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Jewels of the Windward Islands
Nov 27, 2026 — Dec 4, 2026
Starting from
Beyond Inclusive Package
BRIDGETOWN, BARBADOS → BRIDGETOWN, BARBADOS
7 Nights on Star Legend
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.





Popular Highlights
Enjoy St. Lucia's beachside resorts and national park.
Walk up Mount Pleasant and see the amazing view from Fort Hamilton on Bequia.
Make time for a visit to Grand Etang National Park on Grenada.
Savor the beauty of scenic sailing around St. Vincent & the Grenadines.
Indulge yourself at Windstar's Signature Beach Party with plenty of Caribbean flavors and spirit to savor and share.
Stand on deck for scenic sailing past the UNESCO World Heritage Site Pitons on St. Lucia.

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.
Available Excursions
Bridgetown
Time
7:30 AMDuration
4.5 HoursActivity Level
ModerateAdd during booking
$129

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.
Available Excursions
Anse Mitan
Time
9:00 AMDuration
3 HoursActivity Level
StrenuousAdd during booking
$209
Anse Mitan
Time
8:30 AMDuration
4 HoursActivity Level
ModerateAdd during booking
$169
Anse Mitan
Time
9:15 AMDuration
3 HoursActivity Level
Moderate-StrenuousAdd during booking
$99
Anse Mitan
Time
8:45 AMDuration
2.5 HoursActivity Level
Moderate-StrenuousAdd during booking
$139
Anse Mitan
Time
9:15 AMDuration
3.5 HoursActivity Level
Easy-ModerateAdd during booking
$259
Anse Mitan
Time
8:45 AMDuration
3.75 HoursActivity Level
ModerateAdd during booking
$159

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.
Available Excursions
Pigeon Island
Time
8:30 AMDuration
4 HoursActivity Level
EasyAdd during booking
$499
Pigeon Island
Time
9:00 AMDuration
3.5 HoursActivity Level
ModerateAdd during booking
$159
Pigeon Island
Time
9:00 AMDuration
3 HoursActivity Level
EasyAdd during booking
$59
Pigeon Island
Time
8:30 AMDuration
4.5 HoursActivity Level
Moderate-StrenuousAdd during booking
$119
Pigeon Island
Time
8:30 AMDuration
8 HoursActivity Level
EasyAdd during booking
$699
Pigeon Island
Time
8:30 AMDuration
5 HoursActivity Level
EasyAdd during booking
$159
Pigeon Island
Time
10:00 AMDuration
3.5 HoursActivity Level
Easy-ModerateAdd during booking
$189
Pigeon Island
Time
8:30 AMDuration
8 HoursActivity Level
EasyAdd during booking
$899
Pigeon Island
Time
8:30 AMDuration
4 HoursActivity Level
EasyAdd during booking
$399
Pigeon Island
Time
9:30 AMDuration
3 HoursActivity Level
Moderate-StrenuousAdd during booking
$129

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.

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.
Available Excursions
Castries
Time
8:30 AMDuration
3 HoursActivity Level
EasyAdd during booking
$69
Castries
Time
8:30 AMDuration
4 HoursActivity Level
EasyAdd during booking
$159
Castries
Time
8:30 AMDuration
4 HoursActivity Level
Moderate-StrenuousAdd during booking
$119
Castries
Time
8:30 AMDuration
2.5 HoursActivity Level
Easy-ModerateAdd during booking
$129
Castries
Time
8:30 AMDuration
4 HoursActivity Level
EasyAdd during booking
$769
Castries
Time
8:30 AMDuration
3.5 HoursActivity Level
Easy-ModerateAdd during booking
$209
Castries
Time
8:30 AMDuration
4.25 HoursActivity Level
Easy-ModerateAdd during booking
$179
Castries
Time
8:30 AMDuration
3.5 HoursActivity Level
ModerateAdd during booking
$69
Castries
Time
8:30 AMDuration
4 HoursActivity Level
EasyAdd during booking
$599

Located near the town of Soufriere, St. Lucia the Pitons are a UNESCO World Heritage Site and a spectacular landmark. Gros Piton is 2,619 feet high (798 meters) and Petit Piton is 2,438 feet high (743 meters). Gros Piton is home to at least 148 plant species and 27 bird species (5 of them endemic) and Petit Piton has 97 plant species with 8 rare tree species.

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.
Available Excursions
Mayreau
Time
8:30 AMDuration
3.5 HoursActivity Level
ModerateAdd during booking
$89

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.
Available Excursions
St. George's
Time
8:30 AMDuration
7.5 HoursActivity Level
EasyAdd during booking
$169
St. George's
Time
8:30 AMDuration
3 HoursActivity Level
Moderate-StrenuousAdd during booking
$89
St. George's
Time
8:30 AMDuration
4 HoursActivity Level
Easy-ModerateAdd during booking
$69
St. George's
Time
8:30 AMDuration
2 HoursActivity Level
Moderate-StrenuousAdd during booking
$119
St. George's
Time
8:30 AMDuration
3.5 HoursActivity Level
Moderate-StrenuousAdd during booking
$215
St. George's
Time
8:30 AMDuration
4.5 HoursActivity Level
ModerateAdd during booking
$279
St. George's
Time
8:30 AMDuration
4.25 HoursActivity Level
Moderate-StrenuousAdd during booking
$319
St. George's
Time
8:30 AMDuration
3.5 HoursActivity Level
ModerateAdd during booking
$99
St. George's
Time
8:30 AMDuration
3 HoursActivity Level
Easy-ModerateAdd during booking
$119
St. George's
Time
8:30 AMDuration
3.5 HoursActivity Level
Moderate-StrenuousAdd during booking
$99

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.
Available Excursions
Bequia
Time
8:30 AMDuration
3 HoursActivity Level
StrenuousAdd during booking
$119
Bequia
Time
8:30 AMDuration
3.5 HoursActivity Level
Easy-ModerateAdd during booking
$149
Bequia
Time
8:30 AMDuration
2.5 HoursActivity Level
Easy-ModerateAdd during booking
$89
Bequia
Time
8:30 AMDuration
3 HoursActivity Level
Easy-ModerateAdd during booking
$99
Bequia
Time
8:30 AMDuration
3 HoursActivity Level
ModerateAdd during booking
$169
Bequia
Time
8:30 AMDuration
6 HoursActivity Level
ModerateAdd during booking
$269

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.
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