Lush & Lovely Islands of the Lesser Antilles

Jan 11, 2026 — Jan 18, 2026

Starting from

See more routes around Caribbean

PHILIPSBURG, ST. MAARTEN → BRIDGETOWN, BARBADOS

7 Nights on Wind Surf

Enjoy the perfect mix of must-see Caribbean towns and harbors off the beaten path as you cruise and sail the royal beauties of the Lesser Antilles islands. Explore colonial history in pastel waterfronts, weathered forts and former sugar plantations. See the Caribbean at its most wild and beautiful on Dominica, St. Lucia and St. Kitts. Join the jetsetters on St. Barts, and make a rare visit to Montserrat, the “Pompeii of the Caribbean.” And everywhere you go, find delicious white beaches that turn rose and orange under Caribbean sunsets.

1
JAN 11, 2026
EMBARK
1:00 PM
DEPART
7:00 PM
MARINA
NO
SHORE EXCURSIONS
0
2
JAN 12, 2026
ARRIVE
8:00 AM
DEPART
9:00 PM
MARINA
NO
SHORE EXCURSIONS
2

Basseterre, Island History & Rum Tasting

Time
8:00 AM
Duration
2.5 Hours
Activity Level
Moderate
Price
$59

Basseterre, Irie Rider Speed Boat

Time
8:00 AM
Duration
3.25 Hours
Activity Level
Moderate-Strenuous
Price
$119
3
JAN 13, 2026
ARRIVE
8:00 AM
DEPART
10:00 PM
MARINA
YES
SHORE EXCURSIONS
9

St. Barts: Independent Explorer by Car

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

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

Gustavia, Concierge Collection: Scuba Dive 1 Tank

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

Gustavia, Concierge Collection: Savor St Barts

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

St. Barts: Intimate Island Tour

Time
8:30 AM
Duration
1 Hours
Activity Level
Easy
Price
$139

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, Concierge Collection: Sunset Cruise

Time
5:00 PM
Duration
1.5 Hours
Activity Level
Easy-Moderate
Price
$199
4
JAN 14, 2026
ARRIVE
8:00 AM
DEPART
10:00 PM
MARINA
NO
SHORE EXCURSIONS
8

St. Johns, Open Course Canopy Challenge

Time
8:30 AM
Duration
4 Hours
Activity Level
Strenuous
Price
$139

St. Johns, Beach Escape

Time
9:00 AM
Duration
4 Hours
Activity Level
Easy
Price
$89

St Johns, Swim with the Stingrays

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

St. Johns: Presidents Tour

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

St. Johns, Spectacular Antigua

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

St. Johns, Concierge Collection: Antigua Helicopter Adventure

Time
8:30 AM
Duration
2 Hours
Activity Level
Easy
Price
$429

St John's , Caribbean Cooking Culinary Experience

Time
10:45 AM
Duration
4 Hours
Activity Level
Easy-Moderate
Price
$239

St Johns, Concierge Collection, Jet Ski Adventure

Time
8:30 AM
Duration
1.75 Hours
Activity Level
Moderate-Strenuous
Price
$379
5
JAN 15, 2026
ARRIVE
8:00 AM
DEPART
5:00 PM
MARINA
YES
SHORE EXCURSIONS
7

Les Saintes, Terre de Haut Panoramic Tour

Time
9:00 AM
Duration
1 Hours
Activity Level
Easy
Price
$119

Les Saintes, Blue Escape Kayaking *

Time
8:30 AM
Duration
2 Hours
Activity Level
Strenuous
Price
$149

Les Saintes, Relax & Snorkel *

Time
9:00 AM
Duration
3 Hours
Activity Level
Moderate-Strenuous
Price
$179

Les Saintes, Historic Tastes & Treasures of Fort Napoleon

Time
12:30 PM
Duration
2.5 Hours
Activity Level
Moderate
Price
$129

Les Saintes, Explore Terra de Haut by Foot

Time
9:30 AM
Duration
1.25 Hours
Activity Level
Moderate
Price
$109

Les Saintes, Sample Culinary Treasures of Guadeloupe

Time
10:00 AM
Duration
3 Hours
Activity Level
Easy-Moderate
Price
$209

Les Saintes, Sailing the Bay

Time
8:30 AM
Duration
3 Hours
Activity Level
Moderate-Strenuous
Price
$249
6
JAN 16, 2026
ARRIVE
8:00 AM
DEPART
4:00 PM
MARINA
NO
SHORE EXCURSIONS
10

Roseau, Dominica in a Day

Time
9:30 AM
Duration
4.5 Hours
Activity Level
Strenuous
Price
$159

Roseau, Whale & Dolphin Adventure

Time
9:30 AM
Duration
3.5 Hours
Activity Level
Easy
Price
$159

Roseau, Champagne Reef Snorkel Adventure

Time
9:30 AM
Duration
2 Hours
Activity Level
Strenuous
Price
$79

Roseau, 4X4 Waterfall & Rainforest

Time
9:30 AM
Duration
3 Hours
Activity Level
Strenuous
Price
$89

Roseau, Trafalgar Falls & Hot Springs

Time
9:30 AM
Duration
3 Hours
Activity Level
Moderate
Price
$99

Roseau, River Tubing Adventure

Time
9:30 AM
Duration
4 Hours
Activity Level
Moderate-Strenuous
Price
$109

Roseau, Concierge Collection: Cooking Caribbean Flavors & Lifestyles

Time
9:30 AM
Duration
3.5 Hours
Activity Level
Easy
Price
$129

Roseau, A Historical Roseau Walking Tour

Time
9:30 AM
Duration
2.5 Hours
Activity Level
Moderate
Price
$59

Roseau, Concierge Collection: Wet & Rugged Dominica

Time
9:30 AM
Duration
5.5 Hours
Activity Level
Strenuous
Price
$225

Roseau, Indian River Rowboat

Time
9:30 AM
Duration
4.5 Hours
Activity Level
Easy-Moderate
Price
$99
7
JAN 17, 2026
ARRIVE
8:00 AM
DEPART
5:00 PM
MARINA
NO
SHORE EXCURSIONS
0

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

Available Dates

Date Yacht
Starting from
Actions
Feb 28 (Sat) – Mar 7 (Sat), 2026February 28 (Sat) – March 7 (Sat), 2026Wind Spirit$7,240