Top Mediterranean Trips & Tours in September 2026

from $3,945

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Dalmatian Paradise

Roundtrip Trogir - 8 Day Itinerary aboard Avangard

• Discover Mljet’s lakes
• Walk Dubrovnik’s old walls
• Visit Scedro’s quiet shores
• Explore Trogir’s medieval core

Starts / Ends

Trogir / Trogir

Activities

Small Ship Sailing

Activity Level

Variable

Experience an 8-day cruise from Trogir on the Avangard, exploring Croatia's stunning southern Adriatic, including Dubrovnik, Hvar, and Mljet. Enjoy a blend of relaxation and guided excursions while the crew manages the details for a worry-free adventure.

Cruise Details

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from $2,410

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Southern Cyclades

Roundtrip Piraeus - 8 Day Itinerary aboard Star Flyer

• Explore Piraeus vibrant port city
• Wander Rhodes medieval streets
• Discover Bodrum rich history
• Admire Santorini whitewashed cliffs

Starts / Ends

Piraeus / Piraeus

Activity Level

Variable

Set sail for 8 days on the Star Flyer, exploring historic Aegean ports from Piraeus to Rhodes and Bodrum while enjoying stunning views in Santorini and Hydra. Experience local culture, cuisine, and relaxation, culminating in a memorable return to Piraeus.

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from $3,090

10% EBD

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Jewels of the Cyclades

Roundtrip Athens - 8 Day Itinerary aboard Galileo

• Capture Santorini’s caldera views
• Swim Poliegos turquoise waters
• Stroll Folegandros cliffside views
• Tour Delos sacred temples

Starts / Ends

Athens / Athens

Activity Level

Variable

Set sail on an 8-day cruise aboard the Galileo, exploring the beautiful Cyclades from Athens to islands like Santorini, Mykonos, and Folegandros. Enjoy swim stops, cultural experiences, and delightful Cycladic cuisine on this unforgettable journey.

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from $1,985

Up to 20%

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Dubrovnik to Split

Dubrovnik - Split - 8 Day Itinerary aboard M/S Splendid

• Tour Split’s Diocletian Palace
• Enter Bisevo’s magical Blue Cave
• Relax on Bol’s Zlatni Rat beach
• Explore historic Dubrovnik

Starts / Ends

Dubrovnik / Split

Activities

Urban Exploration

Activity Level

Variable

Set sail on an 8-day cruise from Dubrovnik to Split aboard M/S Splendid, exploring Croatia’s stunning islands, historic cities, and vibrant culture. Enjoy medieval towns, crystal-clear waters, and timeless traditions.

Cruise Details

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from $3,150

Savings

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Highlights of Sicily

Italy Small Group Tour - 9 Day Itinerary

• Visit the Island of Sicily
• Discover the Valley of the Temples
• Visit Taormina's ancient ruins
• See the Mount Etna in Sicily
• Explore the coastal town of Cefalu
• Visit Syracuse's Archeological Park
• Discover the Zingaro Nature Reserve

Starts / Ends

Viagrande / Taormina

Activity Level

Relaxed

Spend 9 days on this small group journey through the highlights of Sicily to step into a world where ancient ruins stand alongside vibrant cities and picturesque landscapes. Discover ancient ruins, bask in the island's natural beauty, and indulge in Sicily's culinary delights.

Tour Details

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from $2,550

Savings

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Highlights of the Amalfi Coast

Italy Small Group Tour - 8 Day Itinerary

• Admire the Amalfi Coastline
• Explore Positano on foot
• Visit Herculaneum and Pompeii
• Ride a boat to the island of Capri
• Walk the Path of the Gods
• Explore the village of Ravello

Starts / Ends

Naples / Naples

Activity Level

Easy Active

Discover one of the most fascinating and romantic destinations in the world, the Amalfi Coast. On this small 8-day group adventure, visit both Herculaneum and Pompeii, see the romantic coastal towns of Amalfi, Positano, and Ravello, and explore the island of Capri on this best-selling tour.

