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Windward Islands Surf & Sunsets
Mar 27, 2028 — Apr 3, 2028
Starting from
SAN JUAN → SAN JUAN
7 Nights on Star Pride
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 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
3.5 HoursActivity Level
ModerateAdd during booking
$99
St. George's
Time
9:30 AMDuration
2 HoursActivity Level
Moderate-StrenuousAdd during booking
$119
St. George's
Time
9:30 AMDuration
4 HoursActivity Level
Easy-ModerateAdd during booking
$69
St. George's
Time
9:30 AMDuration
3 HoursActivity Level
ModerateAdd during booking
$79
St. George's
Time
9:30 AMDuration
3 HoursActivity Level
Moderate-StrenuousAdd during booking
$89
St. George's
Time
9:30 AMDuration
3.5 HoursActivity Level
Moderate-StrenuousAdd during booking
$109
St. George's
Time
9:30 AMDuration
3 HoursActivity Level
Easy-ModerateAdd during booking
$119
St. George's
Time
9:30 AMDuration
4.5 HoursActivity Level
ModerateAdd during booking
$289

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
Time
10:00 AMDuration
3 HoursActivity Level
ModerateAdd during booking
$169
Bequia
Time
8:30 AMDuration
2.5 HoursActivity Level
Easy-ModerateAdd during booking
$89
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
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
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
Time
10:00 AMDuration
3 HoursActivity Level
Easy-ModerateAdd during booking
$109

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
8:30 AMDuration
5 HoursActivity Level
Easy-ModerateAdd during booking
$349
Marigot, St. Martin
Time
8:30 AMDuration
5 HoursActivity Level
EasyAdd during booking
$279
Marigot, St. Martin
Time
8:30 AMDuration
4 HoursActivity Level
EasyAdd during booking
$299
Marigot, St. Martin
Time
9:00 AMDuration
4 HoursActivity Level
Easy-ModerateAdd during booking
$99

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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