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Masterpieces at Sea: Gems of the Leeward Islands
Oct 28, 2026 — Nov 8, 2026
Starting from
7-For-7:
Beyond Inclusive Package
SAN JUAN → SAN JUAN
11 Nights on Star Pride
On your Caribbean voyage to the Leeward Islands, everywhere you look is another cover shot image. Dazzling white sand turns the shallows mesmerizing shades of peacock and mermaid, weathered fortresses point canons at long-vanished schooners, natural pools warm gently under the mid-day sun. On your private yacht, you’re equally at home in exclusive harbors and anchored off barefoot beaches, so you can see it all. Snorkel or dive on vibrant coral reefs. Follow your siren inland to rainforest adventures or delightful boutiques. Thank your lucky Star Pride for bringing you here.




Popular Highlights
Delve into the history of pirates and colonists in San Juan.
On Antigua, explore Nelson’s Dockyard, the only Georgian dockyard in the world.
Absorb the distinctive French charm of enchanting Les Saintes.
Enjoy your day on Jost Van Dyke and let the azure waters wash your cares away.
Sail past the stunning emerald Pitons on St. Lucia, a UNESCO World Heritage Site.
Mingle with the glitterati in St. Barts.
Discover the culinary delights of both the Signature Beach Party and the Signature Onboard Barbecue.
Sail, swim and kayak from your yacht’s Marina Platform.

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.
Available Excursions
San Juan
Time
8:30 AMDuration
4 HoursActivity Level
Moderate-StrenuousAdd during booking
$159
San Juan
Time
8:30 AMDuration
4 HoursActivity Level
EasyAdd during booking
$829
San Juan
Time
8:30 AMDuration
3.25 HoursActivity Level
Moderate-StrenuousAdd during booking
$159
San Juan
Time
8:30 AMDuration
4 HoursActivity Level
N/AAdd during booking
$729
CRUZ BAY, ST. JOHN, Virgin Islands (U.S.)
Available Excursions
CRUZ BAY, ST. JOHN, Virgin Islands (U.S.)
Time
8:30 AMDuration
3.5 HoursActivity Level
ModerateAdd during booking
$139
CRUZ BAY, ST. JOHN, Virgin Islands (U.S.)
Time
8:30 AMDuration
2.5 HoursActivity Level
EasyAdd during booking
$99
CRUZ BAY, ST. JOHN, Virgin Islands (U.S.)
Time
8:30 AMDuration
3 HoursActivity Level
ModerateAdd during booking
$149
CRUZ BAY, ST. JOHN, Virgin Islands (U.S.)
Time
8:30 AMDuration
3 HoursActivity Level
ModerateAdd during booking
$129
CRUZ BAY, ST. JOHN, Virgin Islands (U.S.)
Time
8:30 AMDuration
3 HoursActivity Level
ModerateAdd during booking
$149

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.
Available Excursions
Gustavia
Time
9:45 AMDuration
6 HoursActivity Level
Easy-ModerateAdd during booking
$519
Gustavia
Time
10:30 AMDuration
2 HoursActivity Level
StrenuousAdd during booking
$509
Gustavia
Time
9:00 AMDuration
1 HoursActivity Level
EasyAdd during booking
$139
Gustavia
Time
8:30 AMDuration
3 HoursActivity Level
StrenuousAdd during booking
$349
Gustavia
Time
9:30 AMDuration
6 HoursActivity Level
Easy-ModerateAdd during booking
$349
Gustavia
Time
9:00 AMDuration
3 HoursActivity Level
ModerateAdd during booking
$299
Gustavia
Time
8:30 AMDuration
4 HoursActivity Level
StrenuousAdd during booking
$499
Gustavia
Time
5:00 PMDuration
1.5 HoursActivity Level
Easy-ModerateAdd during booking
$199
Gustavia
Time
8:30 AMDuration
2.5 HoursActivity Level
ModerateAdd during booking
$349

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.
Available Excursions
Basseterre
Time
8:30 AMDuration
2.5 HoursActivity Level
ModerateAdd during booking
$59
Basseterre
Time
8:30 AMDuration
4 HoursActivity Level
StrenuousAdd during booking
$119
Basseterre
Time
8:30 AMDuration
3 HoursActivity Level
ModerateAdd during booking
$99
Basseterre
Time
8:30 AMDuration
3 HoursActivity Level
StrenuousAdd during booking
$129
Basseterre
Time
8:30 AMDuration
3.25 HoursActivity Level
Easy-ModerateAdd during booking
$79
Basseterre
Time
8:30 AMDuration
3 HoursActivity Level
EasyAdd during booking
$109
Basseterre
Time
8:30 AMDuration
5 HoursActivity Level
Easy-ModerateAdd during booking
$139
Basseterre
Time
8:30 AMDuration
3.5 HoursActivity Level
EasyAdd during booking
$99