Tour Details

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from $2,570

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Voiles de Saint Tropez

Roundtrip Nice - 8 Day Itinerary aboard Royal Clipper

• Explore Nice’s coastal charm
• Discover Lerici’s seaside villages
• Visit Portoferraio’s vineyards
• Swim Sant'Amanza’s crystal waters

Starts / Ends

Nice / Nice

Activity Level

Variable

Set sail on an 8-day cruise aboard the Royal Clipper, exploring the stunning Mediterranean coasts of France, Italy, and Corsica. Journey from Nice to Lerici, Portoferraio, and St. Tropez, enjoying historical sites, breathtaking views, and vibrant local culture.

Cruise Details

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from $3,350

Save 10%

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Classical Greece

Roundtrip Athens - 8 Day Itinerary aboard Harmony G

• Explore Kea’s charming port
• Discover Delos archaeological site
• Visit Monemvasia’s medieval streets
• Stroll Nafplion’s old town

Starts / Ends

Athens / Athens

Activity Level

Variable

Set sail on an 8-day cruise from Athens aboard the Harmony G, exploring the Cyclades, Crete, and the hidden gem of Kythira. Discover historic charm in Monemvasia and Nafplion while enjoying a unique blend of cruising and yachting.

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from $3,499

Up to 50%

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La Dolce Vita

Naples - Valletta - 8 Day Itinerary aboard M/Y Callisto

• Discover Lipari panoramic viewpoint
• Stroll Taormina’s alleys
• Experience Sicilian wines
• Wander Syracuse’s historic streets

Starts / Ends

Naples / Valletta

Activity Level

Variable

Set sail on an 8-day cruise aboard the MY Callisto, starting in Naples and exploring the glamorous island of Capri. Discover Sicily's rich history, including Mount Etna and Taormina, before heading to Malta's UNESCO sites, like Valletta and Gozo's ancient temples.

Cruise Details

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from $3,405

Up to 25%

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Divine Cyclades

Roundtrip Lavrion - 8 Day Itinerary aboard Elysium

• Discover Ios golden beach
• Swim Naxos crystal waters
• Wander Mykonos vibrant alleys
• Explore Delos sacred ruins

Starts / Ends

Lavrion / Lavrion

Activities

Hiking

Activity Level

Variable

Embark on an 8-day cruise aboard the Elysium through the enchanting Cyclades. Discover this enchanting paradise, holding ancient secrets, and embark on a journey to explore its beauty.

Cruise Details

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from $2,410

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Northern Cyclades

Roundtrip Piraeus - 8 Day Itinerary aboard Star Flyer

• Explore Piraeus bustling port city
• Discover Kusadasi grand ruins
• Visit Amorgos soaring cliffs
• Stroll Mykonos harbor

Starts / Ends

Piraeus / Piraeus

Activity Level

Variable

Set sail on an 8-day cruise aboard the Star Flyer to explore Greece’s ancient ruins and beautiful islands, starting in Piraeus. Experience vibrant destinations like Kusadasi, Patmos, and Mykonos while enjoying guided tours and hands-on sailing activities.

Cruise Details

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from $3,093

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Croatia and Montenegro

Dubrovnik Roundtrip - 8 Day Itinerary aboard MV La Belle de L'Adriatique

• Discover Dubrovnik
• Explore beautiful Mljet
• Enjoy Veneto-Byzantine tradition
• Visit the gorgeous Krka Falls

Starts / Ends

Dubrovnik / Dubrovnik

Activities

Biking

Activity Level

Variable

Discover Mediterranean charm on this 8-day cruise aboard the MV La Belle de L'Adriatique. Start and end in the historical city of Dubrovnik. Explore all the wonders this famous region has to offer as you sail through clear-blue waters & enchanting coastal towns, including architectural diversity and Skradinkski buk & Krka National Park.

