Star Collector: Ivory Beaches & Sapphire Seas of the Caribbean

Dec 2, 2025 — Dec 14, 2025

Starting from $7,004 Displayed pricing is based off of double occupancy per person. Pricing subject to change based on occupancy and cabin selection.

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PHILIPSBURG, ST. MAARTEN → PHILIPSBURG, ST. MAARTEN

12 Nights in Wind Surf

1
DEC 02, 2025
Philipsburg, St. Maarten
EMBARK
1:00 PM
DEPART
7:00 PM
MARINA
NO
SHORE EXCURSIONS
0

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.

2
DEC 03, 2025
Soper's Hole
ARRIVE
8:00 AM
DEPART
6:00 PM
MARINA
NO
SHORE EXCURSIONS
4

Arrive at the boardwalk of Pusser's Landing and mingle with other yachtsmen in the utterly charming marina at Soper's Hole. Find a deserted stretch of beach to kick back and ponder this tiny port's rich heritage of romance, pirates, and adventure. An evening departure features a once-in-a-lifetime romantic sunset Sail Away. 

Soper's Hole: Cane Garden Bay Beach Break

Time
8:30 AM
Duration
4 Hours
Activity Level
Moderate
Price
$89

Tortola, Scenic Drive & Beach

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

Tortola, Snorkel Adventure at Peter Island

Time
8:30 AM
Duration
3 Hours
Activity Level
Moderate-Strenuous
Price
$135

Tortola, Tortola Jeep & Beach Tour

Time
8:30 AM
Duration
4 Hours
Activity Level
Moderate
Price
$199
Jost Van Dyke, Great Harbour
ARRIVE
7:00 PM
DEPART
11:59 PM
MARINA
NO
SHORE EXCURSIONS
0

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.

3
DEC 04, 2025
Jost Van Dyke, Great Harbour
ARRIVE
12:00 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
8:15 AM
Duration
4.5 Hours
Activity Level
Moderate-Strenuous
Price
$259
4
DEC 05, 2025
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
8:15 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
$239
5
DEC 06, 2025
Gustavia
ARRIVE
8:00 AM
DEPART
10:00 PM
MARINA
NO
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 2 Tank

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

St Barts, Concierge Collection: St. Barthelemy Beach Day

Time
10:30 AM
Duration
6 Hours
Activity Level
Easy-Moderate
Price
$499

Gustavia, Concierge Collection: Scuba Dive 1 Tank

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

Gustavia, Concierge Collection: Savor St Barts

Time
8:30 AM
Duration
2.5 Hours
Activity Level
Moderate
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

Gustavia, Concierge Collection: Jet Ski

Time
8:30 AM
Duration
2 Hours
Activity Level
Strenuous
Price
$269

St. Barts: Sailing Catamaran Adventure

Time
9:00 AM
Duration
3 Hours
Activity Level
Moderate
Price
$299
6
DEC 07, 2025
Philipsburg, St. Maarten
ARRIVE
6:00 AM
DEPART
7:00 PM
MARINA
NO
SHORE EXCURSIONS
4

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, Post Island Tour with Transfer to Airport

Time
8:00 AM
Duration
4.5 Hours
Activity Level
Easy
Price
$99

St. Maarten: Americas Cup Sailboat Racing with Transfer to Windstar Hotel

Time
8:30 AM
Duration
2.5166666666666666 Hours
Activity Level
Moderate-Strenuous
Price
$179

St. Maarten, Post Island Tour with Transfer to Hotel

Time
8:00 AM
Duration
4.5 Hours
Activity Level
Easy-Moderate
Price
$99

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

Time
8:30 AM
Duration
2.5166666666666666 Hours
Activity Level
Moderate-Strenuous
Price
$179
7
DEC 08, 2025
Charlestown
ARRIVE
8:00 AM
DEPART
5:00 PM
MARINA
NO
SHORE EXCURSIONS
6

This capital of Nevis with its narrow streets and brightly painted Victorian and Georgian stone buildings is full of colonial history. Alexander Hamilton lived here as a child and you can see the ruins of the Hamilton Estate. Lovely Pinney's Beach is nearby and a group of volunteers work at night tagging sea turtles here and on the other beautiful beaches. Walk the main street and check out the Museum of Nevis History, St. Thomas Lowland Church and the Nevisian Heritage Village to name a few of the historic sites here.

Charlestown, Concierge Collection: Deep Sea Fishing

Time
8:30 AM
Duration
4 Hours
Activity Level
Moderate-Strenuous
Price
$479

Charlestown, Coastal Boat Cruise Snorkel Adventure

Time
8:30 AM
Duration
3 Hours
Activity Level
Strenuous
Price
$85

Charlestown, Nevis Half Island & Botanical Garden

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

Charlestown, Yachtsman Grill Beach Escape

Time
8:30 AM
Duration
3.5 Hours
Activity Level
Easy-Moderate
Price
$69

Charlestown, Quad Biking Adventure

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

Charlestown, Montravers Hike & Beach Break with Lunch

Time
8:30 AM
Duration
5 Hours
Activity Level
Moderate-Strenuous
Price
$89

Wind Surf

number of decks
6 Decks
yacht length
535 ft (163 meters)
yacht crew size
191 Crew Members
yacht guest capacity
342 Guests

Available Staterooms

Category A

Cabin
29 Cabins
Max. Occupancy
2 Passengers
Room Size
188 Sqft
Amenities

Category AX Deluxe

Cabin
34 Cabins
Max. Occupancy
2 Passengers
Room Size
188 Sqft
Amenities

Category BX Deluxe

Cabin
34 Cabins
Max. Occupancy
3 Passengers
Room Size
188 Sqft
Amenities

Suite

Cabin
18 Cabins
Max. Occupancy
3 Passengers
Room Size
376 Sqft
Amenities

Category B

Cabin
21 Cabins
Max. Occupancy
2 Passengers
Room Size
188 Sqft
Amenities

Category TX Deluxe

Cabin
32 Cabins
Max. Occupancy
2 Passengers
Room Size
188 Sqft
Amenities

Available Dates