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Star Collector: Lovely Leewards
Nov 1, 2027 — Nov 15, 2027
Starting from
Complimentary All-In Package
Free Laundry for Collectors:
Reduced Deposit
SAN JUAN → SAN JUAN
14 Nights on Star Pride
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
Take a stroll in the St. John’s National Park which covers over half of the islands.
Pick up tempting souvenirs at the pastel-colored buildings and shops of duty-free Philipsburg.
Enjoy the spice market and some of the best snorkeling around Grenada, the Spice Island.
The Piton's two volcanic peaks, rising more than 2,400, feet welcome you to St. Lucia.
Walk up Mount Pleasant with a spectacular view of Bequia's Admiral Bay.
Discover the imposing façade of El Morrow Fortress, a UNESCO site in San Juan.
Enjoy a relaxing beach day in St. Barts, long the haunt of the rich.
Pack light with complimentary daily laundry service.

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.
CRUZ BAY, ST. JOHN, Virgin Islands (U.S.)
Available Excursions
CRUZ BAY, ST. JOHN, Virgin Islands (U.S.)
Time
8:30 AMDuration
2.5 HoursActivity Level
EasyAdd during booking
$99
CRUZ BAY, ST. JOHN, Virgin Islands (U.S.)
Time
8:30 AMDuration
3 HoursActivity Level
ModerateAdd during booking
$149
CRUZ BAY, ST. JOHN, Virgin Islands (U.S.)
Time
8:30 AMDuration
3.5 HoursActivity Level
ModerateAdd during booking
$139
CRUZ BAY, ST. JOHN, Virgin Islands (U.S.)
Time
8:30 AMDuration
3 HoursActivity Level
ModerateAdd during booking
$139

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.
Available Excursions
Basseterre
Time
8:30 AMDuration
3 HoursActivity Level
StrenuousAdd during booking
$139
Basseterre
Time
8:30 AMDuration
4 HoursActivity Level
StrenuousAdd during booking
$129
Basseterre
Time
8:30 AMDuration
3.25 HoursActivity Level
Easy-ModerateAdd during booking
$89
Basseterre
Time
9:00 AMDuration
3.5 HoursActivity Level
EasyAdd during booking
$99
Basseterre
Time
10:30 AMDuration
2.5 HoursActivity Level
ModerateAdd during booking
$69

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.

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.

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.

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
Available Excursions
Virgin Gorda / Prickly Pear, British Virgin Islands
Time
8:30 AMDuration
4 HoursActivity Level
StrenuousAdd during booking
$99
Virgin Gorda / Prickly Pear, British Virgin Islands
Time
8:30 AMDuration
2.75 HoursActivity Level
Moderate-StrenuousAdd during booking
$299

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.

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
9:30 AMDuration
3 HoursActivity Level
Easy-ModerateAdd during booking
$119
St. George's
Time
9:30 AMDuration
4.25 HoursActivity Level
Moderate-StrenuousAdd during booking
$329
St. George's
Time
9:30 AMDuration
4.5 HoursActivity Level
ModerateAdd during booking
$289
St. George's
Time
9:30 AMDuration
3 HoursActivity Level
Moderate-StrenuousAdd during booking
$89
St. George's
Time
9:30 AMDuration
7.5 HoursActivity Level
EasyAdd during booking
$179
St. George's
Time
9:30 AMDuration
3.5 HoursActivity Level
Moderate-StrenuousAdd during booking
$229
St. George's
Time
9:30 AMDuration
3.5 HoursActivity Level
ModerateAdd during booking
$99
St. George's
Time
9:30 AMDuration
3 HoursActivity Level
ModerateAdd during booking
$79
St. George's
Time
9:30 AMDuration
4 HoursActivity Level
Easy-ModerateAdd during booking
$69
St. George's
Time
9:30 AMDuration
2 HoursActivity Level
Moderate-StrenuousAdd during booking
$119
St. George's
Time
9:30 AMDuration
3.5 HoursActivity Level
Moderate-StrenuousAdd during booking
$109

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
A boat excursion to the exclusive island of Mustique for beach time, shopping, and a waterfront lunch at the famous Basil's Bar.
Time
10:00 AMDuration
6 HoursActivity Level
ModerateAdd during booking
$299
Bequia
A scenic powerboat cruise along Bequia's coastline with a snorkeling stop at Petit Nevis.
Time
10:00 AMDuration
3 HoursActivity Level
StrenuousAdd during booking
$129
Bequia
Time
8:30 AMDuration
2.5 HoursActivity Level
Easy-ModerateAdd during booking
$89
Bequia
Time
10:00 AMDuration
3 HoursActivity Level
Easy-ModerateAdd during booking
$109
Bequia
A guided walking and culinary tour through Bequia's waterfront restaurants, sampling authentic Caribbean dishes and cocktails.
Time
10:00 AMDuration
3.5 HoursActivity Level
Easy-ModerateAdd during booking
$149
Bequia
Time
10:00 AMDuration
3 HoursActivity Level
ModerateAdd during booking
$169

Mayreau is the smallest inhabited island of St. Vincent and the Grenadines, covering just about 1.5 square miles with a population of only a few hundred people. Tucked between Union Island and the Tobago Cays in the southern Grenadines, it's known for its laid-back, off-the-grid charm—there are no airports, no banks, and only one small village (Old Wall) perched on a hillside.

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.
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.
Available Excursions
Marigot, St. Martin
Time
9:30 AMDuration
5 HoursActivity Level
EasyAdd during booking
$279
Marigot, St. Martin
Time
9:00 AMDuration
4 HoursActivity Level
Easy-ModerateAdd during booking
$99
Marigot, St. Martin
Time
10:00 AMDuration
5 HoursActivity Level
Easy-ModerateAdd during booking
$349

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.
Staterooms
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