Masterpieces at Sea: Gems of the Leeward Islands

Oct 28, 2026 — Nov 8, 2026

Starting from

See more routes around Caribbean

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.

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 Windstar Hotel

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

Time
8:30 AM
Duration
4 Hours
Activity Level
N/A
Price
$729

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, 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 Airport

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

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

Time
8:30 AM
Duration
5 Hours
Activity Level
Moderate-Strenuous
Price
$199
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, Lind Point Trail Eco Hike

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

St. John, Trunk Bay Snorkeling Experience

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

St. John, Cinnamon Beach Getaway

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, 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: Independent Explorer by Car

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

St. Barts: Intimate Island Tour

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

Gustavia, Concierge Collection: Scuba Dive 2 Tank

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

St Barts, Concierge Collection: St. Barthelemy Beach Day

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

Gustavia, Concierge Collection: Scuba Dive 1 Tank

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

Sailing Catamaran to St Barth Nature Reserve

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

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

Gustavia, Concierge Collection: Jet Ski

Time
10:30 AM
Duration
2 Hours
Activity Level
Strenuous
Price
$509
4
OCT 31, 2026
Basseterre
ARRIVE
8:00 AM
DEPART
6:00 PM
MARINA
NO
SHORE EXCURSIONS
7

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

Time
8:30 AM
Duration
3.5 Hours
Activity Level
Easy
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: Snorkel Safari

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

Basseterre, Nevis Panoramic and Beach Tour

Time
8:30 AM
Duration
5 Hours
Activity Level
Easy-Moderate
Price
$139
5
NOV 01, 2026
Falmouth Harbour
ARRIVE
8:00 AM
DEPART
6:00 PM
MARINA
YES
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, Spectacular Antigua Island Tour

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

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, Concierge Collection, Jet Ski Adventure

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

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, Make Your Own Rum

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

Falmouth Harbour, Presidents Tour

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

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, Blue Escape Kayaking *

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

Les Saintes, Historic Tastes & Treasures of Fort Napoleon

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

Les Saintes, Sailing the Bay

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

Les Saintes, Sample Culinary Treasures of Guadeloupe

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

Les Saintes, Snorkel Experience in Les Saintes *

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

Les Saintes, Terre de Haut Panoramic Tour

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

Les Saintes, Explore Terra de Haut by Foot

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

Les Saintes, Relax & Snorkel *

Time
8:30 AM
Duration
3 Hours
Activity Level
Moderate-Strenuous
Price
$179
7
NOV 03, 2026
Rodney Bay
ARRIVE
8:00 AM
DEPART
9:30 PM
MARINA
NO
SHORE EXCURSIONS
0

Rodney Bay, Saint Lucia

Star Pride

number of decks
6 Decks
yacht length
522 ft (159 meters)
yacht crew size
200 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

Room Size 277 sq ft
Max. Occupancy 3 Passengers
Amenities

Starting from

Room Size 277 sq ft
Max. Occupancy 2 Passengers
Amenities

Starting from

Room Size 277 sq ft
Max. Occupancy 3 Passengers
Amenities

Starting from

Room Size 277 sq ft
Max. Occupancy 3 Passengers
Amenities

Starting from

Room Size 277 sq ft
Max. Occupancy 3 Passengers
Amenities

Starting from

Room Size 277 sq ft
Max. Occupancy 3 Passengers
Amenities

Starting from

Room Size 277 sq ft
Max. Occupancy 3 Passengers
Amenities

Starting from

Room Size 277 sq ft
Max. Occupancy 3 Passengers
Amenities

Starting from

Room Size 277 sq ft
Max. Occupancy 2 Passengers
Amenities

Starting from

Room Size 277 sq ft
Max. Occupancy 2 Passengers
Amenities

Starting from

Room Size 277 sq ft
Max. Occupancy 2 Passengers
Amenities
Expand all

Available Dates

No other dates are available.