Bucket-List Cruise Adventures

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

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Showing 24 of 24 sailings
Azamara · Azamara JourneyOne-way
Caribbean 7 nights Nov 7 – Nov 14, 2026 from San Juan, Puerto Rico to Bridgetown, Barbados
San Juan, Puerto Rico · Virgin Gorda, British Virgin Islands · … · Bridgetown, Barbados8 ports
San Juan, Puerto Rico · Virgin Gorda, British Virgin Islands · St. John's, Antigua · Saint- Pierre · Port Elizabeth, Saint Vincent · St. Georges, Grenada, West Indies · Scarborough, Tobago · Bridgetown, Barbados
★ Bucket-list Walk El Morro & Old San Juan's City WallsPrivate Half-Day Island Adventure & Trunk Bay BeachSchotia Private Game ReserveGrenada Private Taxi Tour +1 more
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from $2,059
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Seabourn · Seabourn OvationOne-way
Caribbean 8 nights Nov 20 – Nov 28, 2026 from Miami, Florida to Bridgetown, Barbados
Miami, Florida · San Juan, Puerto Rico · … · Bridgetown, Barbados7 ports
Miami, Florida · San Juan, Puerto Rico · Great Harbor, Peter Island, BVI · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Roseau, Dominica · Port Elizabeth, Saint Vincent · Bridgetown, Barbados
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Walk El Morro & Old San Juan's City WallsMt. Liamuiga Volcano Crater HikeBoiling Lake Hike +2 more
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from $4,098
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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'Mt. Liamuiga Volcano Crater HikeSchotia Private Game ReserveGrenada Private Taxi Tour +2 more
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from $6,798
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Seabourn · Seabourn OvationOne-way
Caribbean 7 nights Dec 26 – Jan 2, 2027 from Philipsburg, St. Maarten to Bridgetown, Barbados
Philipsburg, St. Maarten · Sopers Hole, British Virgin Islands · … · Bridgetown, Barbados7 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
★ Bucket-list Random Wind 'Paradise Day Sail'Mt. Liamuiga Volcano Crater HikeSchotia Private Game ReserveGrenada Private Taxi Tour +1 more
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from $5,998
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Azamara · Azamara JourneyOne-way
Caribbean 11 nights Jan 14 – Jan 25, 2027 from Miami, Florida to Bridgetown, Barbados
Miami, Florida · Saint John, New Brunswick · … · Bridgetown, Barbados10 ports
Miami, Florida · Saint John, New Brunswick · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · Philipsburg, St. Maarten · Port of Charlestown, Nevis, St. Kitts and Nevis · St. John's, Antigua · Saint- Pierre · Port Elizabeth, Saint Vincent · St. Georges, Grenada, West Indies · Bridgetown, Barbados
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Reversing Falls & Fundy Tidal BorePrivate Full-Day Boat CharterRandom Wind 'Paradise Day Sail' +5 more
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from $3,116
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Seabourn · Seabourn OvationOne-way
Caribbean 7 nights Jan 16 – Jan 23, 2027 from Philipsburg, St. Maarten to Bridgetown, Barbados
Philipsburg, St. Maarten · Sopers Hole, British Virgin Islands · … · Bridgetown, Barbados7 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
★ Bucket-list Random Wind 'Paradise Day Sail'Mt. Liamuiga Volcano Crater HikeSchotia Private Game ReserveGrenada Private Taxi Tour +1 more
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from $5,798
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Regent · Seven Seas VoyagerOne-way
Australia & South Pacific 15 nights Jan 17 – Feb 1, 2027 from Port Louis, Mauritius to Cape Town, South Africa
Port Louis, Mauritius · Pointe des Galets, Reunion Island · … · Cape Town, South Africa14 ports
