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Star Pride — 14-night Eastern Caribbean
Oceanview · per person
$5,624 37
$11,248 for two
14
nights
11
ports
3
dates

14-Night Eastern Caribbean on Star Pride

San Juan, PR→
Cruz Bay→
Gustavia→
Basseterre, KN→
St. Maarten, SX→
Great Harbour→
Virgin Gorda/prickly Pear→
St. George’s, GD→
Bequia→
Mayreau→
Deshaies→
Marigot Bay
Priced high — 13% above its 90-day average
Overpaying ~$654/person vs its usual — a cheaper date does better. How scoring works
Star Pride
Launched 1988
14 nights
Roundtrip San Juan, PR
Tracked daily since Jul 2026

What's special

14 nights round-trip from San Juan, PR calling at Cruz Bay, Gustavia, Basseterre, KN, St. Maarten, SX, Great Harbour, Virgin Gorda/prickly Pear, St. George’s, GD, Bequia, Mayreau, Deshaies and Marigot Bay. 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

13% above its 90-day averageOceanview · tracked daily since Jul 2026
$4,900
$5,700
$6,500
$7,300
90-day avg $4,970
JulAugSepOct

Good to know

Is this a good price?
Not really — Oceanview is currently about 13% above its 90-day average, roughly $654 a person over, scoring 37. 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 Pride to itself, never to other ships · Independent, not affiliated with Windstar Cruises.