Star Collector: Caribbean Explorations

Jan 2, 2027 — Jan 16, 2027

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PHILIPSBURG, ST. MAARTEN → PHILIPSBURG, ST. MAARTEN

14 Nights on Wind Surf

Skip the usual Caribbean cruise stops and discover the small harbors, overlooked havens and most remote secrets among the Leeward Islands. Whether you’re looking for hidden shops, sampling new cuisine or seeking a local place to sip rum cocktails over the melodic beat of steel drums, this highly personalized adventure is an intimate opportunity to familiarize yourself with the lesser-known charms of Barbuda, Soper’s Hole in Tortola, Gustavia in St. Barthémy, St. Lucia’s Pigeon Island and much more.

1
JAN 02, 2027
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
JAN 03, 2027
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, Antigua Beach Escape *

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

Falmouth Harbour , Concierge Collection, Tuk Tuk Rainforest and Beach

Time
8:30 AM
Duration
3.5 Hours
Activity Level
Easy
Price
$379

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

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, Swim with the Stingrays

Time
8:30 AM
Duration
3 Hours
Activity Level
Moderate
Price
$119
3
JAN 04, 2027
Road Bay
ARRIVE
8:00 AM
DEPART
6:00 PM
MARINA
YES
SHORE EXCURSIONS
6

With its protected shoreline, calm surf, spectacular coral reefs and sugar-soft beaches, Road Bay has become a destination for boaters, with its delightful restaurants, bars, and shops. Anguilla has some of the most beautiful sunsets and delicious rum punch to be found in the Caribbean.  It is also home to Cuban tree frogs, red-footed tortoise, green iguanas and five species of bats.  Worth checking out is Wallblake House, a heritage plantation house and museum said to be the oldest building on the island and located nearby.

Road Bay, French Invasion Hike

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

Road Bay, Concierge Collection: Relaxing Day at Savi with Lunch

Time
8:30 AM
Duration
5 Hours
Activity Level
Easy-Moderate
Price
$459

Concierge Collection: Road Bay, Snorkel Adventure by Speedboat

Time
8:30 AM
Duration
3 Hours
Activity Level
Moderate-Strenuous
Price
$329

Road Bay, Iconic Island Highlights with Salt Tasting and Beach Time

Time
8:30 AM
Duration
4 Hours
Activity Level
Easy
Price
$199

Road Bay, Island Exploration by Moke

Time
9:00 AM
Duration
2.5 Hours
Activity Level
Strenuous
Price
$579

Road Bay, Shoal Bay Beach Transfer

Time
8:30 AM
Duration
4 Hours
Activity Level
Easy
Price
$129
4
JAN 05, 2027
Soper's Hole
ARRIVE
8:00 AM
DEPART
6:00 PM
MARINA
YES
SHORE EXCURSIONS
5

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. 

Tortola, Tortola Jeep & Beach Tour

Time
8:30 AM
Duration
4 Hours
Activity Level
Moderate
Price
$199

Jost Van Dyke, Catamaran Cruise & Swim to Norman Island

Time
7:30 PM
Duration
Invalid Duration
Activity Level
Moderate-Strenuous
Price
$259

Soper's Hole: Cane Garden Bay Beach Break

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

Tortola, Scenic Drive & Beach

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

Tortola, Snorkel Adventure at Peter Island

Time
8:30 AM
Duration
3 Hours
Activity Level
Moderate-Strenuous
Price
$149
Jost Van Dyke, Great Harbour
ARRIVE
7:00 PM
DEPART
11:59 PM
MARINA
YES
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.

5
JAN 06, 2027
Jost Van Dyke, Great Harbour
ARRIVE
12:00 AM
DEPART
10:00 PM
MARINA
YES
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.

6
JAN 07, 2027
Virgin Gorda / Prickly Pear, British Virgin Islands
ARRIVE
8:00 AM
DEPART
5:00 PM
MARINA
YES
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
8:30 AM
Duration
2.75 Hours
Activity Level
Moderate-Strenuous
Price
$269

Virgin Gorda: Highlights & Bath Tour

Time
8:00 AM
Duration
4 Hours
Activity Level
Strenuous
Price
$89
7
JAN 08, 2027
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: Sunset Cruise

Time
8:30 AM
Duration
1.5 Hours
Activity Level
Easy-Moderate
Price
$199

St. Barts: Sailing Catamaran Adventure

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

Gustavia, Concierge Collection: Jet Ski

Time
8:30 AM
Duration
2 Hours
Activity Level
Strenuous
Price
$509

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
8:30 AM
Duration
2.5 Hours
Activity Level
Moderate
Price
$349

