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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Filtering Caribbean ×Visits Port Elizabeth ×6–8 nights × Clear all
Showing 13 of 13 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 WallsThe Baths National ParkPrivate Half-Day Island Adventure & Trunk Bay BeachSchotia Private Game Reserve +2 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 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
Book This Cruise@ Cruisebound
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
Book This Cruise@ Cruisebound
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
Book This Cruise@ Cruisebound
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
Book This Cruise@ Cruisebound
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
Book This Cruise@ Cruisebound
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
Book This Cruise@ Cruisebound
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
Book This Cruise@ Cruisebound
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 WallsThe Baths National ParkPrivate Half-Day Island Adventure & Trunk Bay BeachSchotia Private Game Reserve +2 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
View →
from $4,798
Book This Cruise@ Cruisebound
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
View →
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
View →
from $4,998
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