Classic Caribbean

Jan 9, 2027 — Jan 16, 2027

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
JAN 09, 2027
EMBARK
1:00 PM
DEPART
7:00 PM
MARINA
NO
SHORE EXCURSIONS
0
2
JAN 10, 2027
ARRIVE
8:00 AM
DEPART
5:00 PM
MARINA
NO
SHORE EXCURSIONS
6

Charlestown, Montravers Hike & Beach Break with Lunch

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

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, Coastal Boat Cruise Snorkel Adventure

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

Charlestown, Concierge Collection: Deep Sea Fishing

Time
8:30 AM
Duration
4 Hours
Activity Level
Moderate-Strenuous
Price
$479
3
JAN 11, 2027
ARRIVE
7:00 AM
DEPART
1:00 PM
MARINA
YES
SHORE EXCURSIONS
8

Les Saintes, Explore Terra de Haut by Foot

Time
7:30 AM
Duration
1.25 Hours
Activity Level
Moderate
Price
$109

Les Saintes, Blue Escape Kayaking *

Time
7:30 AM
Duration
2 Hours
Activity Level
Strenuous
Price
$149

Les Saintes, Sample Culinary Treasures of Guadeloupe

Time
7:30 AM
Duration
3 Hours
Activity Level
Easy-Moderate
Price
$209

Les Saintes, Historic Tastes & Treasures of Fort Napoleon

Time
7:30 AM
Duration
2.5 Hours
Activity Level
Moderate
Price
$129

Les Saintes, Snorkel Experience in Les Saintes *

Time
7:30 AM
Duration
2 Hours
Activity Level
Strenuous
Price
$119

Les Saintes, Terre de Haut Panoramic Tour

Time
7:30 AM
Duration
1 Hours
Activity Level
Easy
Price
$119

Les Saintes, Relax & Snorkel *

Time
7:30 AM
Duration
3 Hours
Activity Level
Moderate-Strenuous
Price
$179

Les Saintes, Sailing the Bay

Time
7:30 AM
Duration
3 Hours
Activity Level
Moderate-Strenuous
Price
$249
4
JAN 12, 2027
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
JAN 13, 2027
ARRIVE
8:00 AM
DEPART
4:00 PM
MARINA
NO
SHORE EXCURSIONS
4

Roseau, 4X4 Waterfall & Rainforest

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

Roseau, Concierge Collection: Cooking Caribbean Flavors & Lifestyles

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

Roseau, Champagne Reef Snorkel Adventure

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

Roseau, River Tubing Adventure

Time
8:30 AM
Duration
4 Hours
Activity Level
Moderate-Strenuous
Price
$109
6
JAN 14, 2027
ARRIVE
8:00 AM
DEPART
10:00 PM
MARINA
NO
SHORE EXCURSIONS
8

Basseterre: St Kitts Quad ATV Adventure

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

Basseterre: Sky Safari Zipline Adventure

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

Basseterre, Island History & Rum Tasting

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

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, Nevis Panoramic and Beach Tour

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

Basseterre: Caribbean Scenic Railway

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

Basseterre: Snorkel Safari

Time
8:30 AM
Duration
3 Hours
Activity Level
Moderate
Price
$99
7
JAN 15, 2027
ARRIVE
8:00 AM
DEPART
10:00 PM
MARINA
YES
SHORE EXCURSIONS
10

St. Barts: Sailing the Leeward Coast

Time
8:30 AM
Duration
3 Hours
Activity Level
Easy-Moderate
Price
$209

Gustavia, Concierge Collection: Scuba Dive 2 Tank

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

Gustavia, Concierge Collection: Jet Ski

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

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

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

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

St Barts, Concierge Collection: St. Barthelemy Beach Day

Time
8:30 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 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