San Juan, Puerto Rico
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7-night Caribbean cruise from San Juan, Puerto Rico on Star Pride
The Windward Islands Surf & Sunsets is a 7-night Caribbean cruise aboard Star Pride, operated by Windstar Cruises. Departing San Juan, Puerto Rico on November 8, 2027, the voyage visits 5 ports including St Georges, Grenada, Bequia, Mayreau. Fares start from $2,411 per person.
- Length
- 7 nights
- Departs
- Nov 8, 2027
- Returns
- Nov 15, 2027
- Ports of call
- 5
- Days at sea
- 2
Voyage code PR20271108-7D
7 nights · Caribbean
Why this route stands out
A closer look at the journey
Price tracking
Today’s fare, in context
Price history
Cheaper than 36%30 days
Current prices
Per person · 2 guests
Tax and fee inclusion varies by fare source. Confirm the total, including any additional charges, before booking.
Inside
No recorded fare
Oceanview
from $2,411
$344 / night
Fare rows
Star Porthole Suite
Cabin grade
from $2,411
$344 / night
per person
Observed 14 Oct 2026, 08:33 UTC
Rate details
Rate name not supplied
Rate code not supplied
Rate conditions not supplied. Confirm the rate and its terms before booking.
Ocean View Suite
Cabin grade
from $2,586
$369 / night
per person
Observed 14 Oct 2026, 08:33 UTC
Rate details
Rate name not supplied
Rate code not supplied
Rate conditions not supplied. Confirm the rate and its terms before booking.
Ocean View Suite
Cabin grade
from $2,691
$384 / night
per person
Observed 14 Oct 2026, 08:33 UTC
Rate details
Rate name not supplied
Rate code not supplied
Rate conditions not supplied. Confirm the rate and its terms before booking.
Star Ocean View Suite
Cabin grade
from $2,796
$399 / night
per person
Observed 14 Oct 2026, 08:33 UTC
Rate details
Rate name not supplied
Rate code not supplied
Rate conditions not supplied. Confirm the rate and its terms before booking.
Ocean View Suite
Cabin grade
from $2,866
$409 / night
per person
Observed 14 Oct 2026, 08:33 UTC
Rate details
Rate name not supplied
Rate code not supplied
Rate conditions not supplied. Confirm the rate and its terms before booking.
Ocean View Suite
Cabin grade
from $3,006
$429 / night
per person
Observed 14 Oct 2026, 08:33 UTC
Rate details
Rate name not supplied
Rate code not supplied
Rate conditions not supplied. Confirm the rate and its terms before booking.
Balcony
from $3,951
$564 / night
Fare rows
Balcony Suite
Cabin grade
from $3,951
$564 / night
per person
Observed 14 Oct 2026, 08:33 UTC
Rate details
Rate name not supplied
Rate code not supplied
Rate conditions not supplied. Confirm the rate and its terms before booking.
Star Balcony Suite
Cabin grade
from $4,021
$574 / night
per person
Observed 14 Oct 2026, 08:33 UTC
Rate details
Rate name not supplied
Rate code not supplied
Rate conditions not supplied. Confirm the rate and its terms before booking.
Balcony Suite
Cabin grade
from $4,161
$594 / night
per person
Observed 14 Oct 2026, 08:33 UTC
Rate details
Rate name not supplied
Rate code not supplied
Rate conditions not supplied. Confirm the rate and its terms before booking.
Star Balcony Suite
Cabin grade
from $4,266
$609 / night
per person
Observed 14 Oct 2026, 08:33 UTC
Rate details
Rate name not supplied
Rate code not supplied
Rate conditions not supplied. Confirm the rate and its terms before booking.
Suite
from $6,051
$864 / night
Fare rows
Deluxe Suite
Cabin grade
from $6,051
$864 / night
per person
Observed 14 Oct 2026, 08:33 UTC
Rate details
Rate name not supplied
Rate code not supplied
Rate conditions not supplied. Confirm the rate and its terms before booking.
Classic Suite
Cabin grade
from $7,801
$1,114 / night
per person
Observed 14 Oct 2026, 08:33 UTC
Rate details
Rate name not supplied
Rate code not supplied
Rate conditions not supplied. Confirm the rate and its terms before booking.
Owner's Suite
Cabin grade
from $9,446
$1,349 / night
per person
Observed 14 Oct 2026, 08:33 UTC
Rate details
Rate name not supplied
Rate code not supplied
Rate conditions not supplied. Confirm the rate and its terms before booking.
This sailing
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The journey
7 nights, in order
San Juan, Puerto Rico
Explore San Juan, Puerto RicoDay by day
The full itinerary
Your ship
Star Pride
With only 212 guests, a Star Pride cruise will make you feel like you're on board your own private small ship almost as soon as you step aboard. The sitting area of your spacious, newly refurbished suite gives you an expansive ocean view — making it a welcome retreat. When you're ready to make an appearance, the lounges, club, screening room, and library are waiting to be explored. Take some "you" time in the tranquil WindSpa . . . enjoy a dip in the pool . . . work off that decadent dessert in the Fitness Center . . . and, of course, you are always welcome to visit the Bridge to examine navigation charts with the Captain. Star Pride is large enough to pamper and entertain you, yet small enough to tuck into delightful tiny harbors and hidden coves that others can’t reach.
4★
9,975 GT
212 Passengers
Built 1988
Star Pride
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