Windstar Cruises · 14 nights
Wind Surf weather: 14-night cruise from Philipsburg, December 19, 2026
The Wind Surf (Windstar Cruises) leaves Philipsburg on December 19, 2026 for a 14-night cruise, with stops in Gustavia, English Harbour, Road Bay, Tortola, Jost Van Dyke, Virgin Gorda and 5 more. It returns to Philipsburg on January 2, 2027. Typical afternoon highs along the route run from 80°F to 83°F (27°C to 28°C), with no days at sea.
Open the interactive forecast for this sailing
This page shows typical conditions for these dates. The interactive forecast adds a live day-by-day forecast, wave heights and weather alerts as the sailing gets closer.
Day-by-day itinerary and typical weather
| Day | Port | High / low | Rain days | Wind | Typical seas |
|---|---|---|---|---|---|
| Day 1Sat, Dec 19 | Philipsburg Embark | 80 / 78°F27 / 25°C | 31% | 18 mph29 km/h | – |
| Day 2Sun, Dec 20 | Gustavia | 81 / 78°F27 / 25°C | 36% | 19 mph31 km/h | – |
| Day 3Mon, Dec 21 | English Harbour | 82 / 75°F28 / 24°C | 39% | 14 mph23 km/h | – |
| Day 4Tue, Dec 22 | Road Bay | 81 / 78°F27 / 26°C | 20% | 17 mph27 km/h | – |
| Day 5Wed, Dec 23 | Tortola | 80 / 77°F27 / 25°C | 31% | 19 mph31 km/h | – |
| Day 6Thu, Dec 24 | Jost Van Dyke | 80 / 77°F27 / 25°C | 33% | 19 mph31 km/h | – |
| Day 7Fri, Dec 25 | Virgin Gorda | 80 / 77°F27 / 25°C | 39% | 19 mph31 km/h | – |
| Day 8Sat, Dec 26 | Philipsburg | 80 / 78°F27 / 25°C | 31% | 18 mph29 km/h | – |
| Day 9Sun, Dec 27 | Gustavia | 81 / 78°F27 / 25°C | 36% | 19 mph31 km/h | – |
| Day 10Mon, Dec 28 | Charlestown | 83 / 76°F28 / 24°C | 30% | 12 mph20 km/h | – |
| Day 11Tue, Dec 29 | Roseau | 82 / 75°F28 / 24°C | 58% | 13 mph21 km/h | – |
| Day 12Wed, Dec 30 | Mayreau | 82 / 79°F28 / 26°C | 48% | 19 mph31 km/h | – |
| Day 13Thu, Dec 31 | Les Saintes | 81 / 78°F27 / 25°C | 44% | 21 mph33 km/h | – |
| Day 14Fri, Jan 1 | Basseterre | 82 / 76°F28 / 24°C | 51% | 13 mph21 km/h | – |
| Day 15Sat, Jan 2 | Philipsburg Disembark | 80 / 77°F27 / 25°C | 36% | 18 mph29 km/h | – |
Seas are significant wave height, the average of the highest third of waves, on the Douglas sea state scale. What that means on board.
Ports on this cruise
- GustaviaWeather by month
- English HarbourWeather by month
- Road BayWeather by month
- TortolaWeather by month
- Jost Van DykeWeather by month
- Virgin GordaWeather by month
- CharlestownWeather by month
- RoseauWeather by month
- MayreauWeather by month
- Les SaintesWeather by month
- BasseterreWeather by month
- PhilipsburgWeather by month
More Wind Surf sailings
This is the last scheduled sailing we have for this ship.