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Beach Fun & Sun: A Remote Caribbean Getaway St. Maarten 2023

from $2699

Beach Fun & Sun: A Remote Caribbean Getaway St. Maarten 2023

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Bask on remote beaches resplendent in natural beauty during this relaxing, unrushed, and uncrowded 7-day getaway to secluded Caribbean destinations Windstar spe Read More

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8 Days / 6

Cruise Line:

Windstar Cruises

from $2699 per person

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Boston Sights, Warm Caribbean Nights Boston St. Maarten 2023

from $2599

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Venture from cosmopolitan Boston to warm Bermuda beaches and the picturesque Caribbean shorelines during this 11-day cruise. Kayak amid gliding sea turtles and Read More

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10 Days / 8

Cruise Line:

Windstar Cruises

from $2599 per person

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Colombian & Southern Caribbean Coastlines Colón Bridgetown 2024

from $2999

Colombian & Southern Caribbean Coastlines Colón Bridgetown 2024

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Venture from Colombia to the quiet solitude of the Caribbean’s southern islands during this 11-day cruise. Explore a restored Spanish colonial house and master Read More

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12 Days / 10

Cruise Line:

Windstar Cruises

from $2999 per person

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Jewels of the Windward Islands Bridgetown 2023

from $2699

Jewels of the Windward Islands Bridgetown 2023

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This is the Caribbean of days gone by – deep blue waters, quiet coves and tropical islands dotted with powdery beaches and lush green hillsides. Sail from the r Read More

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8 Days / 6

Cruise Line:

Windstar Cruises

from $2699 per person

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Jewels of the Windward Islands Bridgetown 2024

from $2699

Jewels of the Windward Islands Bridgetown 2024

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This is the Caribbean of days gone by – deep blue waters, quiet coves and tropical islands dotted with powdery beaches and lush green hillsides. Sail from the r Read More

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8 Days / 6

Cruise Line:

Windstar Cruises

from $2699 per person

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Lush & Lovely Islands of the Lesser Antilles St. Maarten Bridgetown 2023

from $2599

Lush & Lovely Islands of the Lesser Antilles St. Maarten Bridgetown 2023

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Enjoy the perfect mix of must-see Caribbean towns and harbors off the beaten path as you cruise and sail the royal beauties of the Lesser Antilles islands. Expl Read More

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8 Days / 6

Cruise Line:

Windstar Cruises

from $2599 per person

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Ocean Crossings Bridgetown Lisbon 2023

from $1999

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This is a place where dreams really do come true. The place where nothing comes between you and your fondest wishes. Where no schedules intrude, where day-to-da Read More

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16 Days / 14

Cruise Line:

Windstar Cruises

from $1999 per person

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Ocean Crossings Bridgetown Lisbon 2024

from $2299

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Ship:

This is a place where dreams really do come true. The place where nothing comes between you and your fondest wishes. Where no schedules intrude, where day-to-da Read More

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16 Days / 14

Cruise Line:

Windstar Cruises

from $2299 per person

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Ocean Crossings Lisbon Bridgetown 2023

from $2199

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Ship:

This is a place where dreams really do come true. The place where nothing comes between you and your fondest wishes. Where no schedules intrude, where day-to-da Read More

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15 Days / 13

Cruise Line:

Windstar Cruises

from $2199 per person

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Ocean Crossings Lisbon Bridgetown 2024

from $2199

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Ship:

This is a place where dreams really do come true. The place where nothing comes between you and your fondest wishes. Where no schedules intrude, where day-to-da Read More

Check Availability

15 Days / 13

Cruise Line:

Windstar Cruises

from $2199 per person

View all 42 dates

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View all 42 dates

Caribbean

Hot Tip: Look for the Golden Corners!