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Windward Islands Surf & Sunsets

Windward Islands Surf & Sunsets

At a glance

Duration: 8 Days, 7 Nights

Coverage: Roundtrip San Juan, Puerto Rico

From: $1,999

Season: November - December

Activities: Adventure, Culture, History, Wildlife

Book this Trip › or call us toll-free 1-888-815-5428

Wind Star Cruises

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. Stroll the weather-beaten parapets of the citadel of El Morro near San Juan, Puerto Rico and run your fingers along the stone scars left by Dutch invasions and American bombardments. Then clip into a zip line and hang on as moss-covered limbs and colorful wild birds rush by your head as you glide through St. Lucia’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.

Popular Highlights

  • Walk up Mount Pleasant with a spectacular view of Bequia's Admiral Bay
  • Shop for spices, especially nutmeg and cinnamon in St. George’s local markets
  • See San Juan’s UNESCO site El Morrow Fortress
  • Discover the underwater world of Les Saintes
  • Enjoy some of the best snorkeling around in the deep blue waters of Guadeloupe
  • The UNESCO site Piton's two volcanic peaks, rising more than 2,400 feet, welcome you to St. Lucia
  • Shop the 100% duty free island of two nations, St. Maarten and St. Martin

Day-to-Day Itinerary

Day 1 - San Juan, Puerto Rico

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 - 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 - Les Saintes, Guadeloupe

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 4 - Bequia, St. Vincent & the Grenadines

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 - St. George's, Grenada

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 6 - Pigeon Island, St. Lucia

The UNESCO site Pitons’ 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 8 - San Juan, Puerto Rico

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.

Windward Islands Surf & Sunsets itinerary map

Dates & Rates

Dates Ocean View Suite Ocean View Suite 1 Ocean View Suite 2 Ocean View Suite 3 Balcony Suite Balcony Suite 1 Classic Suite Owner's Suite
Nov 3, 2018 $1,999 $2,099 $2,299 $2,499 $2,899 $3,099 $4,499 $5,499
Nov 17, 2018 $1,999 $2,099 $2,299 $2,499 $2,899 $3,099 $4,499 $5,499
Dec 1, 2018 $1,999 $2,099 $2,299 $2,499 $2,899 $3,099 $4,499 $5,499
Dec 15, 2018 $1,999 $2,099 $2,299 $2,499 $2,899 $3,099 $4,499 $5,499
Dec 29, 2018 $2,799 $2,899 $3,099 $3,299 $3,699 $3,899 $5,299 $6,299

Ships

Star Pride

Star Pride The graceful, suite-only Star Pride is the first of Windstar's three new power yachts. With only 212 guests, you begin to feel like it's your own private yacht almost as soon as you step aboard. View ship details...

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