Bucket-List Cruise Adventures

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Showing 36 of 507 sailings
Explora Journeys · EXPLORA IIIRound-trip
Caribbean 14 nights Oct 25, 2026 from Miami, Florida
Miami, Florida · Saint John/cruz Bay · … · Miami, Florida11 ports
Miami, Florida · Saint John/cruz Bay · St. John's, Antigua · Terre-de-haut, Guadeloupe · Philipsburg, St. Maarten · San Juan, Puerto Rico · Road Town, Tortola, B.V.I. · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Gustavia, St. Barts · Road Bay, Anguilla · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Private Half-Day Island Adventure & Trunk Bay BeachPrivate Catamaran Sail & SnorkelRandom Wind 'Paradise Day Sail' +5 more
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from $12,280
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Windstar · Star PrideRound-trip
Caribbean 11 nights Oct 28 – Nov 8, 2026 from San Juan, Puerto Rico
San Juan, Puerto Rico · Cruz Bay, St. John · … · San Juan, Puerto Rico11 ports
San Juan, Puerto Rico · Cruz Bay, St. John · Gustavia, St. Barts · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Falmouth Harbour, Antigua · Les Saintes, Guadeloupe · Rodney Bay, St. Lucia · St. Georges, Grenada, West Indies · Jost Van Dyke, British Virgin Islands · Virgin Gorda, British Virgin Islands · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsTrunk Bay Underwater Snorkel Trail & VI National P…Private Open-Top Mini Moke Island Tour of St. BartsMt. Liamuiga Volcano Crater Hike +6 more
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from $3,930
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MSC Cruises · MSC OperaOne-way
Mediterranean 25 nights Oct 29 – Nov 23, 2026 from Civitavecchia (Rome), Italy to La Romana, Dominican Republic
Civitavecchia (Rome), Italy · Genoa, Italy · … · La Romana, Dominican Republic16 ports
Civitavecchia (Rome), Italy · Genoa, Italy · Livorno (Florence/Pisa), Italy · Marseille, France · Barcelona, Spain · Tangier, Morocco · St. John's, Antigua · Philipsburg, St. Maarten · Port of Charlestown, Nevis, St. Kitts and Nevis · La Romana, Dominican Republic · Catalina Island, Dominican Republic · Bridgetown, Barbados · Fort-de-France, Martinique · Pointe-a-Pitre, Guadeloupe · Road Town, Tortola, B.V.I. · La Romana, Dominican Republic
★ Bucket-list Vatican, Sistine Chapel & Colosseum in One DaySail straight to Portofino from the cruise dockClimb the Leaning Tower of PisaCalanques National Park Boat Cruise from the Old P… +10 more
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from $4,730
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Costa · Costa FavolosaOne-way
Mediterranean 18 nights Nov 8 – Nov 26, 2026 from Hamburg, Germany to Pointe-a-Pitre, Guadeloupe
Hamburg, Germany · Ijmuiden, Netherlands · … · Pointe-a-Pitre, Guadeloupe9 ports
Hamburg, Germany · Ijmuiden, Netherlands · Dover (London), England · Le Havre (Paris), France · Lisbon, Portugal · Cadiz (Seville), Spain · Las Palmas, Gran Canaria, Canary Islands · Fort-de-France, Martinique · Pointe-a-Pitre, Guadeloupe
★ Bucket-list Private Full-Day Hamburg Shore Excursion with Loca…Rijksmuseum & CanalsWhite Cliffs of DoverPrivate Paris Highlights & Seine River Cruise from… +5 more
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from $1,539
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Windstar · Star PrideRound-trip
Caribbean 7 nights Nov 8 – Nov 15, 2026 from San Juan, Puerto Rico
San Juan, Puerto Rico · St. Georges, Grenada, West Indies · … · San Juan, Puerto Rico7 ports
San Juan, Puerto Rico · St. Georges, Grenada, West Indies · Bequia, Grenadines · Mayreau, Grenadines · Les Saintes, Guadeloupe · Marmaris, Turkey · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsGrenada Private Taxi TourTobago Cays & Mystique Full-Day Private SailSalt Whistle Bay +2 more
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from $2,411
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Costa · Costa FavolosaOne-way
