10-Day Eastern Sicily Cultural and Wine Tasting Itinerary from Palermo

Day 1: Arrival and Exploration

Palermo, Italy on June 3, 2025

9:00am

Breakfast at Antico Caffè Spinnato

Start your day with traditional Sicilian pastries and excellent coffee in this historic Palermo café, a favourite with locals.
EUR10, 1h

10:30am

Visit Palermo Cathedral

Explore Palermo’s impressive cathedral, a blend of architectural styles reflecting Sicily’s diverse history. Opens 7:00am-7:00pm.
EUR5, 1h30m

12:30pm

Lunch at Osteria dei Vespri

Enjoy authentic Sicilian cuisine using local ingredients, including seafood specialties in a charming setting.
EUR30, 1h30m

2:30pm

Palazzo dei Normanni and Cappella Palatina

Discover Norman history and stunning Byzantine mosaics inside one of Palermo’s most important landmarks (8:15am-6:40pm).
EUR12, 2h

5:00pm

Stroll through the Mercato di Ballarò

Experience the vibrant local market with fresh produce, street food and local character.
Free, 1h

8:00pm

Dinner at Il Mirto e la Rosa

Dine on innovative Sicilian dishes with local wines in a refined atmosphere near Teatro Massimo.
EUR40, 2h
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Day 2: Culture and Food

Palermo, Italy on June 4, 2025

8:30am

Breakfast at Bar Alba

Savour cappuccino and fresh cornetti to energise for the day.
EUR8, 30m

9:30am

Teatro Massimo Guided Tour

Tour the largest opera house in Italy and admire its neoclassical architecture (9:00am-6:00pm).
EUR10, 1h

11:00am

Visit Catacombe dei Cappuccini

Explore the eerie underground catacombs with mummified remains dating back centuries (9:00am-12:00pm).
EUR6, 1h

1:00pm

Lunch at Trattoria ai Cascinari

Relish traditional Palermo dishes in a cozy, authentic trattoria.
EUR25, 1h30m

3:00pm

Travel to Cefalù

Drive or take train (approx. 1h) east along the coast to the charming seaside town of Cefalù for the next two nights.
EUR10, 1h

4:30pm

Explore Cefalù Old Town and Beach

Wander medieval streets, visit the Norman Cathedral, and relax by the sandy beach.
Free, 2h

8:00pm

Dinner at La Brace

Enjoy grilled local seafood and Sicilian wines in a lively downtown restaurant.
EUR35, 2h
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Day 3: Coastal Scenic and Cultural

Cefalù, Italy on June 5, 2025

8:00am

Breakfast at Caffè Cordiano

Try Sicilian pastries with a seafront view to start the day.
EUR8, 30m

9:00am

Visit Cefalù Cathedral

Admire the UNESCO-listed Norman Cathedral with its exquisite mosaics (8:00am-7:00pm).
EUR5, 1h

10:30am

Climb La Rocca

Hike the rocky hill overlooking Cefalù for panoramic views and ancient ruins.
Free, 2h

1:00pm

Lunch at Ristorante Le Chat Noir

Enjoy modern Sicilian cuisine with fresh ingredients in a romantic setting.
EUR30, 1h30m

3:00pm

Travel to Taormina

Drive approx. 2h30m along the coast, preparing for your wine and cultural experiences over the coming days.
EUR0, 2h30m

6:00pm

Check into hotel and relax

Stay in a boutique hotel such as Hotel Villa Carlotta, known for stunning views of Mount Etna and the sea.
EUR150/night, Rest

8:00pm

Dinner at Ristorante Otto Geleng

Savour fine Sicilian dining with spectacular views, perfect to soak in Taormina’s atmosphere.
EUR45, 2h
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Day 4: Taormina Culture & Wine

Taormina, Italy on June 6, 2025

8:30am

Breakfast at Bam Bar

Famous for granita and fresh pastries to energise before sightseeing.
EUR8, 30m

9:30am

Visit Teatro Antico di Taormina

Explore the ancient Greco-Roman theatre with stunning views of Mount Etna and the coast (9:00am-7:00pm).
EUR10, 1h30m

11:30am

Wine Tasting at Azienda Agricola Feudo Maccari

Enjoy a wine tour and tasting at this nearby renowned winery specialising in Sicilian varietals like Nero d’Avola. Book ahead.
EUR25, 2h

2:00pm

Lunch at Ristorante La Capinera

Michelin-starred restaurant serving creative local dishes with excellent wine pairings.
EUR60, 1h30m

4:00pm

Leisurely afternoon at Isola Bella

Relax on the beach or explore the nature reserve on the small island connected by a narrow strip of sand.
Entrance free, 2h

8:00pm

Dinner at Trattoria Don Camillo

Casual dining focusing on fresh seafood and Sicilian family recipes in a relaxed setting.
EUR35, 2h
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Day 5: Etna Wine & Nature

Mount Etna Region, Italy on June 7, 2025

8:00am

Breakfast at hotel

Start with a hearty breakfast featuring local produce before heading to Etna.
Included, 1h

9:30am

Travel to Zafferana Etnea

Short drive (~40min) to the base of Mount Etna, a centre for wine production and climbing adventures.
EUR0, 40m

