Bucket-List Cruise Adventures

Pick your sailing — we plan the whole adventure

Bucket-list adventures at every port — where to fly in, and what to do the day(s) before and after.

When are you free? — only cruises that fit entirely inside your dates
My result then click any cruise row to open it
Where to? tap as many as you like Caribbean Mediterranean Alaska Bahamas Mexico Northern Europe Hawaii Bermuda Europe Asia Australia & South Pacific Panama Canal South America North America Pacific Middle East Africa
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Length tap one or more 3–5 nights 6–8 nights 9–12 nights 13+ nights
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+ pick specific cruise lines · 2 selected
Luxury Azamara Oceania Regent Seabourn Viking Ocean River AmaWaterways Avalon Viking River Premium Celebrity Cunard Disney Holland America Princess Virgin Voyages Contemporary Carnival Costa MSC Cruises Norwegian Royal Caribbean
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Filtering Holland America ×Oceania ×From Trieste, Italy × Clear all
Showing 17 of 17 sailings
Oceania · Oceania AlluraOne-way
Mediterranean 21 nights Jul 7 – Jul 28, 2026 from Trieste, Italy to Piraeus (Athens), Greece
Trieste, Italy · Hvar, Croatia · … · Piraeus (Athens), Greece20 ports
Trieste, Italy · Hvar, Croatia · Bari, Italy · Kotor, Montenegro · Dubrovnik, Croatia · Corfu, Greece · Chania, Greece · Rhodes, Greece · Santorini (Thira), Greece · Piraeus (Athens), Greece · Mykonos, Greece · Kusadasi (Ephesus), Turkey · Istanbul, Turkey · Bozcaada, Turkey · Mytilene, Lesbos, Greece · Izmir, Turkey · Chios, Greece · Kos, Greece · Santorini (Thira), Greece · Piraeus (Athens), Greece
★ Bucket-list Miramare CastleBlue Cave & Vis Island Private Speedboat DayMatera & the Sassi cave city with a licensed Basil…Climb the City Walls to San Giovanni Fortress +14 more
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from $12,349
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Holland America · OosterdamOne-way
Mediterranean 10 nights Sep 23 – Oct 3, 2026 from Trieste, Italy to Piraeus (Athens), Greece
Trieste, Italy · Rijeka, Croatia · … · Piraeus (Athens), Greece8 ports
Trieste, Italy · Rijeka, Croatia · Split, Croatia · Santorini (Thira), Greece · Bodrum, Turkey · Kusadasi (Ephesus), Turkey · Istanbul, Turkey · Piraeus (Athens), Greece
★ Bucket-list Miramare CastlePostojna Cave & Predjama CastleDiocletian's PalaceSemi-Private Caldera Catamaran with Hot Springs &… +4 more
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from $2,149
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Oceania · Oceania AlluraOne-way
Mediterranean 7 nights Oct 3 – Oct 10, 2026 from Trieste, Italy to Piraeus (Athens), Greece
Trieste, Italy · Ravenna, Italy · … · Piraeus (Athens), Greece8 ports
Trieste, Italy · Ravenna, Italy · Rijeka, Croatia · Split, Croatia · Brindisi, Italy · Corfu, Greece · Gythion, Greece · Piraeus (Athens), Greece
★ Bucket-list Miramare CastlePrivate Ravenna UNESCO Mosaics Walk with a Local E…Postojna Cave & Predjama CastleDiocletian's Palace +4 more
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from $3,740
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Oceania · Oceania MarinaOne-way
Mediterranean 11 nights Apr 17 – Apr 28, 2027 from Trieste, Italy to Barcelona, Spain
Trieste, Italy · Koper, Slovenia · … · Barcelona, Spain11 ports
Trieste, Italy · Koper, Slovenia · Zadar, Croatia · Kotor, Montenegro · Corfu, Greece · Argostoli, Kephalonia · Catania, Sicily, Italy · Salerno, Italy · Civitavecchia (Rome), Italy · Marseille, France · Barcelona, Spain
★ Bucket-list Miramare CastlePostojna Cave & Predjama CastleKornati National Park & TelašćicaClimb the City Walls to San Giovanni Fortress +7 more
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from $3,060
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Oceania · Oceania AlluraOne-way
Mediterranean 7 nights Apr 30 – May 7, 2027 from Trieste, Italy to Piraeus (Athens), Greece
Trieste, Italy · Zadar, Croatia · … · Piraeus (Athens), Greece8 ports
Trieste, Italy · Zadar, Croatia · Dubrovnik, Croatia · Corfu, Greece · Gythion, Greece · Santorini (Thira), Greece · Mykonos, Greece · Piraeus (Athens), Greece
