Have questions? We're here.
Explore ruins in Sicily

Sicily Sailing Cruises

Travel made your way
Talk with an expert
Build your ideal Mediterranean trip. Call 1.406.541.2677
Start Planning My Trip
Experience the wonders of Italy, Montenegro, and Croatia on a small ship sailing adventure with Adventure Life this year. Explore the heavenly scent of lavender in the fields of Hvar, witness the awe-inspiring beauty of Dubrovnik, and sail through the narrow Strait of Otranto. From archaeological site visits to snorkeling excursions and optional tours to Pompeii, this cruise offers a relaxed pace suitable for all travelers. Delight in the charming cobbled villages, grand cathedrals, and breathtaking landscapes of the Eastern Mediterranean. Don't miss this opportunity to immerse yourself in the cultural and natural treasures of this enchanting region. Contact one of Adventure Life's tour specialists for help planning your next seamless trip.
Filter (23 Results)
  • Start Date
    OR, More specific start
  • Length
    to
  • Price
    to
  • Activity Levels
  • Experiences
  • Activities
  • Ships
  • Destinations
    • Sicily
Coast of Ortigia island at city of Syracuse
from $3,195
EXPLORE

The Best of the Mediterranean

Roundtrip Valletta - 8 Day Itinerary aboard MV La Belle de L'Adriatique
  • Explore Saint John's Baroque
  • Taste chocolate in Modica
  • Ascend mighty Mount Etna
  • Stroll Mdina’s medieval streets
Starts / Ends
Valletta / Valletta
Activity Level
Variable
Discover the best of the Mediterranean as you explore the magic of Malta and Sicily on an 8-day cruise aboard La Belle de l’Adriatique, featuring UNESCO sites, historic towns, and local flavors. From Valletta to Syracuse, enjoy every excursions, cultural treasures, and vibrant onboard festivities.
Cruise Details
0
Visit Rome's famed Colosseum
from $12,795
EBD
EXPLORE

The Amalfi, Sicily and Malta: The Godfather

Rome - Valletta - 12 Day Itinerary aboard MV Douglas Mawson
  • Discover Rome’s imperial relics
  • Explore Gaeta’s medieval fortress
  • Wander Naples’ ancient streets
  • Marvel at Pompeii’s ruins
Starts / Ends
Rome / Valletta
Activities
Wine Tasting
Activity Level
Variable
Join this 12-day cruise on the Douglas Mawson, exploring Southern Italy, Sicily, and Malta's stunning history and culture. Experience the Amalfi Coast, ancient cities, and Malta's heritage while savoring local cuisine and vibrant Mediterranean life.
Cruise Details
0
Beautiful Amalfi Coast
from $2,660
EXPLORE

Amalfi & Sicily

Roundtrip Civitavecchia - 8 Day Itinerary aboard Royal Clipper
  • Reach Civitavecchia
  • View Sorrento’s city walls
  • Wander Agropoli’s medieval center
  • Admire Lipari’s Acropolis
Starts / Ends
Civitavecchia / Civitavecchia
Activity Level
Variable
Experience an 8-day Mediterranean cruise from Civitavecchia, Rome, on the Royal Clipper, visiting Sorrento, Agropoli, Taormina, and the stunning Pontine Islands. Explore ancient ruins, enjoy the scenic Amalfi Coast, and snorkel the vibrant coral beaches before returning to Rome.
Cruise Details
0
Athens Acropolis
from $1,740
EXPLORE

Sicily & Greece

Piraeus - Valletta - 6 Day Itinerary aboard Star Clipper
  • Explore Athens ancient Agora
  • Walk Monemvasia twisting alleys
  • Wander Syracuse baroque piazzas
  • Discover Valletta capital
Starts / Ends
Piraeus / Valletta
Activity Level
Variable
Embark on a 6-day Mediterranean cruise from Piraeus to Valletta aboard the Star Clipper, visiting historic sites in Greece, Italy, and Malta. Highlights include Monemvasia, Pilos, and Syracuse, concluding in Valletta, a UNESCO World Heritage site.
Cruise Details
0
Explore the ancient Acropolis
from $2,290
SS 25%
EXPLORE

Sicily & Greece

Piraeus - Valletta - 7 Day Itinerary aboard Royal Clipper
  • Wander Athens Ancient Agora
  • Explore Pylos Navarino Bay
  • Explore Syracuse’s historical ruins
  • Visit Valletta’s museums palaces
Starts / Ends
Piraeus / Valletta
Activity Level
Variable
Set sail on a 7-day Mediterranean cruise from Piraeus to Valletta aboard the Royal Clipper, exploring historic Athens, Monemvasia's Byzantine fortress, and Pylos, famous for King Nestor’s Palace. Discover Sicily's Syracuse and Malta's Gozo, known for diving and coastal caves, before concluding in the fortified capital of Valletta.
Cruise Details
0
Beautiful Amalfi Coast
from $2,320
SS 25%
EXPLORE

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.
Cruise Details
0
Explore Agropoli, Italy
from $3,350
EXPLORE

