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 (13 Results)
  • Start Date
    OR, More specific start
  • Length
    to
  • Price
    to
  • Activity Levels
  • Experiences
  • Activities
  • Ships
  • Destinations
    • Sicily
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
Relax in beautiful Sicily
from $8,490
65% OFF
EXPLORE

Longing for La Dolce Vita

Sicily - Italy - 8 Day Itinerary aboard Sea Cloud Spirit
  • Visit Taormina
  • Discover Palermo
  • Explore Lipari
  • Explore Amalfi
Starts / Ends
Catania / Naples
Activity Level
Variable
Embark on an 8-day "Longing for La Dolce Vita" cruise aboard the Sea Cloud Spirit. Begin in Taormina, a town known for its blend of cultures and varied cuisine. Explore Palermo and discover its historic palazzi and gold mosaics, then head to Lipari, an island with volcanic landscapes and a lively harbor town. The trip concludes in Amalfi.
Cruise Details
0
Cruise into charming Sicily
from $2,460
EXPLORE

Amalfi & Sicily

Civitavecchia Round-trip - 8 Day Itinerary aboard Royal Clipper
  • Gaze upon the Sistine Chapel
  • Snorkel at Palmarola
  • Visit historical Pompeii
  • Wander through the grand Duomo
Starts / Ends
Civitavecchia / Civitavecchia
Activity Level
Variable
Board the Royal Clipper on this 8-day cruise to Amalfi & Sicily of the Mediterranean. Admire the perfect architecture and magical landscapes that this region is famous for, visiting Sorrento, Taormina, Amalfi, Ponza, Palmarola, and more! Explore the Sistine Chapel, and the ancient ruins of Pompeii, and even wander through the Pontine Islands.
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
Coast of Ortigia island at city of Syracuse
from $2,590
EXPLORE

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
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
0
Visit Rome's famed Colosseum
from $12,795
EXPLORE

The Amalfi, Sicily and Malta: The Godfather

Rome - Valletta - 12 Day Itinerary aboard 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
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 Taormina, Italy, with Mt. Etna in the background
from $9,920
EXPLORE

Epicurean Delights of Sicily and the Adriatic Coast of Italy

Valletta to Venice - 9 Day Itinerary aboard Le Bougainville
  • Visit Valletta's UNESCO sites
  • Explore ancient Syracuse ruins
  • Visit Taormina's Greek Theater
  • Savor Apulian wine and food
  • Discover Venice’s hidden gardens
  • Enjoy Ravenna's stunning mosaics
  • Mount Etna wine tasting
Starts / Ends
Valletta / Venice
Activities
Archaeological Site Visits, Small Ship Sailing, Wine Tasting
Activity Level
Variable
Embark on a 9-day Le Bougainville trip through Sicily and Italy’s Adriatic coast, visiting UNESCO sites like Valletta, Syracuse, and Venice. Explore ancient ruins, Baroque cities, and medieval towns, while enjoying local wines, cheeses, and dishes prepared by chef Denny Imbroisi.
Cruise Details
0
Beautiful Amalfi Coast
from $2,120
EXPLORE

Amalfi & Sicily

Rome Roundtrip - 7 Day Itinerary aboard Royal Clipper
  • Explore Rome
  • Discover Sorrento
  • Explore Lipari
  • Explore Amalfi
Starts / Ends
Civitavecchia / Civitavecchia
Activity Level
Variable
Embark on a 7-day cruise aboard the Royal Clipper from Civitavecchia. Explore iconic landmarks like St. Peter's and the Colosseum before venturing to Sorrento, Pompeii, and Amalfi. From Taormina's breathtaking Mount Etna views to Lipari's volcanic fireworks, followed by tranquil discoveries in Ponza and Palmarola, it's a captivating cruise that melds history, culture, and nature.
Cruise Details
0
Relax by the sea in sunny Nice
from $7,990
EXPLORE

Isle of Beauty, Italian shores & Malta

Nice - Valletta - 11 Day Itinerary aboard Le Dumont-d'Urville
  • Stroll Promenade des Anglais
  • Explore Napoleon’s exile home
  • Visit Lipari’s obsidian quarries
  • See Valletta’s Grandmasters Palace
Starts / Ends
Nice / Valletta
Activities
Village Visits, Local Market Visits, Spa Relaxation
Activity Level
Variable
Embark on this 11-day cruise across the Mediterranean from Nice to Valletta aboard Le Dumont-d'Urville. Explore Corsica’s charming ports, Sicily’s historical treasures, and the natural beauty of the Aeolian Islands. Visit iconic landmarks like the Calvi Citadel, Portofino’s harbor, and Lipari’s obsidian quarries.
Cruise Details
0
Wander the cobbled streets of Rovinj
from $11,795
EXPLORE

Valletta to Venice: An Adriatic Renaissance

Valletta - Venice - 12 Day Itinerary aboard Douglas Mawson
  • Unveil Valletta’s history
  • Wander Reggio Calabria's sea views
  • Uncover Gallipoli’s coastal charm
  • Visit Bari’s unique Trulli Houses
Starts / Ends
Malta / Venice
Activity Level
Variable
Join a 12-day cruise on the Douglas Mawson, exploring historic routes from Valletta to Venice. Discover the rich legacies of knights and explorers in cities like Split, Dubrovnik, and Ravenna while experiencing the Adriatic's history and culture.
Cruise Details
0
Wander through Rome
from $4,600
EXPLORE

Grand Voyage: Venice to Rome

Venice - Civitavecchia - 16 Day Itinerary aboard Royal Clipper
  • Glide in a gondola in Grand Canal
  • Explore ruins and architecture
  • Swim in Dubrovnik's waters
  • Join an optional tour to Pompeii
Starts / Ends
Venice / Civitavecchia
Activity Level
Variable
On this 16-day Grand Voyage cruise from Venice to Rome, explore the waters across Hvar, Dubrovnik, Civitavecchia, East Corsica, and more. Discover the culture and the beauty of the Mediterranean!
Cruise Details
0
Cruise into charming Sicily
from $4,500
EXPLORE

Grand Voyage: Venice to Rome

17 Day Itinerary aboard Star Flyer
  • Explore Venice's canals
  • Explore ruins and architecture
  • Swim in Dubrovnik's waters
  • Join an optional tour to Pompeii
Starts / Ends
Venice / Civitavecchia
Activity Level
Variable
Embark on a 17-day Grand Voyage from Venice to Rome aboard the Star Flyer. Experience the romantic charm of Venice, the historic allure of Dubrovnik, and the stunning beauty of Sicily. Discover unspoiled beaches, medieval towns, and cultural treasures across Croatia, Montenegro, and Italy.
Cruise Details
0
Piazza Navona, Rome, Italy
from $3,450
EXPLORE

Italy, Montenegro & Croatia

12 Day Itinerary aboard Star Flyer
  • Explore the Sistine Chapel
  • Visit the medieval city of Kotor
  • Cruise through Venice's canals
  • Discover Amalfi's majestic Duomo
Starts / Ends
Civitavecchia / Venice
Activity Level
Variable
Embark on a 12-day cruise aboard Star Flyer, cruising through Italy, Montenegro, and Croatia. Experience historic ports, Mediterranean cuisine, and scenic beauty while enjoying the comfort of a traditional sailing ship.
Cruise Details
0
1-13 of 13 Results
  • 1

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

More Reasons

Why Travel With Adventure Life

All News

Recognized By