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.
Available Excursions
Falmouth Harbour
Time
8:30 AMDuration
3 HoursActivity Level
ModerateAdd during booking
$119
Falmouth Harbour
Time
9:30 AMDuration
4 HoursActivity Level
StrenuousAdd during booking
$139
Falmouth Harbour
Time
8:30 AMDuration
3 HoursActivity Level
Easy-ModerateAdd during booking
$79
Falmouth Harbour
Time
8:30 AMDuration
3 HoursActivity Level
Moderate-StrenuousAdd during booking
$129
Falmouth Harbour
Time
10:45 AMDuration
2 HoursActivity Level
Easy-ModerateAdd during booking
$139
Falmouth Harbour
Time
8:30 AMDuration
1.75 HoursActivity Level
Moderate-StrenuousAdd during booking
$379
Falmouth Harbour
Time
9:00 AMDuration
3.5 HoursActivity Level
ModerateAdd during booking
$99
Falmouth Harbour
Time
8:30 AMDuration
4 HoursActivity Level
EasyAdd during booking
$89

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.
Available Excursions
Les Saintes
Time
8:30 AMDuration
1 HoursActivity Level
EasyAdd during booking
$119
Les Saintes
Time
8:30 AMDuration
3 HoursActivity Level
Moderate-StrenuousAdd during booking
$179
Les Saintes
Time
8:30 AMDuration
1.25 HoursActivity Level
ModerateAdd during booking
$109
Les Saintes
Time
8:30 AMDuration
2.5 HoursActivity Level
ModerateAdd during booking
$129
Les Saintes
Time
8:30 AMDuration
2 HoursActivity Level
StrenuousAdd during booking
$149
Les Saintes
Time
8:30 AMDuration
3 HoursActivity Level
Easy-ModerateAdd during booking
$209
Les Saintes
Time
8:30 AMDuration
3 HoursActivity Level
Moderate-StrenuousAdd during booking
$249
Les Saintes
Time
8:30 AMDuration
2 HoursActivity Level
StrenuousAdd during booking
$119

The UNESCO site Pitons' with their two majestic volcanic peaks and 24 miles of vibrant coral reef welcome you to St. Lucia. Nearby Pigeon Island National Park features impressive ruins of English forts, archaeological relics of Arawak Indians, and splendid beaches.
Available Excursions
Pigeon Island
Time
9:00 AMDuration
3 HoursActivity Level
EasyAdd during booking
$59
Pigeon Island
Time
8:30 AMDuration
4.5 HoursActivity Level
Moderate-StrenuousAdd during booking
$119
Pigeon Island
Time
9:00 AMDuration
3.5 HoursActivity Level
ModerateAdd during booking
$159
Pigeon Island
Time
10:00 AMDuration
3.5 HoursActivity Level
Easy-ModerateAdd during booking
$189
Pigeon Island
Time
8:30 AMDuration
4 HoursActivity Level
EasyAdd during booking
$399
Pigeon Island
Time
8:30 AMDuration
8 HoursActivity Level
EasyAdd during booking
$699
Pigeon Island
Time
8:30 AMDuration
8 HoursActivity Level
EasyAdd during booking
$899
Pigeon Island
Time
8:30 AMDuration
4 HoursActivity Level
EasyAdd during booking
$499
Pigeon Island
Time
8:30 AMDuration
5 HoursActivity Level
EasyAdd during booking
$159
Pigeon Island
Time
9:30 AMDuration
3 HoursActivity Level
Moderate-StrenuousAdd during booking
$129
Pigeon Island
Time
8:30 AMDuration
2.5 HoursActivity Level
ModerateAdd during booking
$109

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.
Available Excursions
St. George's
Time
10:30 AMDuration
4.25 HoursActivity Level
Moderate-StrenuousAdd during booking
$319
St. George's
Time
10:30 AMDuration
3.5 HoursActivity Level
ModerateAdd during booking
$99
St. George's
Time
10:30 AMDuration
3.5 HoursActivity Level
Moderate-StrenuousAdd during booking
$215
St. George's
Time
10:30 AMDuration
3.5 HoursActivity Level
Moderate-StrenuousAdd during booking
$99
St. George's
Time
10:30 AMDuration
2 HoursActivity Level
Moderate-StrenuousAdd during booking
$119
St. George's
Time
10:30 AMDuration
3 HoursActivity Level
Moderate-StrenuousAdd during booking
$89
St. George's
Time
10:30 AMDuration
4 HoursActivity Level
Easy-ModerateAdd during booking
$69
St. George's
Time
10:30 AMDuration
4.5 HoursActivity Level
ModerateAdd during booking
$279
St. George's
Time
10:30 AMDuration
3 HoursActivity Level
Easy-ModerateAdd during booking
$119

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.
Available Excursions
Jost Van Dyke, Great Harbour
Time
8:30 AMDuration
4.5 HoursActivity Level
Moderate-StrenuousAdd during booking
$259

The beautiful Bank Barrier coral reef wavers just beneath you as your ship makes the break to the bird sanctuary of Prickly Pear Island, so named because it is dotted with prickly pear cacti. Althought uninhabited, it does have a beach bar and water sports facilities. Not far away lies the curious assembly of house-sized boulders called "The Baths," which form huge underground pools and caverns
Available Excursions
Virgin Gorda / Prickly Pear, British Virgin Islands
Time
8:00 AMDuration
4 HoursActivity Level
StrenuousAdd during booking
$89
Virgin Gorda / Prickly Pear, British Virgin Islands
Time
8:30 AMDuration
2.75 HoursActivity Level
Moderate-StrenuousAdd during booking
$269

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.
Staterooms
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Available Dates
No other dates are available.