Sicily Unveiled with Italian Treasures

Roundtrip Civitavecchia - 11 Day Itinerary aboard Star Clipper
  • Sail coastlines of Sicily
  • Cruise Aeolian Islands
  • Visit Trapani port
  • Explore Palermo streets
Starts / Ends
Civitavecchia / Civitavecchia
Activities
Local Market Visits
Activity Level
Variable
Sail Italy’s southern coast on an 11-day cruise aboard Star Clipper. Experience Sicily, the Aeolian Islands, Calabria, and the Amalfi Coast, navigating volcanic landscapes, historic ports, and small island harbors for an intimate sailing experience.
Cruise Details
0
Explore Sibenik on the Dalmatian Coast
from $3,870
EXPLORE

Italy, Montenegro & Croatia

Venice - Civitavecchia - 12 Day Itinerary aboard Royal Clipper
  • Admire Venice’s domes
  • Wander Rovinj’s medieval streets
  • Discover Sibenik’s coastal lanes
  • Explore Kotor’s medieval town
Starts / Ends
Venice / Civitavecchia
Activities
Snorkeling
Activity Level
Variable
Set sail on a 12-day Royal Clipper cruise through the Mediterranean, visiting stunning destinations like Venice, Dubrovnik, and Syracuse. Experience rich history and culture while enjoying scenic views and a relaxing day at sea before concluding in Civitavecchia, near Rome.
Cruise Details
0
Monemvasia - View from the Top
from $3,740
EXPLORE

Athens to Rome

Piraeus - Civitavecchia - 12 Day Itinerary aboard Star Clipper
  • Explore Athens ancient Agora
  • Discover Hydra Monastery of Ilias
  • Tour Monemvasia Byzantine port
  • Visit Gythio picturesque streets
Starts / Ends
Piraeus / Civitavecchia
Activities
Archaeological Site Visits, Small Ship Sailing, Village Visits
Activity Level
Variable
Set sail on a 12-day Mediterranean cruise aboard the Star Clipper, exploring historic sites from the Acropolis in Athens to the ruins of Olympia, and enjoying charming towns like Taormina and Ponza. Experience ancient culture and stunning vistas before disembarking in Civitavecchia.
Cruise Details
0
Relax in beautiful Sicily
from $3,610
EXPLORE

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
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
0
Clifftop towns on Italy's Tyrrhenian coast
from $2,500
SS 25%
EXPLORE

Icons of the Italian Coast

Roundtrip Civitavecchia - 8 Day Itinerary aboard Star Clipper
  • Stroll Ponza to see pastel houses
  • Admire Sorrento on the Amalfi Coast
  • Wander Agropoli’s medieval center
  • Visit Lipari to see the Acropolis
Starts / Ends
Civitavecchia / Civitavecchia
Activity Level
Variable
Embark on an 8-day roundtrip cruise from Civitavecchia on the Star Clipper, visiting stunning volcanic islands and charming coastal towns. Highlights include Lipari's Acropolis, Stromboli's volcano, Taormina near Mount Etna, Agropoli's medieval charm, Sorrento with Pompeii access, and the picturesque Pontine Islands.
Cruise Details
0
Athens Acropolis
from $2,820
EXPLORE

Sicily & Greece

Piraeus - Valletta - 9 Day Itinerary aboard Star Flyer
  • Explore Milos Sarakiniko Bay
  • Visit Chania Venetian harbor
  • Walk Gythio streets
  • Explore Valletta the walled city
Starts / Ends
Piraeus / Valletta
Activity Level
Variable
Experience a 9-day Mediterranean sailing cruise on the Star Flyer, exploring ancient Athens, stunning Milos, and the charming alleys of Chania. Visit historic sites in Gythio, Pylos, Syracuse, Gozo, and end in Valletta, famous for its fortified city and gardens.
Cruise Details
0
1-12 of 23 Results
  • 1
  • 2

Real experience. Honest advice.

Talk with an expert trip planner 1.800.344.6118

Plan My Trip
Tilly Pearson employee headshot
Tilly P.
Sail to the stunning city of Taormina, Sicily.
Mediterranean

Chat Sicily with a specialist

Our team is waiting and ready to talk with you about your next adventure. So go ahead and book an appointment with one of our specialized trip planners.

Let's Chat
1.800.344.6118

Where is your next adventure?

Contact Chat Call

Why Travel With Us?

Unbiased Cruise Expertise

We're not tied to any one cruise line, so you receive honest guidance on the best ship and itinerary for you—not a sales pitch.

Rewards That Go Further

Secure your 5% Past Traveler Rewards across a wide range of ships and destinations - not a single brand and not just cruises.

More Value, Less Risk

Our extensive travel experience helps you avoid common pitfalls, maximize your time, and get the most out of every part of your trip.

As Featured In

How it Works

Connect

No cost, no commitment. Talk with our experts about your dream trip.

Plan

Share your travel style—we match you with the right itinerary or create one just for you.

Book

Lock in knowing every detail is handled and you’re fully supported.

Travel

Enjoy a seamless journey—and unlock 5% off your next adventure.