Star Collector: Lovely Leewards

Feb 14, 2028 — Feb 28, 2028

Starting from

DATA ART TEST PROMO

Free Laundry for Collectors:

See more routes around Caribbean

SAN JUAN → SAN JUAN

14 Nights on Star Legend

Whether you’re passionate about swimming among undersea wildlife or the intricate cultures and intertwined European histories of the Leeward Islands, this 2-week cruise offers the best combinations of charm, island heritage and natural beauty. Shop unique designer apparel in St. Barts, where you’ll discover a fashionable confluence of high-end brands. Stare in wonder at the glow from miniscule bioluminescent organisms stirred by your kayak paddle during a tour of the Fajardo Bio Bay nature reserve near San Juan. Master the art of cooking with distinct spices like nutmeg, cloves and allspice in authentic Caribbean cuisine while taking direction from a highly-skilled native chef in Philipsburg. This Caribbean getaway is the perfect duration for lovers of island life and those who want to spend more time exploring the Windward Islands overlooked by other cruise lines.

Popular Highlights

Map routes may vary by sailing. Actual itineraries are listed below.
1
FEB 14, 2028
San Juan
EMBARK
1:00 PM
DEPART
7:00 PM
MARINA
NO
SHORE EXCURSIONS
0

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.

2
FEB 15, 2028
CRUZ BAY, ST. JOHN, Virgin Islands (U.S.)
ARRIVE
8:00 AM
DEPART
6:00 PM
MARINA
NO
SHORE EXCURSIONS
0

CRUZ BAY, ST. JOHN, Virgin Islands (U.S.)

3
FEB 16, 2028
Philipsburg, St. Maarten
ARRIVE
8:00 AM
DEPART
10:00 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.

4
FEB 17, 2028
Gustavia
ARRIVE
7:00 AM
DEPART
10:00 PM
MARINA
YES
SHORE EXCURSIONS
0

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.

5
FEB 18, 2028
Basseterre
ARRIVE
8:00 AM
DEPART
5:00 PM
MARINA
NO
SHORE EXCURSIONS
0

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.

6
FEB 19, 2028
Jost Van Dyke, Great Harbour
ARRIVE
9:00 AM
DEPART
10:00 PM
MARINA
YES
SHORE EXCURSIONS
0

For an island comprised of a mere eight square miles, it's amazing how much there is to do on Jost Van Dyke. Visit the national park on nearby Diamond Cay, snorkel among swaying sponges and angelfish at Sandy Spit, or pilot your own boat around Sir Francis  Drake Waterway. After all that, you'll be ready for an evening drink on the beach - where you can admire your Windstar ship aglow in the harbor.

7
FEB 20, 2028
Virgin Gorda / Prickly Pear, British Virgin Islands
ARRIVE
8:00 AM
DEPART
5:00 PM
MARINA
YES
SHORE EXCURSIONS
0

The  beautiful Bank Barrier coral reef wavers just beneath you as your ship makes the break to the bird sanctuary of Prickly Pear Island, so named because it is dotted with prickly pear cacti. Althought uninhabited, it does have a beach bar and water sports facilities. Not far away lies the curious assembly of house-sized boulders called "The Baths," which form huge underground pools and caverns

8
FEB 21, 2028
San Juan
ARRIVE
7:00 AM
DEPART
7:00 PM
MARINA
NO
SHORE EXCURSIONS
0

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.

9
FEB 22, 2028
AT SEA
10
FEB 23, 2028
St. George's
ARRIVE
9:00 AM
DEPART
10:00 PM
MARINA
NO
SHORE EXCURSIONS
0

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.

11
FEB 24, 2028
Bequia
ARRIVE
8:00 AM
DEPART
10:00 PM
MARINA
YES
SHORE EXCURSIONS
0

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.

12
FEB 25, 2028
Mayreau
ARRIVE
8:00 AM
DEPART
5:00 PM
MARINA
NO
SHORE EXCURSIONS
0

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.

