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 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
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Filtering Princess ×One-way ×9–12 nights × Clear all
Showing 29 of 29 sailings
Princess · Sapphire PrincessOne-way
North America 10 nights Sep 3 – Sep 13, 2026 from Boston, Massachusetts to Quebec City, Quebec
Boston, Massachusetts · Portland, Maine · … · Quebec City, Quebec8 ports
Boston, Massachusetts · Portland, Maine · Saint John, New Brunswick · Halifax, Nova Scotia · Sydney, Nova Scotia · Charlottetown, Prince Edward Island · Saguenay Fjord, Canada · Quebec City, Quebec
★ Bucket-list Private Luxury Boston TourPeggy's Cove & LunenburgBridgeClimb Sydney
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from $1,344
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Princess · Sapphire PrincessOne-way
North America 10 nights Sep 13 – Sep 23, 2026 from Quebec City, Quebec to Boston, Massachusetts
Quebec City, Quebec · Saguenay Fjord, Canada · … · Boston, Massachusetts7 ports
Quebec City, Quebec · Saguenay Fjord, Canada · Charlottetown, Prince Edward Island · Sydney, Nova Scotia · Halifax, Nova Scotia · Saint John, New Brunswick · Boston, Massachusetts
★ Bucket-list BridgeClimb SydneyPeggy's Cove & LunenburgPrivate Luxury Boston Tour
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from $1,137
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Princess · Enchanted PrincessOne-way
Mediterranean 10 nights Sep 15 – Sep 25, 2026 from Civitavecchia (Rome), Italy to Piraeus (Athens), Greece
Civitavecchia (Rome), Italy · Naples, Italy · … · Piraeus (Athens), Greece10 ports
Civitavecchia (Rome), Italy · Naples, Italy · Dubrovnik, Croatia · Split, Croatia · Kotor, Montenegro · Corfu, Greece · Katakolon (Olympia), Greece · Heraklion, Crete, Greece · Mykonos, Greece · Piraeus (Athens), Greece
★ Bucket-list Vatican, Sistine Chapel & Colosseum in One DayPompeii with a Licensed ArchaeologistWalk Dubrovnik's Ancient City WallsDiocletian's Palace +6 more
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from $1,769
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Princess · Sapphire PrincessOne-way
North America 10 nights Sep 23 – Oct 3, 2026 from Boston, Massachusetts to Quebec City, Quebec
Boston, Massachusetts · Portland, Maine · … · Quebec City, Quebec8 ports
Boston, Massachusetts · Portland, Maine · Saint John, New Brunswick · Halifax, Nova Scotia · Sydney, Nova Scotia · Charlottetown, Prince Edward Island · Saguenay Fjord, Canada · Quebec City, Quebec
★ Bucket-list Private Luxury Boston TourPeggy's Cove & LunenburgBridgeClimb Sydney
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from $1,229
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Princess · Enchanted PrincessOne-way
Mediterranean 11 nights Sep 25 – Oct 6, 2026 from Piraeus (Athens), Greece to Civitavecchia (Rome), Italy
Piraeus (Athens), Greece · Santorini (Thira), Greece · … · Civitavecchia (Rome), Italy8 ports
Piraeus (Athens), Greece · Santorini (Thira), Greece · Kusadasi (Ephesus), Turkey · Istanbul, Turkey · Rhodes, Greece · Messina, Sicily, Italy · Valletta, Malta · Civitavecchia (Rome), Italy
★ Bucket-list The Acropolis & Parthenon, Guided Skip-the-LineSemi-Private Caldera Catamaran with Hot Springs &…Ephesus + the Terrace Houses with a licensed archa…Hagia Sophia + the upper gallery mosaics with a li… +4 more
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from $2,155
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Princess · Sapphire PrincessOne-way
North America 10 nights Oct 3 – Oct 13, 2026 from Quebec City, Quebec to Boston, Massachusetts
Quebec City, Quebec · Saguenay Fjord, Canada · … · Boston, Massachusetts8 ports