Cruise Details

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from $3,145

Up to 20%

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Dubrovnik to Split

8 Day Itinerary aboard M/S Mama Marija

• Explore Mljet National Park
• Visit Korčula Island
• Enjoy Trogir's heritage
• Stroll through relaxing Omiš

Activities

Fishing

Activity Level

Variable

On this 8-day Adriatic cruise, sail from Dubrovnik to Split and discover the beauty of enchanting Croatia. The M/S Mama Marija takes you on this cruise, starting in Dubrovnik, hugging the Adriatic Sea. Swim in the Adriatic Sea, explore Mljet National Park, visit Kor?ula Island, and tour cities that are considered UNESCO Heritage Sites.

Cruise Details

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from $5,440

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Aegean Escape

Roundtrip Lavrion - 8 Day Itinerary aboard Gemaya

• Explore Sifnos scenic trails
• Discover Sikinos landscapes
• Relax on Ios with pristine beaches
• Visit Serifos with rugged landscape

Starts / Ends

Lavrion / Lavrion

Activity Level

Variable

Set sail on an 8-day cruise to the Aegean aboard the Gemaya, exploring stunning islands like Santorini and Milos. Discover whitewashed villages, hidden coves, and the rich traditions of Greece amidst a backdrop of beauty and myth.

Cruise Details

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from $5,440

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Saronic Gems

Roundtrip Lavrion - 8 Day Itinerary aboard Gemaya

• Explore Epidaurus’ ancient theater
• Visit Aegina’s neoclassical charm
• Swim Porto Cheli’s waters
• Wander Nafplion’s old town

Starts / Ends

Lavrion / Lavrion

Activities

Scuba Diving

Activity Level

Variable

Set sail for an 8-day cruise from Lavrion on the Gemaya, exploring the historic Saronic Islands. Enjoy stunning landscapes and rich culture, from the lush charm of Spetses to the UNESCO beauty of Hydra and Aegina's ancient Temple of Aphaia.

Cruise Details

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from $3,499

Up to 50%

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Sicilian Sunsets & Amalfi Delights

Valletta - Naples - 8 Day Itinerary aboard M/Y Callisto

• Explore Valletta’s historic port
• Stroll Trapani’s cobbled streets
• Visit medieval Erice
• Indulge in Palermo’s vibrant market

Starts / Ends

Valletta / Naples

Activities

Archaeological Site Visits, Village Visits, Local Market Visits, Wine Tasting

Activity Level

Variable

Embark on an 8-day cruise aboard the MY Callisto 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

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from $4,523

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Greece Island Hopping

9 Day Itinerary

• Visit Athens, the capital of Greece
• See iconic landmark in Athens
• Visit the charming town of Naoussa
• Relax in Paros' beautiful beaches
• Capture the famous Santorini sunset
• Sample local wines in Santorini
• Enjoy the beauty of Santorini

Starts / Ends

Athens / Athens

Activity Level

Relaxed

Embark on an unforgettable 9-day Greece island-hopping adventure, exploring the stunning islands of Athens, Paros, and Santorini. This journey will take you through a perfect blend of ancient history and breathtaking landscapes. Be ready for a trip filled with azure waters, sun-drenched beaches, delicious cuisine, and picturesque villages.

Tour Details

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from $11,395

EBD

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Classic Greece: To Antiquity and Beyond

Roundtrip Athens - 10 Day Itinerary aboard Douglas Mawson

• Explore Athens’ ancient wonders
• Discover Delphi’s ruins
• Wander Zakynthos’ streets
• Stroll Gytheio’s harbor

Starts / Ends

Athens / Piraeus

Activity Level

Variable

Experience a 10-day cruise from Athens on the Douglas Mawson, exploring the historic Peloponnese. Visit ancient sites like Olympia and Monemvasia, where the rich heritage of Greece unfolds at every turn.

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