Mediterranean 20 nights Nov 12 – Dec 2, 2026 from Le Havre (Paris), France to Pointe-a-Pitre, Guadeloupe
Le Havre (Paris), France · Lisbon, Portugal · … · Pointe-a-Pitre, Guadeloupe12 ports
Le Havre (Paris), France · Lisbon, Portugal · Cadiz (Seville), Spain · Las Palmas, Gran Canaria, Canary Islands · Fort-de-France, Martinique · Pointe-a-Pitre, Guadeloupe · Sea Of Antilles Darkest Spot · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Antigua, Antigua & Barbuda · Road Town, Tortola, B.V.I. · Santo Domingo, Dominican Republic · Pointe-a-Pitre, Guadeloupe
★ Bucket-list Private Paris Highlights & Seine River Cruise from…SintraReal Alcázar de SevillaRoque Nublo & Tejeda +6 more
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from $1,735
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Explora Journeys · EXPLORA IIIRound-trip
Caribbean 7 nights Nov 15, 2026 from San Juan, Puerto Rico
San Juan, Puerto Rico · Road Bay, Anguilla · … · San Juan, Puerto Rico12 ports
San Juan, Puerto Rico · Road Bay, Anguilla · St. John's, Antigua · Frederikstad, St. Croix · Ain Sokhna, Egypt · Puerto Plata, Dominican Republic · Miami, Florida · Saint John/cruz Bay · St. John's, Antigua · Terre-de-haut, Guadeloupe · Philipsburg, St. Maarten · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsPrivate Island HoppingPrivate Half-Day Island Adventure & Trunk Bay BeachPrivate Pyramids of Giza, Sphinx & Grand Egyptian… +4 more
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from $10,200
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MSC Cruises · MSC OperaRound-trip
Caribbean 7 nights Nov 16 – Nov 23, 2026 from La Romana, Dominican Republic
La Romana, Dominican Republic · Catalina Island, Dominican Republic · … · La Romana, Dominican Republic7 ports
La Romana, Dominican Republic · Catalina Island, Dominican Republic · Bridgetown, Barbados · Fort-de-France, Martinique · Pointe-a-Pitre, Guadeloupe · Road Town, Tortola, B.V.I. · La Romana, Dominican Republic
★ Bucket-list Saona Island Private Speedboat & Natural Pool DaySwim with wild green sea turtles + two shipwrecks…Mount Pelée & Saint-PierreDeath in Paradise Filming Locations & Botanical Ga… +1 more
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from $982
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MSC Cruises · MSC World EuropaRepositioning
Caribbean 19 nights Nov 17 – Dec 6, 2026 from Marseille, France to Pointe-a-Pitre, Guadeloupe
Marseille, France · Barcelona, Spain · … · Pointe-a-Pitre, Guadeloupe11 ports
Marseille, France · Barcelona, Spain · Puerto del Rosario, Spain · Santa Cruz de Tenerife, Canary Islands · Philipsburg, St. Maarten · Port of Charlestown, Nevis, St. Kitts and Nevis · Port of Kingstown, St. Vincent & the Grenadines · Bridgetown, Barbados · St. Georges, Grenada, West Indies · Fort-de-France, Martinique · Pointe-a-Pitre, Guadeloupe
★ Bucket-list Calanques National Park Boat Cruise from the Old P…Sagrada FamiliaFuerteventuraTeide National Park +7 more
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from $1,274
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MSC Cruises · MSC OperaRound-trip
Caribbean 14 nights Nov 19 – Dec 3, 2026 from Bridgetown, Barbados
Bridgetown, Barbados · Fort-de-France, Martinique · … · Bridgetown, Barbados13 ports
Bridgetown, Barbados · Fort-de-France, Martinique · Pointe-a-Pitre, Guadeloupe · Road Town, Tortola, B.V.I. · La Romana, Dominican Republic · Samana, Dominican Republic · Virgin Gorda, British Virgin Islands · Philipsburg, St. Maarten · Port of Charlestown, Nevis, St. Kitts and Nevis · Catalina Island, Dominican Republic · La Romana, Dominican Republic · Catalina Island, Dominican Republic · Bridgetown, Barbados
★ Bucket-list Swim with wild green sea turtles + two shipwrecks…Mount Pelée & Saint-PierreDeath in Paradise Filming Locations & Botanical Ga…Norman Island +5 more
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from $1,515
