Classic Caribbean
Sail-assisted small-ship cruising
- Sails Dec 26, 2026
- 7 nights · small ship
- Roundtrip from PHILIPSBURG, ST. MAARTEN
- Wind Surf
- Caribbean
Honest booking disclosure: Tripbase may earn advisor or affiliate revenue if you ask for help booking. Every range below is visible before contact details, and is a sourced estimate — not a live personalized fare.
True-cost starter range
$9,484–$11,164
For 2 adults in a oceanview cabin, before editable optional extras.
Prices observed 2026-09-28 at windstarcruises.com
Oceanview fare trend
40% higher vs 7 weeks ago($3,377 → $4,742)
| Cabin | Fare per person | Taxes & fees |
|---|---|---|
| Oceanview | $4,742–$5,582 | — |
| Suite | $7,332–$10,832 | — |
What the trip actually costs
oceanview fare
$9,484–$11,164
Specialty dining
Included
This fare includes
Day by day
The route
Day 17:00 PM
Day 28:00 AM – 10:00 PM
Day 38:00 AM – 5:00 PM
Day 48:00 AM – 4:00 PM
Day 58:00 AM – 5:00 PM
Day 612:00 PM – 6:00 PM
Day 78:00 AM – 10:00 PM
Day 86:00 AM
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The ship
Wind Surf
Ship details · flagged in The Bahamas
- Tonnage
- 14,745
- Capacity
- 308
- Built
- 1,989
- Length
- 188 m
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Sailing with
Windstar Cruises
Sail-assisted small-ship cruising
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Ask for help only after seeing the range — an advisor can confirm live pricing, cabins, perks, and whether a group rate beats retail.
Sources
- windstarcruises.com · as of 2026-09-28
- Windstar Cruises inclusion policy · as of 2026-06-28