Windstar Cruises

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Windward Islands Surf & Sunsets

Jan 24, 2028 — Jan 31, 2028

Starting from

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See more routes around Caribbean

SAN JUAN → SAN JUAN

7 Nights on Star Legend

Revel in seven days of surf, sand and sunsets during this leisurely cruise up and down the Caribbean’s Windward Islands. It’s a perfect vacation getaway for anyone craving a quick escape from life’s everyday obligations. Swim among sea turtles and glide above dazzling coral reefs with a highly skilled diving guide off the coast of Les Saintes’ volcanic shoreline. Vacation time is always well spent among the Windward Islands, but nothing makes it more perfect than the personalized attention and unique excursion opportunities offered by Windstar.

Popular Highlights

Find aromatic spices, especially nutmeg and cinnamon in St. George’s local markets.

"Discover the underwater world of Les Saintes. Enjoy some of the best snorkeling around in the deep blue waters of Guadeloupe. "

Shop the 100% duty free island of two nations, St. Maarten and St. Martin.

St. Barts has plenty of water activities, designer boutiques, stunning beaches, and delightful restaurants.

Beautiful Bequia’s Admiralty Bay is only for small yachts and ships like ours and the island is famous for its model miniature boat builders.

Additional Information

The Story

One of the most sought-after yachting destinations in the Caribbean, the Windward Islands give you a glimpse of what the West Indies looked like in days of old. Technicolor travel posters come to life in its lush green mountains, shimmering blue waters, swaying palm trees and uncrowded beaches. Colorful fishing boats bob in the harbor next to private yachts, and resorts give way to charming boutique hotels and B&Bs.

Pastel Georgian buildings, crumbling forts, and rusting canons recall the days when pirates roamed the seas and Britain and France fought over who would rule these islands. And while each island has its unique charms, the pace of life is almost universally slow, with time to absorb the copious amounts of natural beauty and chat with people who are genuinely welcoming.

Sip a local Carib beer in the shade of sea grape trees. Dive off the Watersports Platform and snorkel above coral gardens entirely undisturbed by your passage. Stand on the ramparts of forts that have seen centuries come and go staring out at a view that never grows old. Discover islands that perfectly match your dreams.

Insider Tips

An island’s windward side faces the trade winds, which come from across the Atlantic. On the leeward side, the Caribbean Sea is calmer. As a result, you’ll usually find the best beaches on the west side of each island.

Check out the nutmeg ice cream on Grenada, the Spice Island. It’s like a summer version of eggnog.
In tiny Bequia, an island of just 7 square miles, all beaches are public. They’re also clean and uncrowded, so take your pick.

The incredibly beautiful twin pitons on Saint Lucia are a UNESCO World Heritage Site. You can climb Gros Piton (with a guide), but it’s an exhausting climb and you’ll need good hiking shoes and plenty of water.

The people you meet in Les Saintes are descended from Breton corsairs (pirates), and they’re skilled sailors. Their distinctive shallow white hats are called salacos. If you would like to take a photo, be sure to ask first.

JAN 24, 2028

San Juan

EMBARK

1:00 PM

DEPART

7:00 PM

MARINA

SHORE EXCURSIONS

Details

The imposing façade of El Morro fortress is just one of the many UNESCO World Heritage Sites in San Juan. Admire the colorful colonial buildings from your casually elegant ship, docked right in the heart of Old San Juan.

JAN 25, 2028

AT SEA

JAN 26, 2028

St. George's

ARRIVE

9:00 AM

DEPART

10:00 PM

MARINA

SHORE EXCURSIONS

Details

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.

JAN 27, 2028

Bequia

ARRIVE

8:00 AM

DEPART

10:00 PM

MARINA

YES

SHORE EXCURSIONS

Details

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.

JAN 28, 2028

Mayreau

ARRIVE

8:00 AM

DEPART

5:00 PM

MARINA

SHORE EXCURSIONS

Details

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.

