San Juan & the Virgin Islands

Feb 20, 2026 — Feb 27, 2026

Starting from $6,924 Displayed pricing is based off of double occupancy per person. Pricing subject to change based on occupancy and cabin selection.

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SAN JUAN → SAN JUAN

7 Nights in Star Seeker

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
FEB 20, 2026
San Juan
EMBARK
1:00 PM
DEPART
7:00 PM
MARINA
NO
SHORE EXCURSIONS
0

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.

2
FEB 21, 2026
CRUZ BAY, ST. JOHN, Virgin Islands (U.S.)
ARRIVE
8:00 AM
DEPART
6:00 PM
MARINA
NO
SHORE EXCURSIONS
0

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

3
FEB 22, 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, Concierge Collection: Caribbean Cooking, History & Folklore in St. Kitts

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

Basseterre, Island History & Rum Tasting

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

Basseterre: Caribbean Scenic Railway

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

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, Nevis Panoramic and Beach Tour

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

Basseterre: Sky Safari Zipline Adventure

Time
8:30 AM
Duration
4 Hours
Activity Level
Strenuous
Price
$119
4
FEB 23, 2026
Philipsburg, St. Maarten
ARRIVE
8:00 AM
DEPART
10:00 PM
MARINA
NO
SHORE EXCURSIONS
7

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: Under Two Flags Island Tour

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

St. Maarten: Soualiga Sky Explorer & 360 Views

Time
8:30 AM
Duration
4.5 Hours
Activity Level
Easy-Moderate
Price
$219

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: Soualiga Sky Explorer & Flying Dutchman

Time
8:30 AM
Duration
4.25 Hours
Activity Level
Strenuous
Price
$339

St. Maarten: Americas Cup Sailboat Racing

Time
8:30 AM
Duration
3.5 Hours
Activity Level
Moderate-Strenuous
Price
$149

Philipsburg, Savor St. Maarten Foodie Tour

Time
8:30 AM
Duration
4.5 Hours
Activity Level
Easy-Moderate
Price
$189

St. Maarten: Americas Cup Sailboat Racing with Transfer to Airport

Time
8:30 AM
Duration
2.5166666666666666 Hours
Activity Level
Moderate-Strenuous
Price
$179
5
FEB 24, 2026
Gustavia
ARRIVE
7:00 AM
DEPART
6:00 PM
MARINA
NO
SHORE EXCURSIONS
8

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: Jet Ski

Time
7:30 AM
Duration
2 Hours
Activity Level
Strenuous
Price
$269

Gustavia, Concierge Collection: Scuba Dive 1 Tank

Time
7:30 AM
Duration
3 Hours
Activity Level
Strenuous
Price
$339

St. Barts: Independent Explorer by Car

Time
8:30 AM
Duration
6 Hours
Activity Level
Easy-Moderate
Price
$349

Gustavia, Concierge Collection: Savor St Barts

Time
7:30 AM
Duration
2.5 Hours
Activity Level
Moderate
Price
$349

St. Barts: Sailing Catamaran Adventure

Time
8:30 AM
Duration
3 Hours
Activity Level
Moderate
Price
$299

Gustavia, Concierge Collection: Scuba Dive 2 Tank

Time
7:30 AM
Duration
4 Hours
Activity Level
Strenuous
Price
$499

St. Barts: Intimate Island Tour

Time
8:30 AM
Duration
1 Hours
Activity Level
Easy
Price
$139

St Barts, Concierge Collection: St. Barthelemy Beach Day

Time
8:30 AM
Duration
6 Hours
Activity Level
Easy-Moderate
Price
$499
6
FEB 25, 2026
Jost Van Dyke, Great Harbour
ARRIVE
8:00 AM
DEPART
10:00 PM
MARINA
NO
SHORE EXCURSIONS
2

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, Sail and Snorkel

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

Jost Van Dyke, Catamaran Cruise & Swim to Norman Island

Time
8:30 AM
Duration
4.5 Hours
Activity Level
Moderate-Strenuous
Price
$259
7
FEB 26, 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: Snorkel Adventure

Time
9:00 AM
Duration
2.75 Hours
Activity Level
Moderate-Strenuous
Price
$239

Virgin Gorda: Highlights & Bath Tour

Time
8:15 AM
Duration
4 Hours
Activity Level
Strenuous
Price
$89

Star Seeker

number of decks
6 Decks
yacht length
ft (0 meters)
yacht crew size
Crew Members
yacht guest capacity
224 Guests

Available Staterooms

Vista Veranda Suite

Cabin
10 Cabins
Max. Occupancy
2 Passengers
Room Size
268 Sqft
Amenities

Classic Suite

Cabin
2 Cabins
Max. Occupancy
2 Passengers
Room Size
353 Sqft
Amenities

Premier Veranda Suite VS1

Cabin
6 Cabins
Max. Occupancy
2 Passengers
Room Size
Sqft
Amenities

Star Suite

Cabin
4 Cabins
Max. Occupancy
2 Passengers
Room Size
380 Sqft
Amenities

Deluxe Suite

Cabin
4 Cabins
Max. Occupancy
2 Passengers
Room Size
288 Sqft
Amenities

Veranda Suite

Cabin
16 Cabins
Max. Occupancy
2 Passengers
Room Size
225 Sqft
Amenities

Oceanview Suite

Cabin
10 Cabins
Max. Occupancy
2 Passengers
Room Size
203 Sqft
Amenities

Triple Infinity Suite

Cabin
2 Cabins
Max. Occupancy
3 Passengers
Room Size
301 Sqft
Amenities

Premier Veranda Suite VSS

Cabin
12 Cabins
Max. Occupancy
2 Passengers
Room Size
Sqft
Amenities

Premier Veranda Suite

Cabin
14 Cabins
Max. Occupancy
2 Passengers
Room Size
225 Sqft
Amenities

Triple Infinity Suite IN3

Cabin
2 Cabins
Max. Occupancy
3 Passengers
Room Size
Sqft
Amenities

Vista Infinity Suite

Cabin
4 Cabins
Max. Occupancy
2 Passengers
Room Size
280 Sqft
Amenities

Available Dates