★ Bucket-list Miramare CastleKornati National Park & TelašćicaWalk Dubrovnik's Ancient City WallsPaleokastritsa Blue Caves & coves by speedboat +4 more
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from $4,649
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Holland America · OosterdamOne-way
Mediterranean 10 nights May 15 – May 25, 2027 from Trieste, Italy to Barcelona, Spain
Trieste, Italy · Zadar, Croatia · … · Barcelona, Spain9 ports
Trieste, Italy · Zadar, Croatia · Dubrovnik, Croatia · Kotor, Montenegro · Kefalonia, Greece · Messina, Sicily, Italy · Naples, Italy · Civitavecchia (Rome), Italy · Barcelona, Spain
★ Bucket-list Miramare CastleKornati National Park & TelašćicaWalk Dubrovnik's Ancient City WallsClimb the City Walls to San Giovanni Fortress +5 more
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from $1,909
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Oceania · Oceania AlluraOne-way
Mediterranean 10 nights May 23 – Jun 2, 2027 from Trieste, Italy to Barcelona, Spain
Trieste, Italy · Split, Croatia · … · Barcelona, Spain10 ports
Trieste, Italy · Split, Croatia · Kotor, Montenegro · Corfu, Greece · Gythion, Greece · Piraeus (Athens), Greece · Katakolon (Olympia), Greece · Messina, Sicily, Italy · Palma de Mallorca, Spain · Barcelona, Spain
★ Bucket-list Miramare CastleDiocletian's PalaceClimb the City Walls to San Giovanni FortressPaleokastritsa Blue Caves & coves by speedboat +6 more
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from $4,549
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Oceania · Oceania AlluraOne-way
Mediterranean 7 nights Jun 18 – Jun 25, 2027 from Trieste, Italy to Piraeus (Athens), Greece
Trieste, Italy · Zadar, Croatia · … · Piraeus (Athens), Greece8 ports
Trieste, Italy · Zadar, Croatia · Dubrovnik, Croatia · Kotor, Montenegro · Argostoli, Kephalonia · Monemvasia, Greece · Mykonos, Greece · Piraeus (Athens), Greece
★ Bucket-list Miramare CastleKornati National Park & TelašćicaWalk Dubrovnik's Ancient City WallsClimb the City Walls to San Giovanni Fortress +4 more
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from $3,285
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Oceania · Oceania AlluraOne-way
Mediterranean 10 nights Jul 27 – Aug 6, 2027 from Trieste, Italy to Barcelona, Spain
Trieste, Italy · Split, Croatia · … · Barcelona, Spain10 ports
Trieste, Italy · Split, Croatia · Bar, Montenegro · Corfu, Greece · Gythion, Greece · Piraeus (Athens), Greece · Katakolon (Olympia), Greece · Messina, Sicily, Italy · Palma de Mallorca, Spain · Barcelona, Spain
★ Bucket-list Miramare CastleDiocletian's PalacePaleokastritsa Blue Caves & coves by speedboatDiros Caves +5 more
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from $4,699
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Oceania · Oceania AlluraOne-way
Mediterranean 7 nights Aug 20 – Aug 27, 2027 from Trieste, Italy to Piraeus (Athens), Greece
Trieste, Italy · Zadar, Croatia · … · Piraeus (Athens), Greece8 ports
Trieste, Italy · Zadar, Croatia · Dubrovnik, Croatia · Kotor, Montenegro · Argostoli, Kephalonia · Katakolon (Olympia), Greece · Heraklion, Crete, Greece · Piraeus (Athens), Greece
★ Bucket-list Miramare CastleKornati National Park & TelašćicaWalk Dubrovnik's Ancient City WallsClimb the City Walls to San Giovanni Fortress +4 more
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from $3,349
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Oceania · Oceania SonataOne-way
Mediterranean 9 nights Aug 21 – Aug 30, 2027 from Trieste, Italy to Barcelona, Spain
Trieste, Italy · Split, Croatia · … · Barcelona, Spain9 ports
Trieste, Italy · Split, Croatia · Dubrovnik, Croatia · Sorrento, Italy · Civitavecchia (Rome), Italy · Bastia, France · Florence, Italy · Marseille, France · Barcelona, Spain
★ Bucket-list Miramare CastleDiocletian's PalaceWalk Dubrovnik's Ancient City WallsPompeii Private Excavation Tour with Archaeologist… +5 more
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from $4,949
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Holland America · OosterdamOne-way
Mediterranean 11 nights Sep 21 – Oct 2, 2027 from Trieste, Italy to Piraeus (Athens), Greece
