Lush & Lovely Islands of the Lesser Antilles

Feb 28, 2026 — Mar 7, 2026

Starting from

See more routes around Caribbean

PHILIPSBURG, ST. MAARTEN → BRIDGETOWN, BARBADOS

7 Nights on Wind Spirit

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
FEB 28, 2026
Philipsburg, St. Maarten
EMBARK
1:00 PM
DEPART
7:00 PM
MARINA
NO
SHORE EXCURSIONS
0

Pastel-colored buildings and shops filled with tempting souvenirs herald your arrival to bustling Philipsburg. Situated near the harbor on the Dutch side of St. Maarten, Philipsburg owes its discovery to Christopher Columbus in 1493. Today, celebrated Front Street is home to a number of local Creole restaurants as well as jewelry stores, stylish boutiques, and lively casinos for visitors seeking an upbeat island experience.

2
MAR 01, 2026
Basseterre
ARRIVE
8:00 AM
DEPART
9:00 PM
MARINA
NO
SHORE EXCURSIONS
8

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, Island History & Rum Tasting

Time
9:00 AM
Duration
2.5 Hours
Activity Level
Moderate
Price
$59

Basseterre, Brimstone Hill Fortress & Fairview Great House

Time
8:30 AM
Duration
3.25 Hours
Activity Level
Easy-Moderate
Price
$79

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

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

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

Basseterre: Sky Safari Zipline Adventure

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

Basseterre: St Kitts Quad ATV Adventure

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

Basseterre, Nevis Panoramic and Beach Tour

Time
8:30 AM
Duration
5 Hours
Activity Level
Easy-Moderate
Price
$139
3
MAR 02, 2026
Gustavia
ARRIVE
8:00 AM
DEPART
10:00 PM
MARINA
YES
SHORE EXCURSIONS
9

Affectionately known as St. Barts, the Caribbean's most chic island adds a French flair to Riviera-like beaches and duty-free boutiques. Walk past gingerbread cottages in search of celebrities, shop for designer fashions, or sip the island's signature ti punch as kite surfers fly by.

Gustavia, Concierge Collection: Savor St Barts

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

St. Barts, Concierge Collection: Sunset Cruise

Time
5:00 PM
Duration
1.5 Hours
Activity Level
Easy-Moderate
Price
$199

Gustavia, Concierge Collection: Scuba Dive 2 Tank

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

St. Barts: Sailing Catamaran Adventure

Time
9:00 AM
Duration
3 Hours
Activity Level
Moderate
Price
$299

Gustavia, Concierge Collection: Jet Ski

Time
8:30 AM
Duration
2 Hours
Activity Level
Strenuous
Price
$509

Gustavia, Concierge Collection: Scuba Dive 1 Tank

Time
8:30 AM
Duration
3 Hours
Activity Level
Strenuous
Price
$349

St. Barts: Independent Explorer by Car

Time
9:30 AM
Duration
6 Hours
Activity Level
Easy-Moderate
Price
$349

St Barts, Concierge Collection: St. Barthelemy Beach Day

Time
2:45 PM
Duration
6 Hours
Activity Level
Easy-Moderate
Price
$519

St. Barts: Intimate Island Tour

Time
9:00 AM
Duration
1 Hours
Activity Level
Easy
Price
$139
4
MAR 03, 2026
Falmouth Harbour
ARRIVE
8:00 AM
DEPART
9:00 PM
MARINA
NO
SHORE EXCURSIONS
7

It's said that Antigua has 365 beaches - one for every day of the year. See how many you can discover as our stay in port stretches into the evening to accommodate them all. Watch the stars come out as darkness falls and imagine how residents of Andromeda must envy you.

Falmouth Harbour, Concierge Collection, Jet Ski Adventure

Time
12:30 PM
Duration
1.75 Hours
Activity Level
Moderate-Strenuous
Price
$379

Falmouth Harbour, Presidents Tour

Time
1:00 PM
Duration
3 Hours
Activity Level
Moderate-Strenuous
Price
$129

Falmouth Harbour, Antigua Beach Escape *

Time
10:00 AM
Duration
4 Hours
Activity Level
Easy
Price
$89

Falmouth Harbour, Swim with the Stingrays

Time
12:15 PM
Duration
3 Hours
Activity Level
Moderate
Price
$119

Falmouth Harbour, Make Your Own Rum

Time
8:45 AM
Duration
2 Hours
Activity Level
Easy-Moderate
Price
$139

Falmouth Harbour, Spectacular Antigua Island Tour

Time
9:00 AM
Duration
3.5 Hours
Activity Level
Moderate
Price
$99

Falmouth Harbour, Open Course Canopy Zipline

Time
11:30 AM
Duration
4 Hours
Activity Level
Strenuous
Price
$139
5
MAR 04, 2026
Les Saintes
ARRIVE
8:00 AM
DEPART
5:00 PM
MARINA
YES
SHORE EXCURSIONS
5

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, Terre de Haut Panoramic Tour

Time
8:30 AM
Duration
1 Hours
Activity Level
Easy
Price
$119

Les Saintes, Relax & Snorkel *

Time
8:30 AM
Duration
3 Hours
Activity Level
Moderate-Strenuous
Price
$179

Les Saintes, Blue Escape Kayaking *

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

Les Saintes, Sample Culinary Treasures of Guadeloupe

Time
8:30 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
MAR 05, 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, 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, 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, Beach Break

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

Roseau, Whale & Dolphin Adventure

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

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 06, 2026
Mayreau
ARRIVE
8:00 AM
DEPART
4:00 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.