Beach Fun & Sun: A Remote Caribbean Getaway

Dec 19, 2026 — Dec 26, 2026

Starting from

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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 19, 2026
EMBARK
1:00 PM
DEPART
7:00 PM
MARINA
NO
SHORE EXCURSIONS
0
2
DEC 20, 2026
ARRIVE
8:00 AM
DEPART
10:00 PM
MARINA
YES
SHORE EXCURSIONS
0
3
DEC 21, 2026
ARRIVE
8:00 AM
DEPART
6:00 PM
MARINA
NO
SHORE EXCURSIONS
0
4
DEC 22, 2026
ARRIVE
8:00 AM
DEPART
6:00 PM
MARINA
YES
SHORE EXCURSIONS
6

Concierge Collection: Road Bay, Snorkel Adventure by Speedboat

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

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, French Invasion Hike

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

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, Shoal Bay Beach Transfer

Time
8:30 AM
Duration
4 Hours
Activity Level
Easy
Price
$129
5
DEC 23, 2026
ARRIVE
8:00 AM
DEPART
6:00 PM
MARINA
YES
SHORE EXCURSIONS
5

Jost Van Dyke, Catamaran Cruise & Swim to Norman Island

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

Tortola, Scenic Drive & Beach

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

Soper's Hole: Cane Garden Bay Beach Break

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

Tortola, Tortola Jeep & Beach Tour

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

Tortola, Snorkel Adventure at Peter Island

Time
8:30 AM
Duration
3 Hours
Activity Level
Moderate-Strenuous
Price
$149
ARRIVE
7:00 PM
DEPART
11:59 PM
MARINA
YES
SHORE EXCURSIONS
1

Jost Van Dyke, Sail and Snorkel

Time
7:30 PM
Duration
4 Hours
Activity Level
Strenuous
Price
$189
6
DEC 24, 2026
ARRIVE
12:00 AM
DEPART
10:00 PM
MARINA
YES
SHORE EXCURSIONS
0
7
DEC 25, 2026
ARRIVE
8:00 AM
DEPART
5:00 PM
MARINA
YES
SHORE EXCURSIONS
2

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

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 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