Have questions? We're here.
Visit charming Sicily

Trapani Small Ship Cruises

Travel made your way ™
Talk with an expert
Build your ideal Mediterranean trip. Call 800.344.6118
Start Planning My Trip
Experience the enchanting allure of Sicily with Adventure Life's small ship cruises. Join us on a cruise journey where you can discover the beautiful cities and archaeological wonders of this Mediterranean gem, from Trapani to Valletta. Whether you're exploring ancient sites in Syracuse, marveling at the historic charm of Palermo, or enjoying a relaxing cruise around the island aboard luxurious expedition ships, each moment offers a unique opportunity to immerse yourself in the wonders of Sicily. Engage in archaeological site visits, village tours, and more, all while surrounded by the natural splendor that has captivated travelers for centuries. With tours starting at $2,770 to $35,195, begin your adventure to Sicily today and contact one of Adventure Life's tour specialists for help planning your next seamless trip.
Filter (13 Results)
  • Start Date
    Months
    Years
  • Length
    to
  • Price
    to
  • Activity Levels
  • Experiences
  • Activities
  • Ships
  • Destinations
    • Trapani
Relax in beautiful Sicily
from $3,390
EXPLORE

Sicilian Sunsets & Amalfi Delights

Malta - Naples - 8 Day Itinerary aboard Variety Voyager
  • Explore Agrigento’s Temple Valley
  • Marvel at Trapani’s medieval street
  • Discover Erice’s Venus Castle
  • Taste Palermo’s food delights
Starts / Ends
Valletta / Naples
Activity Level
Variable
Embark on an 8-day cruise aboard the Variety Voyager 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
0
Explore ruins in Sicily
from $6,280
EXPLORE

Authentic Mediterranean Shores

Valletta Roundtrip - 8 Day Itinerary aboard Le Bougainville
  • Explore Valletta’s Historic Streets
  • Discover Segesta’s Ancient Ruins
  • Visit Palermo’s Norman Heritage
  • Explore Syracuse’s Ancient Sites
Starts / Ends
Valletta / Valletta
Activities
Urban Exploration
Activity Level
Variable
Explore Malta and Sicily on an 8-day cruise from Valletta aboard Le Bougainville, visiting Trapani, Erice, Palermo, Monreale, Lipari, Reggio di Calabria, Taormina, Syracuse and Noto, with historic sites, archaeological landmarks and cultural excursions.
Cruise Details
0
Mura di Tramontana (Tramontana Walls) and the Bastione Conca along the historic coastline of Trapani, Sicily, Italy
from $2,770
EXPLORE

Sicily & Malta

Roundtrip Valletta - 8 Day Itinerary aboard Royal Clipper
  • Admire Valletta’s grand churches
  • Discover ancient Syracuse
  • Stroll hillside Taormina
  • Sail the Strait of Messina
Starts / Ends
Valletta / Valletta
Activity Level
Variable
Take an 8-day Sicily and Malta sailing cruise on the Royal Clipper round-trip from Valletta, with stops around Sicily in Syracuse, Taormina, the Aeolian Islands, Palermo, and Trapani. Explore ancient Syracuse, sail the Strait of Messina, and admire the mosaics of Palermo’s Palatine Chapel.
Cruise Details
0
Corso Vittorio Emanuele in the historic center of Trapani, Sicily, Italy
from $3,630
EXPLORE

3 Islands Malta, Sicily & Corsica

Valletta - Civitavecchia - 10 Day Itinerary aboard Royal Clipper
  • Visit the watchtowers of Gozo
  • Discover ancient Syracuse
  • Stroll hillside Taormina
  • Sail the Strait of Messina
Starts / Ends
Valletta / Civitavecchia
Activity Level
Variable
Take a 10-day Mediterranean sailing cruise on the Royal Clipper from Valletta to Civitavecchia. Explore ancient Syracuse, sail the Strait of Messina, stroll hillside Taormina, and spend beach days at Sant’Amanza and L’Arinella before visiting clifftop Bonifacio and lively Bastia.
Cruise Details
0
Cagliari’s historic guardian: the majestic Basilica of Our Lady of Bonaria standing tall above the sparkling Sardinian sea.
from $4,020
EXPLORE

3 Islands Sicily, Sardinia & Corsica

Valletta - Civitavecchia - 11 Day Itinerary aboard Royal Clipper
  • Visit the watchtowers of Gozo
  • Discover ancient Syracuse
  • Explore Cagliari’s Castello quarter
  • Stroll pastel Carloforte
Starts / Ends
Valletta / Civitavecchia
Activity Level
Variable
Take an 11-day Mediterranean cruise on the Royal Clipper from Valletta to Civitavecchia, linking Malta, Sicily, Sardinia, Corsica, and Elba. Explore ancient Syracuse, stroll the medieval old towns of Cagliari and Alghero, and spend a beach day at Sant’Amanza before visiting clifftop Bonifacio.
Cruise Details
0
Explore Italy's Tyrrhenian coast
from $4,020
EXPLORE