Quebec City, Quebec · Saguenay Fjord, Canada · Charlottetown, Prince Edward Island · Sydney, Nova Scotia · Halifax, Nova Scotia · Saint John, New Brunswick · Portland, Maine · Boston, Massachusetts
★ Bucket-list BridgeClimb SydneyPeggy's Cove & LunenburgPrivate Luxury Boston Tour
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from $1,421
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Princess · Royal PrincessOne-way
Asia 12 nights Oct 4 – Oct 16, 2026 from Tokyo, Japan to Singapore, Singapore
Tokyo, Japan · Shimizu, Japan · … · Singapore, Singapore7 ports
Tokyo, Japan · Shimizu, Japan · Osaka (Kyoto and Nara), Japan · Keelung (Taipei), Taiwan · Hong Kong, Hong Kong SAR, China · Chan May, Vietnam · Singapore, Singapore
★ Bucket-list Private Licensed Tokyo ExpertPrivate Mt. Fuji & Hakone Full-Day Tour from Shimi…Victoria Peak at DuskGardens by the Bay
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from $2,315
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Princess · Sapphire PrincessOne-way
North America 10 nights Oct 13 – Oct 23, 2026 from Boston, Massachusetts to Quebec City, Quebec
Boston, Massachusetts · Portland, Maine · … · Quebec City, Quebec8 ports
Boston, Massachusetts · Portland, Maine · Saint John, New Brunswick · Halifax, Nova Scotia · Sydney, Nova Scotia · Charlottetown, Prince Edward Island · Saguenay Fjord, Canada · Quebec City, Quebec
★ Bucket-list Private Luxury Boston TourPeggy's Cove & LunenburgBridgeClimb Sydney
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from $1,074
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Princess · Caribbean PrincessOne-way
Caribbean 12 nights Oct 18 – Oct 30, 2026 from Port Canaveral, Florida to Fort Lauderdale (Port Everglades), Florida
Port Canaveral, Florida · Port of Oranjestad, Aruba, Caribbean · … · Fort Lauderdale (Port Everglades), Florida8 ports
Port Canaveral, Florida · Port of Oranjestad, Aruba, Caribbean · Curacao, Caribbean · Kralendijk, Bonaire, Dutch Antilles · Amber Cove, Dominican Republic · Grand Turk, Turks and Caicos · Nassau, Bahamas · Fort Lauderdale (Port Everglades), Florida
★ Bucket-list Kennedy Space Center Visitor ComplexArubaKlein Bonaire27 Charcos of Damajagua +3 more
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from $824
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Princess · Enchanted PrincessOne-way
Mediterranean 10 nights Oct 31 – Nov 10, 2026 from Piraeus (Athens), Greece to Civitavecchia (Rome), Italy
Piraeus (Athens), Greece · Santorini (Thira), Greece · … · Civitavecchia (Rome), Italy10 ports
Piraeus (Athens), Greece · Santorini (Thira), Greece · Chania, Greece · Katakolon (Olympia), Greece · Corfu, Greece · Split, Croatia · Dubrovnik, Croatia · Kotor, Montenegro · Naples, Italy · Civitavecchia (Rome), Italy
★ Bucket-list The Acropolis & Parthenon, Guided Skip-the-LineSemi-Private Caldera Catamaran with Hot Springs &…Samaria GorgeAncient Olympia +6 more
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from $1,336
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Princess · Grand PrincessOne-way
Australia & South Pacific 12 nights Mar 8 – Mar 20, 2027 from Brisbane, Australia to Sydney, Australia
Brisbane, Australia · Airlie Beach · … · Sydney, Australia9 ports
Brisbane, Australia · Airlie Beach · Townsville, Australia · Port Douglas, Australia · Cairns, Australia · Willis Island · Brisbane, Australia · Newcastle, Australia · Sydney, Australia
★ Bucket-list Lone Pine Koala SanctuaryOuter Great Barrier ReefZodiac Circumnavigation of Willis IslandBridgeClimb Sydney
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from $1,231
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Princess · Crown PrincessOne-way
