Beach Fun & Sun: A Remote Caribbean Getaway

Dec 14, 2025 — Dec 21, 2025

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PHILIPSBURG, ST. MAARTEN → PHILIPSBURG, ST. MAARTEN

7 Nights on Wind Surf

Bask on remote beaches resplendent in natural beauty during this relaxing and uncrowded getaway to secluded Caribbean destinations Windstar specializes in. Board a private speedboat bound for Little Bay, Anguilla’s smallest and most private beach, then snorkel among flitting grunts, wrasses and snappers. Guide your own rigid inflatable boat (RIB) through Sir Francis Drake Waterway bays and isles around Jost Van Dyke. Sink in solitude to the silent depths where an 1867 steamship rests, an iconic Tortola dive site that doubled as an underwater movie set. Embark from our yacht’s onboard Marina Platform on your own self-directed snorkeling and kayaking adventures. Find the warm sunset twilight during an overnight port stay at Virgin Gorda. Windstar invites you to join us for our private Signature Beach Party, a fun in the sun affair, full of the rhythm and joy of the Caribbean.

1
DEC 14, 2025
EMBARK
1:00 PM
DEPART
7:00 PM
MARINA
NO
SHORE EXCURSIONS
0
2
DEC 15, 2025
ARRIVE
8:00 AM
DEPART
6:00 PM
MARINA
NO
SHORE EXCURSIONS
8

Falmouth Harbour, Spectacular Antigua Island Tour

Time
8:30 AM
Duration
3.5 Hours
Activity Level
Moderate
Price
$79

Falmouth Harbour, Swim with the Stingrays

Time
8:30 AM
Duration
3 Hours
Activity Level
Moderate
Price
$119

Falmouth Harbour, Antigua Beach Escape *

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

Falmouth Harbour, Concierge Collection, Jet Ski Adventure

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

Falmouth Harbour, Presidents Tour

Time
8:30 AM
Duration
3 Hours
Activity Level
Moderate-Strenuous
Price
$119

Falmouth Harbour, Open Course Canopy Zipline

Time
9:30 AM
Duration
4 Hours
Activity Level
Strenuous
Price
$139

Falmouth Harbour, Make Your Own Rum

Time
10:45 AM
Duration
2 Hours
Activity Level
Easy-Moderate
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
3
DEC 16, 2025
ARRIVE
8:00 AM
DEPART
6:00 PM
MARINA
YES
SHORE EXCURSIONS
6

Road Bay, Island Exploration by Moke

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

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

Time
9:30 AM
Duration
5 Hours
Activity Level
Easy-Moderate
Price
$459

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, French Invasion Hike

Time
9:00 AM
Duration
2.5 Hours
Activity Level
Strenuous
Price
$159

Road Bay, Shoal Bay Beach Transfer

Time
8:30 AM
Duration
4 Hours
Activity Level
Easy
Price
$129

Concierge Collection: Road Bay, Snorkel Adventure by Speedboat

Time
8:30 AM
Duration
3 Hours
Activity Level
Moderate-Strenuous
Price
$329
4
DEC 17, 2025
ARRIVE
8:00 AM
DEPART
6:00 PM
MARINA
YES
SHORE EXCURSIONS
4

Tortola, Tortola Jeep & Beach Tour

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

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

Soper's Hole: Cane Garden Bay Beach Break

Time
8:30 AM
Duration
4 Hours
Activity Level
Moderate
Price
$109
ARRIVE
7:00 PM
DEPART
11:59 PM
MARINA
YES
SHORE EXCURSIONS
0
5
DEC 18, 2025
ARRIVE
12:00 AM
DEPART
10:00 PM
MARINA
YES
SHORE EXCURSIONS
1

Jost Van Dyke, Catamaran Cruise & Swim to Norman Island

Time
8:15 AM
Duration
4.5 Hours
Activity Level
Moderate-Strenuous
Price
$259
6
DEC 19, 2025
ARRIVE
8:00 AM
DEPART
5:00 PM
MARINA
YES
SHORE EXCURSIONS
2

Virgin Gorda: Highlights & Bath Tour

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

Virgin Gorda: Snorkel Adventure

Time
9:00 AM
Duration
2.75 Hours
Activity Level
Moderate-Strenuous
Price
$269
7
DEC 20, 2025
ARRIVE
8:00 AM
DEPART
10:00 PM
MARINA
YES
SHORE EXCURSIONS
9

St. Barts, Concierge Collection: Sunset Cruise

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

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

St. Barts: Sailing Catamaran Adventure

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

Gustavia, Concierge Collection: Scuba Dive 1 Tank

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

St. Barts: Independent Explorer by Car

Time
9:30 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: Jet Ski

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

St Barts, Concierge Collection: St. Barthelemy Beach Day

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

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

Staterooms description here

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 2 Passengers
Amenities

Starting from