Bucket-List Cruise Adventures

Pick your sailing — we plan the whole adventure

34 sailings across 23 cruise lines, each one priced and planned end to end: the ports it calls at, the one unmissable thing to do at each, and the flights and nights either side. A balcony averages about $166 a night on Carnival and about $414 on Disney, per person with taxes in — what a night costs on every line. Leaving within three weeks?

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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Showing 34 of 34 sailings
12-night Caribbean from MiamiRound-trip
Silversea · Silver Shadow
Suite: above average 15% over usual↑ 21% suite, 39d
Caribbean 12 nights Nov 18 – Nov 30, 2026
Miami, Florida · San Juan, Puerto Rico · … · Miami, Florida9 ports
Miami, Florida · San Juan, Puerto Rico · Cruz Bay, St. John, U.S. Virgin Islands · Gustavia, St. Barts · Codrington, Barbuda · Little Bay, Montserrat, Leeward Islands · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Jost Van Dyke, British Virgin Islands · Miami, Florida
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7-night Caribbean from BridgetownRound-trip
Silversea · Silver Spirit
Suite: low fare 5% under usual
Caribbean 7 nights Dec 5 – Dec 12, 2026
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
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7-night Caribbean from BridgetownRound-trip
Silversea · Silver Spirit
Suite: low fare 5% under usual↑ 9% suite, 39d
Caribbean 7 nights Dec 12 – Dec 19, 2026
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
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8-night San Juan to MiamiOne-way
Silversea · Silver Nova
Suite: above average 99% over usual↑ 54% suite, 39d
Caribbean 8 nights Dec 29 – Jan 6, 2027
San Juan, Puerto Rico · Cruz Bay, St. John, U.S. Virgin Islands · … · Miami, Florida7 ports
San Juan, Puerto Rico · Cruz Bay, St. John, U.S. Virgin Islands · Port of Charlestown, Nevis, St. Kitts and Nevis · Roseau, Dominica · Codrington, Barbuda · Jost Van Dyke, British Virgin Islands · Miami, Florida
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7-night Caribbean from San JuanRound-trip
Silversea · Silver Shadow
Suite: typical fare in the usual range
Caribbean 7 nights Jan 3 – Jan 10, 2027
San Juan, Puerto Rico · Cruz Bay, St. John, U.S. Virgin Islands · … · San Juan, Puerto Rico8 ports
San Juan, Puerto Rico · Cruz Bay, St. John, U.S. Virgin Islands · Gustavia, St. Barts · Codrington, Barbuda · Little Bay, Montserrat, Leeward Islands · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Jost Van Dyke, British Virgin Islands · San Juan, Puerto Rico
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11-night Caribbean from BridgetownRound-trip
Silversea · Silver Spirit
Suite: above average 13% over usual↑ 10% suite, 38d
Caribbean 11 nights Jan 4 – Jan 15, 2027
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
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11-night Caribbean from MiamiRound-trip
Silversea · Silver Ray
Suite: typical fare in the usual range
Caribbean 11 nights Jan 5 – Jan 16, 2027
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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10-night San Juan to BridgetownOne-way
Silversea · Silver Shadow
Suite: typical fare in the usual range
Caribbean 10 nights Jan 10 – Jan 20, 2027
San Juan, Puerto Rico · Jost Van Dyke, British Virgin Islands · … · Bridgetown, Barbados11 ports
San Juan, Puerto Rico · Jost Van Dyke, British Virgin Islands · Gustavia, St. Barts · Codrington, Barbuda · Little Bay, Montserrat, Leeward Islands · Iles des Saintes, Guadeloupe · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Trois Ilets · Castries, St. Lucia · St. Georges, Grenada, West Indies · Bridgetown, Barbados
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11-night Caribbean from MiamiRound-trip
Silversea · Silver Ray
Suite: typical fare in the usual range↓ 27% suite, 57d
Caribbean 11 nights Jan 27 – Feb 7, 2027
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
