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Masterpieces at Sea: Gems of the Leeward Islands
Oct 28, 2026 — Nov 8, 2026
Starting from
Complimentary All-In Package
Reduced Deposit
SAN JUAN → SAN JUAN
11 Nights on Star Pride
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 mesmerizing shades of blue, and fiery sunsets provide a canvas of rich oranges and reds.





Popular Highlights
Learn to create your own original art piece while onboard, guided by a talented artist, and join lively artist-led Draw & Sip socials.
Watch a Fountainhead artist transform the ship with a live mural that evolves day by day as you sail.
Attend engaging presentations led by an Art Historian, thoughtfully tailored to the theme of your cruise and the destinations you’ll explore.
Enhance your artistic journey ashore with specially curated, art-focused excursions designed to immerse you in the creativity of each destination.
Join coffee chats inspired by The Artist’s Way—a renowned guide to unlocking creativity—and take part in intimate meet-the-artist dinners for a unique opportunity to connect with the creators behind the art.
Meet a local artist onboard, experience their creative process firsthand, and gain meaningful insight into their culture, inspiration, and artistic vision.

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
9:01 AMDuration
3.25 HoursActivity Level
Moderate-StrenuousAdd during booking
$159
San Juan
Time
8:30 AMDuration
4 HoursActivity Level
N/AAdd during booking
$729
San Juan
Time
9:01 AMDuration
3 HoursActivity Level
Easy-ModerateAdd during booking
$259
San Juan
Time
9:01 AMDuration
3 HoursActivity Level
Easy-ModerateAdd during booking
$259
San Juan
Time
8:30 AMDuration
4 HoursActivity Level
EasyAdd during booking
$829
San Juan
Time
8:30 AMDuration
4 HoursActivity Level
Moderate-StrenuousAdd during booking
$159
CRUZ BAY, ST. JOHN, Virgin Islands (U.S.)
Available Excursions
CRUZ BAY, ST. JOHN, Virgin Islands (U.S.)
Time
8:30 AMDuration
3 HoursActivity Level
ModerateAdd during booking
$139
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
3.5 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

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
Explore the island at your own pace with a self-drive adventure through lush countryside and scenic hidden gems.
Time
9:30 AMDuration
6 HoursActivity Level
Easy-ModerateAdd during booking
$359
Gustavia
Enjoy an exclusive island panorama tour — explore local highlights at your pace with a private driver and guide!
Time
9:00 AMDuration
1 HoursActivity Level
EasyAdd during booking
$149
Gustavia
Dive St. Barth’s Protected Marine Reserve and discover vibrant coral reefs, tropical fish, and incredible marine life.
Time
8:30 AMDuration
4 HoursActivity Level
StrenuousAdd during booking
$499
Gustavia
Relax at Le Barthélemy Resort — unwind on a stunning St. Barts beach, swim, savor lunch, and enjoy luxury by the sea.
Time
9:45 AMDuration
6 HoursActivity Level
Easy-ModerateAdd during booking
$579
Gustavia
Dive into St. Barth’s Protected Marine Reserve and discover vibrant reefs, colorful marine life, and crystal-clear waters.
Time
8:30 AMDuration
3 HoursActivity Level
StrenuousAdd during booking
$359
Gustavia
Leisurely sail St. Barth’s coast to crystal-clear waters of Colombier Beach, relax in crystal waters & spot colorful marine life.
Time
9:00 AMDuration
3 HoursActivity Level
ModerateAdd during booking
$319
Gustavia
Toast the sunset aboard a sailing catamaran, cruise Gustavia Harbor & admire mega yachts with Champagne and scenic views.
Time
5:00 PMDuration
1.5 HoursActivity Level
Easy-ModerateAdd during booking
$209
Gustavia
Savor Gustavia’s French-Caribbean flavors with crêpes, Le Select, gourmet bites & Champagne as you explore the town.
Time
8:30 AMDuration
2.5 HoursActivity Level
ModerateAdd during booking
$369
Gustavia
Jet ski from Gustavia to Shell, Gouverneur & Salines beaches, then swim in the crystal-clear waters near Coco Island.
Time
10:30 AMDuration
2 HoursActivity Level
StrenuousAdd during booking
$529

