In the Caribbean, the best ports are the ones you’ve never heard of — until now
The Caribbean is a sensory feast: impossibly blue water, vibrant reefs teeming with life, landscapes that shift from lush rainforest to sun-bleached desert within a single island chain. But the real magic happens at the harbors themselves — the intimate coves and storied ports where the islands reveal their character up close.
This is where Windstar’s small ships have the advantage. Rather than crowding into the same mega-ports as the big cruise lines, our yachts slip into harbors too small, too shallow, or simply too special for larger vessels.
Before diving into these picturesque harbors, it’s worth noting that the Caribbean can be tricky to parse, since it’s made up of three main archipelagos (sometimes called the West Indies collectively):
- The Greater Antilles — the big islands: Cuba, Jamaica, Hispaniola (Haiti/Dominican Republic), and Puerto Rico. These aren’t referred to as Leeward or Windward at all. Aside from Puerto Rico, where San Juan is a hub for some Leeward Islands itineraries, Windstar doesn’t currently visit this group.
- The Lesser Antilles — the best-known group, running from the Virgin Islands to Grenada, split into two sub-groups. The Leewards arc down from the north: the Virgin Islands through Anguilla, St. Maarten/St. Martin, St. Barts, St. Kitts, Nevis, Antigua, and Guadeloupe. The Windwards lie further south: Dominica down through Martinique, St. Lucia, St. Vincent and the Grenadines, and Grenada.
- The Leeward Antilles — a separate, often-confused third group: islands off Venezuela’s coast like Aruba, Curaçao, and Bonaire, plus Venezuela’s own island territories.
Windstar itineraries may focus on just one region or mix and match across overlapping areas. And it’s important to note that most of Windstar’s best off-the-path yacht harbor ports are located in either the Greater Antilles or Lesser Antilles. These are places that transport travelers’ experiences beyond the usual big ship ports in the region.
Here’s a look at some of the most scenic harbors along Windstar’s Caribbean routes.
The Leeward Islands
Anguilla:
Known for its pristine, sugar-white beaches and laid-back glamour, Anguilla offers the ultimate Caribbean retreat. It’s a destination reserved largely for small ship cruise lines, which anchor in the intimate Road Bay, its low-key harbor lined with beach shacks and cafés. Snorkeling at Little Bay offers calm, clear waters, and the beaches throughout the island are soft and pristine.
Here’s a tip: it’s no longer a secret that Anguilla is one of the Caribbean’s culinary magnets. This tiny island has roughly 100 restaurants, including acclaimed spots like Blanchards — now celebrating more than 30 years on the island and widely credited with kickstarting its culinary reputation — the newer L’Étoile at Manoah Boutique Hotel, and Celeste by Kerth Gumbs at the Malliouhana Resort. Just as central to Anguilla’s food-lover reputation are its casual beach shack eateries (Blanchard’s, in fact, operates a fine-dining restaurant and a casual spot side by side).
Planning tip: Anguilla is included on Windstar itineraries such as:
- Beach, Fun and Sun
- San Juan and the Virgin Islands
Antigua:
Antigua is a little more than 100 square miles — about the size of Shreveport, Louisiana — yet it boasts 365 beaches. Its coastline is exquisite, thanks to an abundance of coral that keeps the water clear.
St. John’s, Antigua’s capital, is the usual port for big-ship visitors, but Windstar anchors in Falmouth Harbour, a world away, alongside other yachts and sailing vessels. The tender dock is within walking distance of Nelson’s Dockyard, a charming Georgian-era village also known as Antigua Naval Dockyard and Related Archaeological Sites.
Another option on this more pastoral side of the island: Antigua’s Rainforest Canopy Zipline, with 13 ziplines and two suspension bridges. For a gourmet afternoon on the beach, take a short taxi ride to Catherine’s Café on Pigeon Point Beach. And because Windstar’s yachts anchor in the harbor itself, its marinas are often open for swimming, sunbathing, and water sports.