JAN 29, 2028

Les Saintes

ARRIVE

10:00 AM

DEPART

5:00 PM

MARINA

YES

SHORE EXCURSIONS

Details

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.

JAN 30, 2028

Marigot, St. Martin

ARRIVE

8:00 AM

DEPART

3:00 PM

MARINA

SHORE EXCURSIONS

Details

Established around 1689, Marigot is the attractive capital of French St. Martin, with its brightly colored houses, a lively open-air market, secluded beaches, and pretty waterfront promenade. Because of its tax-free status, Marigot is a popular center for duty-free shopping, where all of the world's most prestigious brands can be found. Originally the area was marshy, and surrounded by mangroves. In the 1970s part of the bay was filled in to extend Marigot into a larger city with a marina. Overlooking Marigot is Fort St. Louis, the largest historical monument in St. Martin with an impressive panoramic view of the bay.

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Star Legend

6 Decks

440 ft (134 meters)

140 Crew Members

312 Guests

See More Voyages

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

Date	Yacht	Starting from
Feb 13 (Fri) – Feb 20 (Fri), 2026 February 13 (Fri) – February 20 (Fri), 2026	Star Seeker	$5,927
Feb 27 (Fri) – Mar 6 (Fri), 2026 February 27 (Fri) – March 6 (Fri), 2026	Star Seeker	$5,836
Mar 13 (Fri) – Mar 20 (Fri), 2026 March 13 (Fri) – March 20 (Fri), 2026	Star Seeker	$5,733
Nov 8 (Sun) – Nov 15 (Sun), 2026 November 8 (Sun) – November 15 (Sun), 2026	Star Pride	$3,330
Nov 22 (Sun) – Nov 29 (Sun), 2026 November 22 (Sun) – November 29 (Sun), 2026	Star Pride	$3,330
Dec 6 (Sun) – Dec 13 (Sun), 2026 December 6 (Sun) – December 13 (Sun), 2026	Star Pride	$3,130
Dec 20 (Sun) – Dec 27 (Sun), 2026 December 20 (Sun) – December 27 (Sun), 2026	Star Pride	$3,330
Jan 3 (Sun) – Jan 10 (Sun), 2027 January 3 (Sun) – January 10 (Sun), 2027	Star Pride	$4,030
Nov 8 (Mon) – Nov 15 (Mon), 2027 November 8 (Mon) – November 15 (Mon), 2027	Star Pride	$2,930
Nov 22 (Mon) – Nov 29 (Mon), 2027 November 22 (Mon) – November 29 (Mon), 2027	Star Pride	$2,930
Dec 27 (Mon) – Jan 3 (Mon), 2028 December 27 (Mon) – January 3 (Mon), 2028	Star Legend	$3,230
Jan 10 (Mon) – Jan 17 (Mon), 2028 January 10 (Mon) – January 17 (Mon), 2028	Star Legend	$3,030
Feb 7 (Mon) – Feb 14 (Mon), 2028 February 7 (Mon) – February 14 (Mon), 2028	Star Legend	$3,030
Feb 21 (Mon) – Feb 28 (Mon), 2028 February 21 (Mon) – February 28 (Mon), 2028	Star Legend	$3,030
Mar 13 (Mon) – Mar 20 (Mon), 2028 March 13 (Mon) – March 20 (Mon), 2028	Star Pride	$3,030
Mar 27 (Mon) – Apr 3 (Mon), 2028 March 27 (Mon) – April 3 (Mon), 2028	Star Pride	$3,030

Windward Islands Surf & Sunsets

SAN JUAN → SAN JUAN

Popular Highlights

Additional Information

Star Legend

Staterooms

Owner's Suite

Classic Suite

Deluxe Suite

Star Balcony Suite 1

Balcony Suite 1

Star Balcony Suite

Balcony Suite

Ocean View Suite 3

Ocean View Suite 2

Star Ocean View Suite 1

Ocean View Suite 1

Ocean View Suite

Star Porthole Suite

Guaranteed Suite** (chosen by Windstar)

Available Dates