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
10:30 AMDuration
2.5 HoursActivity Level
ModerateAdd during booking
$69
Basseterre
Time
1:00 PMDuration
3.25 HoursActivity Level
Moderate-StrenuousAdd during booking
$119
Basseterre
Time
8:30 AMDuration
4 HoursActivity Level
StrenuousAdd during booking
$129
Basseterre
Time
9:00 AMDuration
3.5 HoursActivity Level
EasyAdd during booking
$99
Basseterre
Time
8:30 AMDuration
3 HoursActivity Level
StrenuousAdd during booking
$139
Basseterre
Time
9:00 AMDuration
3.25 HoursActivity Level
Easy-ModerateAdd during booking
$89
Basseterre
Time
9:00 AMDuration
3 HoursActivity Level
ModerateAdd 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
10:15 AMDuration
3 HoursActivity Level
ModerateAdd during booking
$129
Falmouth Harbour
Time
8:45 AMDuration
4 HoursActivity Level
StrenuousAdd during booking
$149
Falmouth Harbour
Time
9:00 AMDuration
3 HoursActivity Level
Easy-ModerateAdd during booking
$89
Falmouth Harbour
Time
8:45 AMDuration
2 HoursActivity Level
Easy-ModerateAdd during booking
$149
Falmouth Harbour
Time
10:15 AMDuration
4 HoursActivity Level
EasyAdd during booking
$99

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
2 HoursActivity Level
StrenuousAdd during booking
$149
Les Saintes
Time
8:30 AMDuration
3 HoursActivity Level
Moderate-StrenuousAdd during booking
$269
Les Saintes
Time
8:30 AMDuration
1 HoursActivity Level
EasyAdd during booking
$129
Les Saintes
Time
8:30 AMDuration
3 HoursActivity Level
Moderate-StrenuousAdd during booking
$179

Rodney Bay, Saint Lucia
Available Excursions
Rodney Bay
Time
9:00 AMDuration
2.5 HoursActivity Level
ModerateAdd during booking
$109
Rodney Bay
Time
8:30 AMDuration
5 HoursActivity Level
EasyAdd during booking
$169
Rodney Bay
Time
9:45 AMDuration
3 HoursActivity Level
Easy-ModerateAdd during booking
$189
Rodney Bay
Time
9:30 AMDuration
3 HoursActivity Level
Moderate-StrenuousAdd during booking
$139
Rodney Bay
Time
8:30 AMDuration
5 HoursActivity Level
Moderate-StrenuousAdd during booking
$119
Rodney Bay
Time
9:30 AMDuration
2 HoursActivity Level
Easy-ModerateAdd during booking
$129
Rodney Bay
Time
9:00 AMDuration
3.5 HoursActivity Level
ModerateAdd during booking
$159
Rodney Bay
Time
9:00 AMDuration
3 HoursActivity Level
EasyAdd during booking
$59

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
3 HoursActivity Level
Moderate-StrenuousAdd during booking
$89
St. George's
Time
10:30 AMDuration
3 HoursActivity Level
Easy-ModerateAdd during booking
$119
St. George's
Time
10:30 AMDuration
4.5 HoursActivity Level
ModerateAdd during booking
$289
St. George's
Time
10:30 AMDuration
2 HoursActivity Level
Moderate-StrenuousAdd during booking
$119
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
$109
St. George's
Time
10:30 AMDuration
4 HoursActivity Level
Easy-ModerateAdd during booking
$69
St. George's
Time
10:30 AMDuration
3.5 HoursActivity Level
Moderate-StrenuousAdd during booking
$229
St. George's
Time
10:30 AMDuration
4.25 HoursActivity Level
Moderate-StrenuousAdd during booking
$329

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
$99

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.