Bucket-List Cruise Adventures

Pick your sailing — we plan the whole adventure

8 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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Filtering Visits Falmouth Harbour × Clear all
Showing 8 of 8 sailings
7-night Caribbean from PhilipsburgRound-trip
Windstar · Wind Surf
Suite: low fare 9% under usual↓ 22% suite, 26d
Caribbean 7 nights Dec 19 – Dec 26, 2026
Philipsburg, St. Maarten · Gustavia, St. Barts · … · Philipsburg, St. Maarten9 ports
Philipsburg, St. Maarten · Gustavia, St. Barts · Falmouth Harbour, Antigua · Road Bay, Anguilla · Jost Van Dyke, British Virgin Islands · Sopers Hole, British Virgin Islands · Jost Van Dyke, British Virgin Islands · Virgin Gorda, British Virgin Islands · Philipsburg, St. Maarten
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7-night Caribbean from PhilipsburgRound-trip
Windstar · Wind Surf
Suite: typical fare in the usual range
Caribbean 7 nights Jan 2 – Jan 9, 2027
Philipsburg, St. Maarten · Falmouth Harbour, Antigua · … · Philipsburg, St. Maarten8 ports
Philipsburg, St. Maarten · Falmouth Harbour, Antigua · Road Bay, Anguilla · Sopers Hole, British Virgin Islands · Jost Van Dyke, British Virgin Islands · Virgin Gorda, British Virgin Islands · Gustavia, St. Barts · Philipsburg, St. Maarten
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7-night Caribbean from PhilipsburgRound-trip
Windstar · Wind Surf
Suite: typical fare in the usual range↓ 13% suite, 38d
Caribbean 7 nights Jan 16 – Jan 23, 2027
Philipsburg, St. Maarten · Road Bay, Anguilla · … · Philipsburg, St. Maarten9 ports
Philipsburg, St. Maarten · Road Bay, Anguilla · Jost Van Dyke, British Virgin Islands · Sopers Hole, British Virgin Islands · Jost Van Dyke, British Virgin Islands · Virgin Gorda, British Virgin Islands · Gustavia, St. Barts · Falmouth Harbour, Antigua · Philipsburg, St. Maarten
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7-night Caribbean from PhilipsburgRound-trip
Windstar · Wind Surf
Suite: above average 24% over usual↑ 24% suite, 24d
Caribbean 7 nights Jan 30 – Feb 6, 2027
Philipsburg, St. Maarten · Road Bay, Anguilla · … · Philipsburg, St. Maarten9 ports
Philipsburg, St. Maarten · Road Bay, Anguilla · Jost Van Dyke, British Virgin Islands · Sopers Hole, British Virgin Islands · Jost Van Dyke, British Virgin Islands · Virgin Gorda, British Virgin Islands · Gustavia, St. Barts · Falmouth Harbour, Antigua · Philipsburg, St. Maarten
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7-night Caribbean from PhilipsburgRound-trip
Windstar · Wind Surf
Suite: above average 11% over usual↑ 12% outside, 27d
Caribbean 7 nights Feb 13 – Feb 20, 2027
Philipsburg, St. Maarten · Falmouth Harbour, Antigua · … · Philipsburg, St. Maarten8 ports
Philipsburg, St. Maarten · Falmouth Harbour, Antigua · Road Bay, Anguilla · Sopers Hole, British Virgin Islands · Jost Van Dyke, British Virgin Islands · Virgin Gorda, British Virgin Islands · Gustavia, St. Barts · Philipsburg, St. Maarten
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7-night Caribbean from PhilipsburgRound-trip
Windstar · Wind Surf
Suite: typical fare in the usual range
Caribbean 7 nights Feb 27 – Mar 6, 2027
Philipsburg, St. Maarten · Sopers Hole, British Virgin Islands · … · Philipsburg, St. Maarten8 ports
Philipsburg, St. Maarten · Sopers Hole, British Virgin Islands · Jost Van Dyke, British Virgin Islands · Virgin Gorda, British Virgin Islands · Gustavia, St. Barts · Road Bay, Anguilla · Falmouth Harbour, Antigua · Philipsburg, St. Maarten
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6-night Caribbean from PhilipsburgRound-trip
Windstar · Wind Surf
Suite: above average 23% over usual
Caribbean 6 nights Mar 13 – Mar 19, 2027
Philipsburg, St. Maarten · Falmouth Harbour, Antigua · … · Philipsburg, St. Maarten9 ports
Philipsburg, St. Maarten · Falmouth Harbour, Antigua · Road Bay, Anguilla · Jost Van Dyke, British Virgin Islands · Sopers Hole, British Virgin Islands · Jost Van Dyke, British Virgin Islands · Virgin Gorda, British Virgin Islands · Gustavia, St. Barts · Philipsburg, St. Maarten
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11-night Philipsburg to BridgetownOne-way
Seabourn · Seabourn Ovation
Suite: typical fare in the usual range
Caribbean 11 nights Dec 28 – Jan 8, 2028
Philipsburg, St. Maarten · Sopers Hole, British Virgin Islands · … · Bridgetown, Barbados10 ports
Philipsburg, St. Maarten · Sopers Hole, British Virgin Islands · Road Bay, Anguilla · Falmouth Harbour, Antigua · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Terre-de-haut, Guadeloupe · Port of Oranjestad, Aruba, Caribbean · Willemstad, Curacao · Kralendijk, Bonaire, Dutch Antilles · Bridgetown, Barbados
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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.