Have questions? We're here.
Beautiful Amalfi Coast

Sailing Trips in Mediterranean

Travel made your way ™
Talk with an expert
Build your ideal Mediterranean trip. Call 1.406.541.2677
Start Planning My Trip
Talk with an expert
Filter (46 Results)
  • Start Date
    OR, More specific start
  • Length
    to
  • Price
    to
  • Activity Level
  • Experiences
  • Activities
  • Ships
  • Destinations
    • Mediterranean
Bonifacio, Corsica, France
$1,880
EXPLORE

Corsica & French Riviera

7 Day Itinerary aboard Royal Clipper
  • Discover Portofino
  • Explore Bastia
  • Discover Sant' Amanza
  • Experience East Corsica
Starts / Ends:
Cannes / Cannes
Activities:
Small Ship Cruises, Small Ship Sailing
Activity Level:
Variable
Embark on a 7-day cruise aboard the Royal Clipper in Cannes, France. This glamorous city is known for its luxurious lifestyle and the famous Cannes Film Festival. Next, visit the picturesque fishing village of Portofino, Italy, with its colorful houses and stunning views. Explore the beautiful …
Cruise Details
0
Calvi, Corsica, France
$1,320
EXPLORE

Corsica & French Riviera

5 Day Itinerary aboard Royal Clipper
  • Discover Cannes
  • Experience Calvi
  • Explore Monaco
  • Experience St. Tropez
Starts / Ends:
Cannes / Cannes
Activities:
Small Ship Cruises, Small Ship Sailing
Activity Level:
Variable
Embark on a 5-day cruise aboard the Royal Clipper through the Mediterranean, starting in the glamorous city of Cannes, France. Known for its glittering lifestyle and prestigious Cannes Film Festival, this resort city offers luxury and elegance. From there, sail to Calvi, Corsica, where this …
Cruise Details
0
Coast of Ortigia island at city of Syracuse
$2,280
EXPLORE

Sicily & Greece

Piraeus - Valletta - 9 Day Itinerary aboard Star Clipper
  • See Nafplio's Venetian buildings
  • Visit Monemvasia, a Byzantine city
  • See historic Taormina and Syracuse
  • Explore Malta's cultural heritage
Starts / Ends:
Piraeus / Valletta
Activities:
Archaeological Site Visits, Small Ship Cruises, Small Ship Sailing
Activity Level:
Variable
On this 9-day Sicily & Greece cruise from Piraeus to Valletta aboard the Star Clipper, embark on an adventure through ancient and historic destinations, starting in Athens, the birthplace of democracy. Visit Nafplio, a charming seaport town in Greece, followed by the fortified Byzantine city of …
Cruise Details
0
An aerial view of the city Malaga
$2,590
EXPLORE

Malta, Balearic Islands & Spain

11 Day Itinerary aboard Star Flyer
  • Relax aboard a majestic tall ship
  • Gaze upon Palma's Gothic cathedral
  • Visit the World Heritage City
  • Explore Cagliari, Sardinia
Starts / Ends:
Valletta / Malaga
Activities:
Small Ship Cruises, Small Ship Sailing
Activity Level:
Variable
Join us on a delightful sailing experience and relax in some of the most historical and magical destinations in the Mediterranean. Enjoy the easy-going informality aboard your tall ship, finding that there are no rigid schedules and you are free to do as you wish with your days and evenings. Start …
Cruise Details
0
Donkeys are a traditional form of transportation in Greece
$3,030
$100 OBC
EXPLORE

Greece, Montenegro & Croatia

Piraeus - Venice - 12 Day Itinerary aboard Star Flyer
  • Discover Mykonos
  • Experience Santorini
  • Explore Corfu
  • Discover Kotor
Starts / Ends:
Piraeus / Venice
Activities:
Archaeological Site Visits, Small Ship Cruises, Small Ship Sailing
Activity Level:
Variable
Embark on a 12-day cruise aboard the Star Flyer through the stunning destinations of Piraeus, Mykonos, Santorini, Katakolon, Corfu, Kotor, Dubrovnik, Korcula, Hvar, Cres, and Venice. Explore the ancient wonders of Athens, where the Agora whispers tales of great philosophers. Immerse yourself in the …
Cruise Details
0
Cannes at sunset
$3,640
EXPLORE

Grand Voyage: Malaga to Cannes

16 Day Itinerary aboard Star Flyer
  • Gaze upon Malaga's architecture
  • Explore luxurious Ibiza
  • Try your hand at sailing
  • Admire St. Tropez's famous beaches
Starts / Ends:
Malaga / Cannes
Activities:
Local Market Visits, Small Ship Cruises, Small Ship Sailing, Village Visits
Activity Level:
Variable
On this 15-day sailing voyage, admire Palma's enormous Gothic cathedral, a powerful symbol of the religious fervor which gripped all of Spain shortly after the defeat of the Moors. Discover Mahon's heritage, including the invention of mayonnaise and the first distillation of gin from …
Cruise Details
0
Hydra Island, Greece
$2,170
EXPLORE