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MSC Cruises · MSC OperaRound-trip
Caribbean 14 nights Nov 20 – Dec 4, 2026 from Fort-de-France, Martinique
Fort-de-France, Martinique · Pointe-a-Pitre, Guadeloupe · … · Fort-de-France, Martinique13 ports
Fort-de-France, Martinique · Pointe-a-Pitre, Guadeloupe · Road Town, Tortola, B.V.I. · La Romana, Dominican Republic · Samana, Dominican Republic · Virgin Gorda, British Virgin Islands · Philipsburg, St. Maarten · Port of Charlestown, Nevis, St. Kitts and Nevis · Catalina Island, Dominican Republic · La Romana, Dominican Republic · Catalina Island, Dominican Republic · Bridgetown, Barbados · Fort-de-France, Martinique
★ Bucket-list Mount Pelée & Saint-PierreDeath in Paradise Filming Locations & Botanical Ga…Norman IslandSaona Island Private Speedboat & Natural Pool Day +5 more
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from $1,324
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Explora Journeys · EXPLORA IIIOne-way
Caribbean 7 nights Nov 22, 2026 from Miami, Florida to San Juan, Puerto Rico
Miami, Florida · Saint John/cruz Bay · … · San Juan, Puerto Rico6 ports
Miami, Florida · Saint John/cruz Bay · St. John's, Antigua · Terre-de-haut, Guadeloupe · Philipsburg, St. Maarten · San Juan, Puerto Rico
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Private Half-Day Island Adventure & Trunk Bay BeachPrivate Catamaran Sail & SnorkelRandom Wind 'Paradise Day Sail' +1 more
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from $4,200
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Seabourn · Seabourn QuestRound-trip
Caribbean 14 nights Nov 22 – Dec 6, 2026 from Miami, Florida
Miami, Florida · San Juan, Puerto Rico · … · Miami, Florida11 ports
Miami, Florida · San Juan, Puerto Rico · Road Bay, Anguilla · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Roseau, Dominica · Fort-de-France, Martinique · Terre-de-haut, Guadeloupe · Little Bay, Montserrat, Leeward Islands · Virgin Gorda, British Virgin Islands · Great Harbor, Peter Island, BVI · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Walk El Morro & Old San Juan's City WallsPrivate Island HoppingMt. Liamuiga Volcano Crater Hike +6 more
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from $5,599
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Costa · Costa FavolosaRound-trip
Caribbean 8 nights Nov 25 – Dec 3, 2026 from Fort-de-France, Martinique
Fort-de-France, Martinique · Pointe-a-Pitre, Guadeloupe · … · Fort-de-France, Martinique9 ports
Fort-de-France, Martinique · Pointe-a-Pitre, Guadeloupe · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Antigua, Antigua & Barbuda · Sea Of Antilles Darkest Spot · Road Town, Tortola, B.V.I. · Santo Domingo, Dominican Republic · Pointe-a-Pitre, Guadeloupe · Fort-de-France, Martinique
★ Bucket-list Mount Pelée & Saint-PierreDeath in Paradise Filming Locations & Botanical Ga…Mt. Liamuiga Volcano Crater HikeAdventure Antigua +2 more
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from $1,227
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Oceania · Oceania VistaRound-trip
Caribbean 12 nights Nov 25 – Dec 7, 2026 from Miami, Florida
Miami, Florida · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · … · Miami, Florida9 ports
Miami, Florida · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · Philipsburg, St. Maarten · Gustavia, St. Barts · Fort-de-France, Martinique · Pointe-a-Pitre, Guadeloupe · St. John's, Antigua · Tortola, B.V.I. · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Private Full-Day Boat CharterRandom Wind 'Paradise Day Sail'Private Open-Top Mini Moke Island Tour of St. Barts +4 more
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from $4,025
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Costa · Costa FavolosaRound-trip
Caribbean 6 nights Nov 26 – Dec 2, 2026 from Pointe-a-Pitre, Guadeloupe
Pointe-a-Pitre, Guadeloupe · Port of Basseterre, St. Kitts, St. Kitts and Nevis · … · Pointe-a-Pitre, Guadeloupe7 ports
