Masterpieces at Sea: Gems of the Leeward Islands

Oct 28, 2026 — Nov 8, 2026

Starting from

Beyond Inclusive Package

Now available on select voyages sailing through March 2027, Windstar’s complimentary Beyond Inclusive Package features a pre-cruise hotel stay, transfer from hotel to yacht, All-Inclusive perks and up to $1,000 onboard credit per guest.
See more routes around Caribbean

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

1
OCT 28, 2026
San Juan
EMBARK
1:00 PM
DEPART
7:00 PM
MARINA
NO
SHORE EXCURSIONS
6

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.

San Juan: Old San Juan Natl Historic Parks Walking Tour with Transfer to Airport

Time
8:30 AM
Duration
4 Hours
Activity Level
Moderate-Strenuous
Price
$159

San Juan, Concierge Collection: Half Day Private SUV with Guide

Time
8:30 AM
Duration
4 Hours
Activity Level
Easy
Price
$829

San Juan: Old San Juan Natl Historic Parks Walking Tour with Transfer to Windstar Hotel

Time
8:30 AM
Duration
3.25 Hours
Activity Level
Moderate-Strenuous
Price
$159

San Juan: Rainforest Eco Wonder Tour with Transfer to Airport

Time
8:30 AM
Duration
5 Hours
Activity Level
Moderate-Strenuous
Price
$199

San Juan: Rainforest Eco Wonder Tour with Transfer to Windstar Hotel

Time
8:30 AM
Duration
5 Hours
Activity Level
Moderate-Strenuous
Price
$199

Time
8:30 AM
Duration
4 Hours
Activity Level
N/A
Price
$729
2
OCT 29, 2026
CRUZ BAY, ST. JOHN, Virgin Islands (U.S.)
ARRIVE
8:00 AM
DEPART
6:00 PM
MARINA
NO
SHORE EXCURSIONS
5

CRUZ BAY, ST. JOHN, Virgin Islands (U.S.)

St. John, Champagne Catamaran Sail

Time
8:30 AM
Duration
3.5 Hours
Activity Level
Moderate
Price
$139

St. John, Island tour Featuring Annaberg Ruins

Time
8:30 AM
Duration
2.5 Hours
Activity Level
Easy
Price
$99

St. John, Trunk Bay Snorkeling Experience

Time
8:30 AM
Duration
3 Hours
Activity Level
Moderate
Price
$149

St. John, Lind Point Trail Eco Hike

Time
8:30 AM
Duration
3 Hours
Activity Level
Moderate
Price
$129

St. John, Champagne Catamaran Sail

Time
8:30 AM
Duration
3 Hours
Activity Level
Moderate
Price
$149
3
OCT 30, 2026
Gustavia
ARRIVE
8:00 AM
DEPART
10:00 PM
MARINA
YES
SHORE EXCURSIONS
9

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.

St Barts, Concierge Collection: St. Barthelemy Beach Day

Time
9:45 AM
Duration
6 Hours
Activity Level
Easy-Moderate
Price
$519

Gustavia, Concierge Collection: Jet Ski

Time
10:30 AM
Duration
2 Hours
Activity Level
Strenuous
Price
$509

St. Barts: Intimate Island Tour

Time
9:00 AM
Duration
1 Hours
Activity Level
Easy
Price
$139

Gustavia, Concierge Collection: Scuba Dive 1 Tank

Time
8:30 AM
Duration
3 Hours
Activity Level
Strenuous
Price
$349

St. Barts: Independent Explorer by Car

Time
9:30 AM
Duration
6 Hours
Activity Level
Easy-Moderate
Price
$349

St. Barts: Sailing Catamaran Adventure

Time
9:00 AM
Duration
3 Hours
Activity Level
Moderate
Price
$299

Gustavia, Concierge Collection: Scuba Dive 2 Tank

Time
8:30 AM
Duration
4 Hours
Activity Level
Strenuous
Price
$499

St. Barts, Concierge Collection: Sunset Cruise

Time
5:00 PM
Duration
1.5 Hours
Activity Level
Easy-Moderate
Price
$199

Gustavia, Concierge Collection: Savor St Barts

Time
8:30 AM
Duration
2.5 Hours
Activity Level
Moderate
Price
$349
4
OCT 31, 2026
Basseterre
ARRIVE
8:00 AM
DEPART
6:00 PM
MARINA
NO
SHORE EXCURSIONS
8

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.

Basseterre, Island History & Rum Tasting

Time
8:30 AM
Duration
2.5 Hours
Activity Level
Moderate
Price
$59

Basseterre: Sky Safari Zipline Adventure

Time
8:30 AM
Duration
4 Hours
Activity Level
Strenuous
Price
$119

Basseterre: Snorkel Safari

Time
8:30 AM
Duration
3 Hours
Activity Level
Moderate
Price
$99

Basseterre: St Kitts Quad ATV Adventure

Time
8:30 AM
Duration
3 Hours
Activity Level
Strenuous
Price
$129

Basseterre, Brimstone Hill Fortress & Fairview Great House

Time
8:30 AM
Duration
3.25 Hours
Activity Level
Easy-Moderate
Price
$79

Basseterre: Caribbean Scenic Railway

Time
8:30 AM
Duration
3 Hours
Activity Level
Easy
Price
$109

Basseterre, Nevis Panoramic and Beach Tour

Time
8:30 AM
Duration
5 Hours
Activity Level
Easy-Moderate
Price
$139

Basseterre, Concierge Collection: Caribbean Cooking, History & Folklore in St. Kitts

Time
8:30 AM
Duration
3.5 Hours
Activity Level
Easy
Price
$99
5
NOV 01, 2026
Falmouth Harbour
ARRIVE
8:00 AM
DEPART
6:00 PM
MARINA
NO
SHORE EXCURSIONS
8

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.

