Sicily and Its Isles

Sicily and Its Isles

May 14th-28th, 2026

Small Group Tour (Maximum 24 people)

 

Days 1 | Thursday, May 14, 2026 | 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 | Friday, May 15, 2026 | Palermo: Arrive 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. (D)

 

Day 3 | Saturday, May 16, 2026 | Palermo: Begin your adventure tasting your way through Palermo’s lively markets on a walking tour unveiling the city's historical center and introducing you to traditional Sicilian street food. Palermo's culinary heritage layers Arab and Norman influences with local produce such as wild fennel, olives, and spices. This afternoon, head to Monreale Cathedral, ascending on foot to see its majestic Byzantine mosaics. Then, it's your choice! Explore the cathedral’s cloisters, taking in their serene atmosphere of the monastic complex or ascend the southern tower to the panoramic terraces for a bird’s-eye view over Palermo. (B, L)

 

 

Day 4 | Sunday, May 17, 2026 | Palermo - Marsala | Make your way to Alcamo, a hilltop town deeply nestled in Sicily's largest wine-producing region. Venture off the beaten path and meet a local winemaker. Learn about the local types of grapes and production techniques, before joining a hands-on cooking class. Share the meal you prepared for lunch, paired with the farm's own wines. Late this afternoon, settle into your hotel in coastal marsala for a three-night stay. Perhaps you'll take a sunset walk along the waterfront before heading out for an evening at leisure. (B, L)

 

Day 5 | Monday, May 18, 2026 | Marsala: Discover the ancient craft of sea-salt harvesting during a guided visit to the salt pans of the Stagnone Lagoon.

 

Hop on a boat and take in views of the lagoon. Discover the city of Marsala’s numerous wineries or join an optional full-day excursion to Favignana Island a short waterjet ride from Sicily’s mainland.

 

Day 7: Explore the olive gardens today where we meet an olive oil maker and hear his story about how he stands up against the rules that the Mafia tries to impose on local farmers. Tonight we rest in Agrigento.

 

Days 8-9: Today we wander through the imposing Greek ruins of Agrigento’s Valley of the Temples, travel to Sicily’s northern coast and enjoy a two night stay at a cliffside resort. We visit Cefalu and stroll the medieval streets. You can dip your feet in the Mediterranean at our resort’s private beach!

Days 10-11: Today includes a ferry ride to Aeolian Islands-Isle of Salina. Sail by Vulcano and Lipan on your way. Start your 2 night stay and slow your rhythm to the gentle pace of this small island. Visit Pollara, famous for its traditional caper cultivation. Wander through fields tasting the salted flower buds accompanied by a glass of Malvasia, a locally produced dessert wine. You may find a cafe by the sea and soak in the local life while sampling their every flavor of granita ice slush.

 

Days 12-13: Today we will ferry back to mainland Sicily. Journey along the Ionian Coast to Taormina, a seaside hub of Ancient Greek theaters and hilly walkways, for a two-night stay. See Sicily’s wilder side on an off-road adventure to Mount Etna. Stare at the iconic peak as your vehicle climbs along the sides of Europe’s largest active volcano. Dinner this evening will be surrounded by local musicians.

Day 14: We return home full of lifelong memories.

 

Luggage fees NOT included in price of trip

 

 

Timi's Tours offers Travel Protection through Trip Mate. The Pre-Existing Medical Condition Exclusion Waiver is available if Travel Protection is purchased at the same time you make your Timi's Tours deposit (or within 15 days). For questions about coverage please call our office.

Travel Insurance price per person:

Single: $811.35

Double: $721.15

 

Activity Level: 4

*Our Activity levels are a 1-4 scale. To view what each level includes, please go to the  “Policy” tab on the website*