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San Juan, Puerto Rico
- Best Nov – Apr
- 11 lines sailing from here
- 394 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
Sailings that start in San Juan, Puerto Rico
All 394 →| Ship & line | Itinerary | Departs | Nights | From |
|---|---|---|---|---|
| Rhapsody of the SeasRoyal Caribbean | Caribbean | Sep 12, 2026 | 7 | — |
| Rhapsody of the SeasRoyal Caribbean | Caribbean | Sep 19, 2026 | 7 | — |
| Rhapsody of the SeasRoyal Caribbean | Caribbean | Sep 26, 2026 | 7 | — |
| Rhapsody of the SeasRoyal Caribbean | Caribbean | Oct 03, 2026 | 7 | — |
| Rhapsody of the SeasRoyal Caribbean | Caribbean | Oct 10, 2026 | 7 | — |
| Rhapsody of the SeasRoyal Caribbean | Caribbean | Oct 17, 2026 | 7 | — |
| Rhapsody of the SeasRoyal Caribbean | Caribbean | Oct 24, 2026 | 7 | — |
| Rhapsody of the SeasRoyal Caribbean | Caribbean | Oct 31, 2026 | 7 | — |
| Valiant LadyVirgin Voyages | Caribbean | Oct 31, 2026 | 7 | — |
| Vision of the SeasRoyal Caribbean | Caribbean | Nov 01, 2026 | 7 | — |
| EXPLORA IIIExplora Journeys | Central America | Nov 01, 2026 | 7 | — |
| EXPLORA IIIExplora Journeys | Caribbean | Nov 01, 2026 | 14 | — |
Where you go next
The ports these sailings call at most often.
- Philipsburg, Sint Maartenon 214 of these sailings
- Bridgetownon 166 of these sailings
- Charlotte Amalie, St. Thomason 135 of these sailings
- St John's, Antiguaon 126 of these sailings
- Basseterre, St. Kittson 116 of these sailings
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