Port Louis, Mauritius · Pointe des Galets, Reunion Island · Willis Island · Fort Dauphin, Madagascar · Willis Island · Toliara, Madagascar · Willis Island · Maputo, Mozambique · Willis Island · Durban, South Africa · East London, South Africa · Port Elizabeth, South Africa · Mossel Bay, South Africa · Cape Town, South Africa
★ Bucket-list Île aux CerfsZodiac Circumnavigation of Willis IslandSani Pass 4x4 AscentSchotia Private Game Reserve +1 more
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from $12,399
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Seabourn · Seabourn OvationOne-way
Caribbean 7 nights Jan 30 – Feb 6, 2027 from Philipsburg, St. Maarten to Bridgetown, Barbados
Philipsburg, St. Maarten · Sopers Hole, British Virgin Islands · … · Bridgetown, Barbados7 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
★ Bucket-list Random Wind 'Paradise Day Sail'Mt. Liamuiga Volcano Crater HikeSchotia Private Game ReserveGrenada Private Taxi Tour +1 more
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from $4,798
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Regent · Seven Seas VoyagerOne-way
Australia & South Pacific 15 nights Feb 1 – Feb 16, 2027 from Cape Town, South Africa to Port Louis, Mauritius
Cape Town, South Africa · Willis Island · … · Port Louis, Mauritius11 ports
Cape Town, South Africa · Willis Island · Port Elizabeth, South Africa · Willis Island · Durban, South Africa · Willis Island · Mayotte, Comoros Isles · Nosy Be, Madagascar · Diego Suarez (Antsiranana), Madagascar · Willis Island · Port Louis, Mauritius
★ Bucket-list Table MountainZodiac Circumnavigation of Willis IslandSchotia Private Game ReserveSani Pass 4x4 Ascent +1 more
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from $13,999
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Seabourn · Seabourn OvationOne-way
Caribbean 7 nights Feb 20 – Feb 27, 2027 from Philipsburg, St. Maarten to Bridgetown, Barbados
Philipsburg, St. Maarten · Sopers Hole, British Virgin Islands · … · Bridgetown, Barbados7 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
★ Bucket-list Random Wind 'Paradise Day Sail'Mt. Liamuiga Volcano Crater HikeSchotia Private Game ReserveGrenada Private Taxi Tour +1 more
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from $5,998
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Seabourn · Seabourn OvationOne-way
Caribbean 7 nights Mar 6 – Mar 13, 2027 from Philipsburg, St. Maarten to Bridgetown, Barbados
Philipsburg, St. Maarten · Sopers Hole, British Virgin Islands · … · Bridgetown, Barbados7 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
★ Bucket-list Random Wind 'Paradise Day Sail'Mt. Liamuiga Volcano Crater HikeSchotia Private Game ReserveGrenada Private Taxi Tour +1 more
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from $4,798
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Regent · Seven Seas NavigatorOne-way
Australia & South Pacific 28 nights Mar 9 – Apr 6, 2027 from Cape Town, South Africa to Singapore, Singapore
Cape Town, South Africa · Willis Island · … · Singapore, Singapore20 ports
Cape Town, South Africa · Willis Island · Port Elizabeth, South Africa · Willis Island · Maputo, Mozambique · Willis Island · Nosy Be, Madagascar · Willis Island · Dar es Salaam, Tanzania · Willis Island · Mahe, Seychelles Islands · Willis Island · Male, Maldives · Willis Island · Hambantota, Sri Lanka · Willis Island · Phuket, Thailand · Penang, Malaysia · Port Klang (Kuala Lumpur), Malaysia · Singapore, Singapore
★ Bucket-list Table MountainZodiac Circumnavigation of Willis IslandSchotia Private Game ReservePrivate Overwater Sandbank Picnic & Snorkel by Spe… +4 more
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from $16,899
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Seabourn · Seabourn OvationOne-way
Caribbean 7 nights Mar 20 – Mar 27, 2027 from Philipsburg, St. Maarten to Bridgetown, Barbados
Philipsburg, St. Maarten · Sopers Hole, British Virgin Islands · … · Bridgetown, Barbados7 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
★ Bucket-list Random Wind 'Paradise Day Sail'Mt. Liamuiga Volcano Crater HikeSchotia Private Game ReserveGrenada Private Taxi Tour +1 more
