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San Juan, Puerto Rico
- Best Nov – Apr
- 9 lines sailing from here
- 359 sailings
Why sail from here
The most forgiving cruise there is: warm water all season and ports where the day plan can be a beach and a taxi. Southern loops from Barbados or San Juan reach the smaller, greener islands; eastern loops from Florida work the busier ones.
Winter sun and the itineraries where the ship is as much the point as the islands.
This guidance covers the Caribbean region as a whole.
Ships sailing from San Juan, Puerto Rico
Vision of the Seas
Royal Caribbean · 47 sailings
Next departure Nov 08, 2026 · 7 nights
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Norwegian Prima
Norwegian Cruise Line · 45 sailings
Next departure Nov 15, 2026 · 7 nights
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Rhapsody of the Seas
Royal Caribbean · 39 sailings
Next departure Nov 07, 2026 · 7 nights
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Valiant Lady
Virgin Voyages · 22 sailings
Next departure Nov 07, 2026 · 7 nights
About Virgin Voyages →
Sailings that start in San Juan, Puerto Rico
All 359 →| Ship & line | Itinerary | Departs | Nights | From |
|---|---|---|---|---|
| Rhapsody of the SeasRoyal Caribbean | Caribbean | Nov 07, 2026 | 7 | $469pp · excludes taxes & fees |
| Valiant LadyVirgin Voyages | Caribbean | Nov 07, 2026 | 7 | $1,043pp · excludes taxes & fees |
| Azamara JourneyAzamara | Caribbean | Nov 07, 2026 | 7 | $3,109pp · excludes taxes & fees |
| Azamara JourneyAzamara | Caribbean | Nov 07, 2026 | 14 | — |
| Vision of the SeasRoyal Caribbean | Caribbean | Nov 08, 2026 | 7 | $678pp · excludes taxes & fees |
| Rhapsody of the SeasRoyal Caribbean | Caribbean | Nov 14, 2026 | 7 | — |
| Valiant LadyVirgin Voyages | Caribbean | Nov 14, 2026 | 6 | $774pp · excludes taxes & fees |
| Norwegian PrimaNorwegian Cruise Line | Caribbean | Nov 15, 2026 | 7 | $709pp · excludes taxes & fees |
| EXPLORA IIIExplora Journeys | Central America | Nov 15, 2026 | 7 | $4,270pp · excludes taxes & fees |
| EXPLORA IIIExplora Journeys | Caribbean | Nov 15, 2026 | 14 | $10,115pp · excludes taxes & fees |
| Vision of the SeasRoyal Caribbean | Caribbean | Nov 15, 2026 | 7 | $665pp · excludes taxes & fees |
| Celebrity ConstellationCelebrity Cruises | Caribbean | Nov 17, 2026 | 11 | $1,221pp · excludes taxes & fees |
Where you go next
The ports these sailings call at most often.
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