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Top Sicily Trips & Tours in October 2025

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Balate Dorin
Visit charming Sicily
Amalfi
Explore Italy's colorful Amalfi coast
Venice
See the famed Rialto bridge in Venice
Rome
The Roman Colosseum in autumn
Naples
Naples at Sunset, Italy
Capri
Sail around the beautiful Italian island of Capri
Civitavecchia
Aleksander Nalbantjan
Visit the Forum Romanum, the center of ancient Rome
Sorrento
Sorrento, Italy
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Discover Sicily in October 2025 on one of these 5 tours hand-selected by the travel experts at Adventure Life. Explore the best of during October 2025 as you enjoy Archaeological Site Visits, Hiking, Village Visits, Wine Tasting, and Local Market Visits. Prices for trips in October 2025 range from $2,590 to $18,000 for a vacation of 8 to 9 days. Choose any of the below 5 itineraries in October 2025 and customize it when you contact one of Adventure Life's expert Sicily trip planners.
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    • Sicily
Visit charming Sicily
from $3,000
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Treasures of Sicily

Italy Small Group Tour - 9 Day Itinerary
  • Visit the Island of Sicily
  • Discover the Valley of the Temples
  • Visit Taormina's ancient ruins
  • See the Mount Etna in Sicily
  • Explore the coastal town of Cefalu
  • Visit Syracuse's Archeological Park
  • Discover the Zingaro Nature Reserve
Starts / Ends
Viagrande / Taormina
Activities
Hiking, Wine Tasting, Village Visits
Activity Level
Relaxed
Spend 9 days on this small group journey through the treasures of Sicily to step into a world where ancient ruins stand alongside vibrant cities and picturesque landscapes. Discover ancient ruins, bask in the island's natural beauty, and indulge in Sicily's culinary delights.
Tour Details
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Colorful villages line the shores of the Italian riviera
from $4,357
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Aeolian Archipelago

Lipari to Salina - 8 Day Itinerary
  • Discover Lipari and Salina
  • Visit a local winery
  • Enjoy a scenic hike in Vulcano
  • Swim in Cala Junco nature reserve
  • Take a walking tour in Stromboli
  • Relax on the beaches of Salina
Starts / Ends
Milazzo / Milazzo
Activity Level
Relaxed
Experience the nature and culture of the Aeolian Archipelago on this 8-day tour. Visit Lipari, Vulcano, Panarea, Stromboli, Filicidu, and Salina, which form one of the most active geological structures in the Mediterranean. Explore these beautiful coastal towns, visiting incredible volcanic rock formations and seafront black sand beaches.
Tour Details
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Coast of Ortigia island at city of Syracuse
from $2,590
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Sicily & Greece

Piraeus - Valletta - 9 Day Itinerary aboard Star Clipper
  • Explore Piraeus port city
  • Wander Nafplio charming town
  • Discover Monemvasia fortress
  • Visit Syracuse ruins
Starts / Ends
Piraeus / Valletta
Activities
Archaeological Site Visits, Small Ship Sailing
Activity Level
Variable
Set sail on a 9-day cruise with Star Clipper, exploring Greece, Sicily, and Malta. Discover ancient sites, stunning landscapes, and cultural gems from Athens to Valletta while enjoying the charm of your ship.
Cruise Details
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Explore ruins in Sicily
from $6,330
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Cruising the Mediterranean: Sicily, Sardinia, and Mallorca – with Smithsonian Journeys

Valletta - Tarragona - 8 Day Itinerary aboard L'Austral
  • Visit UNESCO charm in Valletta
  • Explore Tarragona's Roman ruins
  • Indulge in Sicilian seafood
  • Stroll Mahon's colorful streets
Starts / Ends
Valletta / Tarragona
Activities
Local Market Visits
Activity Level
Variable
Experience an 8-day cruise aboard L'Austral, exploring cultural treasures in the Mediterranean's historic ports. From UNESCO-listed Valletta to the Roman ruins of Tarragona, delve into the region's rich heritage and scenic beauty.
Cruise Details
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Beautiful Taormina, Italy, with Mt. Etna in the background
from $5,750
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Ancient Jewels of the Mediterranean

Valletta - Athens - 8 Day Itinerary aboard Le Bougainville
  • Meet a famous puppeteer in Syracuse
  • Immerse in Southern Italy
  • Wander through the ancient streets
  • Visit the Taormina in Sicily
Starts / Ends
Valletta / Athens
Activity Level
Variable
Set sail on an 8-day Ancient Jewels of the Mediterranean cruise aboard Le Bougainville. Explore Malta's coast and Greece's treasures. Discover Syracuse's puppetry, Paros' villages, and Taormina's ancient theatre. Experience Gallipoli, Galaxidi, Hydra, and Paros.
Cruise Details
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