Windward Islands Surf & Sunsets

From $2,349 per person

8 days

Ships: Star Pride, Star Seeker

Windward Islands Surf & Sunsets
Windstar Cruises logo

Journey Summary

  • Day 1 - San Juan
  • Day 2 -
  • Day 3 - St. George's
  • Day 4 - Bequia
  • Day 5 - Mayreau
  • Day 6 - Les Saintes
  • Day 7 - Marigot, St. Martin
  • Day 8 - San Juan

Detailed Itinerary

Day-by-day description of your cruise and cruise activities.

Day 1

San Juan

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.

Day 2

Day 3

St. George's

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.

Day 4

Bequia

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.

Day 5

Mayreau

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.

Day 6

Les Saintes

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.

Day 7

Marigot, St. Martin

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.

Day 8

San Juan

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.

Dates and Prices

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Available dates:

Nov 23, 2025

Ship

Your cruise ship

The Star Pride ship sails serenely on calm waters under a clear blue sky, showcasing its elegant design.
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About this ship

Star Pride

Star Pride is an elegant, all-suite yacht that delivers Windstar Cruises’ signature small-ship experience with sophistication and style. Designed for just 312 guests, the ship offers a refined alternative to larger cruise vessels—combining personalized service, expansive accommodations, and a relaxed onboard ambiance with the ability to explore some of the world’s most captivating and hard-to-reach destinations.

As part of Windstar’s $250 million Star Plus Initiative, Star Pride underwent a transformative renovation in 2021. The ship was lengthened by 84 feet, resulting in expanded public areas, new culinary venues, and additional suites. Upgrades also included new eco-friendly engines and enhanced environmental systems, positioning the vessel at the forefront of sustainable luxury travel. Though refreshed and modernized, Star Pride retains the intimate, yachting spirit that defines the Windstar experience.

All 156 suites on board are ocean-facing, offering spacious layouts ranging from 277 to over 800 square feet. Designed with a blend of contemporary elegance and classic comfort, each suite features plush bedding, walk-in closets, marble-accented bathrooms with dual vanities, and thoughtful amenities such as Illy espresso machines and L’Occitane bath products. Many suites include private verandas or French balconies, creating a seamless connection to the sea and surrounding landscapes.

Dining on Star Pride is elevated, globally inspired, and entirely complimentary. Amphora, the ship’s main dining room, offers ever-changing menus rooted in fresh, seasonal ingredients. Candles transforms the deck into a romantic open-air steakhouse by night, while Cuadro 44 by chef Anthony Sasso offers bold, modern Spanish cuisine in an intimate, tapas-style setting. Star Grill by Steven Raichlen serves barbecue with international flair in a casual al fresco setting, and the Yacht Club Café is a favorite for fresh pastries, coffee, and light bites throughout the day. In-suite dining is available 24 hours a day for added flexibility.

The ship’s amenities cater to both active travelers and those seeking rest and rejuvenation. A full-service spa and wellness complex offers a variety of treatments, a thermal suite, and a well-equipped fitness center. Open decks and lounges provide ample space for relaxation, while the watersports platform at the stern gives guests direct access to complimentary activities such as kayaking, paddleboarding, and snorkeling when conditions allow.

Thanks to its size and shallow draft, Star Pride is able to navigate narrow waterways and dock in smaller ports that are inaccessible to larger ships. Whether cruising the Norwegian fjords, the coastal towns of the Mediterranean, or the islands of Southeast Asia, the ship brings guests closer to the cultural and natural heart of each destination.

Deckplans

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