Pointe-a-Pitre, Guadeloupe · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Antigua, Antigua & Barbuda · Sea Of Antilles Darkest Spot · Road Town, Tortola, B.V.I. · Santo Domingo, Dominican Republic · Pointe-a-Pitre, Guadeloupe
★ Bucket-list Death in Paradise Filming Locations & Botanical Ga…Mt. Liamuiga Volcano Crater HikeAdventure AntiguaNorman Island +1 more
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from $927
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Costa · Costa FavolosaRound-trip
Caribbean 7 nights Nov 30 – Dec 7, 2026 from Santo Domingo, Dominican Republic
Santo Domingo, Dominican Republic · Pointe-a-Pitre, Guadeloupe · … · Santo Domingo, Dominican Republic8 ports
Santo Domingo, Dominican Republic · Pointe-a-Pitre, Guadeloupe · Fort-de-France, Martinique · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Antigua, Antigua & Barbuda · Sea Of Antilles Darkest Spot · Road Town, Tortola, B.V.I. · Santo Domingo, Dominican Republic
★ Bucket-list Zona ColonialDeath in Paradise Filming Locations & Botanical Ga…Mount Pelée & Saint-PierreMt. Liamuiga Volcano Crater Hike +2 more
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from $2,399
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MSC Cruises · MSC OperaRound-trip
Caribbean 7 nights Nov 30 – Dec 7, 2026 from La Romana, Dominican Republic
La Romana, Dominican Republic · Catalina Island, Dominican Republic · … · La Romana, Dominican Republic7 ports
La Romana, Dominican Republic · Catalina Island, Dominican Republic · Bridgetown, Barbados · Fort-de-France, Martinique · Pointe-a-Pitre, Guadeloupe · Road Town, Tortola, B.V.I. · La Romana, Dominican Republic
★ Bucket-list Saona Island Private Speedboat & Natural Pool DaySwim with wild green sea turtles + two shipwrecks…Mount Pelée & Saint-PierreDeath in Paradise Filming Locations & Botanical Ga… +1 more
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from $698
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Costa · Costa FavolosaRound-trip
Caribbean 8 nights Dec 2 – Dec 10, 2026 from Pointe-a-Pitre, Guadeloupe
Pointe-a-Pitre, Guadeloupe · Fort-de-France, Martinique · … · Pointe-a-Pitre, Guadeloupe10 ports
Pointe-a-Pitre, Guadeloupe · Fort-de-France, Martinique · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Antigua, Antigua & Barbuda · Sea Of Antilles Darkest Spot · Road Town, Tortola, B.V.I. · Santo Domingo, Dominican Republic · Fort-de-France, Martinique · Martinique Bay · Pointe-a-Pitre, Guadeloupe
★ Bucket-list Death in Paradise Filming Locations & Botanical Ga…Mount Pelée & Saint-PierreMt. Liamuiga Volcano Crater HikeAdventure Antigua +2 more
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from $1,221
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MSC Cruises · MSC World EuropaRound-trip
Caribbean 13 nights Dec 2 – Dec 15, 2026 from Bridgetown, Barbados
Bridgetown, Barbados · St. Georges, Grenada, West Indies · … · Bridgetown, Barbados12 ports
Bridgetown, Barbados · St. Georges, Grenada, West Indies · Fort-de-France, Martinique · Pointe-a-Pitre, Guadeloupe · St. John's, Antigua · Philipsburg, St. Maarten · Port of Charlestown, Nevis, St. Kitts and Nevis · Roseau, Dominica · Fort-de-France, Martinique · Pointe-a-Pitre, Guadeloupe · Castries, St. Lucia · Bridgetown, Barbados
★ Bucket-list Swim with wild green sea turtles + two shipwrecks…Grenada Private Taxi TourMount Pelée & Saint-PierreDeath in Paradise Filming Locations & Botanical Ga… +5 more
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from $5,271
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MSC Cruises · MSC OperaRound-trip
Caribbean 14 nights Dec 3 – Dec 17, 2026 from Bridgetown, Barbados
Bridgetown, Barbados · Fort-de-France, Martinique · … · Bridgetown, Barbados13 ports