Planning tip: Antigua is a highlight of several Caribbean itineraries, including:
- Beach, Fun and Sun
- Masterpieces at Sea: Gems of the Leeward Islands
- Star Collector: Caribbean Explorations
British Virgin Islands:
The British Virgin Islands of Tortola, Jost Van Dyke, and Virgin Gorda are a mainstay of Windstar’s intimate Caribbean voyages and are among the most laid-back places any small cruise ship visits.
Soper’s Hole, Tortola
Tortola is one of the only British Virgin Islands to accept larger cruise ships (at Road Town, its main city), but, as with Anguilla, Windstar docks instead at Soper’s Hole, a tiny harbor with a restaurant, a bar, and colorful West Indian buildings. This stop is a low-key jumping-off point for beach adventures at spots like Long Bay Beach or Smuggler’s Cove.
Prickly Pear Cay, Virgin Gorda
In Virgin Gorda’s North Sound, Prickly Pear Cay is an uninhabited national park island — and, on Windstar’s itineraries, typically the site of its famous beach barbecues. Travelers usually spend the morning exploring Virgin Gorda by shore excursion (unless spending the whole day at the beach, since there’s no independent transportation on the cay). The must-see experience is a trip to Virgin Gorda’s The Baths: massive granite boulders spread across Devil’s Bay on the island’s north shore, threaded by a series of steps and ropes that guide adventurers through grottos from beach to bay. It’s also an excellent spot for snorkeling.
As BVI Insider explains, these boulders — found along the shoreline from Devil’s Bay to Spring Bay — were formed by volcanic uplift. Roughly 45 million years ago, an intrusion of hot liquid magma (a batholith) pushed ancient seafloor sediments above sea level.
Jost Van Dyke
At just three-square miles, Jost Van Dyke is the smallest of the BVI’s main islands. For visitors, there are two main destinations. Great Harbour holds Jost’s small town — government offices, a church, and the famous Foxy’s Tamarind Bar. Foxy’s is far more than a beach bar; it’s set right on the sand, with a barbecue, hammocks, and live music.
On the other side of the hill is White Bay, entirely pleasure-oriented, lined with beach bars and cafés such as the Soggy Dollar Bar, birthplace of the beloved Painkiller cocktail.
Framing both waterfronts is a mountain ridge that tops out around 1,000 feet.
Because ships anchor in Great Harbour alongside sailboats and yachts, its marinas are often open to guests.
Planning tips: Numerous ports here find their way into Windstar’s itineraries. They include:
- Beach Fun and Sun (Jost van Dyke, Soper’s Hole and Virgin Gorda/Prickly Pear Cay)
- San Juan and the Virgin Islands (Jost van Dyke and Virgin Gorda/Prickly Pear Cay)
- Star Collector: Caribbean Explorations (Jost van Dyke, Soper’s Hole, Virgin Gorda/Prickly Pear Cay)
- Star Collector: Caribbean Collection: ABC, BVI & the Windwards (Jost van Dyke, Virgin Gorda)
- Star Collector: Atlantic Crossing to the British Virgin Islands (Jost Van Dyke, Virgin Gorda)
- Star Collector: Windward Islands, ABC Islands, and the Virgin Islands (Jost Van Dyke, Virgin Gorda)
United States Virgin Islands: St. John
St. John, a far more intimate island than the USVI’s St. Thomas, offers smaller cruise ships an anchorage that’s more working harbor than postcard bay. Even so, views of the surrounding mountainous islands, an abundance of gorgeous beaches and bays, and a vibrant downtown known for distinctive eateries and boutiques make it a lovely — and rare — port of call for small ships.
