Windward Ways & Tobago Cays

Dec 4, 2026 — Dec 12, 2026

Starting from

Beyond Inclusive Package

Now available on select voyages sailing through March 2027, Windstar’s complimentary Beyond Inclusive Package features a pre-cruise hotel stay, transfer from hotel to yacht, All-Inclusive perks and up to $1,000 onboard credit per guest.
See more routes around Caribbean

BRIDGETOWN, BARBADOS → ORANJESTAD, ARUBA

8 Nights on Star Legend

Dive, snorkel and swim with fish and sea turtles in Tobago Cays Marine Park, Bonaire National Marine Park and the proposed Speyside Marine Protected Area. Swim in a picture-perfect waterfall pool surrounded by the oldest protected rainforest in the Western Hemisphere, the Main Ridge Forest Reserve. Take in the volcanic beauty of the Pitons on St. Lucia, where rainforest meets some of the healthiest coral reefs in the Caribbean. And discover Bonaire, with its stunning desert-palette motifs like pink flamingos on white salt pans. Those who are looking for the classic Caribbean will find it in Mayreau — fewer than 300 inhabitants, and just 1.5 square miles, making it a port exclusive to yachts. And those who love colonial harbors will enjoy British Bridgetown as well as the triple Dutch treat of Kralendijk, Willemstad and Oranjestad.

Popular Highlights

Additional Information

1
DEC 04, 2026
Bridgetown
EMBARK
1:00 PM
DEPART
6:00 PM
MARINA
NO
SHORE EXCURSIONS
1

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.

Bridgetown: Barbados Island Tour with Airport Transfer

Time
6:30 AM
Duration
4.5 Hours
Activity Level
Moderate
Price
$129
2
DEC 05, 2026
Rodney Bay
TYPE
Sail
DETAIL
RODNEY BAY

Rodney Bay, Saint Lucia

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.

3
DEC 06, 2026
Scarborough, Tobago
ARRIVE
8:00 AM
DEPART
5:00 PM
MARINA
NO
SHORE EXCURSIONS
0

Scarborough, Tobago

4
DEC 07, 2026
Bequia
ARRIVE
8:00 AM
DEPART
10:00 PM
MARINA
YES
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, Taste of Bequia

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

Bequia, Bequia Fort & Lower Beach Getaway *

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

Bequia Highlights

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

Bequia Snorkel Adventure

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

Bequia, Mustique Magic with Lunch

Time
8:30 AM
Duration
6 Hours
Activity Level
Moderate
Price
$269
5
DEC 08, 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 09, 2026
AT SEA
7
DEC 10, 2026
Kralendijk
ARRIVE
8:00 AM
DEPART
10:00 PM
MARINA
NO
SHORE EXCURSIONS
0

The ice cream colors of the stucco houses will draw your lens, as will the pink flamingos on the salt pans. But you'll need a waterproof camera to complete the portrait since more than 400 fish species and 50 types of coral wait beneath the surface

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 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 400 sq ft
Max. Occupancy 2 Passengers
Amenities

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

Available Dates

No other dates are available.