Sicily & Greece

Piraeus to Valletta - 9 Day Itinerary aboard Star Flyer
  • Ride a donkey on Hydra
  • Visit Sicily's archaeological sites
  • Explore historic Pilos
  • Discover Gozo, a diving destination
Activities:
Archaeological Site Visits, Small Ship Cruises, Small Ship Sailing
Activity Level:
Variable
Start your tall ship sailing expedition in the ancient city of Athens, the birthplace of democracy and epicenter of western civilization, a city for all eternity. Visit Syracuse, a city on the Ionian coast of Sicily that's known for its ancient ruins. It was once the largest city in the world, …
Cruise Details
0
Wander through the vibrant streets of Barcelona
$7,940
EXPLORE

A Solar Eclipse at Sea: Voyage Across the Western Mediterranean - with Smithsonian Journeys

Barcelona - Nice - 9 Day Itinerary aboard Le Dumont-d'Urville
  • Witness solar eclipse in Palma
  • Explore Palma de Mallorca’s coves
  • Discover Mahon’s colorful streets
  • See Portofino’s harbor
Starts / Ends:
Barcelona / Nice
Activities:
Local Market Visits, Small Ship Sailing, Village Visits
Activity Level:
Variable
This 9-day Mediterranean cruise from Barcelona to Nice aboard Le Dumont-d'Urville offers a blend of history, culture, and natural beauty, with a once-in-a-lifetime celestial event. On August 12, 2026, experience a total solar eclipse aboard Le Dumont-d'Urville as it sails near Palma de …
Cruise Details
0
A beautiful marina, Cannes at night
$2,030
EXPLORE

Corsica & French Riviera

8 Day Itinerary aboard Star Flyer
  • Experience Cannes
  • Discover Ile Rousse
  • Explore Calvi
  • Enjoy St. Tropez
Starts / Ends:
Cannes / Cannes
Activities:
Small Ship Cruises, Small Ship Sailing
Activity Level:
Variable
Embark on an 8-day cruise to and from Cannes aboard the Star Flyer. Discover the Mediterranean's charm with visits to glamorous Cannes, scenic Portofino, the quaint towns of Ile Rousse and Calvi in Corsica, the serene beauty of Plage Saint Antoine and Saint-Raphaël, and the vibrant …
Cruise Details
0
City of Dubrovnik
$2,375
EXPLORE

Dalmatian Paradise

Split Roundtrip - 8 Day Itinerary aboard Nautilus
  • Stroll to Mljet National Park
  • Enjoy the spectacular views
  • Explore remote beaches
  • Wander along Korcula
Starts / Ends:
Split / Split
Activities:
Archaeological Site Visits, Small Ship Sailing, Village Visits
Activity Level:
Relaxed
Join Nautilus on this 8-day luxurious Croatian cruise that departs from Split, Dalmatian Paradise, and is a round-trip journey that includes stops in Dubrovnik and notable Croatian islands. In the mornings, you can unwind on sizable decks, sunbathe, or cool yourself in the Adriatic Sea. The …
Cruise Details
0
Korcula Island
$2,825
EXPLORE

Dalmatian Paradise

Split Roundtrip - 8 Day Itinerary aboard MV Futura
  • Stroll to Mljet National Park
  • Enjoy the spectacular views
  • Explore remote beaches
  • Wander along Korcula
Starts / Ends:
Split / Split
Activities:
Archaeological Site Visits, Small Ship Sailing, Village Visits
Activity Level:
Variable
Join MV Futura on this 8-day luxurious Croatian cruise that departs from Split, Dalmatian Paradise, and is a round-trip journey that includes stops in Dubrovnik and notable Croatian islands. In the mornings, you can unwind on sizable decks, sunbathe, or cool yourself in the Adriatic Sea. The …
Cruise Details
0
Rock of Gibraltar
$3,860
EXPLORE

Spain, Morocco & Portugal

14 Day Itinerary aboard Royal Clipper
  • View Bonifacio's natural beauty
  • Explore luxurious Ibiza
  • Discover charming Motril
  • Visit Malaga to view architecture
Starts / Ends:
Civitavecchia / Lisbon
Activities:
Small Ship Cruises, Small Ship Sailing
Activity Level:
Variable
Embark on a 14-day cruise aboard the Royal Clipper, discovering the Mediterranean, starting in Civitavecchia, and exploring Rome's iconic landmarks. Visit picturesque Bonifacio in Corsica, elegant Mahon in Menorca, and historic Palma de Mallorca. Sail to vibrant Ibiza, discover Cartagena's …
Cruise Details
0
Cruise into charming Sicily
$2,190
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
Activities:
Archaeological Site Visits, Small Ship Cruises, Small Ship Sailing
Activity Level:
Variable
Embark on an 8-day cruise aboard Royal Clipper through Amalfi and Sicily! Explore Rome's iconic landmarks like St. Peter's and the Colosseum before hitting Sorrento's stunning coast. Dive into history at Pompeii and relish Amalfi's medieval charm, from its Duomo to the picturesque …
Cruise Details
0
View of Valletta
$4,060
EXPLORE

