Windstar’s Windward Islands Surf & Sunsets Cruise Explores Hidden Gems in the Caribbean

Windstar’s Windward Islands Surf & Sunsets cruise takes you deep into the heart of the Caribbean, visiting islands off the beaten path, plus small ports that are big on culture and island vibes. It’s the trip you take when you want to be in places where everyone else is not.  

You’ll visit independent nations, and foreign territories all set against the backdrop of dramatic lush coastlines, sun-kissed beaches, and azure waves. You’ll learn about the deeply rooted history of colonialism, slavery, and how a unique culture was born from its history. You’ll delight your senses with spice and rum.  

This is an itinerary appealing to sun seekers, nature lovers, history buffs, and foodies who crave unique blends. Here are some of the highlights. 

San Juan, Puerto Rico

Your Caribbean adventure starts in the colorful hub of San Juan, Puerto Rico. Established in 1521, San Juan is the second-oldest European-founded settlement in the Americas and the oldest under US jurisdiction. The city was inaugurated almost a century before the Mayflower laid anchor, and it is now a place of colonial-era artifacts and historical authenticity mixed with the modern world.  

When the Spaniards arrived in the early 1500s, San Juan was just a deserted spit of land dominated by strong trade winds and dramatic headlands. They settled it, built a city, built forts to protect it, and maintained the city as the primary military and legislative outpost for the Spanish Empire in the Caribbean. That was until 1898 after the Spanish-American War when the US annexed the island as a territory.  

From port, you’re only a 10-minute walk away from the colorful and well-preserved streets of Old San Juan. Within walking distance are also the two main attractions of the city, Castillo San Cristobal, and Castillo San Felipe del Morro (El Morro). El Morro is said to be the oldest Spanish architecture example in the New World. Construction of this fort took almost 200 years to complete.  

Sea Day

Who doesn’t love a sea day during their cruise? Take this day to sleep in, hit the gym, get a spa treatment, read in the Yacht Club, or lounge on the deck and watch the world go by. The day is yours to relax and enjoy life at sea. 

St George’s, Grenada

From the moment you set foot in St George’s you will quickly realize that Grenada is not a cliché Caribbean destination. While it offers sparkling white beaches such as Grand Anse and a plethora of untouched diving locations under the waves, it is the lush interior and rich culture that set this island nation apart.  

To truly experience the best of Grenada, you’ll want to consider the Best of Grenada excursion that will soak you in the richness of the island with a visit to the Diamond Chocolate Factory, the shallow crater Lake Antoine, Grand Etang National Park, a nutmeg factory, you’ll savor a creole lunch at a former plantation, and lastly enjoy time at one of the many beautiful waterfalls on the island.  

If you’d rather spend your day in the water, head out to the Statue Park in Mango Back. The installation is located 16.5 feet (5 meters) below the surface and is comprised of 14 statues. The sculptures aid in reef restoration and it’s not uncommon to see several species of fish while snorkeling or diving at the park. 

Bequia, St Vincent & the Grenadines

Bequia is considered to be the most perfect island in the Grenadines. The island is outlined by stunning beaches, colorful buildings line the streets of Port Elizabeth, and life embraces the island vibes creating an environment that is truly unforgettable. It’s an island paradise and the best part is that you and your fellow Windstar cruisers will enjoy it with few other people. 

The tender pier is located right in the heart of Port Elizabeth, and once onshore, you can visit the entirety of the area by foot. The highlight is the Belmont Walkway, a paved island-style path that follows the shoreline past several local cafes, restaurants, and takes you to two beautiful beaches. The best beach near to the port is Princess Margaret Beach.  

If you’re into rubbing elbows with the rich and famous, or at least trying, you could opt for an excursion to the superbly upscale Mustique Island. This excursion takes you by speed boat alongside Bequia before making the open water crossing to Mustique. Once on the island, you’ll enjoy a 4×4 tour that stops at several beaches, and points of interest, all while allowing you to gawk at the celebrity homes along the way. It includes a traditional lunch with a view before having some free time at the dockside bar. You’ll then cross back to Bequia for an hour at Princess Margaret Beach. It’s a lovely way to spend your day in paradise.  