13
FEB 26, 2028
Les Saintes
ARRIVE
10:00 AM
DEPART
5:00 PM
MARINA
YES
SHORE EXCURSIONS
0

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.

14
FEB 27, 2028
Marigot, St. Martin
ARRIVE
8:00 AM
DEPART
3:00 PM
MARINA
NO
SHORE EXCURSIONS
0

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.

15
FEB 28, 2028
San Juan
ARRIVE
7:00 AM
DISEMBARK
8:00 AM
MARINA
NO
SHORE EXCURSIONS
0

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.

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

Date Yacht
Starting from
Actions
Nov 8 (Sun) – Nov 22 (Sun), 2026November 8 (Sun) – November 22 (Sun), 2026Star Pride
Nov 15 (Sun) – Nov 29 (Sun), 2026November 15 (Sun) – November 29 (Sun), 2026Star Pride
Nov 22 (Sun) – Dec 6 (Sun), 2026November 22 (Sun) – December 6 (Sun), 2026Star Pride
Nov 29 (Sun) – Dec 13 (Sun), 2026November 29 (Sun) – December 13 (Sun), 2026Star Pride
Dec 6 (Sun) – Dec 20 (Sun), 2026December 6 (Sun) – December 20 (Sun), 2026Star Pride
Dec 13 (Sun) – Dec 27 (Sun), 2026December 13 (Sun) – December 27 (Sun), 2026Star Pride
Dec 20 (Sun) – Jan 3 (Sun), 2027December 20 (Sun) – January 3 (Sun), 2027Star Pride
Dec 27 (Sun) – Jan 10 (Sun), 2027December 27 (Sun) – January 10 (Sun), 2027Star Pride
Jan 3 (Sun) – Jan 17 (Sun), 2027January 3 (Sun) – January 17 (Sun), 2027Star Pride
Nov 1 (Mon) – Nov 15 (Mon), 2027November 1 (Mon) – November 15 (Mon), 2027Star Pride
Nov 8 (Mon) – Nov 22 (Mon), 2027November 8 (Mon) – November 22 (Mon), 2027Star Pride
Nov 15 (Mon) – Nov 29 (Mon), 2027November 15 (Mon) – November 29 (Mon), 2027Star Pride
Dec 20 (Mon) – Jan 3 (Mon), 2028December 20 (Mon) – January 3 (Mon), 2028Star Legend
Dec 27 (Mon) – Jan 10 (Mon), 2028December 27 (Mon) – January 10 (Mon), 2028Star Legend
Jan 3 (Mon) – Jan 17 (Mon), 2028January 3 (Mon) – January 17 (Mon), 2028Star Legend
Jan 10 (Mon) – Jan 24 (Mon), 2028January 10 (Mon) – January 24 (Mon), 2028Star Legend
Jan 17 (Mon) – Jan 31 (Mon), 2028January 17 (Mon) – January 31 (Mon), 2028Star Legend
Jan 24 (Mon) – Feb 7 (Mon), 2028January 24 (Mon) – February 7 (Mon), 2028Star Legend
Jan 31 (Mon) – Feb 14 (Mon), 2028January 31 (Mon) – February 14 (Mon), 2028Star Legend
Feb 7 (Mon) – Feb 21 (Mon), 2028February 7 (Mon) – February 21 (Mon), 2028Star Legend
Mar 13 (Mon) – Mar 27 (Mon), 2028March 13 (Mon) – March 27 (Mon), 2028Star Pride
Mar 20 (Mon) – Apr 3 (Mon), 2028March 20 (Mon) – April 3 (Mon), 2028Star Pride

Star Collector: Lovely Leewards

SAN JUAN → SAN JUAN

14 Nights on Star Legend

Feb 14, 2028 — Feb 28, 2028

Whether you’re passionate about swimming among undersea wildlife or the intricate cultures and intertwined European histories of the Leeward Islands, this 2-week cruise offers the best combinations of charm, island heritage and natural beauty. Shop unique designer apparel in St. Barts, where you’ll discover a fashionable confluence of high-end brands. Stare in wonder at the glow from miniscule bioluminescent organisms stirred by your kayak paddle during a tour of the Fajardo Bio Bay nature reserve near San Juan. Master the art of cooking with distinct spices like nutmeg, cloves and allspice in authentic Caribbean cuisine while taking direction from a highly-skilled native chef in Philipsburg. This Caribbean getaway is the perfect duration for lovers of island life and those who want to spend more time exploring the Windward Islands overlooked by other cruise lines.

