Masterpieces at Sea: Gems of the Leeward Islands
Everywhere you look is another cover-worthy image on this Caribbean voyage — scenes so striking they’ll inspire your inner artist. Dazzling white sand turns the shallows mesmerizin...
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Ports of Call & Itinerary
11-night voyage departing San Juan (Puerto Rico).
Printable Itinerary (PDF)Route Map
Masterpieces at Sea: Gems of the Leeward Islands
9 ports plotted · click a marker for details
Day 1
San Juan (Puerto Rico) , Puerto Rico
Wednesday, 28/10/2026
The imposing façade of El Morro fortress is just one of the many UNESCO World Heritage Sites in San Juan. Admire the colorful colonial buildings from your casually elegant ship, docked right in the heart of Old San Juan.
Day 3
Gustavia , Saint Barthélemy
Friday, 30/10/2026
Affectionately known as St. Barts, the Caribbean's most chic island adds a French flair to Riviera-like beaches and duty-free boutiques. Walk past gingerbread cottages in search of celebrities, shop for designer fashions, or sip the island's signature ti punch as kite surfers fly by.
Day 4
Basseterre, Saint Kitts , Saint Kitts and Nevis
Saturday, 31/10/2026
With Georgian architecture situated against an irresistible backdrop of emerald green hills, Basseterre is one of the loveliest of the Caribbean's small capitals. Beyond town, more than a quarter of St. Kitts has been set aside as Brimstone Hill Fortress national Park, a UNESCO World Heritage Site.
Day 5
Falmouth , Antigua and Barbuda
Sunday, 01/11/2026
It's said that Antigua has 365 beaches - one for every day of the year. See how many you can discover as our stay in port stretches into the evening to accommodate them all. Watch the stars come out as darkness falls and imagine how residents of Andromeda must envy you.
Day 6
Terre-de-Haut , Guadeloupe
Monday, 02/11/2026
This is the Caribbean as you've always imagined it, with yacht-filled harbors set against volcanic mountains and endless stretches of palm-fringed beach. The underwater world here attracted the likes of Jacques Cousteau, but even novice snorkelers will enjoy exploring these impossibly blue waters.
Day 7
Rodney Bay , Saint Lucia
Tuesday, 03/11/2026
Rodney Bay, Saint Lucia
Day 8
Saint George's , Grenada
Wednesday, 04/11/2026
Inhale the intoxicating aroma of the "Isle of Spice" as your eyes feast on what is widely claimed to be the most beautiful city in the Caribbean. Spend the day on 2-mile-long Grand Anse beach, and before you go, a taste of nutmeg ice cream is a must.
Day 10
Great Harbour, Jost Van Dyke , British Virgin Islands
Friday, 06/11/2026
For an island comprised of a mere eight square miles, it's amazing how much there is to do on Jost Van Dyke. Visit the national park on nearby Diamond Cay, snorkel among swaying sponges and angelfish at Sandy Spit, or pilot your own boat around Sir Francis Drake Waterway. After all that, you'll be ready for an evening drink on the beach - where you can admire your Windstar ship aglow in the harbor.
Day 12
San Juan (Puerto Rico) , Puerto Rico
Sunday, 08/11/2026
The imposing façade of El Morro fortress is just one of the many UNESCO World Heritage Sites in San Juan. Admire the colorful colonial buildings from your casually elegant ship, docked right in the heart of Old San Juan.
Room Type & Prices
All prices per person based on double occupancy. Solo traveller prices — single occupancy. Contact our cruise experts for the latest availability and best fares.
Star Ocean View Suite
277 sqft · Up to 2 guests
Balcony Suite
277 sqft · Up to 2 guests
Star Porthole Suite
277 sqft · Up to 2 guests
Ocean View Suite
277 sqft · Up to 2 guests
Star Balcony Suite
277 sqft · Up to 2 guests
Deluxe Suite
468 sqft · Up to 2 guests
Broadmoor Suite/Sea Island Suite
400 sqft · Up to 2 guests
Owner's Suite
575 sqft · Up to 2 guests
Oceanview
| Cabin | Grade | Per Person | Avail. | |
|---|---|---|---|---|
| Star Ocean View Suite · 277 sqft | SS1 | Enquire → |
Star Ocean View Suite · 277 sqft
SS1
Balcony
Suite
| Cabin | Grade | Per Person | Avail. | |
|---|---|---|---|---|
| Star Porthole Suite · 277 sqft | SP | Enquire → | ||
| Ocean View Suite · 277 sqft | S Ocean View Suite (Deck 4, forward) | Enquire → | ||
| S1 Ocean View Suite 1 (Deck 4) | Enquire → | |||
| S2 Ocean View Suite 2 (Deck 5) | Enquire → | |||
| S3 Ocean View Suite 3 (Deck 6) | Enquire → | |||
| Star Balcony Suite (Deck 5) | SBS | Enquire → | ||
| Star Balcony Suite · 277 sqft | SBS1 Star Balcony Suite 1 (Deck 6) | Enquire → | ||
| Deluxe Suite · 468 sqft | DS | Enquire → | ||
| Broadmoor Suite/Sea Island Suite · 400 sqft | CS Classic Suite | Enquire → | ||
| Owner's Suite · 575 sqft | OW Owner's Suite | Enquire → |
Star Porthole Suite · 277 sqft
SP
Ocean View Suite · 277 sqft
S Ocean View Suite (Deck 4, forward)
Ocean View Suite · 277 sqft
S1 Ocean View Suite 1 (Deck 4)
Ocean View Suite · 277 sqft
S2 Ocean View Suite 2 (Deck 5)
Ocean View Suite · 277 sqft
S3 Ocean View Suite 3 (Deck 6)
Star Balcony Suite (Deck 5)
SBS
Star Balcony Suite · 277 sqft
SBS1 Star Balcony Suite 1 (Deck 6)
Deluxe Suite · 468 sqft
DS
Broadmoor Suite/Sea Island Suite · 400 sqft
CS Classic Suite
Owner's Suite · 575 sqft
OW Owner's Suite
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Your Ship
Star Pride
Serving just 312 guests, Star Pride is the perfect size — small enough to offer unique experiences that set Windstar apart from other cruise lines (like our complimentary Signature Beach Party), yet large enough for you to make plenty of new connections on board — all without ever feeling crowded.
