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
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Where to? tap as many as you like 1 selected · clear Caribbean Mediterranean Alaska Bahamas Mexico Northern Europe Hawaii Bermuda Europe Asia Australia & South Pacific Panama Canal South America North America Pacific Middle East Africa
Trip tap one or more Round-trip One-way Repositioning
Length tap one or more 3–5 nights 6–8 nights 9–12 nights 13+ nights
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+ pick specific cruise lines · 1 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 Mediterranean ×Holland America ×9–12 nights × Clear all
Showing 8 of 8 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 CastleDiocletian's PalaceSemi-Private Caldera Catamaran with Hot Springs &…Ephesus + the Terrace Houses with a licensed archa… +2 more
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from $2,149
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Holland America · OosterdamRound-trip
Mediterranean 11 nights Oct 3 – Oct 14, 2026 from Piraeus (Athens), Greece
Piraeus (Athens), Greece · Nafplion, Greece · … · Piraeus (Athens), Greece8 ports
Piraeus (Athens), Greece · Nafplion, Greece · Istanbul, Turkey · Kusadasi (Ephesus), Turkey · Santorini (Thira), Greece · Rhodes, Greece · Souda Bay · Piraeus (Athens), Greece
★ Bucket-list The Acropolis & Parthenon, Guided Skip-the-LineHagia Sophia + the upper gallery mosaics with a li…Ephesus + the Terrace Houses with a licensed archa…Semi-Private Caldera Catamaran with Hot Springs &… +1 more
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from $1,514
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Holland America · OosterdamRound-trip
Mediterranean 10 nights Oct 14 – Oct 24, 2026 from Piraeus (Athens), Greece
Piraeus (Athens), Greece · Mykonos, Greece · … · Piraeus (Athens), Greece7 ports
Piraeus (Athens), Greece · Mykonos, Greece · Istanbul, Turkey · Kusadasi (Ephesus), Turkey · Kos, Greece · Rhodes, Greece · Piraeus (Athens), Greece
★ Bucket-list The Acropolis & Parthenon, Guided Skip-the-LineDelosHagia Sophia + the upper gallery mosaics with a li…Ephesus + the Terrace Houses with a licensed archa… +1 more
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from $1,629
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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 +4 more
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from $1,909
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Holland America · OosterdamRound-trip
Mediterranean 11 nights May 25 – Jun 5, 2027 from Barcelona, Spain
Barcelona, Spain · Malaga, Spain · … · Barcelona, Spain10 ports
Barcelona, Spain · Malaga, Spain · Tangier, Morocco · Almeria, Spain · Cagliari, Sardinia, Italy · Civitavecchia (Rome), Italy · Livorno (Florence/Pisa), Italy · Ajaccio, Corsica, France · Marseille, France · Barcelona, Spain
★ Bucket-list Sagrada FamiliaGranada & the AlhambraTangier Kasbah, Medina & American Legation Private…Su Nuraxi di Barumini +4 more
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from $2,124
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Holland America · OosterdamOne-way
Mediterranean 10 nights Sep 11 – Sep 21, 2027 from Civitavecchia (Rome), Italy to Trieste, Italy
Civitavecchia (Rome), Italy · Naples, Italy · … · Trieste, Italy9 ports
Civitavecchia (Rome), Italy · Naples, Italy · Palermo, Sicily, Italy · Messina, Sicily, Italy · Kefalonia, Greece · Kotor, Montenegro · Dubrovnik, Croatia · Split, Croatia · Trieste, Italy
★ Bucket-list Vatican, Sistine Chapel & Colosseum in One DayPompeii with a Licensed ArchaeologistCappella Palatina & the Norman PalaceTaormina's Ancient Greek Theatre, framed by Mount… +4 more
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from $1,902
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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 &… +4 more
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from $2,327
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Holland America · OosterdamOne-way
Mediterranean 10 nights Oct 2 – Oct 12, 2027 from Piraeus (Athens), Greece to Civitavecchia (Rome), Italy
Piraeus (Athens), Greece · Mykonos, Greece · … · Civitavecchia (Rome), Italy7 ports
Piraeus (Athens), Greece · Mykonos, Greece · Istanbul, Turkey · Santorini (Thira), Greece · Souda Bay · Messina, Sicily, Italy · Civitavecchia (Rome), Italy
★ Bucket-list The Acropolis & Parthenon, Guided Skip-the-LineDelosHagia Sophia + the upper gallery mosaics with a li…Semi-Private Caldera Catamaran with Hot Springs &… +2 more
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from $1,882
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