Jewels of the Windward Islands

Jan 18, 2026 — Jan 25, 2026

Starting from

See more routes around Caribbean

BRIDGETOWN, BARBADOS → BRIDGETOWN, BARBADOS

7 Nights on Wind Surf

This is the Caribbean of days gone by — deep blue waters, quiet coves and tropical islands dotted with powdery beaches and lush green hillsides. Sail from the rugged natural beauty of St. Lucia to little-known isles that are off the tourist radar. From colorful Bequia and Mayreau in St. Vincent & the Grenadines to the open-air markets of exotic St. George’s, you’ll discover a part of the Caribbean that remains authentic and unspoiled. This is everything that makes the Caribbean synonymous with paradise.

1
JAN 18, 2026
EMBARK
1:00 PM
DEPART
6:00 PM
MARINA
NO
SHORE EXCURSIONS
0
2
JAN 19, 2026
ARRIVE
9:00 AM
DEPART
11:00 PM
MARINA
NO
SHORE EXCURSIONS
5

Anse Mitan, Creole Village

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

Anse Mitan, Kayaking Mangrove Discovery

Time
9:30 AM
Duration
2.5 Hours
Activity Level
Moderate-Strenuous
Price
$139

Anse Mitan, Snorkel Adventure Long

Time
9:30 AM
Duration
3 Hours
Activity Level
Strenuous
Price
$209

Anse Mitan, VIP Experience at La Mauny Plantation and Rum Tasting

Time
9:15 AM
Duration
3.5 Hours
Activity Level
Easy-Moderate
Price
$259

Anse Mitan, Southern Panoramic Martinique

Time
9:30 AM
Duration
3.75 Hours
Activity Level
Moderate
Price
$159
3
JAN 20, 2026
ARRIVE
8:00 AM
DEPART
4:00 PM
MARINA
NO
SHORE EXCURSIONS
11

Castries, Rainforest Canopy Zip Line Adventure

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

Castries, Flavors of St. Lucia - Food & Rum

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

Castries, Concierge Collection: Half Day Private Van with Guide

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

Castries, Creole Day in the Eyes of a FarmHer (Moderate)

Time
8:30 AM
Duration
2.5 Hours
Activity Level
Moderate
Price
$129

Castries, Panoramic St. Lucia

Time
8:30 AM
Duration
3 Hours
Activity Level
Easy
Price
$69

Castries, Concierge Collection: Lets Make Chocolate

Time
8:30 AM
Duration
2.5 Hours
Activity Level
Easy-Moderate
Price
$129

Castries, Heritage Highlights

Time
8:30 AM
Duration
3.5 Hours
Activity Level
Moderate
Price
$69

Castries, Bamboo River Rafting & Rum (Easy-Moderate)

Time
8:30 AM
Duration
4.25 Hours
Activity Level
Easy-Moderate
Price
$179

Castries, Catamaran Cruise to the Pitons

Time
8:30 AM
Duration
4 Hours
Activity Level
Easy
Price
$149

Castries, St. Lucian Walking Food Tour

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

Castries, Concierge Collection: Half Day Private Sedan with Guide

Time
8:30 AM
Duration
4 Hours
Activity Level
Easy
Price
$399
ARRIVE
6:00 PM
DEPART
11:59 PM
MARINA
NO
SHORE EXCURSIONS
0
4
JAN 21, 2026
ARRIVE
12:00 AM
DEPART
6:00 PM
MARINA
NO
SHORE EXCURSIONS
10

