Windward Islands Surf & Sunsets

From $3,299 per person

7 days

Ship: Star Seeker

Windward Islands Surf & Sunsets
Windstar Cruises

Revel in seven days of surf, sand and sunsets during this leisurely cruise up and down the Caribbean&rsquo;s Windward Islands. It&rsquo;s a perfect vacation getaway for anyone craving a quick escape from life&rsquo;s everyday obligations. Clip into a zipline and hang on as moss-covered limbs and colorful wild birds rush by your head as you glide through St. Lucia&rsquo;s rainforest canopy. 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.<br />
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Journey Summary

  • Day 1 - Feb. 27, 2026, Fri. - San Juan
  • Day 2 - Feb. 28, 2026, Sat. - Philipsburg, St. Maarten
  • Day 3 - Mar. 1, 2026, Sun. - Les Saintes
  • Day 4 - Mar. 2, 2026, Mon. - Mayreau
  • Day 5 - Mar. 3, 2026, Tue. - Bequia
  • Day 6 - Mar. 4, 2026, Wed. - Mayreau
  • Day 7 - Mar. 5, 2026, Thu. -
  • Day 8 - Mar. 6, 2026, Fri. - San Juan

Itinerary Highlights

Tour St. Barts to find a chic collection of designer boutiques, stunning beaches, and delightful restaurants

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Detailed Itinerary

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

Day 1 - February 27, 2026

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 - February 28, 2026

Philipsburg, St. Maarten

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.

Day 3 - March 01, 2026

Les Saintes

This is the Caribbean as you&rsquo;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 4 - March 02, 2026

Mayreau

With fewer than 300 inhabitants and miles of secluded beaches, it&#39;s easy to feel as if you&#39;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 5 - March 03, 2026

Bequia

The only ships in port are those small enough to anchor alongside the yachts and fishing boats in Admiralty Bay. Bequia&rsquo;s whaling heritage is on display in the museum in pretty Port Elizabeth, or watch the island&rsquo;s famed model boat builders at work on their miniature masterpieces.

Day 6 - March 04, 2026

Mayreau

With fewer than 300 inhabitants and miles of secluded beaches, it&#39;s easy to feel as if you&#39;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 7 - March 05, 2026

Day 8 - March 06, 2026

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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Feb 27, 2026

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