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7-night Caribbean from San JuanRound-trip
Silversea · Silver Shadow
Suite: typical fare in the usual range↓ 24% suite, 57d
Caribbean 7 nights Jan 30 – Feb 6, 2027
San Juan, Puerto Rico · Cruz Bay, St. John, U.S. Virgin Islands · … · San Juan, Puerto Rico8 ports
San Juan, Puerto Rico · Cruz Bay, St. John, U.S. Virgin Islands · Little Bay, Montserrat, Leeward Islands · Codrington, Barbuda · Gustavia, St. Barts · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Jost Van Dyke, British Virgin Islands · San Juan, Puerto Rico
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12-night Miami to BridgetownOne-way
Silversea · Silver Ray
Suite: above average 18% over usual
Caribbean 12 nights Feb 7 – Feb 19, 2027
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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7-night Caribbean from San JuanRound-trip
Silversea · Silver Shadow
Suite: low fare 12% under usual↑ 7% suite, 39d
Caribbean 7 nights Feb 26 – Mar 5, 2027
San Juan, Puerto Rico · Cruz Bay, St. John, U.S. Virgin Islands · … · San Juan, Puerto Rico8 ports
San Juan, Puerto Rico · Cruz Bay, St. John, U.S. Virgin Islands · Gustavia, St. Barts · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Codrington, Barbuda · Little Bay, Montserrat, Leeward Islands · Jost Van Dyke, British Virgin Islands · San Juan, Puerto Rico
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7-night Caribbean from BridgetownRound-trip
Silversea · Silver Spirit
Suite: above average 16% over usual↑ 10% suite, 39d
Caribbean 7 nights Feb 28 – Mar 7, 2027
Bridgetown, Barbados · Castries, St. Lucia · … · Bridgetown, Barbados8 ports
Bridgetown, Barbados · Castries, St. Lucia · Gustavia, St. Barts · Cruz Bay, St. John, U.S. Virgin Islands · Codrington, Barbuda · Roseau, Dominica · Bequia, Grenadines · Bridgetown, Barbados
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14-night San Juan to LisbonOne-way
Silversea · Silver Shadow
Suite: low fare 52% under usual↓ 12% suite, 39d
Mediterranean 14 nights Mar 9 – Mar 23, 2027
San Juan, Puerto Rico · Jost Van Dyke, British Virgin Islands · … · Lisbon, Portugal6 ports
San Juan, Puerto Rico · Jost Van Dyke, British Virgin Islands · Codrington, Barbuda · Santa Cruz de La Palma, Spain · Santa Cruz de Tenerife, Canary Islands · Lisbon, Portugal
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10-night Caribbean from San JuanRound-trip
Silversea · Silver Dawn
Suite: above average 7% over usual
Caribbean 10 nights Dec 11 – Dec 21, 2027
San Juan, Puerto Rico · Jost Van Dyke, British Virgin Islands · … · San Juan, Puerto Rico11 ports
San Juan, Puerto Rico · Jost Van Dyke, British Virgin Islands · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Gustavia, St. Barts · Fort-de-France, Martinique · St. Georges, Grenada, West Indies · Bequia, Grenadines · Castries, St. Lucia · Codrington, Barbuda · Cruz Bay, St. John, U.S. Virgin Islands · San Juan, Puerto Rico
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8-night Bridgetown to San JuanOne-way
Silversea · Silver Ray
Suite: typical fare in the usual range
Caribbean 8 nights Dec 18 – Dec 26, 2027
Bridgetown, Barbados · Castries, St. Lucia · … · San Juan, Puerto Rico8 ports
Bridgetown, Barbados · Castries, St. Lucia · St. Georges, Grenada, West Indies · Bequia, Grenadines · Fort-de-France, Martinique · Roseau, Dominica · Codrington, Barbuda · San Juan, Puerto Rico
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7-night Caribbean from San JuanRound-trip
Silversea · Silver Dawn
Suite: typical fare in the usual range
Caribbean 7 nights Dec 21 – Dec 28, 2027
San Juan, Puerto Rico · Cruz Bay, St. John, U.S. Virgin Islands · … · San Juan, Puerto Rico7 ports
San Juan, Puerto Rico · Cruz Bay, St. John, U.S. Virgin Islands · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Castries, St. Lucia · Codrington, Barbuda · Jost Van Dyke, British Virgin Islands · San Juan, Puerto Rico
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8-night San Juan to MiamiOne-way
Silversea · Silver Ray
Suite: above average 22% over usual
