Windward Islands Surf & Sunsets

From $2,999 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 />
<br />
<!--<strong>NOTE: All departures on Star Pride through April 11, 2022 will be on her sister yacht, Star Legend</strong><br />
<br />
<a href="https://www.windstarcruises.com/air-packages-caribbean/"><span style="color:#0000FF;"><u>Caribbean Air + Cruise Packages</u></span></a>-->

Journey Summary

  • Day 1 - Mar. 13, 2026, Fri. - San Juan
  • Day 2 - Mar. 14, 2026, Sat. - Marigot, St. Martin
  • Day 3 - Mar. 15, 2026, Sun. - Les Saintes
  • Day 4 - Mar. 16, 2026, Mon. - Mayreau
  • Day 5 - Mar. 17, 2026, Tue. - Bequia
  • Day 6 - Mar. 18, 2026, Wed. - Pigeon Island
  • Day 7 - Mar. 19, 2026, Thu. - The Pitons
  • Day 8 - Mar. 20, 2026, Fri. -

Itinerary Highlights

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

Book this cruise

Detailed Itinerary

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

Day 1 - March 13, 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 - March 14, 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 3 - March 15, 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 16, 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 17, 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 18, 2026

Pigeon Island

The UNESCO site Pitons&rsquo; with their two majestic volcanic peaks and 24 miles of vibrant coral reef welcome you to St. Lucia. Nearby Pigeon Island National Park features impressive ruins of English forts, archaeological relics of Arawak Indians, and splendid beaches.

Day 7 - March 19, 2026

The Pitons

Located near the town of Soufriere, St. Lucia the Pitons are a UNESCO World Heritage Site and a spectacular landmark. Gros Piton is 2,619 feet high (798 meters) and Petit Piton is 2,438 feet high (743 meters). Gros Piton is home to at least 148 plant species and 27 bird species (5 of them endemic) and Petit Piton has 97 plant species with 8 rare tree species.

Day 8 - March 20, 2026

Dates and Prices

Select year & month:

Unavailable dates are greyed out

JanFebMarAprMayJunJulAugSepOctNovDec

Available dates:

Mar 13, 2026

consultation

Need information to make a decision?

Reach out to our travel concierges today to create your perfect journey.