Jewels of the Windward Islands

Nov 27, 2026 — Dec 4, 2026

Starting from

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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.

1
NOV 27, 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
NOV 28, 2026
Anse Mitan
ARRIVE
8:00 AM
DEPART
6:00 PM
MARINA
NO
SHORE EXCURSIONS
6

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, Creole Village

Time
9:15 AM
Duration
3 Hours
Activity Level
Moderate-Strenuous
Price
$99

Anse Mitan, Southern Panoramic Martinique

Time
8:45 AM
Duration
3.75 Hours
Activity Level
Moderate
Price
$159

Anse Mitan, Kayaking Mangrove Discovery

Time
8:45 AM
Duration
2.5 Hours
Activity Level
Moderate-Strenuous
Price
$139

Anse Mitan, Martinique Heritage

Time
8:30 AM
Duration
4 Hours
Activity Level
Moderate
Price
$169

Anse Mitan, Snorkel Adventure Long

Time
9:00 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
3
NOV 29, 2026
Pigeon Island
ARRIVE
8:00 AM
DEPART
11:59 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, St. Lucian Walking Food Tour

Time
10:00 AM
Duration
3.5 Hours
Activity Level
Easy-Moderate
Price
$189

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

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

Pigeon Island, Panoramic St. Lucia

Time
9:00 AM
Duration
3 Hours
Activity Level
Easy
Price
$59

Pigeon Island, Rainforest Canopy Zip Line Adventure

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

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

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

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

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

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, Aerial Tram Park

Time
9:00 AM
Duration
3.5 Hours
Activity Level
Moderate
Price
$159

Pigeon Island, Catamaran Cruise to the Pitons

Time
8:30 AM
Duration
5 Hours
Activity Level
Easy
Price
$159
4
NOV 30, 2026
Pigeon Island
ARRIVE
12:00 AM
DEPART
6:00 AM
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.

Castries
ARRIVE
8:00 AM
DEPART
3:00 PM
MARINA
NO
SHORE EXCURSIONS
9

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, Heritage Highlights

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

Castries, Panoramic St. Lucia

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

Castries, St. Lucian Walking Food Tour

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

Castries, Concierge Collection: Lets Make Chocolate

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

Castries, Rainforest Canopy Zip Line Adventure

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

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

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

Castries, Concierge Collection: Half Day Private Sedan with Guide

Time
8:30 AM
Duration
4 Hours
Activity Level
Easy
Price
$599

Castries, Concierge Collection: Half Day Private Van with Guide

Time
8:30 AM
Duration
4 Hours
Activity Level
Easy
Price
$769

Castries, Catamaran Cruise to the Pitons

Time
8:30 AM
Duration
4 Hours
Activity Level
Easy
Price
$159
The Pitons
ARRIVE
5:30 PM
DEPART
6:30 PM
MARINA
NO
SHORE EXCURSIONS
0

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.

5
DEC 01, 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
6
DEC 02, 2026
St. George's
ARRIVE
8:00 AM
DEPART
10:00 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, Spice of Our Lives

Time
8:30 AM
Duration
4 Hours
Activity Level
Easy-Moderate
Price
$69

St. Georges, The Best of Grenada

Time
8:30 AM
Duration
7.5 Hours
Activity Level
Easy
Price
$169

St. Georges, Certified Two-Tank Dive

Time
8:30 AM
Duration
4.25 Hours
Activity Level
Moderate-Strenuous
Price
$319

St. Georges, Clear Bottom Kayaking

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

St. Georges, Discover Scuba

Time
8:30 AM
Duration
4.5 Hours
Activity Level
Moderate
Price
$279

St. Georges, Sailing Cruise to the Statue Park

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

St. Georges, Certified One-Tank Dive

Time
8:30 AM
Duration
3.5 Hours
Activity Level
Moderate-Strenuous
Price
$215

St. Georges, Fort Frederick Rainforest & Waterfall

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

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

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

St. Georges, Izzie's Great House Discovery

Time
8:30 AM
Duration
3 Hours
Activity Level
Easy-Moderate
Price
$119
7
DEC 03, 2026
Bequia
ARRIVE
8:00 AM
DEPART
5:00 PM
MARINA
YES
SHORE EXCURSIONS
6

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, Taste of Bequia

Time
8:30 AM
Duration
3.5 Hours
Activity Level
Easy-Moderate
Price
$149

Bequia, Mustique Magic with Lunch

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

Bequia Snorkel Adventure

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

Bequia, Concierge Collection: Rum Tasting at Firefly Plantation

Time
8:30 AM
Duration
3 Hours
Activity Level
Moderate
Price
$169

Bequia, Bequia Fort & Lower Beach Getaway *

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

Star Legend

number of decks
6 Decks
yacht length
440 ft (134 meters)
yacht crew size
140 Crew Members
yacht guest capacity
312 Guests

Staterooms

Room Size 575 sq ft
Max. Occupancy 3 Passengers
Amenities

Starting from

Room Size 400 sq ft
Max. Occupancy 2 Passengers
Amenities

Starting from

Room Size 468 sq ft
Max. Occupancy 3 Passengers
Amenities

Starting from

Room Size 277 sq ft
Max. Occupancy 3 Passengers
Amenities

Starting from

Room Size 277 sq ft
Max. Occupancy 2 Passengers
Amenities

Starting from

Room Size 277 sq ft
Max. Occupancy 3 Passengers
Amenities

Starting from

Room Size 277 sq ft
Max. Occupancy 3 Passengers
Amenities

Starting from

Room Size 277 sq ft
Max. Occupancy 3 Passengers
Amenities

Starting from

Room Size 277 sq ft
Max. Occupancy 3 Passengers
Amenities

Starting from

Room Size 277 sq ft
Max. Occupancy 3 Passengers
Amenities

Starting from

Room Size 277 sq ft
Max. Occupancy 3 Passengers
Amenities

Starting from

Room Size 277 sq ft
Max. Occupancy 2 Passengers
Amenities

Starting from

Room Size 277 sq ft
Max. Occupancy 2 Passengers
Amenities

Starting from

Room Size 277 sq ft
Max. Occupancy 2 Passengers
Amenities
Expand all

Available Dates

No other dates are available.