10:30am

Guided Etna Wine Tour & Tasting

Visit vineyards on the volcanic slopes, tasting local Nerello Mascalese wines while learning about Etna’s unique terroir.
EUR30, 3h

2:00pm

Lunch at Azienda Agricola Contrada Marchesa

Enjoy traditional Sicilian dishes paired perfectly with wines produced on site.
EUR35, 1h30m

4:00pm

Visit Etna Park and Cable Car

Take the cable car up Mount Etna to admire volcanic landscapes and viewpoints (check weather, operates until 6:00pm).
EUR40, 2h

7:00pm

Overnight in Randazzo

Choose a charming hotel like Hotel Villa Sonia as a base in the Etna region.
EUR100/night, Rest

8:00pm

Dinner at Locanda Nerello

Dine on Etna region specialities with excellent local wines in a rustic setting.
EUR40, 2h
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Day 6: Etna & Baroque Gems

Randazzo to Taormina, Italy on June 8, 2025

8:00am

Breakfast at hotel

Enjoy local pastries and espresso to prepare for the day.
Included, 1h

9:15am

Visit Randazzo Old Town

Explore medieval streets, Norman churches, and volcanic stone architecture unique to Randazzo.
Free, 2h

11:30am

Travel back to Taormina

Return drive approximately 1h to Taormina for your second stay before heading further south.
EUR0, 1h

1:00pm

Lunch at Pizzeria Villa Zuccaro

Enjoy traditional wood-fired pizzas and Sicilian dishes with a sea view.
EUR20, 1h

2:30pm

Visit Giardini della Villa Comunale

Relax in beautiful public gardens offering lovely views and shade.
Free, 1h

4:00pm

Free afternoon to explore or relax

Shop in local boutiques, explore art galleries, or enjoy the hotel spa.
Varies, 2h

8:00pm

Dinner at Ristorante al Duomo

Dine on refined Sicilian classics steps from Taormina’s main cathedral.
EUR40, 2h
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Day 7: Baroque Siracusa

Siracusa, Italy on June 9, 2025

8:00am

Breakfast at hotel

Fuel up with Sicilian specialties before travelling south to Siracusa.
Included, 1h

9:30am

Travel to Siracusa

Drive approximately 1h15m to Siracusa, a city rich in Greek history and Baroque architecture.
EUR0, 1h15m

11:00am

Visit the Archaeological Park of Neapolis

Explore ancient Greek ruins including the Greek theatre, Roman amphitheatre, and Ear of Dionysius (8:30am-7:00pm).
EUR10, 2h

1:30pm

Lunch at Apollonion Osteria da Carlo

Enjoy traditional Sicilian recipes in Ortigia, the historic heart of Siracusa.
EUR25, 1h30m

3:00pm

Explore Ortigia Island

Walk the charming streets, visit the Duomo and Fountain of Arethusa.
Free, 2h

7:00pm

Check into Grand Hotel Ortigia

Stay in a luxury hotel on the water with stunning views.
EUR160/night, Rest

8:00pm

Dinner at Don Camillo Siracusa

Sample the best seafood dishes paired with regional wines in the heart of Ortigia.
EUR40, 2h
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Day 8: Wine and History

Siracusa, Italy on June 10, 2025

8:30am

Breakfast at hotel

Enjoy a relaxed breakfast overlooking the harbour before your day begins.
Included, 1h

9:30am

Wine Tasting at Feudo di Santa Tresa

A short drive from Siracusa, this winery offers tours and tastings of renowned Sicilian wines (reservation recommended).
EUR25, 2h

12:00pm

Visit Castello Maniace

Explore this 13th-century fortress at the tip of Ortigia, offering remarkable views and history.
EUR5, 1h

1:30pm

Lunch at Sicilia in Tavola

Experience authentic and creative Sicilian home cooking in Ortigia.
EUR30, 1h30m

3:00pm

Leisure time for shopping and exploring local artisan shops

Discover handmade ceramics, jewellery and island crafts in Ortigia’s narrow streets.
Varies, 2h

8:00pm

Dinner at La Foglia

Enjoy a refined last dinner with innovative Sicilian dishes paired with fine wines.
EUR45, 2h
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Day 9: Leisure and Departure Prep

Siracusa to Palermo, Italy on June 11, 2025

8:00am

Breakfast at hotel

Early breakfast before departure.
Included, 45m

9:00am

Travel back to Palermo

Drive approximately 3h to return to Palermo for the final night.
EUR0, 3h

12:30pm

Lunch at Antica Focacceria San Francesco

Indulge one last time in famous Palermo street food like arancini and panelle.
EUR20, 1h

2:00pm

Afternoon at leisure

Relax at your hotel or explore any remaining sights or shops.
Varies, 3h

8:00pm

Farewell Dinner at Ferro di Cavallo

Enjoy a lively, traditional Sicilian meal in this beloved local eatery.
EUR35, 2h
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Day 10: Departure Day

Palermo, Italy on June 12, 2025

7:00am

Early breakfast and check-out

Have a light breakfast at your hotel before heading to the airport.
Included, 1h

8:30am

Transfer to Palermo Airport

Allow approximately 30 minutes travel time to the airport for your departure.
EUR30 by taxi, 30m
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