti-Mafia nonprofit that supports locals who refuse to pay the Mafia’s protection fees. Visit Capaci and Cinisi, the site of two terrorist acts led by the Mafia, and pay tribute to fallen activists. Chat with locals for a personal perspective and learn how they overcame the Mafia’s reign. As the day draws to a close, settle into Trapani for two nights and watch the sunset fade against the crashing waves and whirling windmills.

Meals: Breakfast & Dinner

Day 5 – Trapani – Isle of Mozia – Marsala – Optional Excursion

Venture to the isle of Mozia, once a great trading port for the Phoenician, Greek and Roman civilizations. On the way, sail next to a submerged Roman road, once traversed on foot. Explore Mozia with a guide, visiting the ruins of its ancient port, and a museum featuring impressive Greek statuary. Then continue to Marsala, heading down into a cellar for a taste of its renowned wine. The remainder of the day is yours. Perhaps you will join an optional tour to Erice to visit Maria Grammatico’s famous bakery for a hands-on pastry-making class.

Meals: Breakfast

Day 6 – Trapani – Gibellina – Agrigento – Valley of the Temples – Agrigento

Begin in Gibellina, a humble countryside village. See how this town rebuilt itself after an earthquake, transforming ruins into a sprawling piece of contemporary art. Head to an award-winning olive grove and learn about the Slow Food movement, which supports local cultures and preserves traditions. Try their unique olive oil at lunch before departing for Agrigento, where ancient roots and medieval buildings blend into modernity. Wander through the Valley of the Temples (UNESCO) with a guide at dusk.

Meals: Breakfast, Lunch & Dinner

Day 7 – Agrigento – Ragusa

Make your way to Ragusa (UNESCO), an ancient city perched upon a hill. Meander through its Baroque neighborhood with an expert guide, passing by winding lanes, cobblestone streets, and wrought iron balconies. Make the most of a free afternoon to explore on your own. As the sun sets, retreat to your countryside resort just outside the city.

Meals: Breakfast & Dinner

Day 8 – Ragusa – Optional Excursion

The entire day is yours. With free time, you might choose to relax in the countryside and enjoy the resort’s amenities. Or, perhaps you will join an optional tour to the picture-perfect towns of Scicli and Modica, where you’ll enjoy a savory brunch at a ricotta farm before continuing to an Aztec chocolate shop for some sweet samples.

Meals: Breakfast & Dinner

Day 9 – Ragusa – Milazzo – Ferry to Aeolian Islands – Isle of Salina – Lingua

Grab your bags* and hop on a ferry in Milazzo. Sail by Vulcano and Lipari on your way to Salina** a far-flung isle surrounded by vibrant blue waters and dark volcanic rock. Somewhat off the beaten path, Salina is one of the less-traveled Aeolian Islands, preserved as a vacation getaway for Italians. Settle into the hamlet of Lingua for a 2-night stay. Get your bearings on a brief tour and visit a local winery*** for a tasting of Malvasia, a locally produced wine.

Meals: Breakfast

Day 10 – Salina – Caper Farm – Optional Excursion

Dramatic landscapes of rocky cliffs and vibrant vineyards pass by on your way to nearby Pollara, famous for its traditional caper cultivation. Wander through the fields, tasting the salted flower buds. The afternoon is yours to do as you please. Perhaps you’ll take an optional cruise to Stromboli, where you’ll swim off your private boat and dine at sunset; relax and watch for the signature glow of the island’s active volcano.

Meals: Breakfast

Day 11 – Salina – Ferry to Milazzo – Taormina

After a relaxing morning, ferry back to mainland Sicilia. Journey along the Ionian Coast to Taormina, a seaside hub of ancient Greek theaters and hilly walkways. Settle into your new home for the next three nights and enjoy a free evening to explore on your own.

Meals: Breakfast

Day 12 – Taormina

Discover Taormina with a local guide, leading you to the city’s Duomo, public gardens, and the well-preserved Greek theater. Walk in the footsteps of ancient attendees and take in an unparalleled viewpoint of the adjacent ocean. Spend the afternoon on your own. Perhaps you’ll grab a bite to eat at a sidewalk café, or peruse the local boutiques for handcrafted souvenirs.

Meals: Breakfast

Day 13 – Taormina – Mount Etna – Taormina

See Sicily’s wilder side on an off-road adventure to Mount Etna. Stare up at the iconic peak as your vehicle climbs along the sides of Europe’s largest active volcano. Spend the day exploring this legendary giant, passing by lava formations and basalt rocks. This evening, toast to your Sicilian sojourn at dinner, surrounded by local musicians.

Meals: Breakfast & Dinner

Day 14 – Taormina – Tour Ends

Your journey through Sicily comes to a close today. Return home with memories of Italy’s favorite island.

Meals: Breakfast

Click here to review the Sicily escorted tour accommodations.

For more Sicily vacation options click Sicily tours packages.

* When all-inclusive Italy vacation prices are quoted to include airfare the price includes fuel surcharges, airport taxes, Italy airport transfers and fees. All prices are per person based on twin occupancy. Italy tours with air & land tour prices apply from the gateway airport. Prices will vary from alternative gateway airports or cities and may be higher. The total price will be emailed to you prior to any deposit being required. Airline baggage fees may apply. Please review all terms and conditions before booking.