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Top Mediterranean Trips & Tours in September 2026

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Discover Mediterranean in September 2026 on one of these 113 tours hand-selected by the travel experts at Adventure Life. Explore the best of during September 2026 as you enjoy Archaeological Site Visits, Village Visits, Wine Tasting, Local Market Visits, and Hiking. Prices for trips in September 2026 range from $734 to $117,000 for a vacation of 5 to 17 days. Choose any of the below 113 itineraries in September 2026 and customize it when you contact one of Adventure Life's expert Mediterranean trip planners.
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Explore the beautifully preserved walled city of Dubrovnik
from $3,990
EXPLORE

Dalmatian Paradise

Roundtrip Trogir - 8 Day Itinerary aboard Avangard
  • Visit Mljet St. Mary's Isle
  • Ride Dubrovnik cable car
  • Stroll Pucisca waterfront
  • Tour Trogir Old Town
Starts / Ends
Trogir / Trogir
Activity Level
Variable
Join an 8-day Adriatic cruise aboard the Avangard, exploring Trogir, Hvar's theater and fortress, and tasting wines on Peljesac Peninsula. Enjoy stunning views from Srd Mountain in Dubrovnik and visit Korcula's stonemasonry school before concluding in Trogir.
Cruise Details
0
Walking in Santorini
from $2,410
Air Credit
EXPLORE

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.
Cruise Details
0
St.Blaise Church, Dubrovnik
from $2,005
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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
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
0
Swim in the clear waters of the Mediterranean
from $2,570
EXPLORE

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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Explore the beautiful walkways of Santorini
from $4,560
EXPLORE

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
Activities
Village Visits, Archaeological Site Visits, Wine Tasting
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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Traditional architecture in Greece.
from $3,090
EBD 10%
EXPLORE

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.
Cruise Details
0
The towering ruins of the Acropolis rise over Athens
from $2,410
Air Credit
EXPLORE

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
Activities
Small Ship Sailing
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
0
The lighthouse of Kotor
from $3,093
$695 off
EXPLORE

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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Visit charming Sicily
from $3,568
EXPLORE

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
Activities
Hiking
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
0
Salona ruins with city of Split in background
from $3,180
EXPLORE

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
0
Relaxing on the Amalfi coast of Italy
from $2,775
EXPLORE

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
0
Greek Monastery on a Rock and Sunny Summer Evening
from $4,522
EXPLORE

Highlights of Classical Greece

7 Day Itinerary
  • Visit Athens, the capital of Greece
  • See iconic landmark in Athens
  • Visit Archaeological site of Mycena
  • See the charming town of Nafplion
  • See iconic site in Olympia
  • Explore Delphi, naval of the world
  • See the rock formation in Meteora
Starts / Ends
Athens / Athens
Activities
Urban Exploration, Local Market Visits
Activity Level
Relaxed
This 7-day tour of classical Greece will explore Athens and its rich cultural heritage. Visit the charming town of Nafplion and its beautiful architecture. Learn about Greek mythology and history at the Temple of Apollo and the Delphi Archaeological Museum. Finally, see the stunning rock formations of Meteora and the monasteries perched atop them.
Tour Details
0
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