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 (29 Results)
  • Start Date
    OR, More specific start
  • Length
    to
  • Price
    to
  • Activity Levels
  • Experiences
  • Activities
  • Ships
  • Destinations
    • Sicily
Sunset over Palermo
from $8,910
EXPLORE

Epicurean Delights: The Food & Wine of Sicily

Valletta Roundtrip - 9 Day Itinerary aboard Le Dumont-d'Urville
  • Visit Valley of Temples
  • Walk Palermo’s historic streets
  • Visit Taormina’s Greco-Roman theatr
  • Wander Syracuse’s old town
Starts / Ends
Valletta / Valletta
Activity Level
Variable
Sail roundtrip from Valletta on a 9-day cruise through Sicily aboard Le Dumont-d’Urville. Discover Palermo, Syracuse, Taormina, and more as you explore UNESCO-listed ruins, charming island villages, and volcanic landscapes rich in history and culture.
Cruise Details
0
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
Sicilian landscape in the early evening
from $2,080
EXPLORE

Amalfi & Sicily

Civitavecchia Roundtrip - 7 Day Itinerary aboard Star Clipper
  • Explore Civitavecchia wonders
  • Discover Lipari lively streets
  • Witness Stromboli’s volcano
  • Experience Amalfi seaside views
Starts / Ends
Civitavecchia / Civitavecchia
Activity Level
Variable
Embark on a 7-day cruise aboard the Star Clipper, starting from Civitavecchia and visiting Italy's beautiful coastal spots like the Aeolian Islands and Amalfi. Conclude your journey with easy access to explore Rome.
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
Explore the colorful villages of Parga
from $7,150
EXPLORE

Ancient Cities of the Mediterranean

Valletta - Athens - 9 Day Itinerary aboard Le Bougainville
  • Explore ancient Syracuse ruins
  • Tour Sparta’s ancient port
  • Wander Monemvasia’s medieval alleys
  • Climb Nafplion’s hill fortress
Starts / Ends
Valletta / Athens
Activity Level
Variable
Embark on a 9-day Ancient Cities of the Mediterranean cruise from Valletta to Athens, exploring Syracuse, Reggio di Calabria, Gallipoli, Parga, Gythio, Monemvasia, and Nafplion. Discover a mix of ancient ruins, medieval towns, and coastal views aboard Le Bougainville. Each stop offers insight into centuries of Mediterranean culture and heritage.
Cruise Details
0
Athens Acropolis
from $1,740
Air Credit
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
Activities
Small Ship Sailing, Archaeological Site Visits
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
View from mount Solaro of Capri island at summer day, Italy
from $11,425
EXPLORE

Early Summer Mediterranean Style

Valletta - Nice - 11 Day Itinerary aboard Sea Cloud Spirit
  • Discover Valletta's architecture
  • Experience Ortigia’s Old Town
  • Explore Corsica, Sardinia and Calvi
  • Discover Amalfi and Amalfi Coast
Starts / Ends
Valletta / Nice
Activity Level
Variable
Sail from Malta to France on an 11-day Early Summer Mediterranean cruise aboard the Sea Cloud Spirit. Visit Valletta’s historic streets, Syracuse’s ancient ruins, and Taormina’s views of Mount Etna. Cruise past the Amalfi Coast, visit Capri’s grottos, Corsica’s cliffs, Sardinia’s Catalan past, and Calvi’s beaches. End in St. Tropez and scenic Nice.
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
Village Visits, 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
Air Credit
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
1-12 of 29 Results

Plan smarter. Spend better.

Talk with an expert trip planner 1.800.344.6118

Plan My Trip
Jason Maynard employee profile
Jason M.
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
More Reasons

Why Travel With Adventure Life

All News

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.

Mediterranean Travel Guide

Favorite Mediterranean Mediterranean All Trips

Top Mediterranean Travel Destinations

Mediterranean Trips by Departure Date

Top Experiences in Mediterranean

Mediterranean Trips by Duration

Mediterranean Trips by Activity