Trieste, Italy · Split, Croatia · … · Piraeus (Athens), Greece9 ports
Trieste, Italy · Split, Croatia · Dubrovnik, Croatia · Santorini (Thira), Greece · Mykonos, Greece · Kos, Greece · Kusadasi (Ephesus), Turkey · Istanbul, Turkey · Piraeus (Athens), Greece
★ Bucket-list Miramare CastleDiocletian's PalaceWalk Dubrovnik's Ancient City WallsSemi-Private Caldera Catamaran with Hot Springs &… +5 more
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from $2,327
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Oceania · Oceania SonataOne-way
Mediterranean 7 nights Oct 7 – Oct 14, 2027 from Trieste, Italy to Piraeus (Athens), Greece
Trieste, Italy · Rijeka, Croatia · … · Piraeus (Athens), Greece8 ports
Trieste, Italy · Rijeka, Croatia · Hvar, Croatia · Sarande, Albania · Argostoli, Kephalonia · Chania, Greece · Mykonos, Greece · Piraeus (Athens), Greece
★ Bucket-list Miramare CastlePostojna Cave & Predjama CastleBlue Cave & Vis Island Private Speedboat DayButrint UNESCO Ruins +4 more
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from $3,499
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Oceania · Oceania SonataOne-way
Mediterranean 9 nights Oct 31 – Nov 9, 2027 from Trieste, Italy to Civitavecchia (Rome), Italy
Trieste, Italy · Ravenna, Italy · … · Civitavecchia (Rome), Italy9 ports
Trieste, Italy · Ravenna, Italy · Zadar, Croatia · Split, Croatia · Kotor, Montenegro · Sarande, Albania · Messina, Sicily, Italy · Salerno, Italy · Civitavecchia (Rome), Italy
★ Bucket-list Miramare CastlePrivate Ravenna UNESCO Mosaics Walk with a Local E…Kornati National Park & TelašćicaDiocletian's Palace +5 more
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from $4,349
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Oceania · Oceania AlluraOne-way
Mediterranean 10 nights Nov 7 – Nov 17, 2027 from Trieste, Italy to Barcelona, Spain
Trieste, Italy · Koper, Slovenia · … · Barcelona, Spain11 ports
Trieste, Italy · Koper, Slovenia · Dubrovnik, Croatia · Igoumenitsa, Greece · Gythion, Greece · Piraeus (Athens), Greece · Argostoli, Kephalonia · Catania, Sicily, Italy · Valletta, Malta · Suez Canal, Egypt · Barcelona, Spain
★ Bucket-list Miramare CastlePostojna Cave & Predjama CastleWalk Dubrovnik's Ancient City WallsPrivate Full-Day Meteora Monasteries Tour from Igo… +7 more
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from $3,699
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Oceania · Oceania MarinaOne-way
Mediterranean 10 nights Nov 7 – Nov 17, 2027 from Trieste, Italy to Piraeus (Athens), Greece
Trieste, Italy · Zadar, Croatia · … · Piraeus (Athens), Greece10 ports
Trieste, Italy · Zadar, Croatia · Split, Croatia · Bar, Montenegro · Sarande, Albania · Chania, Greece · Rhodes, Greece · Kusadasi (Ephesus), Turkey · Mykonos, Greece · Piraeus (Athens), Greece
★ Bucket-list Miramare CastleKornati National Park & TelašćicaDiocletian's PalaceButrint UNESCO Ruins +5 more
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from $2,999
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Oceania · Oceania AureliaOne-way
Mediterranean 12 nights Dec 6 – Dec 18, 2027 from Trieste, Italy to Piraeus (Athens), Greece
Trieste, Italy · Koper, Slovenia · … · Piraeus (Athens), Greece10 ports
Trieste, Italy · Koper, Slovenia · Split, Croatia · Kotor, Montenegro · Brindisi, Italy · Heraklion, Crete, Greece · Rhodes, Greece · Kusadasi (Ephesus), Turkey · Istanbul, Turkey · Piraeus (Athens), Greece
★ Bucket-list Miramare CastlePostojna Cave & Predjama CastleDiocletian's PalaceClimb the City Walls to San Giovanni Fortress +6 more
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from $3,499
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Itineraries from the Cruisebound catalog + our enrichment; schedules cross-checked against official port authorities. Booking via Cruisebound and CruiseDirect — we may earn a commission, at no extra cost to you.

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MSC Cruises Royal Caribbean Carnival Viking River Costa Norwegian AmaWaterways Princess Celebrity Viking Ocean Avalon Disney Holland America Oceania Virgin Voyages Regent Cunard Seabourn Azamara