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from $5,998
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Regent · Seven Seas NavigatorOne-way
Australia & South Pacific 25 nights Oct 26 – Nov 20, 2027 from Singapore, Singapore to Cape Town, South Africa
Singapore, Singapore · Willis Island · … · Cape Town, South Africa19 ports
Singapore, Singapore · Willis Island · Penang, Malaysia · Phuket, Thailand · Willis Island · Hambantota, Sri Lanka · Willis Island · Male, Maldives · Willis Island · Mahe, Seychelles Islands · Willis Island · Nosy Be, Madagascar · Mayotte, Comoros Isles · Willis Island · Maputo, Mozambique · Willis Island · Port Elizabeth, South Africa · Willis Island · Cape Town, South Africa
★ Bucket-list Gardens by the BayZodiac Circumnavigation of Willis IslandCheong Fatt Tze Blue MansionPhang Nga Bay +3 more
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from $13,799
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Azamara · Azamara QuestOne-way
Caribbean 17 nights Oct 28 – Nov 14, 2027 from New York, New York to Bridgetown, Barbados
New York, New York · Hamilton, Bermuda · … · Bridgetown, Barbados13 ports
New York, New York · Hamilton, Bermuda · Philipsburg, St. Maarten · Road Town, Tortola, B.V.I. · San Juan, Puerto Rico · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · Virgin Gorda, British Virgin Islands · St. John's, Antigua · Saint- Pierre · Port Elizabeth, Saint Vincent · St. Georges, Grenada, West Indies · Scarborough, Tobago · Bridgetown, Barbados
★ Bucket-list Manhattan Helicopter TourRandom Wind 'Paradise Day Sail'Norman IslandWalk El Morro & Old San Juan's City Walls +5 more
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from $5,583
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Seabourn · Seabourn OvationOne-way
Caribbean 7 nights Dec 4 – Dec 11, 2027 from Philipsburg, St. Maarten to Bridgetown, Barbados
Philipsburg, St. Maarten · Sopers Hole, British Virgin Islands · … · Bridgetown, Barbados7 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
★ Bucket-list Random Wind 'Paradise Day Sail'Mt. Liamuiga Volcano Crater HikeSchotia Private Game ReserveGrenada Private Taxi Tour +1 more
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from $4,298
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Seabourn · Seabourn OvationOne-way
Caribbean 17 nights Dec 11 – Dec 28, 2027 from Bridgetown, Barbados to Philipsburg, St. Maarten
Bridgetown, Barbados · Rodney Bay, St. Lucia · … · Philipsburg, St. Maarten15 ports
Bridgetown, Barbados · Rodney Bay, St. Lucia · Scarborough, Tobago · Willemstad, Curacao · Kralendijk, Bonaire, Dutch Antilles · Bridgetown, Barbados · St. Georges, Grenada, West Indies · Port Elizabeth, Saint Vincent · Saint-Pierre, Newfoundland, Canada · Terre-de-haut, Guadeloupe · St. John's, Antigua · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Great Harbor, Peter Island, BVI · Road Bay, Anguilla · Philipsburg, St. Maarten
★ Bucket-list Swim with wild green sea turtles + two shipwrecks…Private Full-Day Curaçao Island Tour with Local Ex…Klein BonaireGrenada Private Taxi Tour +4 more
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from $8,998
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Seabourn · Seabourn OvationOne-way
Caribbean 10 nights Dec 18 – Dec 28, 2027 from Bridgetown, Barbados to Philipsburg, St. Maarten
Bridgetown, Barbados · St. Georges, Grenada, West Indies · … · Philipsburg, St. Maarten10 ports
Bridgetown, Barbados · St. Georges, Grenada, West Indies · Port Elizabeth, Saint Vincent · Saint-Pierre, Newfoundland, Canada · Terre-de-haut, Guadeloupe · St. John's, Antigua · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Great Harbor, Peter Island, BVI · Road Bay, Anguilla · Philipsburg, St. Maarten
★ Bucket-list Swim with wild green sea turtles + two shipwrecks…Grenada Private Taxi TourSchotia Private Game ReservePrivate Half-Day Island Adventure & Trunk Bay Beach +2 more