1
FEB 14, 2028
San Juan
EMBARK
1:00 PM
DEPART
7:00 PM
MARINA
NO
SHORE EXCURSIONS
0

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.

2
FEB 15, 2028
CRUZ BAY, ST. JOHN, Virgin Islands (U.S.)
ARRIVE
8:00 AM
DEPART
6:00 PM
MARINA
NO
SHORE EXCURSIONS
0

CRUZ BAY, ST. JOHN, Virgin Islands (U.S.)

3
FEB 16, 2028
Philipsburg, St. Maarten
ARRIVE
8:00 AM
DEPART
10:00 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.

4
FEB 17, 2028
Gustavia
ARRIVE
7:00 AM
DEPART
10:00 PM
MARINA
YES
SHORE EXCURSIONS
0

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.

5
FEB 18, 2028
Basseterre
ARRIVE
8:00 AM
DEPART
5:00 PM
MARINA
NO
SHORE EXCURSIONS
0

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.

6
FEB 19, 2028
Jost Van Dyke, Great Harbour
ARRIVE
9:00 AM
DEPART
10:00 PM
MARINA
YES
SHORE EXCURSIONS
0

For an island comprised of a mere eight square miles, it's amazing how much there is to do on Jost Van Dyke. Visit the national park on nearby Diamond Cay, snorkel among swaying sponges and angelfish at Sandy Spit, or pilot your own boat around Sir Francis  Drake Waterway. After all that, you'll be ready for an evening drink on the beach - where you can admire your Windstar ship aglow in the harbor.

7
FEB 20, 2028
Virgin Gorda / Prickly Pear, British Virgin Islands
ARRIVE
8:00 AM
DEPART
5:00 PM
MARINA
YES
SHORE EXCURSIONS
0

The  beautiful Bank Barrier coral reef wavers just beneath you as your ship makes the break to the bird sanctuary of Prickly Pear Island, so named because it is dotted with prickly pear cacti. Althought uninhabited, it does have a beach bar and water sports facilities. Not far away lies the curious assembly of house-sized boulders called "The Baths," which form huge underground pools and caverns

8
FEB 21, 2028
San Juan
ARRIVE
7:00 AM
DEPART
7:00 PM
MARINA
NO
SHORE EXCURSIONS
0

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.

9
FEB 22, 2028
AT SEA
10
FEB 23, 2028
St. George's
ARRIVE
9:00 AM
DEPART
10:00 PM
MARINA
NO
SHORE EXCURSIONS
0

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.

11
FEB 24, 2028
Bequia
ARRIVE
8:00 AM
DEPART
10:00 PM
MARINA
YES
SHORE EXCURSIONS
0

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.

12
FEB 25, 2028
Mayreau
ARRIVE
8:00 AM
DEPART
5:00 PM
MARINA
NO
SHORE EXCURSIONS
0

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.

13
FEB 26, 2028
Les Saintes
ARRIVE
10:00 AM
DEPART
5:00 PM
MARINA
YES
SHORE EXCURSIONS
0

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.

14
FEB 27, 2028
Marigot, St. Martin
ARRIVE
8:00 AM
DEPART
3:00 PM
MARINA
NO
SHORE EXCURSIONS
0

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.

15
FEB 28, 2028
San Juan
ARRIVE
7:00 AM
DISEMBARK
8:00 AM
MARINA
NO
SHORE EXCURSIONS
0

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.