Caribbean 9 nights Mar 26 – Apr 4, 2027 from Bridgetown, Barbados to Fort Lauderdale (Port Everglades), Florida
Bridgetown, Barbados · San Juan, Puerto Rico · … · Fort Lauderdale (Port Everglades), Florida6 ports
Bridgetown, Barbados · San Juan, Puerto Rico · St. Maarten, Netherlands Antilles · Port of Oranjestad, Aruba, Caribbean · Curacao, Caribbean · Fort Lauderdale (Port Everglades), Florida
★ Bucket-list Swim with wild green sea turtles + two shipwrecks…Walk El Morro & Old San Juan's City WallsMaho BeachAruba +1 more
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from $1,024
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Princess · Star PrincessOne-way
Alaska 9 nights Apr 30 – May 9, 2027 from Vancouver, British Columbia to Seattle, Washington
Vancouver, British Columbia · Glacier Bay, Alaska · … · Seattle, Washington7 ports
Vancouver, British Columbia · Glacier Bay, Alaska · Juneau, Alaska · Skagway, Alaska · Endicott Arm, Alaska · Ketchikan, Alaska · Seattle, Washington
★ Bucket-list Capilano Suspension Bridge ParkPrivate Glacier Bay National Park Charter CruiseHelicopter Glacier Landing & Guided Ice Walk on th…White Pass & Yukon Route Railway +3 more
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from $1,116
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Princess · Enchanted PrincessOne-way
Mediterranean 10 nights May 22 – Jun 1, 2027 from Civitavecchia (Rome), Italy to Piraeus (Athens), Greece
Civitavecchia (Rome), Italy · Salerno, Italy · … · Piraeus (Athens), Greece10 ports
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 Vatican, Sistine Chapel & Colosseum in One DayAmalfi Coast Private BoatTaormina's Ancient Greek Theatre, framed by Mount…St John's Co-Cathedral & the Caravaggio masterpieces +5 more
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from $1,177
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Princess · Enchanted PrincessOne-way
Mediterranean 11 nights Jun 1 – Jun 12, 2027 from Piraeus (Athens), Greece to Civitavecchia (Rome), Italy
Piraeus (Athens), Greece · Heraklion, Crete, Greece · … · Civitavecchia (Rome), Italy11 ports
Piraeus (Athens), Greece · Heraklion, Crete, Greece · Kusadasi (Ephesus), Turkey · Rhodes, Greece · Mykonos, Greece · Chania, Greece · Valletta, Malta · Sicily, Italy · Messina, Sicily, Italy · Naples, Italy · Civitavecchia (Rome), Italy
★ Bucket-list The Acropolis & Parthenon, Guided Skip-the-LinePalace of KnossosEphesus + the Terrace Houses with a licensed archa…Private Full-Day Rhodes Island Highlights & Lindos +6 more
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from $1,008
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Princess · Regal PrincessOne-way
Northern Europe 9 nights Jun 6 – Jun 15, 2027 from Copenhagen, Denmark to Reykjavik, Iceland
Copenhagen, Denmark · Skagen, Denmark · … · Reykjavik, Iceland8 ports
Copenhagen, Denmark · Skagen, Denmark · Skjolden, Norway · Olden, Norway · Seydisfjordur, Iceland · Akureyri, Iceland · Isafjord, Iceland · Reykjavik, Iceland
★ Bucket-list Private Copenhagen Walking Tour with a Local ExpertDynjandi WaterfallInside the Volcano
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from $1,590
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Princess · Regal PrincessOne-way
Northern Europe 10 nights Jun 15 – Jun 25, 2027 from Reykjavik, Iceland to Southampton, England
Reykjavik, Iceland · Isafjord, Iceland · … · Southampton, England9 ports
Reykjavik, Iceland · Isafjord, Iceland · Akureyri, Iceland · Seydisfjordur, Iceland · Kirkwall, Scotland · Invergordon, Scotland · South Queensferry, Scotland · Zeebrugge (Bruges), Belgium · Southampton, England
★ Bucket-list Inside the VolcanoDynjandi WaterfallPrivate Bruges Full-Day Shore Excursion with Canal…Stand Inside Stonehenge & See the Original 1215 Ma…