Sicily Unveiled with Italian Treasures

Roundtrip Civitavecchia - 11 Day Itinerary aboard Royal Clipper
  • Wander Trapani’s old town
  • Snorkel the coves of Palmarola
  • Stroll clifftop Tropea
  • Visit Cefalu’s Norman cathedral
Starts / Ends
Civitavecchia / Civitavecchia
Activities
Archaeological Site Visits, Small Ship Sailing, Spa Relaxation, Snorkeling
Activity Level
Variable
Sail from Rome’s port to Sicily’s baroque towns, the volcanic Aeolian Islands, and the quiet harbors of the Pontine Islands on an 11-day Italy cruise aboard the Royal Clipper. Explore Palermo’s Norman landmarks, snorkel Palmarola’s coves, and join optional trips to Erice, Paestum, and Pompeii.
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
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
Sunset over Palermo
from $9,200
EXPLORE

Culture and islands of the Mediterranean

Tarragona to Valletta - 12 Day Itinerary aboard Le Bougainville
  • Explore Tarragona’s Roman Heritage
  • Discover Mahon’s Menorcan Culture
  • Visit Ancient Carthage
  • Explore Sicily’s Historic Cities
Starts / Ends
Tarragona / Valletta
Activities
Local Market Visits
Activity Level
Variable
Explore a 12-day Mediterranean journey from Tarragona to Valletta aboard Le Bougainville, visiting Mahon, Cagliari, Tunis, Trapani, Palermo, Reggio di Calabria, Catania and Syracuse. Discover Roman, Phoenician, Greek, Arab, Norman and Baroque heritage across Spain, Tunisia and Italy, with a day at sea to enjoy onboard facilities and activities.
Cruise Details
0
from $9,540
EXPLORE

Culture and Islands of the Mediterranean

Barcelona - Valletta - 12 Day Itinerary aboard L'Austral
  • Visit Menorca
  • Explore Sardinia
  • Discover Sicily
  • Experience Catania
  • Discover Syracuse
  • Discover Malta
Starts / Ends
Barcelona / Valletta
Activity Level
Variable
Embark on a 12-day cruise from Barcelona to Malta aboard L’Austral. Enjoy culinary and cultural experiences with an included excursion per port. Highlights include Menorca, Alghero, Cagliari, Trapani, Palermo, Lipari, Catania, Syracuse, Gozo, and ending in Valletta.
Cruise Details
0
Explore Agropoli, Italy
from $4,430
EXPLORE

Sicily Unveiled with Italian Treasures

Roundtrip Civitavecchia - 12 Day Itinerary aboard Royal Clipper
  • Admire Palermo’s Palatine Chapel
  • Wander Trapani’s old town
  • Visit Cefalu’s Norman cathedral
  • Explore Lipari’s acropolis
Starts / Ends
Civitavecchia / Civitavecchia
Activity Level
Variable
Take a 12-day round-trip cruise on the Royal Clipper through Sicily and southern Italy, departing from Civitavecchia and stopping in Trapani, Palermo, the Aeolian Islands, Calabria, and the Amalfi Coast. Explore Palermo’s Norman landmarks, visit Amalfi’s Duomo, and join optional trips to Erice, Paestum, and Pompeii.
Cruise Details
0
Gelato Shop
from $18,695
EBD
EXPLORE

Sailing 'The Med': A Mediterranean Feast

Valletta - Lisbon - 18 Day Itinerary aboard MV Douglas Mawson
  • Wander Valletta Barrakka Gardens
  • Tour Agrigento ancient ruins
  • Taste Tangier street food
  • Sip Portuguese wines
Starts / Ends
Valletta / Lisbon
Activities
Wine Tasting, Village Visits
Activity Level
Variable
Join an 18-day Mediterranean cruise on the Douglas Mawson, exploring the culinary heritage from Malta and Sicily to Spain and Morocco. Discover local traditions, seafood delights, and vibrant markets while visiting charming villages and historic wineries.
Cruise Details
0
Relax in beautiful Sicily
from $9,490
EXPLORE

A Circumnavigation of Sicily with Smithsonian Journeys

Valletta Roundtrip - 9 Day Itinerary aboard Le Dumont-d'Urville
  • Visit Valleta a UNESCO-listed city
  • Visit Valley of Temples
  • Witness a fiery volcano
  • Discover Trapani's diverse heritage
Starts / Ends
Valletta / Valletta
Activity Level
Variable
Set sail on a 9-day Sicily cruise aboard Le Dumont-d'Urville. Visit UNESCO sites like Valletta and the Valley of Temples, admire Stromboli’s volcanic activity, explore vibrant cities such as Palermo and Syracuse, and discover ancient ruins, diverse cultures, and beautiful coastal views.
Cruise Details
0
1-12 of 13 Results
  • 1
  • 2

Let us match you to your best adventure.

Talk with an expert trip planner 800.344.6118

Plan My Trip
Kassandra Magruder Adventure Life employee profile
Kassandra M.
Visit charming Sicily
Mediterranean

Chat Trapani 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
800.344.6118

Where is your next adventure?

Contact Chat Call

Why Travel With Us?

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.

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.

Expert Guidance

With deep destination expertise in complex travel, we advise on how to maximize your time, avoid common pitfalls, 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.