TAA TEST Jewels of the Windward Islands

Jan 18, 2026 — Jan 25, 2026

Starting from $5,444 Displayed pricing is based off of double occupancy per person. Pricing subject to change based on occupancy and cabin selection.

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BRIDGETOWN, BARBADOS → BRIDGETOWN, BARBADOS

7 Nights in 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
Bridgetown
EMBARK
1:00 PM
DEPART
6:00 PM
MARINA
NO
SHORE EXCURSIONS
0

Jolly old England comes to life in the city and its garrison, both UNESCO World Heritage Sites. Further afield, you'll find historic sugar plantations and the fairyland magic of Harrison's Cave.

2
JAN 19, 2026
Anse Mitan
ARRIVE
9:00 AM
DEPART
11:00 PM
MARINA
NO
SHORE EXCURSIONS
5

Martinique offers a delightful and distinctive blend of French and Caribbean influences, with a bounty of historical sites, museums and a wide array of excellent shopping. Be sure to take a tour of the beautiful Jardin de Balata Botanical Gardens with exotic plants from around the world and a treetop walkway affording mountain views.

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
$149

Anse Mitan, Creole Village

Time
9:30 AM
Duration
2.8333333333333335 Hours
Activity Level
Moderate-Strenuous
Price
$99

Anse Mitan, Snorkel Adventure Long

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

Anse Mitan, Kayaking Mangrove Discovery

Time
9:30 AM
Duration
2.5 Hours
Activity Level
Moderate-Strenuous
Price
$139
3
JAN 20, 2026
Castries
ARRIVE
8:00 AM
DEPART
4:00 PM
MARINA
NO
SHORE EXCURSIONS
11

The capital and largest city of St. Lucia is a bustling port where shoppers flock.  Most of the city's historic buildings were destroyed in major fires between 1785 and 1948 but you'll see the beautiful, scenic backdrop of Morne Fortune (elev. 2,795 ft.) and the bustling harbor.  Visit the Castries Market for handicrafts, fruits and vegetables, see the murals painted by a local artist and housed in the Cathedral of the Immaculate Conception, and check out one of the many restaurants or Derek Walcott Square.

Castries, Concierge Collection: Half Day Private Sedan with Guide

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

Castries, Catamaran Cruise to the Pitons

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

Castries, Heritage Highlights

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

Castries, St. Lucian Walking Food Tour

Time
8:30 AM
Duration
3.5 Hours
Activity Level
Easy-Moderate
Price
$189

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, Rainforest Canopy Zip Line Adventure

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

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, Bamboo River Rafting & Rum (Easy-Moderate)

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

Castries, Concierge Collection: Lets Make Chocolate

Time
8:30 AM
Duration
2.5 Hours
Activity Level
Easy-Moderate
Price
$129
Pigeon Island
ARRIVE
6:00 PM
DEPART
11:59 PM
MARINA
NO
SHORE EXCURSIONS
0

The UNESCO site Pitons' with their two majestic volcanic peaks and 24 miles of vibrant coral reef welcome you to St. Lucia. Nearby Pigeon Island National Park features impressive ruins of English forts, archaeological relics of Arawak Indians, and splendid beaches.

4
JAN 21, 2026
Pigeon Island
ARRIVE
12:00 AM
DEPART
6:00 PM
MARINA
NO
SHORE EXCURSIONS
10

The UNESCO site Pitons' with their two majestic volcanic peaks and 24 miles of vibrant coral reef welcome you to St. Lucia. Nearby Pigeon Island National Park features impressive ruins of English forts, archaeological relics of Arawak Indians, and splendid beaches.

Pigeon Island, Rainforest Canopy Zip Line Adventure

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

Pigeon Island, Aerial Tram Park

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

Pigeon Island, Catamaran Cruise to the Pitons

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

Pigeon Island, Panoramic St. Lucia

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

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, Concierge Collection: Full Day Private Van & Guide

Time
8:30 AM
Duration
7.966666666666667 Hours
Activity Level
Easy
Price
$899

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 Car & Guide

Time
8:30 AM
Duration
7.966666666666667 Hours
Activity Level
Easy
Price
$699

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

Time
8:30 AM
Duration
4 Hours
Activity Level
Easy
Price
$499
5
JAN 22, 2026
Bequia
ARRIVE
8:00 AM
DEPART
10:00 PM
MARINA
NO
SHORE EXCURSIONS
5

The only ships in port are those small enough to anchor alongside the yachts and fishing boats in Admiralty Bay. Bequia's whaling heritage is on display in the museum in pretty Port Elizabeth, or watch the island's famed model boat builders at work on their miniature masterpieces.

Bequia Highlights

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

Bequia, Bequia Fort & Lower Beach Getaway *

Time
1:30 PM
Duration
3 Hours
Activity Level
Easy-Moderate
Price
$95

Bequia, Mustique Magic with Lunch

Time
8:30 AM
Duration
6 Hours
Activity Level
Moderate
Price
$269

Bequia, Taste of Bequia

Time
8:30 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
6
JAN 23, 2026
Mayreau
ARRIVE
8:00 AM
DEPART
6:00 PM
MARINA
NO
SHORE EXCURSIONS
1

With fewer than 300 inhabitants and miles of secluded beaches, it's easy to feel as if you're on your own private island. Saline Bay is a delightful anchorage that separates the Caribbean from the Atlantic - and a perfect place to play with some of the toys from the Watersports Platform.

Mayreau, Grenadines Island Escape

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

Inhale the intoxicating aroma of the "Isle of Spice" as your eyes feast on what is widely claimed to be the most beautiful city in the Caribbean. Spend the day on 2-mile-long Grand Anse beach, and before you go, a taste of nutmeg ice cream is a must.

St. Georges, Certified Two-Tank Dive

Time
7:30 AM
Duration
4.25 Hours
Activity Level
Moderate-Strenuous
Price
$309

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

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

St Georges, Spice of Our Lives

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

St. Georges, Certified One-Tank Dive

Time
7:30 AM
Duration
3.5 Hours
Activity Level
Moderate-Strenuous
Price
$209

St. Georges, Izzie's Great House Discovery

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

St. Georges, Fort Frederick Rainforest & Waterfall

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

St. Georges, Adventure River Tubing

Time
7:30 AM
Duration
3 Hours
Activity Level
Moderate
Price
$69

St. Georges, Discover Scuba

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

St. Georges, Sailing Cruise to the Statue Park

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

St. Georges, Clear Bottom Kayaking

Time
7:30 AM
Duration
3 Hours
Activity Level
Moderate-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

Available Staterooms

Category A

Cabin
29 Cabins
Max. Occupancy
2 Passengers
Room Size
188 Sqft
Amenities

Category AX Deluxe

Cabin
34 Cabins
Max. Occupancy
2 Passengers
Room Size
188 Sqft
Amenities

Suite

Cabin
18 Cabins
Max. Occupancy
3 Passengers
Room Size
376 Sqft
Amenities

Category BX Deluxe

Cabin
34 Cabins
Max. Occupancy
3 Passengers
Room Size
188 Sqft
Amenities

Category TX Deluxe

Cabin
32 Cabins
Max. Occupancy
2 Passengers
Room Size
188 Sqft
Amenities

Category B

Cabin
21 Cabins
Max. Occupancy
2 Passengers
Room Size
188 Sqft
Amenities

Available Dates