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from $1,415
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Princess · Regal PrincessOne-way
Northern Europe 10 nights Jul 10 – Jul 20, 2027 from Copenhagen, Denmark to Reykjavik, Iceland
Copenhagen, Denmark · Kristiansund, Norway · … · Reykjavik, Iceland10 ports
Copenhagen, Denmark · Kristiansund, Norway · Skagen, Denmark · Stavanger, Norway · Nordfjordeid, Norway · Molde, Norway · Akureyri, Iceland · Isafjord, Iceland · Grundarfjordur, Iceland · Reykjavik, Iceland
★ Bucket-list Private Copenhagen Walking Tour with a Local ExpertLysefjorden & Pulpit Rock RIB SafariDynjandi WaterfallInside the Volcano
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from $1,534
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Princess · Sun PrincessOne-way
Mediterranean 10 nights Jul 15 – Jul 25, 2027 from Barcelona, Spain to Piraeus (Athens), Greece
Barcelona, Spain · Marseille, France · … · Piraeus (Athens), Greece10 ports
Barcelona, Spain · Marseille, France · Genoa, Italy · Civitavecchia (Rome), Italy · Naples, Italy · Heraklion, Crete, Greece · Santorini (Thira), Greece · Kusadasi (Ephesus), Turkey · Mykonos, Greece · Piraeus (Athens), Greece
★ Bucket-list Sagrada FamiliaCalanques National Park Boat Cruise from the Old P…Sail straight to Portofino from the cruise dockVatican, Sistine Chapel & Colosseum in One Day +6 more
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from $1,286
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Princess · Caribbean PrincessOne-way
North America 10 nights Sep 7 – Sep 17, 2027 from Boston, Massachusetts to Quebec City, Quebec
Boston, Massachusetts · Portland, Maine · … · Quebec City, Quebec8 ports
Boston, Massachusetts · Portland, Maine · Saint John, New Brunswick · Halifax, Nova Scotia · Sydney, Nova Scotia · Charlottetown, Prince Edward Island · Saguenay Fjord, Canada · Quebec City, Quebec
★ Bucket-list Private Luxury Boston TourPeggy's Cove & LunenburgBridgeClimb Sydney
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from $1,200
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Princess · Royal PrincessOne-way
Alaska 10 nights Sep 11 – Sep 21, 2027 from Seattle, Washington to Vancouver, British Columbia
Seattle, Washington · Ketchikan, Alaska · … · Vancouver, British Columbia8 ports
Seattle, Washington · Ketchikan, Alaska · Juneau, Alaska · Skagway, Alaska · Icy Strait, Alaska · Sitka, Alaska · Glacier Bay, Alaska · Vancouver, British Columbia
★ Bucket-list Space Needle & Chihuly Garden of GlassMisty Fjords Floatplane with a Wilderness Water La…Helicopter Glacier Landing & Guided Ice Walk on th…White Pass & Yukon Route Railway +4 more
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from $1,336
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Princess · Caribbean PrincessOne-way
North America 11 nights Sep 17 – Sep 28, 2027 from Quebec City, Quebec to Boston, Massachusetts
Quebec City, Quebec · Saguenay Fjord, Canada · … · Boston, Massachusetts8 ports
Quebec City, Quebec · Saguenay Fjord, Canada · Sept-Iles, Canada · Corner Brook, Newfoundland · Charlottetown, Prince Edward Island · Sydney, Nova Scotia · Halifax, Nova Scotia · Boston, Massachusetts
★ Bucket-list BridgeClimb SydneyPeggy's Cove & LunenburgPrivate Luxury Boston Tour
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from $1,126
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Princess · Caribbean PrincessOne-way
North America 10 nights Sep 28 – Oct 8, 2027 from Boston, Massachusetts to Quebec City, Quebec
Boston, Massachusetts · Portland, Maine · … · Quebec City, Quebec8 ports
