San Juan & the Virgin Islands

Dec 13, 2026 — Dec 20, 2026

Starting from

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SAN JUAN → SAN JUAN

7 Nights on Star Pride

Begin and end your journey where Old World meets New, in historic San Juan, littered with more than 400 restored Spanish colonial buildings. As you continue on this bewitching Caribbean cruise through the Virgin Islands, no two days are alike. One day, you’re shopping chic French boutiques for the latest fashions from Paris. On another, snorkeling a secluded cove known only to lucky yachtsmen — like you. Skip more common and commercial ports like St. Thomas in favor of less-visited destinations like Montserrat. Bypass the major cruise terminals in favor of marinas and anchorages exclusive to small yachts on this Caribbean cruise. And as guests on larger cruise ships take an excursion from Tortola to reach tiny Jost Van Dyke, your elegant yacht is already there.

Additional Information

1
DEC 13, 2026
San Juan
EMBARK
1:00 PM
DEPART
7:00 PM
MARINA
NO
SHORE EXCURSIONS
8

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, Bacardi Rum Tour & Tasting- With Transfer to Windstar Hotel

Time
8:30 AM
Duration
3.5 Hours
Activity Level
Easy-Moderate
Price
$289

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: 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 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

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

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

San Juan, Bacardi Rum Tour & Tasting- With Transfer to Airport

Time
8:30 AM
Duration
3.5 Hours
Activity Level
Easy-Moderate
Price
$289
2
DEC 14, 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 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, Cinnamon Beach Getaway

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

St. John, Trunk Bay Snorkeling Experience

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

St. John, Island tour Featuring Annaberg Ruins

Time
8:30 AM
Duration
2.5 Hours
Activity Level
Easy
Price
$99
3
DEC 15, 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.

Gustavia, Concierge Collection: Scuba Dive 1 Tank

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

St. Barts: Intimate Island Tour

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

St. Barts: Independent Explorer by Car

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

St. Barts, Concierge Collection: Sunset Cruise

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

St Barts, Concierge Collection: St. Barthelemy Beach Day

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

Sailing Catamaran to St Barth Nature Reserve

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

Gustavia, Concierge Collection: Jet Ski

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

Gustavia, Concierge Collection: Scuba Dive 2 Tank

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

Gustavia, Concierge Collection: Savor St Barts

Time
8:30 AM
Duration
2.5 Hours
Activity Level
Moderate
Price
$349
4
DEC 16, 2026
Basseterre
ARRIVE
8:00 AM
DEPART
5:00 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: 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, Island History & Rum Tasting

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

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

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

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

Basseterre: Sky Safari Zipline Adventure

Time
8:30 AM
Duration
4 Hours
Activity Level
Strenuous
Price
$119
5
DEC 17, 2026
Philipsburg, St. Maarten
ARRIVE
8:00 AM
DEPART
10:00 PM
MARINA
NO
SHORE EXCURSIONS
3

Pastel-colored buildings and shops filled with tempting souvenirs herald your arrival to bustling Philipsburg. Situated near the harbor on the Dutch side of St. Maarten, Philipsburg owes its discovery to Christopher Columbus in 1493. Today, celebrated Front Street is home to a number of local Creole restaurants as well as jewelry stores, stylish boutiques, and lively casinos for visitors seeking an upbeat island experience.

St. Maarten, Concierge Collection: Half Day Private Island Tour in SUV or Deluxe Mini Van

Time
8:30 AM
Duration
4 Hours
Activity Level
Easy
Price
$799

St. Maarten: Under Two Flags Island Tour

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

Philipsburg, Savor St. Maarten Foodie Tour

Time
8:30 AM
Duration
4.5 Hours
Activity Level
Easy-Moderate
Price
$189
6
DEC 18, 2026
Jost Van Dyke, Great Harbour
ARRIVE
9:00 AM
DEPART
10:00 PM
MARINA
YES
SHORE EXCURSIONS
1

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.

Jost Van Dyke, Catamaran Cruise & Swim to Norman Island

Time
9:30 AM
Duration
4.5 Hours
Activity Level
Moderate-Strenuous
Price
$259
7
DEC 19, 2026
Virgin Gorda / Prickly Pear, British Virgin Islands
ARRIVE
8:00 AM
DEPART
5:00 PM
MARINA
NO
SHORE EXCURSIONS
2

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

Virgin Gorda: Highlights & Bath Tour

Time
8:00 AM
Duration
4 Hours
Activity Level
Strenuous
Price
$89

Virgin Gorda: Snorkel Adventure

Time
8:30 AM
Duration
2.75 Hours
Activity Level
Moderate-Strenuous
Price
$269

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 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 400 sq ft
Max. Occupancy 2 Passengers
Amenities

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