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Wind Surf — 14-night Eastern Caribbean
Oceanview · per person
$3,900 65
$7,800 for two
14
nights
11
ports
5
dates

14-Night Eastern Caribbean on Wind Surf

St. Maarten, SX→
Charlestown→
Roseau, DM→
Mayreau→
Les Saintes→
Basseterre, KN→
Gustavia→
St. John’s, AG→
Road Bay→
Sopers Hole→
Great Harbour→
Virgin Gorda/prickly Pear
Fair price — 5% below its 90-day average
Roughly $216/person below its usual — a good time to book. How scoring works
Wind Surf
Launched 1990
14 nights
Roundtrip St. Maarten, SX
Tracked daily since Jul 2026

What's special

14 nights round-trip from St. Maarten, SX calling at Charlestown, Roseau, DM, Mayreau, Les Saintes, Basseterre, KN, Gustavia, St. John’s, AG, Road Bay, Sopers Hole, Great Harbour and Virgin Gorda/prickly Pear. We've tracked every cabin and departure on this exact route daily since October — so the score and the “vs 90-day average” above compare it to its own history, never a generic fleet number. Pick a date and cabin above to see whether today’s price is actually a good one.

Fares on

Lead price per person, by cabin · tap to compare · updates daily

5% below its 90-day averageOceanview · tracked daily since Jul 2026
$3,900
$4,100
$4,300
90-day avg $4,116
JulAugSepOct

Good to know

Is this a good price?
Right now, yes — Oceanview is scoring 65 and sits about 5% below what it has averaged on this route over the last 90 days, roughly $216 a person. We only call a price good when its own history says so.
When is the cheapest time to sail this route?
The shoulder months in the chart above tend to run lower than peak summer. We track every departure daily, so you can see which date is actually cheapest — not just which one is advertised.
Does booking through us cost more?
No. The price is identical whether you use our link or go direct. We make money only if you book — and we’ll tell you to wait if the price isn’t good.

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Prices update daily · Every score compares Wind Surf to itself, never to other ships · Independent, not affiliated with Windstar Cruises.