Boston, Massachusetts · Portland, Maine · Saint John, New Brunswick · Halifax, Nova Scotia · Sydney, Nova Scotia · Charlottetown, Prince Edward Island · Saguenay Fjord, Canada · Quebec City, Quebec
★ Bucket-list Private Luxury Boston TourPeggy's Cove & LunenburgBridgeClimb Sydney
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from $1,199
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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
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Princess · Caribbean PrincessOne-way
North America 11 nights Oct 8 – Oct 19, 2027 from Quebec City, Quebec to Boston, Massachusetts
Quebec City, Quebec · Saguenay Fjord, Canada · … · Boston, Massachusetts8 ports
Quebec City, Quebec · Saguenay Fjord, Canada · Sept-Iles, Canada · Corner Brook, Newfoundland · Charlottetown, Prince Edward Island · Sydney, Nova Scotia · Halifax, Nova Scotia · Boston, Massachusetts
★ Bucket-list BridgeClimb SydneyPeggy's Cove & LunenburgPrivate Luxury Boston Tour
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from $1,204
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Princess · Caribbean PrincessOne-way
North America 10 nights Oct 19 – Oct 29, 2027 from Boston, Massachusetts to Quebec City, Quebec
Boston, Massachusetts · Portland, Maine · … · Quebec City, Quebec8 ports
Boston, Massachusetts · Portland, Maine · Saint John, New Brunswick · Halifax, Nova Scotia · Sydney, Nova Scotia · Charlottetown, Prince Edward Island · Saguenay Fjord, Canada · Quebec City, Quebec
★ Bucket-list Private Luxury Boston TourPeggy's Cove & LunenburgBridgeClimb Sydney
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from $1,199
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Princess · Grand PrincessOne-way
Australia & South Pacific 11 nights Oct 20 – Oct 31, 2027 from Sydney, Australia to Fremantle, Australia
Sydney, Australia · Eden, Australia · … · Fremantle, Australia7 ports
Sydney, Australia · Eden, Australia · Melbourne, Australia · Adelaide, Australia · Albany, Australia · Margaret River, Australia · Fremantle, Australia
★ Bucket-list BridgeClimb Sydney
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from $1,879
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Princess · Enchanted PrincessOne-way
Mediterranean 11 nights Oct 26 – Nov 6, 2027 from Ravenna, Italy to Civitavecchia (Rome), Italy
Ravenna, Italy · Kornati National Park, Croatia · … · Civitavecchia (Rome), Italy10 ports
Ravenna, Italy · Kornati National Park, Croatia · Bar, Montenegro · Heraklion, Crete, Greece · Katakolon (Olympia), Greece · Valletta, Malta · Messina, Sicily, Italy · Sicily, Italy · Naples, Italy · Civitavecchia (Rome), Italy
★ Bucket-list Private Ravenna UNESCO Mosaics Walk with a Local E…Palace of KnossosAncient OlympiaSt John's Co-Cathedral & the Caravaggio masterpieces +3 more
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from $1,229
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Princess · Emerald PrincessOne-way
Caribbean 9 nights Mar 24 – Apr 2, 2028 from Bridgetown, Barbados to Fort Lauderdale (Port Everglades), Florida
Bridgetown, Barbados · San Juan, Puerto Rico · … · Fort Lauderdale (Port Everglades), Florida6 ports
Bridgetown, Barbados · San Juan, Puerto Rico · Curacao, Caribbean · Port of Oranjestad, Aruba, Caribbean · Kralendijk, Bonaire, Dutch Antilles · Fort Lauderdale (Port Everglades), Florida
★ Bucket-list Swim with wild green sea turtles + two shipwrecks…Walk El Morro & Old San Juan's City WallsArubaKlein Bonaire +1 more
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from $1,356
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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.

19 lines
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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