Bridgetown, Barbados · Fort-de-France, Martinique · Pointe-a-Pitre, Guadeloupe · Road Town, Tortola, B.V.I. · La Romana, Dominican Republic · Virgin Gorda, British Virgin Islands · Philipsburg, St. Maarten · Port of Charlestown, Nevis, St. Kitts and Nevis · Road Town, Tortola, B.V.I. · Catalina Island, Dominican Republic · La Romana, Dominican Republic · Catalina Island, Dominican Republic · Bridgetown, Barbados
★ Bucket-list Swim with wild green sea turtles + two shipwrecks…Mount Pelée & Saint-PierreDeath in Paradise Filming Locations & Botanical Ga…Norman Island +4 more
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from $1,435
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Costa · Costa FascinosaOne-way
Caribbean 19 nights Dec 4 – Dec 23, 2026 from Marseille, France to Pointe-a-Pitre, Guadeloupe
Marseille, France · Savona (Genoa), Italy · … · Pointe-a-Pitre, Guadeloupe11 ports
Marseille, France · Savona (Genoa), Italy · Barcelona, Spain · Malaga, Spain · Las Palmas, Gran Canaria, Canary Islands · Pointe-a-Pitre, Guadeloupe · Philipsburg, St. Maarten · La Romana, Dominican Republic · 15.9 N, 63.1 W,caribbean Sea · Castries, St. Lucia · Pointe-a-Pitre, Guadeloupe
★ Bucket-list Calanques National Park Boat Cruise from the Old P…Portofino & San Fruttuoso Abbey by the local ferrySagrada FamiliaGranada & the Alhambra +5 more
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from $1,680
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MSC Cruises · MSC OperaRound-trip
Caribbean 14 nights Dec 4 – Dec 18, 2026 from Fort-de-France, Martinique
Fort-de-France, Martinique · Pointe-a-Pitre, Guadeloupe · … · Fort-de-France, Martinique13 ports
Fort-de-France, Martinique · Pointe-a-Pitre, Guadeloupe · Road Town, Tortola, B.V.I. · La Romana, Dominican Republic · Virgin Gorda, British Virgin Islands · Philipsburg, St. Maarten · Port of Charlestown, Nevis, St. Kitts and Nevis · Road Town, Tortola, B.V.I. · Catalina Island, Dominican Republic · La Romana, Dominican Republic · Catalina Island, Dominican Republic · Bridgetown, Barbados · Fort-de-France, Martinique
★ Bucket-list Mount Pelée & Saint-PierreDeath in Paradise Filming Locations & Botanical Ga…Norman IslandSaona Island Private Speedboat & Natural Pool Day +4 more
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from $1,534
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Costa · Costa FascinosaOne-way
Mediterranean 22 nights Dec 5 – Dec 27, 2026 from Savona (Genoa), Italy to La Romana, Dominican Republic
Savona (Genoa), Italy · Barcelona, Spain · … · La Romana, Dominican Republic14 ports
Savona (Genoa), Italy · Barcelona, Spain · Malaga, Spain · Las Palmas, Gran Canaria, Canary Islands · Pointe-a-Pitre, Guadeloupe · Philipsburg, St. Maarten · La Romana, Dominican Republic · 15.9 N, 63.1 W,caribbean Sea · Castries, St. Lucia · Pointe-a-Pitre, Guadeloupe · Antigua, Antigua & Barbuda · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Road Town, Tortola, B.V.I. · La Romana, Dominican Republic
★ Bucket-list Portofino & San Fruttuoso Abbey by the local ferrySagrada FamiliaGranada & the AlhambraRoque Nublo & Tejeda +7 more
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from $1,993
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MSC Cruises · MSC World EuropaRound-trip
Caribbean 7 nights Dec 5 – Dec 12, 2026 from Fort-de-France, Martinique
Fort-de-France, Martinique · Pointe-a-Pitre, Guadeloupe · … · Fort-de-France, Martinique7 ports
Fort-de-France, Martinique · Pointe-a-Pitre, Guadeloupe · St. John's, Antigua · Philipsburg, St. Maarten · Port of Charlestown, Nevis, St. Kitts and Nevis · Roseau, Dominica · Fort-de-France, Martinique
★ Bucket-list Mount Pelée & Saint-PierreDeath in Paradise Filming Locations & Botanical Ga…Private Half-Day Island Adventure & Trunk Bay BeachRandom Wind 'Paradise Day Sail' +2 more
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from $846
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Seabourn · Seabourn OvationOne-way
Caribbean 14 nights Dec 5 – Dec 19, 2026 from Philipsburg, St. Maarten to Bridgetown, Barbados
Philipsburg, St. Maarten · Sopers Hole, British Virgin Islands · … · Bridgetown, Barbados13 ports