Pigeon Island, St Lucia

St Lucia is known for its UNESCO site that features the Pitons, two majestic volcanic peaks and 24 miles (39 kilometers) of vibrant coral reef. This makes them one of the most photographed sites in the Caribbean. However, a commonly overlooked site in St Lucia is Pigeon Island National Park, home to impressive English fort ruins, archaeological relics of Arawak Indians, and lovely beaches. Lucky for you, Windstar makes this island their port of call. 

While you still have the option to take a catamaran cruise to the Pitons, the Windstar crew will be hard at work setting up a fantastic beach barbecue for you to enjoy when you get back! This event means you get to enjoy a private beach with all the amenities you’d have on board. Lounge chairs, watersports, floating mats, beach bar and a lunch buffet along with live local music is yours for the day.  

When you’ve had your fill of beach time, set off on foot to the top of Pigeon Island, where you can enjoy the 18th century ruins of Fort Rodney, along with spectacular views of both Rodney Bay and the lush coastline of St Lucia.   

Les Saintes, Guadaloupe

Les Saintes is a collection of small islands that lies ssix miles (10 kilometers) off the coast of Guadeloupe just south of the town of Basse Terre. They are considered to be the highlight of any visit to Guadeloupe. The islands are volcanic, much the same as other Caribbean islands, and rise sharply from the sea. Only two of the ten islands are inhabited; Terre de Baus, whose residents can trace their roots back to the early days of colonization and slavery, and Terre de Haut, the more popular stop for visitors.  

While not exactly a secret, the islands are still the least explored corner of Guadeloupe and easily one of its most beautiful. Windstar tenders into the stunning Terre de Haut, where you can then explore most of the island on foot. There are two 1,000-foot peaks to be climbed or you can walk square across to the other side for a more exclusive beach experience. Just don’t swim, as the seas are rough on the windward side. The island is also known for its delicious French cuisine with an island twist and the aroma of fresh baguettes will have your mouth watering as you wander the streets.  

The most sought-after excursion is the Historic Tastes & Treasures of Fort Napoleon that offers transportation to the fort and an immersive guided tour that takes you through the entire history of the fort, the islands, and much of the Caribbean. Windstar books exclusive access to the fort in the afternoon, meaning it is not open to the public during your visit.  

Philipsburg, St Maarten

In 1648, France and the Netherlands split this Caribbean Island into Saint Maarten and Sint Martin. Today’s residents and visitors do not pay much attention to the old treaty and just enjoy all that the island has to offer.  

The downtown of Philipsburg is an easy 15-minute walk from the dock, or you can pay for the sometimes-available water taxis that will drop you right on the Philipsburg boardwalk. As with most Caribbean Islands, you’ll find an endless supply of sugary white sand beaches to enjoy, but one place, Maho Beach, is one of the most unique places to visit in all the Caribbean.  

While the beach itself is not the best, people flock here as it’s located directly behind the international airport of St Maarten. This means flights land over Maho Beach all day, including giant jets from Europe. There are a couple beach bars where you can grab a cold one and check flight schedules. It makes for an overall pleasant and unique experience.  

Alternatively, getting out on the water by either taking a leisurely catamaran trip that includes snorkeling and beach hopping or by boarding an America’s Cup Racing sailboat for an adrenaline inducing experience.  

San Juan, Puerto Rico

Your last morning finds you back in colorful San Juan after a successful journey to some of the lesser known and lesser visited windwards islands in the Caribbean. But the fun doesn’t have to stop there. If you didn’t get a chance to visit Old San Juan, this is your time to join the disembarkation walking tour and get to know this fascinating city and its beauty.  

Alternatively, if you did see Old San Juan, then why not take an excursion to one of Puerto Rico’s top shelf rum factories, Rob del Barrilito. Here you’ll learn the history of the beloved Tres Estrellas and tour the estate that continues to produce this rum in the original way. You’ll also enjoy a full-scale rum tasting, with an opportunity to learn about flavors, age and how it affects the drink. It’s the perfect way to end your vacation. 

About the Author: Lina Stock is an award-winning photographer and writer at She has been exploring the world since 2001 and has traveled to more than 100 countries and all 7 continents. 

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