Caribbean 8 nights Dec 26 – Jan 3, 2028
San Juan, Puerto Rico · Cruz Bay, St. John, U.S. Virgin Islands · … · Miami, Florida7 ports
San Juan, Puerto Rico · Cruz Bay, St. John, U.S. Virgin Islands · Codrington, Barbuda · Fort-de-France, Martinique · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Jost Van Dyke, British Virgin Islands · Miami, Florida
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13-night Caribbean from BridgetownRound-trip
Silversea · Silver Spirit
Suite: typical fare in the usual range↓ 8% suite, 38d
Caribbean 13 nights Dec 28 – Jan 10, 2028
Bridgetown, Barbados · St. Georges, Grenada, West Indies · … · Bridgetown, Barbados12 ports
Bridgetown, Barbados · St. Georges, Grenada, West Indies · Bequia, Grenadines · Castries, St. Lucia · Kralendijk, Bonaire, Dutch Antilles · Willemstad, Curacao · Port of Oranjestad, Aruba, Caribbean · Jost Van Dyke, British Virgin Islands · Gustavia, St. Barts · Codrington, Barbuda · Fort-de-France, Martinique · Bridgetown, Barbados
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11-night Caribbean from MiamiRound-trip
Silversea · Silver Nova
Suite: above average 8% over usual↓ 9% suite, 38d
Caribbean 11 nights Dec 29 – Jan 9, 2028
Miami, Florida · Key West, Florida · … · Miami, Florida8 ports
Miami, Florida · Key West, Florida · St. Thomas, U.S. Virgin Islands · Sopers Hole · Gustavia, St. Barts · Codrington, Barbuda · Cruz Bay, St. John, U.S. Virgin Islands · Miami, Florida
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12-night Caribbean from MiamiRound-trip
Silversea · Silver Ray
Suite: low fare 27% under usual
Caribbean 12 nights Jan 3 – Jan 15, 2028
Miami, Florida · San Juan, Puerto Rico · … · Miami, Florida9 ports
Miami, Florida · San Juan, Puerto Rico · Cruz Bay, St. John, U.S. Virgin Islands · Gustavia, St. Barts · Codrington, Barbuda · Fort-de-France, Martinique · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Jost Van Dyke, British Virgin Islands · Miami, Florida
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11-night Caribbean from MiamiRound-trip
Silversea · Silver Nova
Suite: typical fare in the usual range
Caribbean 11 nights Jan 9 – Jan 20, 2028
Miami, Florida · San Juan, Puerto Rico · … · Miami, Florida8 ports
Miami, Florida · San Juan, Puerto Rico · Sopers Hole · Gustavia, St. Barts · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Codrington, Barbuda · Cruz Bay, St. John, U.S. Virgin Islands · Miami, Florida
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10-night Caribbean from San JuanRound-trip
Silversea · Silver Dawn
Suite: typical fare in the usual range
Caribbean 10 nights Jan 15 – Jan 25, 2028
San Juan, Puerto Rico · Jost Van Dyke, British Virgin Islands · … · San Juan, Puerto Rico11 ports
San Juan, Puerto Rico · Jost Van Dyke, British Virgin Islands · Gustavia, St. Barts · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Fort-de-France, Martinique · St. Georges, Grenada, West Indies · Canouan, St. Vincent · Castries, St. Lucia · Codrington, Barbuda · Cruz Bay, St. John, U.S. Virgin Islands · San Juan, Puerto Rico
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11-night Caribbean from MiamiRound-trip
Silversea · Silver Nova
Suite: typical fare in the usual range
Caribbean 11 nights Jan 20 – Jan 31, 2028
Miami, Florida · San Juan, Puerto Rico · … · Miami, Florida8 ports
Miami, Florida · San Juan, Puerto Rico · Sopers Hole · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Gustavia, St. Barts · Codrington, Barbuda · Cruz Bay, St. John, U.S. Virgin Islands · Miami, Florida
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11-night Caribbean from MiamiRound-trip
Silversea · Silver Nova
Suite: typical fare in the usual range
Caribbean 11 nights Jan 31 – Feb 11, 2028
Miami, Florida · Cruz Bay, St. John, U.S. Virgin Islands · … · Miami, Florida8 ports
Miami, Florida · Cruz Bay, St. John, U.S. Virgin Islands · Gustavia, St. Barts · Codrington, Barbuda · Fort-de-France, Martinique · Port of Basseterre, St. Kitts, St. Kitts and Nevis · San Juan, Puerto Rico · Miami, Florida
