What I love about the Caribbean in the shoulder seasons of late fall and early spring, and all winter long, is the just-warm-enough sunshine, tropical breezes, and the delicious sense that the world here often stops still. It’s the best possible peaceful respite from the Northern Hemisphere’s winter.
What might surprise you to learn though is that there’s isn’t just one Caribbean. The region, which incorporates thousands of islands, reefs and keys, not to mention vibrant cultural cities, towns and villages, is essentially divided into two: the Greater Antilles and the Lesser Antilles. There are volcanic islands, rainforests, and a huge agricultural bent, growing sugar and bananas, among others. Populations on the various islands reflect a colonial heritage (Dutch, French, British, Spanish, Portuguese) with indigenous cultures and languages, too.
In a region as diverse as this one, it makes sense that Windstar offers some 24 different itineraries (and you tack on others for even more of a comprehensive experience). It’s a region with immense historical and cultural complexity.
For any traveler contemplating a Caribbean vacation, the big question is what type of trip are you looking for? Are you interested in fun-and-sun? Diving and snorkeling, hiking up volcanoes, trekking through rainforests, seeking out the best rums and vanillas?
Keep reading! We’re happy to help you identify the islands that speak to you for whatever travel mood you happen to be in.
Summer camp for adults
If you’re simply looking to relax, reconnect with friends and family, and indulge in a quick side trip to France, this itinerary is my favorite of all time. Based from St. Maarten, ports could include Antigua, rife with British colonial culture, and St. Barts, the Caribbean’s St. Tropez, along with beachy stops at the British Virgin Islands of Jost van Dyke and Virgin Gorda.
Insider Hint:
Sailing around the hilly and mountainous British Virgin Islands is one of the most beautiful experiences in the Caribbean. And Windstar’s Signature Beach Barbecue, on Jost Van Dyke, is a blast. Another option for this style of sailing is operates out of San Juan.
Nature immersion
Windstar’s Windward Island Delights itinerary is among those that call at Dominica, and the theme of these voyages is wildlife and nature. In Dominica, for instance, the Indian River is a small-scale Amazon in terms of biodiversity (and you can take a ride in a rowboat to experience it). You can go tubing on the Layrou River or jaunt to the island’s Roseau Valley, where experiences include soaking in hot sulphur springs, exploring a nature sanctuary and admiring the Trafalgar waterfalls. Did you know that “Pirates of the Caribbean 2 – Dead Man’s Chest” was filmed at the island’s rainforest?
Other places on the route with a nature emphasis include St. Kitts, where you can try the Sky Safari zipline. On Guadeloupe’s Les Saintes, pilot a clear-bottomed kayak.
Insider Hint:
If your itinerary calls at Martinique’s Fort-de-France, its capital city, make it an urban day; the port has tons of history, including the St. Louis Cathedral and the Schoelcher Library. If you’re in the mood for a swishy beach resort, we also love the nearby village of Les Trois-Îlets.
Culture and culinary:
On a voyage whose itinerary features places like St. Lucia, Bequia and Guadeloupe, not to mention San Juan as its port of embarkation and debarkation, there’s a surprise gourmet component to the nature experiences you’d expect. In Guadeloupe, one of the Caribbean’s French-influenced islands, a culinary-themed outing blends Creole and French ingredients include a tasting of fresh punches, syrups, foie gas and duck breasts alongside bites of smoked fish, sips of rum, and sweets with coffee and chocolate.
Speaking of chocolate, St. Lucia is famous for the cocoa groves of Fond Doux Plantation, where you can stroll through the plantation – and taste its treasures. And in St. Martin’s Marigot, head to the neighborhood of La Case, which has long been home to a cluster of well-regarded French (and sometimes Franco-Caribbean) restaurants, many set right on the beach.
Insider hint:
Visiting local markets on islands in the Caribbean is a great way to embrace local culture.
You want to experience it all – beaches, culture, nature and history
If you want to explore a smattering of islands throughout the region, Star Collector: Caribbean Collection, which is 14 days long, is our favorite option for a just-a-bit-longer voyage. Roundtrip from St. Maarten, it visits the cultural isles of Martinique and St. Barts, several utterly peaceful ports in the British Virgin Islands, and some of the most nature-focused places like Dominica, St. Lucia and Nevis. One place on this cruise that ships don’t often visit is Anguilla, a small, flat island across from St. Maarten with fabulous high-end resorts, gourmet restaurants and the most beautiful beaches, where the sands are often shaded in different colors based on their location in the sea.
For an ultimate Caribbean voyage that pretty much visits every island in Windstar’s collection, we love the option to spend 25 days at sea on Star Collector: Best of the Leeward and Windward Islands. Starting from (and ending in) St. Maarten, it travels north to Anguilla and then heads south to Aruba and the other ABC islands. This itinerary features an overnight visit in Jost van Dyke, the BVI’s best bar scene, and late night stays in St. Barts, St. Lucia and Guadeloupe. It also throws in a few islands that are really off-the-radar, such as Montserrat, Bequia and Tobago.
We also love an 11-day itinerary that spans both the Southern Caribbean and Central America; from Barbados to Panama is Colombia Southern Caribbean Coastlines voyage, that also visits Cartagena, the Grenadines and the ABCs (Aruba, Bonaire, Curacao).
Insider hint:
On the other end of the free time scale, less-than-a-week voyages, some as short as five days, are an option if you’re time crunched or want to combine a sea and land stay. I’m learning, though, to think the longer-the-better and if you want to incorporate a lot of sea days into your voyage, consider combining an Atlantic crossing, as ships reposition between Europe and the Caribbean.