Pigeon Island, Aerial Tram Park

Time
9:00 AM
Duration
3.5 Hours
Activity Level
Moderate
Price
$155

Pigeon Island, Discover Sailing

Time
9:30 AM
Duration
3 Hours
Activity Level
Moderate-Strenuous
Price
$129

Pigeon Island, Concierge Collection: Half Day Private Car & Guide

Time
8:30 AM
Duration
4 Hours
Activity Level
Easy
Price
$399

Pigeon Island, St. Lucian Walking Food Tour

Time
10:30 AM
Duration
3.5 Hours
Activity Level
Easy-Moderate
Price
$179

Pigeon Island, Concierge Collection: Full Day Private Van & Guide

Time
8:30 AM
Duration
8 Hours
Activity Level
Easy
Price
$899

Pigeon Island, Catamaran Cruise to the Pitons

Time
8:30 AM
Duration
5 Hours
Activity Level
Easy
Price
$149

Pigeon Island, Concierge Collection: Half Day Private Van & Guide

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

Pigeon Island, Panoramic St. Lucia

Time
8:30 AM
Duration
3 Hours
Activity Level
Easy
Price
$55

Pigeon Island, Concierge Collection: Full Day Private Car & Guide

Time
8:30 AM
Duration
8 Hours
Activity Level
Easy
Price
$699

Pigeon Island, Rainforest Canopy Zip Line Adventure

Time
8:30 AM
Duration
4.5 Hours
Activity Level
Moderate-Strenuous
Price
$119
5
JAN 22, 2026
ARRIVE
8:00 AM
DEPART
10:00 PM
MARINA
YES
SHORE EXCURSIONS
6

Bequia, Concierge Collection: Rum Tasting at Firefly Plantation

Time
10:30 AM
Duration
3 Hours
Activity Level
Moderate
Price
$165

Bequia, Taste of Bequia

Time
10:00 AM
Duration
3.5 Hours
Activity Level
Easy-Moderate
Price
$149

Bequia Snorkel Adventure

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

Bequia Highlights

Time
8:30 AM
Duration
2.5 Hours
Activity Level
Easy-Moderate
Price
$89

Bequia, Mustique Magic with Lunch

Time
9:30 AM
Duration
6 Hours
Activity Level
Moderate
Price
$269

Bequia, Bequia Fort & Lower Beach Getaway *

Time
1:30 PM
Duration
3 Hours
Activity Level
Easy-Moderate
Price
$99
6
JAN 23, 2026
ARRIVE
8:00 AM
DEPART
6:00 PM
MARINA
NO
SHORE EXCURSIONS
1

Mayreau, Grenadines Island Escape

Time
8:30 AM
Duration
3.5 Hours
Activity Level
Moderate
Price
$89
7
JAN 24, 2026
ARRIVE
7:00 AM
DEPART
2:00 PM
MARINA
NO
SHORE EXCURSIONS
10

St. Georges, Clear Bottom Kayaking

Time
7:30 AM
Duration
3 Hours
Activity Level
Moderate-Strenuous
Price
$89

St. Georges, Certified One-Tank Dive

Time
7:30 AM
Duration
3.5 Hours
Activity Level
Moderate-Strenuous
Price
$215

St Georges, Spice of Our Lives

Time
7:30 AM
Duration
4 Hours
Activity Level
Easy-Moderate
Price
$69

St. Georges, Fort Frederick Rainforest & Waterfall

Time
7:30 AM
Duration
3.5 Hours
Activity Level
Moderate
Price
$99

St. Georges, Powerboat & Snorkeling at the Statues Park *

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

St. Georges, Sailing Cruise to the Statue Park

Time
7:30 AM
Duration
3.5 Hours
Activity Level
Moderate-Strenuous
Price
$99

St. Georges, Certified Two-Tank Dive

Time
7:30 AM
Duration
4.25 Hours
Activity Level
Moderate-Strenuous
Price
$319

St. Georges, Discover Scuba

Time
7:30 AM
Duration
4.5 Hours
Activity Level
Moderate
Price
$279

St. Georges, Adventure River Tubing

Time
7:30 AM
Duration
3 Hours
Activity Level
Moderate
Price
$75

St. Georges, Izzie's Great House Discovery

Time
7:30 AM
Duration
3 Hours
Activity Level
Easy-Moderate
Price
$119

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 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

Available Dates

Date Yacht
Starting from
Actions
Mar 21 (Sat) – Mar 28 (Sat), 2026March 21 (Sat) – March 28 (Sat), 2026Wind Spirit$6,832