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Wind Surf — 6-night Eastern Caribbean
Oceanview · per person
$2,108 42
$4,216 for two
6
nights
5
ports
1
date

6-Night Eastern Caribbean on Wind Surf

St. Maarten, SX→
Road Bay→
Gustavia→
Great Harbour→
Virgin Gorda/prickly Pear→
Sopers Hole
Priced high — 0% above its 90-day average
Overpaying ~$2/person vs its usual — a cheaper date does better. How scoring works
Wind Surf
Launched 1990
6 nights
Roundtrip St. Maarten, SX
Tracked daily since Jul 2026

What's special

6 nights round-trip from St. Maarten, SX calling at Road Bay, Gustavia, Great Harbour, Virgin Gorda/prickly Pear and Sopers Hole. 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

0% below its 90-day averageOceanview · tracked daily since Jul 2026
$2,000
$2,100
$2,200
90-day avg $2,106
JulAugSepOct

Good to know

Is this a good price?
Not really — Oceanview is currently about 0% above its 90-day average, roughly $2 a person over, scoring 42. A cheaper date scores better — open the date picker to compare.
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.

Other Wind Surf itineraries

Eastern Caribbean — Wind Surf14 NIGHTSEastern Caribbean
Windstar Cruises

Wind Surf

73Deal scorelowest fare
from$3,836pp
Save $160 vs 90-day avg
Top deal: 74 Ocean view · $4,046 pp
View 11 dates → Track itinerary
Roundtrip from St. Maarten, SX
Cruise ports Jamaica • Road Bay • Sopers Hole • Great Harbour • Virgin Gorda/prickly Pear • Gustavia • Charlestown • Les Saintes • Mayreau • Roseau, DM • Basseterre, KN
11 sailings · Jan 2027 – Feb 2028
▼ 4% below 90-day avgAt all-time low
View 11 dates → Track itinerary

All routes & dates

View every Wind Surf sailing & deal

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