Windward Islands Surf & Sunsets
Sail-assisted small-ship cruising
- Sails Nov 8, 2026
- 7 nights · small ship
- Roundtrip from SAN JUAN
- Star Pride
- 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
$4,822–$7,062
For 2 adults in a oceanview cabin, before editable optional extras.
Prices observed 2026-09-28 at windstarcruises.com
Oceanview fare trend
0% higher vs 7 weeks ago($2,411 → $2,411)
| Cabin | Fare per person | Taxes & fees |
|---|---|---|
| Oceanview | $2,411–$3,531 | — |
| Balcony | $5,281–$5,596 | — |
| Suite | $6,506–$8,221 | — |
What the trip actually costs
oceanview fare
$4,822–$7,062
Specialty dining
Included
This fare includes
Day by day
The route
Day 17:00 PM
Day 39:00 AM – 10:00 PM
Day 48:00 AM – 10:00 PM
Day 58:00 AM – 5:00 PM
Day 610:00 AM – 5:00 PM
Day 78:00 AM – 3:00 PM
Day 87:00 AM
The ship
Star Pride
Ship details · flagged in The Bahamas
- Tonnage
- 9,975
- Capacity
- 208
- Built
- 1,988
- Length
- 134 m
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