Top Mediterranean Trips & Tours in May 2026

from $2,080

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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

Activities

Small Ship Sailing

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

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from $2,475

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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

Activities

Hiking

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.

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from $3,090

EBD 10%

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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 $2,570

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Grand Prix Trials

Roundtrip Nice - 8 Day Itinerary aboard Royal Clipper

• Stroll Nice’s Promenade
• Explore Lerici’s coastline
• Visit Portoferraio’s historic sites
• Witness Monaco’s Grand Prix

Starts / Ends

Nice / Nice

Activity Level

Variable

Set sail on an 8-day cruise aboard the Royal Clipper, visiting charming coastal towns like Nice, Lerici, and Portoferraio. Explore stunning beaches and rich history, and witness the Monaco Grand Prix trials before returning to Nice.

Cruise Details

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from $4,188

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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 $2,085

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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 $731

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Athens Snapshot Extension

3 Day Itinerary

• Visit Athens, the capital of Greece
• See iconic landmark in Athens
• Take a leisurely walk in Plaka
• Sample local cuisine in Athens
• Visit the new museums of Athens
• See the lovely sea front of Athens

Starts / Ends

Athens / Athens

Activity Level

Relaxed

Discover Athens on this 3-day Athens Snapshot Adventure and discover its rich history, vibrant culture, and stunning beauty as Greece's capital city. This unique experience will take you on a captivating journey through the ancient and modern wonders that define Athens, providing you with a comprehensive snapshot of this extraordinary destination.

Tour Details

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from $4,501

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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

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

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from $2,320

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Amalfi & Sicily

Civitavecchia Roundtrip - 8 Day Itinerary aboard Star Clipper

• Sail across Mediterranean waters
• Visit Lipari for coastal views
• Explore Messina cathedral clock
• See seaside cliffs near Sorrento

Starts / Ends

Civitavecchia / Civitavecchia

Activities

Archaeological Site Visits, Urban Exploration

Activity Level

Variable

Experience an 8-day Mediterranean sailing adventure from Civitavecchia, exploring Sicily, the Amalfi Coast, and the Aeolian and Pontine Islands aboard Star Clipper. Sail past Stromboli’s active volcano, wander historic Messina, and admire the coastal beauty of Amalfi and Sorrento. Explore Ponza’s unspoiled charm before returning to Rome’s port.

Cruise Details

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from $3,093

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Croatia and Montenegro

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

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 $2,376

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Athens City Explorer

4 Day Itinerary

• See iconic landmark in Athens
• Visit Athens, the capital of Greece
• Take a leisurely walk in Plaka
• Visit Archaeological site of Mycena
• See the charming town of Nafplion
• See the lovely sea front of Athens

Starts / Ends

Athens / Athens

Activity Level

Relaxed

Embark on a cultural journey through Athens with the 4-day Athens City Explorer. Experience the unique and captivating journey through the ancient and modern wonders that describe Athens. Discover its rich history, vibrant culture, and stunning beauty as Greece's capital city.

Tour Details

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from $3,350

EBD

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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.

Cruise Details

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from $3,290

Up to 50%

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Yachting in Albania & Croatia

Dubrovnik Roundtrip - 8 Day Itinerary aboard M/Y Callisto

• Explore Korcula’s old town
• Swim Vis Island’s crystal waters
• Wander Bar’s historic ruins
• Relax Orikum Bay’s tranquil waters

Starts / Ends

Dubrovnik / Dubrovnik

Activities

Village Visits, Wine Tasting

Activity Level

Variable

Join the M/Y Callisto for an 8-day cruise through the Adriatic and Ionian seas, exploring sites like Korcula, Vis, Montenegro, and Albania's coast. Enjoy onboard meals, local tastings, and cultural excursions, ending in Dubrovnik with easy transfers.

Cruise Details

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from $9,450

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A Circumnavigation of Sicily with Smithsonian Journeys

Valletta - Valletta - 9 Day Itinerary aboard Le Bougainville

• Take a loop around Sicily
• Discover Sicily's beautiful cities
• Visit Syracuse
• Explore Palermo

Starts / Ends

Valletta / Valletta

Activity Level

Variable

During this 9-day cruise around Sicily aboard the new luxury expedition ship Le Bougainville, you'll be able to explore mythical places at the crossroads of Eastern and Western civilizations. Discover Sicily's most beautiful historic cities and ancient sites.

Cruise Details

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from $5,340

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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 $5,340

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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 $2,570

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Ligurian Sea

Roundtrip Nice - 8 Day Itinerary aboard Royal Clipper

• Stroll Nice’s old town
• Discover Lerici’s villages
• Explore Portoferraio’s vineyards
• Relax on Sant’Amanza’s beach

Starts / Ends

Nice / Nice

Activity Level

Variable

Embark on an 8-day cruise aboard the Royal Clipper, sailing from Nice to Monaco while discovering beautiful coastal towns and rich cultural landmarks. Enjoy vibrant local cuisine, stunning beaches, and history in France, Italy, and Monaco.

Cruise Details

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from $4,090

Up to 50%

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Venetian Horizons

Venice Roudtrip - 8 Day Itinerary aboard M/Y Callisto

• Visit Venice's Grand Canal
• Enjoy fresh seafood in Piran
• Explore Plitvice Lakes in Croatia
• Experience truffle hunting in Koper

Starts / Ends

Venice / Venice

Activities

Local Market Visits

Activity Level

Variable

Embark on an 8-day Adriatic cruise aboard M/Y Callisto, starting in Venice and visiting coastal towns in Slovenia and Croatia before ending in Ravenna. Enjoy guided tours and free time to explore iconic sites, beautiful landscapes, and rich cultural heritage.

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