All Star Legend sailings
Oceanview · per person
$4,271 1
$8,542 for two
21
nights
7
ports
1
date

21-Night Eastern Caribbean on Star Legend

San Juan, PR→
St. George’s, GD→
Bequia→
Mayreau→
Les Saintes→
Marigot Bay→
Funchal→
Casablanca→
Lisbon, PT
Priced high — 1% above its 90-day average
Overpaying ~$50/person vs its usual — a cheaper date does better. How scoring works
Star Legend
Launched 1992
21 nights
San Juan, PR → Lisbon, PT
Tracked daily since Aug 2026

What's special

21 nights from San Juan, PR calling at St. George’s, GD, Bequia, Mayreau, Les Saintes, Marigot Bay, Funchal and Casablanca. 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

1% above its 90-day averageOceanview · tracked daily since Aug 2026
$4,200
$4,300
90-day avg $4,221
AugSepOct

Good to know

Is this a good price?
Not really — Oceanview is currently about 1% above its 90-day average, roughly $50 a person over, scoring 1. 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.

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