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Showing 14 of 14 sailings

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 Sail Mount Pelée & Saint-Pierre Jardin Botanique de Deshaies at Opening Hour +3 more

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from $4,550

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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 Walls Grenada Private Taxi Tour Tobago Cays & Mystique Full-Day Private Sail Salt Whistle Bay +2 more

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from $3,636

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Silversea · Silver RayRound-trip

Caribbean 11 nights Dec 11 – Dec 22, 2026 from Miami, Florida

Miami, Florida · San Juan, Puerto Rico · … · Miami, Florida8 ports

Miami, Florida · San Juan, Puerto Rico · Cruz Bay, St. John, U.S. Virgin Islands · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Gustavia, St. Barts · Deshaies, Guadeloupe · Road Town, Tortola, B.V.I. · Miami, Florida

★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Walk El Morro & Old San Juan's City Walls Trunk Bay Underwater Snorkel Trail & VI National P…Mt. Liamuiga Volcano Crater Hike +3 more

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from $5,450

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Silversea · Silver SpiritRound-trip

Caribbean 7 nights Dec 12 – Dec 19, 2026 from Bridgetown, Barbados

Bridgetown, Barbados · Castries, St. Lucia · … · Bridgetown, Barbados8 ports

Bridgetown, Barbados · Castries, St. Lucia · Fort-de-France, Martinique · Deshaies, Guadeloupe · Codrington, Barbuda · Iles des Saintes, Guadeloupe · Bequia, Grenadines · Bridgetown, Barbados

★ Bucket-list Swim with wild green sea turtles + two shipwrecks…Cosol Tours Mount Pelée & Saint-Pierre Jardin Botanique de Deshaies at Opening Hour +3 more

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from $4,450

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Silversea · Silver SpiritRound-trip

Caribbean 8 nights Dec 27 – Jan 4, 2027 from Bridgetown, Barbados

Bridgetown, Barbados · Bequia, Grenadines · … · Bridgetown, Barbados8 ports

Bridgetown, Barbados · Bequia, Grenadines · Fort-de-France, Martinique · Deshaies, Guadeloupe · Port of Basseterre, St. Kitts, St. Kitts and Nevis · St. Georges, Grenada, West Indies · Castries, St. Lucia · Bridgetown, Barbados

★ Bucket-list Swim with wild green sea turtles + two shipwrecks…Tobago Cays & Mystique Full-Day Private Sail Mount Pelée & Saint-Pierre Jardin Botanique de Deshaies at Opening Hour +3 more

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from $5,750

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Windstar · Star PrideRound-trip

Caribbean 7 nights Jan 3 – Jan 10, 2027 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 Walls Grenada Private Taxi Tour Tobago Cays & Mystique Full-Day Private Sail Salt Whistle Bay +2 more

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from $4,896

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Silversea · Silver SpiritRound-trip

Caribbean 11 nights Jan 4 – Jan 15, 2027 from Bridgetown, Barbados

Bridgetown, Barbados · Castries, St. Lucia · … · Bridgetown, Barbados10 ports

Bridgetown, Barbados · Castries, St. Lucia · Deshaies, Guadeloupe · Codrington, Barbuda · Port of Oranjestad, Aruba, Caribbean · Willemstad, Curacao · Kralendijk, Bonaire, Dutch Antilles · St. Georges, Grenada, West Indies · Bequia, Grenadines · Bridgetown, Barbados

★ Bucket-list Swim with wild green sea turtles + two shipwrecks…Cosol Tours Jardin Botanique de Deshaies at Opening Hour Barbuda's Pink Sand Beach at Dawn, Private & Empty +5 more

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from $4,850

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Silversea · Silver RayRound-trip

Caribbean 11 nights Jan 5 – Jan 16, 2027 from Miami, Florida

Miami, Florida · San Juan, Puerto Rico · … · Miami, Florida8 ports

Miami, Florida · San Juan, Puerto Rico · Cruz Bay, St. John, U.S. Virgin Islands · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Deshaies, Guadeloupe · Codrington, Barbuda · Road Town, Tortola, B.V.I. · Miami, Florida

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from $8,750

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Silversea · Silver RayRound-trip

