Roundtrip

San Juan (Puerto Rico) Caribbean Cruises

32 Cruises 3 Cruise Lines

Route Map

Price Drops & Deals

11.7% OFF

11 Night Southern Caribbean Intensive

Celebrity Cruises
Celebrity Constellation 11 nights Nov 17, 2026
$934 $825 Save $109
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7.7% OFF

West Indies Explorer

Viking Ocean Cruises
Viking Sea 10 nights Feb 24, 2027
$5,195 $4,795 Save $400
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6.1% OFF

West Indies Explorer

Viking Ocean Cruises
Viking Sea 10 nights Nov 15, 2026
$4,895 $4,595 Save $300
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4.1% OFF

West Indies Explorer

Viking Ocean Cruises
Viking Sea 10 nights Jan 5, 2027
$4,895 $4,695 Save $200
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2.4% OFF

West Indies Explorer

Viking Ocean Cruises
Viking Sky 10 nights Nov 29, 2027
$4,090 $3,990 Save $100
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2.4% OFF

West Indies Explorer

Viking Ocean Cruises
Viking Sea 10 nights Dec 7, 2027
$4,090 $3,990 Save $100
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Compare Cruise Lines

Cruise Line Cruises Ships From Duration Next Sailing
Viking Ocean Cruises 28 2 $3,990 10-21 nights Nov 5, 2026
Explora Journeys 2 1 $8,320 15-16 nights Dec 13, 2026
Celebrity Cruises 1 1 $885 11 nights Nov 17, 2026

All Cruises on This Route

Ports on This Route

Basseterre, Saint Kitts

Ascend the iconic Brimstone Hill Fortress to witness sweeping Caribbean views from one of the Western Hemisphere's most impressive 17th-century strongholds.

Saint John's

Explore colorful colonial architecture and pristine beaches while discovering the fascinating history of Nelson's Dockyard National Park.

Castries

Hike through lush rainforest to plunge into emerald mineral pools warmed by volcanic springs.

Philipsburg

Shop and dine in a colorful waterfront village where duty-free treasures meet Caribbean charm and pristine beaches.

Bridgetown

Swim with gentle sea turtles in crystalline Caribbean waters while discovering colonial architecture in the charming historic garrison district.

Charlotte Amalie

Wander through pastel-colored streets lined with duty-free shops, then hike to breathtaking viewpoints overlooking the turquoise Caribbean Sea.

Roseau

Hike through lush rainforest to plunge into the mineral-rich waters of Trafalgar Falls, Dominica's most enchanting natural wonder.

Frederiksted, Saint Croix

Dive into some of the Caribbean's most pristine coral reefs teeming with tropical fish just steps from the historic cruise port.

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