Windward Island Delights

Mar 7, 2026 — Mar 15, 2026

Starting from

See more routes around Caribbean

BRIDGETOWN, BARBADOS → BRIDGETOWN, BARBADOS

8 Nights on Wind Spirit

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
MAR 07, 2026
Bridgetown
EMBARK
1:00 PM
DEPART
5:00 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
MAR 08, 2026
AT SEA
3
MAR 09, 2026
Basseterre
ARRIVE
9:00 AM
DEPART
5:00 PM
MARINA
NO
SHORE EXCURSIONS
9

With Georgian architecture situated against an irresistible backdrop of emerald green hills, Basseterre is one of the loveliest of the Caribbean's small capitals. Beyond town, more than a quarter of St. Kitts has been set aside as Brimstone Hill Fortress national Park, a UNESCO World Heritage Site.

Basseterre, Irie Rider Speed Boat

Time
9:30 AM
Duration
3.25 Hours
Activity Level
Moderate-Strenuous
Price
$119

Basseterre: Snorkel Safari

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

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

Time
9:30 AM
Duration
3.5 Hours
Activity Level
Easy
Price
$99

Basseterre: Caribbean Scenic Railway

Time
9:30 AM
Duration
3 Hours
Activity Level
Easy
Price
$109

Basseterre: St Kitts Quad ATV Adventure

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

Basseterre, Island History & Rum Tasting

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

Basseterre, Nevis Panoramic and Beach Tour

Time
9:30 AM
Duration
5 Hours
Activity Level
Easy-Moderate
Price
$139

Basseterre: Sky Safari Zipline Adventure

Time
9:30 AM
Duration
4 Hours
Activity Level
Strenuous
Price
$119

Basseterre, Brimstone Hill Fortress & Fairview Great House

Time
9:30 AM
Duration
3.25 Hours
Activity Level
Easy-Moderate
Price
$79
4
MAR 10, 2026
St. John's
ARRIVE
8:00 AM
DEPART
6:00 PM
MARINA
NO
SHORE EXCURSIONS
9

St. John's is a city of Old World charm and elegance which lingers in the varied architecture of Georgian, Victorian, Vernacular, Romantic and International flavors.  The picturesque seafront where tiny, colorful boats are moored, the cheerful wooden buildings carefully refurbished to retain their original features, the vibrant Market Street offering vegetables, fruit and fish and the duty-free Heritage Quay shopping area provide a delightful atmosphere to captivate you.  Sites to see include St. John's Cathedral with its white Baroque towers, the Botanical Garden, St. John's Antigua Lighthouse, and Fort James.

St John's , Caribbean Cooking Culinary Experience

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

St. Johns, Spectacular Antigua

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

St Johns, Concierge Collection, Jet Ski Adventure

Time
8:30 AM
Duration
1.75 Hours
Activity Level
Moderate-Strenuous
Price
$379

St. Johns, Concierge Collection: Antigua Helicopter Adventure

Time
1:00 PM
Duration
2 Hours
Activity Level
Easy
Price
$429

St. Johns, Beach Escape

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

St.Johns, Concierge Collection: Sail Snorkel and Beach

Time
9:30 AM
Duration
3 Hours
Activity Level
Easy-Moderate
Price
$389

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
$129

St. Johns, Open Course Canopy Challenge

Time
8:30 AM
Duration
4 Hours
Activity Level
Strenuous
Price
$139
5
MAR 11, 2026
Les Saintes
ARRIVE
9:00 AM
DEPART
10:00 PM
MARINA
YES
SHORE EXCURSIONS
7

This is the Caribbean as you've always imagined it, with yacht-filled harbors set against volcanic mountains and endless stretches of palm-fringed beach. The underwater world here attracted the likes of Jacques Cousteau, but even novice snorkelers will enjoy exploring these impossibly blue waters.

Les Saintes, Sailing the Bay

Time
9:30 AM
Duration
3 Hours
Activity Level
Moderate-Strenuous
Price
$249

Les Saintes, Blue Escape Kayaking *

Time
9:30 AM
Duration
2 Hours
Activity Level
Strenuous
Price
$149

Les Saintes, Relax & Snorkel *

Time
9:30 AM
Duration
3 Hours
Activity Level
Moderate-Strenuous
Price
$179

Les Saintes, Sample Culinary Treasures of Guadeloupe

Time
9:30 AM
Duration
3 Hours
Activity Level
Easy-Moderate
Price
$209

Les Saintes, Terre de Haut Panoramic Tour

Time
9:30 AM
Duration
1 Hours
Activity Level
Easy
Price
$119

Les Saintes, Explore Terra de Haut by Foot

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

Les Saintes, Snorkel Experience in Les Saintes *

Time
9:30 AM
Duration
2 Hours
Activity Level
Strenuous
Price
$119
6
MAR 12, 2026
Roseau
ARRIVE
8:00 AM
DEPART
1:00 PM
MARINA
NO
SHORE EXCURSIONS
8

Get ready for a full day with plenty to do. Snorkel alongside brilliant parrot fish in the bubbly waters of Champagne Beach. Take a break to enjoy more than 150 species of plants and brilliant red-necked Jaco parrots at the botanical gardens. If you're up for an optional hike, don't miss Boiling Lake and the Valley of Desolation at Dominica's Morne Trois Pitons National Park, a UNESCO World Heritage Site.

Roseau, River Tubing Adventure

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

Roseau, Concierge Collection: Cooking Caribbean Flavors & Lifestyles

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

Roseau, Whale & Dolphin Adventure

Time
8:30 AM
Duration
3.5 Hours
Activity Level
Easy
Price
$159

Roseau, Beach Break

Time
10:00 AM
Duration
3 Hours
Activity Level
Easy-Moderate
Price
$89

Roseau, Indian River Rowboat

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

Roseau, Champagne Reef Snorkel Adventure

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

Roseau, 4X4 Waterfall & Rainforest

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

Roseau, Trafalgar Falls & Hot Springs

Time
8:30 AM
Duration
3 Hours
Activity Level
Moderate
Price
$99
7
MAR 13, 2026
Mayreau
ARRIVE
8:00 AM
DEPART
5:00 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

Wind Spirit

number of decks
4 Decks
yacht length
360 ft (110 meters)
yacht crew size
90 Crew Members
yacht guest capacity
148 Guests

Staterooms

Room Size 220 sq ft
Max. Occupancy 3 Passengers
Amenities

Room Size 188 sq ft
Max. Occupancy 2 Passengers
Amenities

Room Size 188 sq ft
Max. Occupancy 2 Passengers
Amenities

Room Size 188 sq ft
Max. Occupancy 3 Passengers
Amenities

Room Size 188 sq ft
Max. Occupancy 3 Passengers
Amenities

Room Size sq ft
Max. Occupancy 2 Passengers
Amenities

Available Dates

No other dates are available.