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9-night Caribbean from San JuanRound-trip
Silversea · Silver Dawn
Suite: low fare 6% under usual
Caribbean 9 nights Feb 10 – Feb 19, 2028
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
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11-night Caribbean from MiamiRound-trip
Silversea · Silver Nova
Suite: typical fare in the usual range
Caribbean 11 nights Feb 11 – Feb 22, 2028
Miami, Florida · San Juan, Puerto Rico · … · Miami, Florida8 ports
Miami, Florida · San Juan, Puerto Rico · Sopers Hole · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Codrington, Barbuda · Gustavia, St. Barts · Cruz Bay, St. John, U.S. Virgin Islands · Miami, Florida
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12-night Caribbean from BridgetownRound-trip
Silversea · Silver Spirit
Suite: low fare 10% under usual
Caribbean 12 nights Feb 17 – Feb 29, 2028
Bridgetown, Barbados · Bequia, Grenadines · … · Bridgetown, Barbados11 ports
Bridgetown, Barbados · Bequia, Grenadines · Castries, St. Lucia · Port of Oranjestad, Aruba, Caribbean · Kralendijk, Bonaire, Dutch Antilles · Willemstad, Curacao · Gustavia, St. Barts · Codrington, Barbuda · Fort-de-France, Martinique · St. Georges, Grenada, West Indies · Bridgetown, Barbados
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11-night Caribbean from MiamiRound-trip
Silversea · Silver Nova
Suite: typical fare in the usual range
Caribbean 11 nights Feb 22 – Mar 4, 2028
Miami, Florida · San Juan, Puerto Rico · … · Miami, Florida8 ports
Miami, Florida · San Juan, Puerto Rico · Sopers Hole · Gustavia, St. Barts · Codrington, Barbuda · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Cruz Bay, St. John, U.S. Virgin Islands · Miami, Florida
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8-night San Juan to MiamiOne-way
Silversea · Silver Dawn
Suite: low fare 11% under usual
Caribbean 8 nights Feb 24 – Mar 3, 2028
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
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11-night Caribbean from BridgetownRound-trip
Silversea · Silver Spirit
Suite: low fare 16% under usual
Caribbean 11 nights Feb 29 – Mar 11, 2028
Bridgetown, Barbados · Bequia, Grenadines · … · Bridgetown, Barbados10 ports
Bridgetown, Barbados · Bequia, Grenadines · St. Georges, Grenada, West Indies · Willemstad, Curacao · Port of Oranjestad, Aruba, Caribbean · Gustavia, St. Barts · Codrington, Barbuda · Fort-de-France, Martinique · Castries, St. Lucia · Bridgetown, Barbados
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11-night Caribbean from MiamiRound-trip
Silversea · Silver Dawn
Suite: typical fare in the usual range
Caribbean 11 nights Mar 3 – Mar 14, 2028
Miami, Florida · San Juan, Puerto Rico · … · Miami, Florida8 ports
Miami, Florida · San Juan, Puerto Rico · Sopers Hole · Gustavia, St. Barts · Codrington, Barbuda · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Jost Van Dyke, British Virgin Islands · Miami, Florida
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10-night Caribbean from MiamiRound-trip
Silversea · Silver Dawn
Suite: typical fare in the usual range
Caribbean 10 nights Mar 14 – Mar 24, 2028
Miami, Florida · San Juan, Puerto Rico · … · Miami, Florida7 ports
Miami, Florida · San Juan, Puerto Rico · Gustavia, St. Barts · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Codrington, Barbuda · Spanish Town · Miami, Florida
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12-night Bridgetown to MiamiOne-way
Silversea · Silver Ray
Suite: typical fare in the usual range
Caribbean 12 nights Mar 20 – Apr 1, 2028
Bridgetown, Barbados · Bequia, Grenadines · … · Miami, Florida11 ports
Bridgetown, Barbados · Bequia, Grenadines · Castries, St. Lucia · Fort-de-France, Martinique · Roseau, Dominica · Codrington, Barbuda · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Gustavia, St. Barts · Jost Van Dyke, British Virgin Islands · San Juan, Puerto Rico · Miami, Florida
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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.