Gustavia, Concierge Collection: Scuba Dive 1 Tank

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

Gustavia, Concierge Collection: Scuba Dive 2 Tank

Time
8:30 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
$519

Wind Surf

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

Staterooms

Room Size 495 sq ft
Max. Occupancy 3 Passengers
Amenities

Starting from

Room Size 242 sq ft
Max. Occupancy 2 Passengers
Amenities

Starting from

Room Size 376 sq ft
Max. Occupancy 3 Passengers
Amenities

Starting from

Room Size 188 sq ft
Max. Occupancy 2 Passengers
Amenities

Starting from

Room Size 188 sq ft
Max. Occupancy 2 Passengers
Amenities

Starting from

Room Size 188 sq ft
Max. Occupancy 2 Passengers
Amenities

Starting from

Room Size 188 sq ft
Max. Occupancy 3 Passengers
Amenities

Starting from

Room Size 188 sq ft
Max. Occupancy 2 Passengers
Amenities

Starting from

Room Size sq ft
Max. Occupancy 2 Passengers
Amenities

Available Dates

Date Yacht
Starting from
Actions
Feb 7 (Sat) – Feb 21 (Sat), 2026February 7 (Sat) – February 21 (Sat), 2026Wind SpiritStarting price not available
Feb 28 (Sat) – Mar 14 (Sat), 2026February 28 (Sat) – March 14 (Sat), 2026Wind SurfStarting price not available
Mar 14 (Sat) – Mar 28 (Sat), 2026March 14 (Sat) – March 28 (Sat), 2026Wind Surf$6,519
Mar 21 (Sat) – Apr 4 (Sat), 2026March 21 (Sat) – April 4 (Sat), 2026Wind Surf$6,719
Dec 19 (Sat) – Jan 2 (Sat), 2027December 19 (Sat) – January 2 (Sat), 2027Wind Surf$5,519
Dec 26 (Sat) – Jan 9 (Sat), 2027December 26 (Sat) – January 9 (Sat), 2027Wind Surf$5,219
Jan 9 (Sat) – Jan 23 (Sat), 2027January 9 (Sat) – January 23 (Sat), 2027Wind Surf$5,819
Jan 16 (Sat) – Jan 30 (Sat), 2027January 16 (Sat) – January 30 (Sat), 2027Wind Surf$5,719
Jan 23 (Sat) – Feb 6 (Sat), 2027January 23 (Sat) – February 6 (Sat), 2027Wind Surf$5,119
Jan 30 (Sat) – Feb 13 (Sat), 2027January 30 (Sat) – February 13 (Sat), 2027Wind Surf$5,219
Feb 6 (Sat) – Feb 20 (Sat), 2027February 6 (Sat) – February 20 (Sat), 2027Wind Surf$5,219
Feb 13 (Sat) – Feb 27 (Sat), 2027February 13 (Sat) – February 27 (Sat), 2027Wind Surf$5,119
Feb 20 (Sat) – Mar 6 (Sat), 2027February 20 (Sat) – March 6 (Sat), 2027Wind Surf$5,119
Feb 27 (Sat) – Mar 13 (Sat), 2027February 27 (Sat) – March 13 (Sat), 2027Wind Surf$5,019
Mar 6 (Sat) – Mar 20 (Sat), 2027March 6 (Sat) – March 20 (Sat), 2027Wind Surf$5,019
Mar 13 (Sat) – Mar 27 (Sat), 2027March 13 (Sat) – March 27 (Sat), 2027Wind Surf$5,119
Nov 28 (Sun) – Dec 12 (Sun), 2027November 28 (Sun) – December 12 (Sun), 2027Wind Surf$4,519
Dec 5 (Sun) – Dec 19 (Sun), 2027December 5 (Sun) – December 19 (Sun), 2027Wind Surf$4,519
Jan 9 (Sun) – Jan 23 (Sun), 2028January 9 (Sun) – January 23 (Sun), 2028Wind Surf$4,819
Jan 16 (Sun) – Jan 30 (Sun), 2028January 16 (Sun) – January 30 (Sun), 2028Wind Surf$4,819
Jan 23 (Sun) – Feb 6 (Sun), 2028January 23 (Sun) – February 6 (Sun), 2028Wind Surf$4,819
Jan 30 (Sun) – Feb 13 (Sun), 2028January 30 (Sun) – February 13 (Sun), 2028Wind Surf$4,819
Feb 6 (Sun) – Feb 20 (Sun), 2028February 6 (Sun) – February 20 (Sun), 2028Wind Surf$4,819
Feb 13 (Sun) – Feb 27 (Sun), 2028February 13 (Sun) – February 27 (Sun), 2028Wind Surf$4,819
Feb 20 (Sun) – Mar 5 (Sun), 2028February 20 (Sun) – March 5 (Sun), 2028Wind Surf$4,819
Feb 27 (Sun) – Mar 12 (Sun), 2028February 27 (Sun) – March 12 (Sun), 2028Wind Surf$4,819
Mar 5 (Sun) – Mar 19 (Sun), 2028March 5 (Sun) – March 19 (Sun), 2028Wind Surf$4,819