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.

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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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Filtering Holland America ×Princess ×From Trieste, Italy × Clear all
Showing 7 of 7 sailings
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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Princess · Enchanted PrincessOne-way
Mediterranean 21 nights May 11 – Jun 1, 2027 from Trieste, Italy to Piraeus (Athens), Greece
Trieste, Italy · Split, Croatia · … · Piraeus (Athens), Greece20 ports
Trieste, Italy · Split, Croatia · Kotor, Montenegro · Corfu, Greece · Katakolon (Olympia), Greece · Santorini (Thira), Greece · Kusadasi (Ephesus), Turkey · Rhodes, Greece · Chania, Greece · Naples, Italy · Civitavecchia (Rome), Italy · Salerno, Italy · Messina, Sicily, Italy · Sicily, Italy · Valletta, Malta · Santorini (Thira), Greece · Mykonos, Greece · Kusadasi (Ephesus), Turkey · Heraklion, Crete, Greece · Piraeus (Athens), Greece
★ Bucket-list Miramare CastleDiocletian's PalaceClimb the City Walls to San Giovanni FortressPaleokastritsa Blue Caves & coves by speedboat +13 more
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from $2,988
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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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Princess · Enchanted PrincessRound-trip
Mediterranean 42 nights Aug 24 – Oct 5, 2027 from Trieste, Italy
Trieste, Italy · Split, Croatia · … · Trieste, Italy37 ports
Trieste, Italy · Split, Croatia · Kotor, Montenegro · Corfu, Greece · Katakolon (Olympia), Greece · Chania, Greece · Santorini (Thira), Greece · Rhodes, Greece · Limassol, Cyprus · Kusadasi (Ephesus), Turkey · Piraeus (Athens), Greece · Santorini (Thira), Greece · Chania, Greece · Katakolon (Olympia), Greece · Messina, Sicily, Italy · Valletta, Malta · Dubrovnik, Croatia · Kotor, Montenegro · Split, Croatia · Trieste, Italy · Kornati National Park, Croatia · Bar, Montenegro · Kotor, Montenegro · Corfu, Greece · Valletta, Malta · Sicily, Italy · Messina, Sicily, Italy · Naples, Italy · Civitavecchia (Rome), Italy · Florence, Italy · Ajaccio, Corsica, France · Sardinia, Italy · Valletta, Malta · Kotor, Montenegro · Dubrovnik, Croatia · Split, Croatia · Trieste, Italy
★ Bucket-list Miramare CastleDiocletian's PalaceClimb the City Walls to San Giovanni FortressPaleokastritsa Blue Caves & coves by speedboat +15 more
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from $6,199
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Princess · Enchanted PrincessOne-way
Mediterranean 42 nights Sep 14 – Oct 26, 2027 from Trieste, Italy to Ravenna, Italy
Trieste, Italy · Kornati National Park, Croatia · … · Ravenna, Italy37 ports
Trieste, Italy · Kornati National Park, Croatia · Bar, Montenegro · Kotor, Montenegro · Corfu, Greece · Valletta, Malta · Sicily, Italy · Messina, Sicily, Italy · Naples, Italy · Civitavecchia (Rome), Italy · Florence, Italy · Ajaccio, Corsica, France · Sardinia, Italy · Valletta, Malta · Kotor, Montenegro · Dubrovnik, Croatia · Split, Croatia · Trieste, Italy · Split, Croatia · Kotor, Montenegro · Corfu, Greece · Katakolon (Olympia), Greece · Mykonos, Greece · Heraklion, Crete, Greece · Kusadasi (Ephesus), Turkey · Santorini (Thira), Greece · Piraeus (Athens), Greece · Kusadasi (Ephesus), Turkey · Rhodes, Greece · Chania, Greece · Katakolon (Olympia), Greece · Valletta, Malta · Messina, Sicily, Italy · Salerno, Italy · Kotor, Montenegro · Kornati National Park, Croatia · Ravenna, Italy
★ Bucket-list Miramare CastleClimb the City Walls to San Giovanni FortressPaleokastritsa Blue Caves & coves by speedboatSt John's Co-Cathedral & the Caravaggio masterpieces +18 more
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from $6,741
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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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Princess · Enchanted PrincessOne-way
Mediterranean 9 nights Oct 5 – Oct 14, 2027 from Trieste, Italy to Piraeus (Athens), Greece
Trieste, Italy · Split, Croatia · … · Piraeus (Athens), Greece10 ports
Trieste, Italy · Split, Croatia · Kotor, Montenegro · Corfu, Greece · Katakolon (Olympia), Greece · Mykonos, Greece · Heraklion, Crete, Greece · Kusadasi (Ephesus), Turkey · Santorini (Thira), Greece · Piraeus (Athens), Greece
★ 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 $1,701
Book This Cruise@ Cruisebound

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