Caribbean 11 nights Jan 27 – Feb 7, 2027 from Miami, Florida

Miami, Florida · San Juan, Puerto Rico · … · Miami, Florida8 ports

Miami, Florida · San Juan, Puerto Rico · Cruz Bay, St. John, U.S. Virgin Islands · Gustavia, St. Barts · Codrington, Barbuda · Deshaies, Guadeloupe · Anguilla, Caribbean · Miami, Florida

★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Walk El Morro & Old San Juan's City Walls Trunk Bay Underwater Snorkel Trail & VI National P…Private Open-Top Mini Moke Island Tour of St. Barts +3 more

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from $9,250

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Silversea · Silver RayOne-way

Caribbean 12 nights Feb 7 – Feb 19, 2027 from Miami, Florida to Bridgetown, Barbados

Miami, Florida · San Juan, Puerto Rico · … · Bridgetown, Barbados11 ports

Miami, Florida · San Juan, Puerto Rico · Cruz Bay, St. John, U.S. Virgin Islands · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Gustavia, St. Barts · Codrington, Barbuda · Deshaies, Guadeloupe · Roseau, Dominica · Fort-de-France, Martinique · Bequia, Grenadines · Bridgetown, Barbados

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from $9,200

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Silversea · Silver RayOne-way

Caribbean 12 nights Feb 26 – Mar 10, 2027 from Bridgetown, Barbados to Miami, Florida

Bridgetown, Barbados · Bequia, Grenadines · … · Miami, Florida11 ports

Bridgetown, Barbados · Bequia, Grenadines · St. Georges, Grenada, West Indies · Fort-de-France, Martinique · Deshaies, Guadeloupe · Soufriere, St. Lucia · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Philipsburg, St. Maarten · Gustavia, St. Barts · Anguilla, Caribbean · Miami, Florida

★ Bucket-list Swim with wild green sea turtles + two shipwrecks…Tobago Cays & Mystique Full-Day Private Sail Grenada Private Taxi Tour Mount Pelée & Saint-Pierre +6 more

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from $8,900

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Silversea · Silver NovaRound-trip

Caribbean 11 nights Dec 18 – Dec 29, 2027 from Miami, Florida

Miami, Florida · Sopers Hole · … · Miami, Florida7 ports

Miami, Florida · Sopers Hole · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Deshaies, Guadeloupe · Fort-de-France, Martinique · Cruz Bay, St. John, U.S. Virgin Islands · Miami, Florida

★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…The Baths of Virgin Gorda Mt. Liamuiga Volcano Crater Hike Jardin Botanique de Deshaies at Opening Hour +2 more

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from $7,850

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Silversea · Silver DawnRound-trip

Caribbean 9 nights Feb 10 – Feb 19, 2028 from San Juan, Puerto Rico

San Juan, Puerto Rico · Spanish Town · … · San Juan, Puerto Rico10 ports

San Juan, Puerto Rico · Spanish Town · Anguilla, Caribbean · Gustavia, St. Barts · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Deshaies, Guadeloupe · Fort-de-France, Martinique · Codrington, Barbuda · Cruz Bay, St. John, U.S. Virgin Islands · San Juan, Puerto Rico

★ Bucket-list Walk El Morro & Old San Juan's City Walls Sandy Island by Private Boat Private Open-Top Mini Moke Island Tour of St. Barts Mt. Liamuiga Volcano Crater Hike +4 more

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from $5,050

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Silversea · Silver DawnOne-way

Caribbean 8 nights Feb 24 – Mar 3, 2028 from San Juan, Puerto Rico to Miami, Florida

San Juan, Puerto Rico · Port of Basseterre, St. Kitts, St. Kitts and Nevis · … · Miami, Florida7 ports

San Juan, Puerto Rico · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Gustavia, St. Barts · Deshaies, Guadeloupe · Codrington, Barbuda · Jost Van Dyke, British Virgin Islands · Miami, Florida

★ Bucket-list Walk El Morro & Old San Juan's City Walls Mt. Liamuiga Volcano Crater Hike Private Open-Top Mini Moke Island Tour of St. Barts Jardin Botanique de Deshaies at Opening Hour +3 more

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from $5,250

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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.

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