Windward Islands Surf & Sunsets

From $2,699 per person

7 days

Ship: Star Pride

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 - Dec. 20, 2026, Sun. - San Juan
  • Day 2 - Dec. 21, 2026, Mon. -
  • Day 3 - Dec. 22, 2026, Tue. - St. George's
  • Day 4 - Dec. 23, 2026, Wed. - Bequia
  • Day 5 - Dec. 24, 2026, Thu. - Mayreau
  • Day 6 - Dec. 25, 2026, Fri. - Les Saintes
  • Day 7 - Dec. 26, 2026, Sat. - Marigot, St. Martin
  • Day 8 - Dec. 27, 2026, Sun. - 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 - December 20, 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 - December 21, 2026

Day 3 - December 22, 2026

St. George's

Inhale the intoxicating aroma of the &ldquo;Isle of Spice&rdquo; 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 - December 23, 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 5 - December 24, 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 6 - December 25, 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 7 - December 26, 2026

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&rsquo;s most prestigious brands can be found. &nbsp;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 - December 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.

Dates and Prices

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Available dates:

Dec 20, 2026

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