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Top Sicily Trips & Tours in September 2026

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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 September 2026 on one of these 6 tours hand-selected by the travel experts at Adventure Life. Explore the best of during September 2026 as you enjoy Archaeological Site Visits, Village Visits, Wine Tasting, Hiking, and Small Ship Sailing. Prices for trips in September 2026 range from $2,320 to $35,480 for a vacation of 8 to 12 days. Choose any of the below 6 itineraries in September 2026 and customize it when you contact one of Adventure Life's expert Sicily trip planners.
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Visit charming Sicily
from $3,568
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Highlights 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
Activity Level
Relaxed
Spend 9 days on this small group journey through the highlights 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.
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Sorrento Landscape
from $3,499
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Sicilian Sunsets & Amalfi Delights

Valletta - Naples - 8 Day Itinerary aboard M/Y Callisto
  • Explore Valletta’s historic port
  • Stroll Trapani’s cobbled streets
  • Visit medieval Erice
  • Indulge in Palermo’s vibrant market
Starts / Ends
Valletta / Naples
Activities
Wine Tasting, Archaeological Site Visits, Village Visits, Local Market Visits
Activity Level
Variable
Embark on an 8-day cruise aboard the MY Callisto from Valletta to Sicily and Southern Italy, exploring historic cities and stunning coastlines. Discover Agrigento, Erice, and Pompeii while enjoying exclusive onboard experiences and authentic Sicilian cuisine.
Cruise Details
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Visit the Baroque Cathedral of Syracuse
from $9,460
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Cruising Southern Italy and Sicily – with Smithsonian Journeys

Valletta - Livorno - 9 Day Itinerary aboard Le Dumont-d'Urville
  • Explore Valletta's heritage
  • Discover Syracuse's history
  • Admire Taormina's scenic views
  • Experience Naples culture
Starts / Ends
Valletta / Livorno
Activity Level
Variable
Sail on this 9-day Southern Italy and Sicily cruise with Smithsonian Journeys aboard Le Dumont-d'Urville. Start in Valletta, Malta, exploring historic landmarks. Visit Syracuse's Greek and cultural sites and Taormina's scenic views and theater. Explore Reggio di Calabria's coast and museum. Visit Civitavecchia, and conclude in Livorno, Tuscany.
Cruise Details
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Beautiful Amalfi Coast
from $2,320
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Amalfi & Sicily

Roundtrip Civitavecchia - 8 Day Itinerary aboard Star Clipper
  • Sail across Mediterranean waters
  • Visit Lipari for coastal views
  • Explore Messina cathedral clock
  • See seaside cliffs near Sorrento
Starts / Ends
Civitavecchia / Civitavecchia
Activities
Urban Exploration
Activity Level
Variable
Experience an 8-day Mediterranean sailing adventure from Civitavecchia, exploring Sicily, the Amalfi Coast, and the Aeolian and Pontine Islands aboard Star Clipper. Sail past Stromboli’s active volcano, wander historic Messina, and admire the coastal beauty of Amalfi and Sorrento. Explore Ponza’s unspoiled charm before returning to Rome’s port.
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Relax in beautiful Sicily
from $3,610
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Rome to Athens

Civitavecchia - Piraeus - 12 Day Itinerary aboard Star Clipper
  • Explore Ponza’s harbor town
  • Discover Sorrento’s ancient cliffs
  • View Lipari’s bustling marina
  • Wander Syracuse’s baroque piazzas
Starts / Ends
Civitavecchia / Piraeus
Activities
Small Ship Sailing
Activity Level
Variable
Join a 12-day cruise on the Star Clipper, starting from Civitavecchia and exploring Italy's Pontine Islands, the Aeolian Islands, and Sicily. Discover Greece's historic sites, including Olympia and picturesque Hydra, before concluding in Athens.
Cruise Details
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Colorful villages line the shores of the Italian riviera
from $4,358
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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.
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