Philipsburg, St. Maarten · Sopers Hole, British Virgin Islands · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Trois Ilets, Martinique · Port Elizabeth, Saint Vincent · St. Georges, Grenada, West Indies · Bridgetown, Barbados · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Terre-de-haut, Guadeloupe · Saint-Pierre, Newfoundland, Canada · Roseau, Dominica · Rodney Bay, St. Lucia · Bridgetown, Barbados
★ Bucket-list Random Wind 'Paradise Day Sail'The Baths of Virgin GordaMt. Liamuiga Volcano Crater HikeLa Savane des Esclaves +7 more
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from $6,319
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Silversea · Silver SpiritRound-trip
Caribbean 7 nights Dec 5 – Dec 12, 2026 from Bridgetown, Barbados
Bridgetown, Barbados · Bequia, Grenadines · … · Bridgetown, Barbados8 ports
Bridgetown, Barbados · Bequia, Grenadines · Fort-de-France, Martinique · Deshaies, Guadeloupe · Gustavia, St. Barts · Codrington, Barbuda · Castries, St. Lucia · Bridgetown, Barbados
★ Bucket-list Swim with wild green sea turtles + two shipwrecks…Tobago Cays & Mystique Full-Day Private SailMount Pelée & Saint-PierreJardin Botanique de Deshaies at Opening Hour +3 more
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from $4,550
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Costa · Costa FascinosaOne-way
Mediterranean 21 nights Dec 6 – Dec 27, 2026 from Barcelona, Spain to La Romana, Dominican Republic
Barcelona, Spain · Malaga, Spain · … · La Romana, Dominican Republic13 ports
Barcelona, Spain · Malaga, Spain · Las Palmas, Gran Canaria, Canary Islands · Pointe-a-Pitre, Guadeloupe · Philipsburg, St. Maarten · La Romana, Dominican Republic · Caribbean Sea Darkest Spot · Castries, St. Lucia · Pointe-a-Pitre, Guadeloupe · Antigua, Antigua & Barbuda · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Road Town, Tortola, B.V.I. · La Romana, Dominican Republic
★ Bucket-list Sagrada FamiliaGranada & the AlhambraRoque Nublo & TejedaDeath in Paradise Filming Locations & Botanical Ga… +6 more
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from $1,871
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Explora Journeys · EXPLORA IIIOne-way
Caribbean 14 nights Dec 6, 2026 from Miami, Florida to San Juan, Puerto Rico
Miami, Florida · Saint John/cruz Bay · … · San Juan, Puerto Rico6 ports
Miami, Florida · Saint John/cruz Bay · St. John's, Antigua · Terre-de-haut, Guadeloupe · Gustavia, St. Barts · San Juan, Puerto Rico
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Private Half-Day Island Adventure & Trunk Bay BeachPrivate Catamaran Sail & SnorkelPrivate Open-Top Mini Moke Island Tour of St. Barts +1 more
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from $4,200
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MSC Cruises · MSC World EuropaRound-trip
Caribbean 7 nights Dec 6 – Dec 13, 2026 from Pointe-a-Pitre, Guadeloupe
Pointe-a-Pitre, Guadeloupe · St. John's, Antigua · … · Pointe-a-Pitre, Guadeloupe7 ports
Pointe-a-Pitre, Guadeloupe · St. John's, Antigua · Philipsburg, St. Maarten · Port of Charlestown, Nevis, St. Kitts and Nevis · Roseau, Dominica · Fort-de-France, Martinique · Pointe-a-Pitre, Guadeloupe
★ Bucket-list Death in Paradise Filming Locations & Botanical Ga…Private Half-Day Island Adventure & Trunk Bay BeachRandom Wind 'Paradise Day Sail'Private Island Tour +2 more
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from $1,175
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Seabourn · Seabourn QuestRound-trip
Caribbean 14 nights Dec 6 – Dec 20, 2026 from Miami, Florida
Miami, Florida · San Juan, Puerto Rico · … · Miami, Florida11 ports
Miami, Florida · San Juan, Puerto Rico · Virgin Gorda, British Virgin Islands · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Roseau, Dominica · Fort-de-France, Martinique · Terre-de-haut, Guadeloupe · Little Bay, Montserrat, Leeward Islands · Road Bay, Anguilla · Great Harbor, Peter Island, BVI · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Walk El Morro & Old San Juan's City WallsThe Baths National ParkMt. Liamuiga Volcano Crater Hike +6 more