Planning tip: Cruz Bay is a port of call on a handful of Windstar’s itineraries, such as:
- San Juan and the Virgin Islands
- Windstar’s Star Collector: Atlantic Crossing to the Virgin Islands
St. Barts: Gustavia
Like every island in the Lesser Antilles, St. Barts (full name Saint-Barthélémy) has plenty of gorgeous bays and beaches, and it’s a great destination for snorkeling and diving. But that’s the least of this swanky, French-flavored isle’s appeal — it’s known just as much as the preeminent Caribbean playground for the rich and famous. Cruise travelers arrive by tender (only small ships are welcome, and all must anchor out in Gustavia Bay), and the main town of Gustavia is packed with pricey boutiques from Louis Vuitton, Prada, Cartier, and Hermès. Its restaurants — aside from the rather touristy Le Select — are equally elegant.
Gustavia is a destination in itself, but you’ll miss much of St. Bart’s charm if you don’t explore further. St. Jean Beach, near Eden Rock, is another wonderful spot for a day out, with tranquil seas alongside numerous boutiques and restaurants. For something more rustic, head to Saline Beach, home to a handful of salt ponds once used to harvest the mineral.
Planning tips: St. Bart’s appears on the following Caribbean itineraries:
- Classic Caribbean
- Star Collector: Caribbean Explorations
- Masterpieces at Sea: Gems of the Leeward Islands
- Star Collector: Atlantic Crossing to the Virgin Islands
- Star Collector: Windward Islands, ABC Islands, and the Virgin Islands
St. Martin: Marigot
Planning tips: If the adjacent island of St. Maarten is the more common port for this two-nation island — particularly as an embarkation/debarkation stop — Marigot itself appears on a few itineraries, including:
- San Juan and the Virgin Islands
- Star Collector: Windward Islands, ABC Islands, and the Virgin Islands
Guadeloupe’s Les Saintes
Small ships skip Guadeloupe’s bustling capital of Pointe-à-Pitre. Instead, they anchor at Les Saintes, an archipelago serving Terre-de-Haut. Its picturesque bay is framed by red-roofed houses, volcanic mountains, and an old fort.
There’s otherwise little to see in this fishing village unless you head out on the water — kayaking, snorkeling, and sailing are the main draws, and Windstar’s marinas are often open here. One sightseeing exception: the Habitation Bellevue Distillery, which has made rum since 1821, offers self-guided tours and tastings; visit between February and April to watch its workers in action.
Planning tip: Guadeloupe appears on the following Windstar itineraries:
- Masterpieces at Sea: Gems of the Leeward Islands
- Classic Caribbean
- Beach, Fun and Sun
The Windward Islands
Bequia, Saint Vincent and the Grenadines: Port Elizabeth
St. Vincent and the Grenadines is an island nation, of which Bequia is one of the larger islands. The official language is English, and the main industry is agriculture, including the harvest of arrowroot — used as a gluten-free thickener.
Bequia — meaning “island of the cloud,” pronounced “beck-way” — is a seven-square-mile speck. Ships can only anchor in Admiralty Bay, since Bequia has no cruise ship pier and only smaller vessels can access the island. From there, you’ll tender into Port Elizabeth, the island’s walkable, low-key capital, full of local color and free of Caribbean crowds.
The star attractions are Bequia’s beaches, including Hope Beach on the island’s windward side — your reward for a lengthy taxi ride from Port Elizabeth and a mile-long hike down to the shore is a real sense of seclusion. Another option is Friendship Bay, a quiet spot on the opposite side of the island from Port Elizabeth; again, plan to bring your own refreshments. As with any unfamiliar beach, ask locals what swimming conditions and skill level are appropriate before taking the plunge.
Another option is Bar One, a floating watering hole in Admiralty Bay. After tendering to the jetty at Port Elizabeth, call ahead to request water taxi pickup (about 5–10 EC dollars). Phone: 1-784-530-8123.
Planning tip: Bequia is a stop on the following Windstar itineraries:
- Windward Ways and Tobago Cays
- Windward Islands Surf and Sunsets
Care to share your own favorite yacht harbor in the Caribbean? Tell us all about it in our comments section.
