Classic Caribbean

Dec 21, 2025 — Dec 28, 2025

Starting from

See more routes around Caribbean

PHILIPSBURG, ST. MAARTEN → PHILIPSBURG, ST. MAARTEN

7 Nights on Wind Surf

From the stunning drama of the Pitons to the captivating charm of Les Saintes; hidden coves and secret beaches to exotic markets and lively cafés, you’ll discover the best of this region with one single Caribbean voyage. Sandy beaches, turquoise waters, lush mountains, and beautiful waterfalls blend with the music, tastes, and joie de vivre unique to the Caribbean life.

1
DEC 21, 2025
EMBARK
1:00 PM
DEPART
7:00 PM
MARINA
NO
SHORE EXCURSIONS
0
2
DEC 22, 2025
ARRIVE
8:00 AM
DEPART
5:00 PM
MARINA
NO
SHORE EXCURSIONS
6

Charlestown, Quad Biking Adventure

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

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, Montravers Hike & Beach Break with Lunch

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

Charlestown, Concierge Collection: Deep Sea Fishing

Time
8:30 AM
Duration
4 Hours
Activity Level
Moderate-Strenuous
Price
$479
3
DEC 23, 2025
ARRIVE
8:00 AM
DEPART
4:00 PM
MARINA
NO
SHORE EXCURSIONS
9

Roseau, Indian River Rowboat

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

Roseau, Concierge Collection: Cooking Caribbean Flavors & Lifestyles

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

Roseau, Trafalgar Falls & Hot Springs

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

Roseau, River Tubing Adventure

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

Roseau, Concierge Collection: Wet & Rugged Dominica

Time
8:30 AM
Duration
5.5 Hours
Activity Level
Strenuous
Price
$225

Roseau, 4X4 Waterfall & Rainforest

Time
8:30 AM
Duration
3 Hours
Activity Level
Strenuous
Price
$89

Roseau, A Historical Roseau Walking Tour

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

Roseau, Champagne Reef Snorkel Adventure

Time
8:30 AM
Duration
2 Hours
Activity Level
Strenuous
Price
$79

Roseau, Whale & Dolphin Adventure

Time
8:30 AM
Duration
3.5 Hours
Activity Level
Easy
Price
$159
4
DEC 24, 2025
ARRIVE
8:00 AM
DEPART
5:00 PM
MARINA
NO
SHORE EXCURSIONS
1

Mayreau, Grenadines Island Escape

Time
8:30 AM
Duration
3.5 Hours
Activity Level
Moderate
Price
$89
5
DEC 25, 2025
ARRIVE
12:00 PM
DEPART
6:00 PM
MARINA
YES
SHORE EXCURSIONS
1

Les Saintes, Historic Tastes & Treasures of Fort Napoleon

Time
12:30 PM
Duration
2.5 Hours
Activity Level
Moderate
Price
$129
6
DEC 26, 2025
ARRIVE
8:00 AM
DEPART
10:00 PM
MARINA
NO
SHORE EXCURSIONS
9

Basseterre: Sky Safari Zipline Adventure

Time
8:30 AM
Duration
4 Hours
Activity Level
Strenuous
Price
$119

Basseterre, Nevis Panoramic and Beach Tour

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

Basseterre, Island History & Rum Tasting

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

Basseterre: Snorkel Safari

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

Basseterre: Caribbean Scenic Railway

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

Basseterre, Concierge Collection: Caribbean Cooking, History & Folklore in St. Kitts

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

Basseterre, Brimstone Hill Fortress & Fairview Great House

Time
8:30 AM
Duration
3.25 Hours
Activity Level
Easy-Moderate
Price
$79

Basseterre: St Kitts Quad ATV Adventure

Time
8:30 AM
Duration
3 Hours
Activity Level
Strenuous
Price
$129

Basseterre, Irie Rider Speed Boat

Time
8:30 AM
Duration
3.25 Hours
Activity Level
Moderate-Strenuous
Price
$119
7
DEC 27, 2025
ARRIVE
8:00 AM
DEPART
10:00 PM
MARINA
YES
SHORE EXCURSIONS
8

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
$339

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: Independent Explorer by Car

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

St Barts, Concierge Collection: St. Barthelemy Beach Day

Time
8:30 AM
Duration
6 Hours
Activity Level
Easy-Moderate
Price
$499

St. Barts, Concierge Collection: Sunset Cruise

Time
5:00 PM
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

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 3 Passengers
Amenities

Starting from

Room Size 188 sq ft
Max. Occupancy 2 Passengers
Amenities

Starting from