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from $5,998
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Azamara · Azamara QuestOne-way
Northern Europe 8 nights Dec 19 – Dec 27, 2027 from San Juan, Puerto Rico to Bridgetown, Barbados
San Juan, Puerto Rico · Virgin Gorda, British Virgin Islands · … · Bridgetown, Barbados8 ports
San Juan, Puerto Rico · Virgin Gorda, British Virgin Islands · St. John's, Antigua · Portsmouth, England · Port Elizabeth, Saint Vincent · St. Georges, Grenada, West Indies · Scarborough, Tobago · Bridgetown, Barbados
★ Bucket-list Walk El Morro & Old San Juan's City WallsPrivate Half-Day Island Adventure & Trunk Bay BeachSchotia Private Game ReserveGrenada Private Taxi Tour +1 more
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from $3,086
Book This Cruise@ Cruisebound
Seabourn · Seabourn OvationOne-way
Caribbean 7 nights Jan 22 – Jan 29, 2028 from Philipsburg, St. Maarten to Bridgetown, Barbados
Philipsburg, St. Maarten · Sopers Hole, British Virgin Islands · … · Bridgetown, Barbados7 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
★ Bucket-list Random Wind 'Paradise Day Sail'Mt. Liamuiga Volcano Crater HikeSchotia Private Game ReserveGrenada Private Taxi Tour +1 more
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from $4,798
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Seabourn · Seabourn OvationOne-way
Caribbean 7 nights Feb 19 – Feb 26, 2028 from Philipsburg, St. Maarten to Bridgetown, Barbados
Philipsburg, St. Maarten · Sopers Hole, British Virgin Islands · … · Bridgetown, Barbados7 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
★ Bucket-list Random Wind 'Paradise Day Sail'Mt. Liamuiga Volcano Crater HikeSchotia Private Game ReserveGrenada Private Taxi Tour +1 more
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from $4,998
Book This Cruise@ Cruisebound
Seabourn · Seabourn OvationOne-way
Caribbean 7 nights Mar 18 – Mar 25, 2028 from Philipsburg, St. Maarten to Bridgetown, Barbados
Philipsburg, St. Maarten · Sopers Hole, British Virgin Islands · … · Bridgetown, Barbados7 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
★ Bucket-list Random Wind 'Paradise Day Sail'Mt. Liamuiga Volcano Crater HikeSchotia Private Game ReserveGrenada Private Taxi Tour +1 more
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from $4,998
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Regent · Seven Seas MarinerOne-way
Asia 31 nights Mar 28 – Apr 28, 2028 from Singapore, Singapore to Cape Town, South Africa
Singapore, Singapore · Port Klang (Kuala Lumpur), Malaysia · … · Cape Town, South Africa23 ports
Singapore, Singapore · Port Klang (Kuala Lumpur), Malaysia · Penang, Malaysia · Phuket, Thailand · Willis Island · Colombo, Sri Lanka · Willis Island · Male, Maldives · Willis Island · Mahe, Seychelles Islands · Willis Island · Diego Suarez (Antsiranana), Madagascar · Willis Island · Port Louis, Mauritius · Pointe des Galets, Reunion Island · Willis Island · Nosy Be, Madagascar · Willis Island · Durban, South Africa · Willis Island · Port Elizabeth, South Africa · Mossel Bay, South Africa · Cape Town, South Africa
★ Bucket-list Gardens by the BayPetronas Twin TowersCheong Fatt Tze Blue MansionPhang Nga Bay +6 more
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from $22,999
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Azamara · Azamara OnwardOne-way
Africa 12 nights Apr 27 – May 9, 2028 from Port Louis, Mauritius to Cape Town, South Africa
Port Louis, Mauritius · Pointe des Galets, Reunion Island · … · Cape Town, South Africa7 ports
Port Louis, Mauritius · Pointe des Galets, Reunion Island · Taolagnaro, Madagascar · Richards Bay, South Africa · Durban, South Africa · Port Elizabeth, South Africa · Cape Town, South Africa
★ Bucket-list Île aux CerfsSani Pass 4x4 AscentSchotia Private Game ReserveTable Mountain
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from $4,974
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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