Grand Voyage: Athens to Malaga

19 Day Itinerary aboard Star Flyer
  • Admire romantic town Nafplio
  • Explore Syracuse's ancient ruins
  • Enjoy leisurely discovery
  • Visit Palma's Gothic cathedral
Starts / Ends:
Piraeus / Malaga
Activities:
Archaeological Site Visits, Local Market Visits, Small Ship Cruises, Small Ship Sailing
Activity Level:
Variable
From the stunning Balearic Islands to quixotic tiny port towns along the Italian Riviera, this 19-day sailing cruise takes you to an impressive collection of ports. Sail through an iron fortress gate to the town of Monemvasia, a perfectly preserved Byzantine fortified port with tons of history and …
Cruise Details
0
Piazza Navona, Rome, Italy
$3,030
$100 OBC
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
Activities:
Archaeological Site Visits, Small Ship Cruises, Small Ship Sailing
Activity Level:
Variable
Cruise from Rome to Venice on this 12-day cruise aboard Star Flyer, exploring Italy, Montenegro, and Croatia's historic ports and cultural landmarks. From Civitavecchia's Roman history to Amalfi's medieval charm and Messina's Sicilian delights, enjoy traditional sailing at sea. …
Cruise Details
0
Admire sun-soaked Malaga
$1,880
EXPLORE

Grand Prix Trials

7 Day Itinerary aboard Royal Clipper
  • Explore Malaga
  • Discover Granada
  • Experience Ibiza
  • Visit Mahon
Starts / Ends:
Malaga / Cannes
Activities:
Small Ship Cruises, Small Ship Sailing
Activity Level:
Variable
Embark on a 7-day cruise aboard the Royal Clipper through the stunning destinations of Malaga, Ibiza, Mahon, Fontvieille, and Cannes. In Malaga, marvel at the magnificent Moorish architecture of the Alcazaba and Castillo de Gibralfaro. Granada awaits with the breathtaking Alhambra Palace, a …
Cruise Details
0
Visit Rome's famed Colosseum
$12,795
EXPLORE

The Amalfi, Sicily and Malta: The Godfather

Rome to Malta - 12 Day Itinerary aboard Douglas Mawson
  • Guided Tour of Rome
  • Vatican City Exploration
  • Sicilian Wine Tasting
  • Explore Pompeii Ruins
  • Discover Amalfi Coast
  • Stroll Baroque Town of Ragusa
  • Valletta’s Historical Sights
Starts / Ends:
Rome / Valletta
Activities:
Archaeological Site Visits, Small Ship Sailing, Village Visits, Wine Tasting
Activity Level:
Variable
This 12-day Douglas Mawson adventure takes you from Rome to Sicily and Malta, blending historical highlights, scenic vistas, and cultural experiences. Start in Rome, where guided tours reveal iconic sites like the Colosseum, Trevi Fountain, and Vatican City. Continue to Sicily’s Porto …
Cruise Details
0
Evening lights of Marseille
$13,595
EXPLORE

Mediterranean Masterpiece

Spain to Rome - 13 Day Itinerary aboard Douglas Mawson
  • Enjoy Flamenco night
  • Explore Barcelona’s Sagrada Familia
  • Stroll Las Ramblas' streets
  • Visit the Vatican Museums
  • Tour historical Rome's sites
Starts / Ends:
Barcelona / Rome
Activities:
Archaeological Site Visits, Festival Visits, Small Ship Sailing, Village Visits, Wine Tasting
Activity Level:
Variable
Experience Spain and Italy on a 13-day Douglas Mawson adventure with personalized excursions at key destinations. Start in Barcelona, where a representative meets you at the airport for a smooth transfer to your hotel. Enjoy an evening Flamenco event that showcases Spain’s dance and music …
Cruise Details
0
19-36 of 46 Results
TrustScore 4.8 | 387 reviews
TrustScore 4.8 of 5
total score
Based on 387 reviews on
review score
1 month ago
This will be the third trip I have arranged with Adventure Life and I find their customer service and helpfulness to be excellent. Sandra has been very knowledgeable in describing the details of the planned trip as well as the signing up process for the trip. I have and will continue to recommend Adventure Life as the best tour vendor I have had the pleasure to work with. Thank you for your continued excellence.
Linda Haugh
review score
2 months ago
I was given all the information that I asked for and my questions were answered quickly. Very pleasant and knowledgeable agent.
Miriam Weininger
review score
3 months ago
Agent was timely and informative
Amy Jordan
review score
5 months ago
The rep Mary was excellent Got back to me rightaway w any info requested Process was easy so far Thank you
Maryellen Pantaleo
review score
6 months ago
I was on a trip to the UK while arranging another trip for next year. Was able to work with email and a short call to secure our spot on a tall ship cruise. Good company to work with so far.
Steve Beal

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

Shannon Fischer-Kendro Adventure Life employee profile
Shannon F
Plan My Trip
We love travel, talk with an expert 1.800.344.6118