All Aboard Deals
Upgrade
All Wind Surf sailings
Wind Surf — 22-night Eastern Caribbean● NEAR 90-DAY LOW
Oceanview · per person
$4,388 45
$8,776 for two
22
nights
8
ports
1
date

22-Night Eastern Caribbean on Wind Surf

St. Maarten, SX→
St. John’s, AG→
Gustavia→
Sopers Hole→
Great Harbour→
Virgin Gorda/prickly Pear→
Road Bay→
Porto Santo→
Funchal→
Lisbon, PT
Priced high — 0% above its 90-day average
Overpaying ~$10/person vs its usual — a cheaper date does better. How scoring works
Wind Surf
Launched 1990
22 nights
St. Maarten, SX → Lisbon, PT
Tracked daily since Sep 2026

What's special

22 nights from St. Maarten, SX calling at St. John’s, AG, Gustavia, Sopers Hole, Great Harbour, Virgin Gorda/prickly Pear, Road Bay, Porto Santo and Funchal. 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 Sep 2026
$4,300
$4,400
90-day avg $4,378
SepOct

Good to know

Is this a good price?
Not really — Oceanview is currently about 0% above its 90-day average, roughly $10 a person over, scoring 45. 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

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.