San Juan, Puerto Rico
One of the places included in this itinerary.
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14-night Caribbean cruise from San Juan, Puerto Rico on Star Pride
The San Juan to San Juan is a 14-night Caribbean cruise aboard Star Pride, operated by Windstar Cruises. Departing San Juan, Puerto Rico on December 27, 2026, the voyage visits 11 ports including Cruz Bay, St. John, Gustavia, Saint Barthelemy, Basseterre, St. Kitts. Fares start from $8,074 per person.
- Length
- 14 nights
- Departs
- Dec 27, 2026
- Returns
- Jan 10, 2027
- Ports of call
- 11
- Days at sea
- 2
Voyage code PR20261227-14D
14 nights · Caribbean
Why this route stands out
A closer look at the journey
Price tracking
Today’s fare, in context
Price history
Cheaper than 71%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 $8,074
$576 / night
Fare rows
Ocean View Suite
Cabin grade
from $8,074
$576 / night
per person
Observed 14 Oct 2026, 08:12 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 $8,424
$601 / night
per person
Observed 14 Oct 2026, 08:12 UTC
Rate details
Rate name not supplied
Rate code not supplied
Rate conditions not supplied. Confirm the rate and its terms before booking.
Balcony
No recorded fare
Suite
No recorded fare
This sailing
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The journey
14 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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Other sailing dates
Same itinerary, different departure dates.
Departs
Nov 29, 2026
Voyage PR20261129-14D
from $7,234
$516 / night