Falmouth Harbour, Swim with the Stingrays

Time
8:30 AM
Duration
3 Hours
Activity Level
Moderate
Price
$119

Falmouth Harbour, Open Course Canopy Zipline

Time
9:30 AM
Duration
4 Hours
Activity Level
Strenuous
Price
$139

Falmouth Harbour, Nelsons Dockyard Walking Tour & Boat around English Harbour

Time
8:30 AM
Duration
3 Hours
Activity Level
Easy-Moderate
Price
$79

Falmouth Harbour, Presidents Tour

Time
8:30 AM
Duration
3 Hours
Activity Level
Moderate-Strenuous
Price
$129

Falmouth Harbour, Make Your Own Rum

Time
10:45 AM
Duration
2 Hours
Activity Level
Easy-Moderate
Price
$139

Falmouth Harbour, Concierge Collection, Jet Ski Adventure

Time
8:30 AM
Duration
1.75 Hours
Activity Level
Moderate-Strenuous
Price
$379

Falmouth Harbour, Spectacular Antigua Island Tour

Time
9:00 AM
Duration
3.5 Hours
Activity Level
Moderate
Price
$99

Falmouth Harbour, Antigua Beach Escape *

Time
8:30 AM
Duration
4 Hours
Activity Level
Easy
Price
$89
6
NOV 02, 2026
Les Saintes
ARRIVE
8:00 AM
DEPART
6:00 PM
MARINA
YES
SHORE EXCURSIONS
8

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.

Les Saintes, Terre de Haut Panoramic Tour

Time
8:30 AM
Duration
1 Hours
Activity Level
Easy
Price
$119

Les Saintes, Relax & Snorkel *

Time
8:30 AM
Duration
3 Hours
Activity Level
Moderate-Strenuous
Price
$179

Les Saintes, Explore Terra de Haut by Foot

Time
8:30 AM
Duration
1.25 Hours
Activity Level
Moderate
Price
$109

Les Saintes, Historic Tastes & Treasures of Fort Napoleon

Time
8:30 AM
Duration
2.5 Hours
Activity Level
Moderate
Price
$129

Les Saintes, Blue Escape Kayaking *

Time
8:30 AM
Duration
2 Hours
Activity Level
Strenuous
Price
$149

Les Saintes, Sample Culinary Treasures of Guadeloupe

Time
8:30 AM
Duration
3 Hours
Activity Level
Easy-Moderate
Price
$209

Les Saintes, Sailing the Bay

Time
8:30 AM
Duration
3 Hours
Activity Level
Moderate-Strenuous
Price
$249

Les Saintes, Snorkel Experience in Les Saintes *

Time
8:30 AM
Duration
2 Hours
Activity Level
Strenuous
Price
$119
7
NOV 03, 2026
Pigeon Island
ARRIVE
8:00 AM
DEPART
9:30 PM
MARINA
NO
SHORE EXCURSIONS
11

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.

Pigeon Island, Panoramic St. Lucia

Time
9:00 AM
Duration
3 Hours
Activity Level
Easy
Price
$59

Pigeon Island, Rainforest Canopy Zip Line Adventure

Time
8:30 AM
Duration
4.5 Hours
Activity Level
Moderate-Strenuous
Price
$119

Pigeon Island, Aerial Tram Park

Time
9:00 AM
Duration
3.5 Hours
Activity Level
Moderate
Price
$159

Pigeon Island, St. Lucian Walking Food Tour

Time
10:00 AM
Duration
3.5 Hours
Activity Level
Easy-Moderate
Price
$189

Pigeon Island, Concierge Collection: Half Day Private Car & Guide

Time
8:30 AM
Duration
4 Hours
Activity Level
Easy
Price
$399

Pigeon Island, Concierge Collection: Full Day Private Car & Guide

Time
8:30 AM
Duration
8 Hours
Activity Level
Easy
Price
$699

Pigeon Island, Concierge Collection: Full Day Private Van & Guide

Time
8:30 AM
Duration
8 Hours
Activity Level
Easy
Price
$899

Pigeon Island, Concierge Collection: Half Day Private Van & Guide

Time
8:30 AM
Duration
4 Hours
Activity Level
Easy
Price
$499

Pigeon Island, Catamaran Cruise to the Pitons

Time
8:30 AM
Duration
5 Hours
Activity Level
Easy
Price
$159

Pigeon Island, Discover Sailing

Time
9:30 AM
Duration
3 Hours
Activity Level
Moderate-Strenuous
Price
$129

Pigeon Island, Sweet Honey Bee Tour

Time
8:30 AM
Duration
2.5 Hours
Activity Level
Moderate
Price
$109

Star Pride

number of decks
6 Decks
yacht length
440 ft (134 meters)
yacht crew size
140 Crew Members
yacht guest capacity
312 Guests

Staterooms

Room Size 575 sq ft
Max. Occupancy 3 Passengers
Amenities

Starting from

Room Size 400 sq ft
Max. Occupancy 2 Passengers
Amenities

Starting from

Room Size 468 sq ft
Max. Occupancy 3 Passengers
Amenities

Starting from

Available Dates

No other dates are available.