All Aboard Deals
Upgrade
All Wind Star sailings
Wind Star — 14-night Southern Caribbean
Oceanview · per person
$7,932 57
$15,864 for two
14
nights
8
ports
1
date

14-Night Southern Caribbean on Wind Star

Lisbon, PT→
Barbados, BB→
Bequia→
St. George’s, GD→
Kralendijk, BQ→
Curacao, CW→
Aruba, AW→
Cartagena→
San Diego, CA→
Colon
Priced high — 20% below its 90-day average
Overpaying ~$2,374/person vs its usual — a cheaper date does better. How scoring works
Wind Star
Launched 1986
14 nights
Lisbon, PT → Colon
Tracked daily since Jul 2026

What's special

14 nights from Lisbon, PT calling at Barbados, BB, Bequia, St. George’s, GD, Kralendijk, BQ, Curacao, CW, Aruba, AW, Cartagena and San Diego, CA. 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

43% above its 90-day averageOceanview · tracked daily since Jul 2026
$3,500
$5,000
$6,500
$8,000
90-day avg $5,558
JulAugSepOct

Good to know

Is this a good price?
Right now, yes — Oceanview is scoring 57 and sits about 20% below what it has averaged on this route over the last 90 days. 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.

Other Wind Star itineraries

All routes & dates

View every Wind Star sailing & deal

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