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from $7,054
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Windstar · Star PrideRound-trip
Caribbean 7 nights Dec 6 – Dec 13, 2026 from San Juan, Puerto Rico
San Juan, Puerto Rico · St. Georges, Grenada, West Indies · … · San Juan, Puerto Rico7 ports
San Juan, Puerto Rico · St. Georges, Grenada, West Indies · Bequia, Grenadines · Mayreau, Grenadines · Deshaies, Guadeloupe · Marmaris, Turkey · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsGrenada Private Taxi TourTobago Cays & Mystique Full-Day Private SailSalt Whistle Bay +2 more
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from $3,636
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Costa · Costa FavolosaRound-trip
Caribbean 7 nights Dec 7 – Dec 14, 2026 from Santo Domingo, Dominican Republic
Santo Domingo, Dominican Republic · Fort-de-France, Martinique · … · Santo Domingo, Dominican Republic9 ports
Santo Domingo, Dominican Republic · Fort-de-France, Martinique · Martinique Bay · Pointe-a-Pitre, Guadeloupe · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Antigua, Antigua & Barbuda · Sea Of Antilles Darkest Spot · Road Town, Tortola, B.V.I. · Santo Domingo, Dominican Republic
★ Bucket-list Zona ColonialMount Pelée & Saint-PierreDeath in Paradise Filming Locations & Botanical Ga…Mt. Liamuiga Volcano Crater Hike +2 more
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from $1,779
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Costa · Costa FavolosaRound-trip
Caribbean 7 nights Dec 9 – Dec 16, 2026 from Fort-de-France, Martinique
Fort-de-France, Martinique · Martinique Bay · … · Fort-de-France, Martinique9 ports
Fort-de-France, Martinique · Martinique Bay · Pointe-a-Pitre, Guadeloupe · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Antigua, Antigua & Barbuda · Sea Of Antilles Darkest Spot · Road Town, Tortola, B.V.I. · Santo Domingo, Dominican Republic · Fort-de-France, Martinique
★ Bucket-list Mount Pelée & Saint-PierreDeath in Paradise Filming Locations & Botanical Ga…Mt. Liamuiga Volcano Crater HikeAdventure Antigua +2 more
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from $1,067
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Costa · Costa FavolosaRound-trip
Caribbean 7 nights Dec 10 – Dec 17, 2026 from Pointe-a-Pitre, Guadeloupe
Pointe-a-Pitre, Guadeloupe · Port of Basseterre, St. Kitts, St. Kitts and Nevis · … · Pointe-a-Pitre, Guadeloupe9 ports
Pointe-a-Pitre, Guadeloupe · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Antigua, Antigua & Barbuda · Sea Of Antilles Darkest Spot · Road Town, Tortola, B.V.I. · Santo Domingo, Dominican Republic · Martinique Bay · Fort-de-France, Martinique · Pointe-a-Pitre, Guadeloupe
★ Bucket-list Death in Paradise Filming Locations & Botanical Ga…Mt. Liamuiga Volcano Crater HikeAdventure AntiguaNorman Island +2 more
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from $1,064
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Silversea · Silver ShadowOne-way
Caribbean 10 nights Dec 10 – Dec 20, 2026 from Miami, Florida to San Juan, Puerto Rico
Miami, Florida · Cruz Bay, St. John, U.S. Virgin Islands · … · San Juan, Puerto Rico9 ports
Miami, Florida · Cruz Bay, St. John, U.S. Virgin Islands · Philipsburg, St. Maarten · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Iles des Saintes, Guadeloupe · Fort-de-France, Martinique · Little Bay, Montserrat, Leeward Islands · Jost Van Dyke, British Virgin Islands · San Juan, Puerto Rico
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Trunk Bay Underwater Snorkel Trail & VI National P…Random Wind 'Paradise Day Sail'Mt. Liamuiga Volcano Crater Hike +5 more
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from $3,850
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