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Wind Surf — 23-night Eastern Caribbean
Oceanview · per person
$4,813 49
$9,626 for two
23
nights
8
ports
1
date

23-Night Eastern Caribbean on Wind Surf

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

What's special

23 nights from Lisbon, PT calling at Funchal, Great Harbour, Gustavia, St. John’s, AG, Deshaies, Road Bay, Sopers Hole 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

0% below its 90-day averageOceanview · tracked daily since Jul 2026
$4,600
$4,700
$4,800
$4,900
90-day avg $4,807
JulAugSepOct

Good to know

Is this a good price?
Not really — Oceanview is currently about 0% above its 90-day average, roughly $6 a person over, scoring 49. 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.