Silversea Cruise of the Southern Caribbean

Debbie's Silversea cruise on Silver Shadow

Philipsburg, Netherlands Antilles (Sint Maarten)- A refined Caribbean capital where Dutch elegance meets island glamour. Philipsburg unfolds along Great Bay with pastel façades, a polished boardwalk, and world-class shopping. Historic Fort Amsterdam crowns the harbor, offering sweeping views as superyachts drift below. Effortlessly chic and cosmopolitan, Philipsburg is a sophisticated gateway to Caribbean luxury.

St. John’s, Antigua & Barbuda- Sun-drenched and steeped in history, St. John’s is the vibrant heart of Antigua. Founded in 1632, its deep natural harbor shaped centuries of maritime heritage, still visible in colonial landmarks like Fort James. Beyond the capital, Antigua reveals pristine white-sand beaches, lush rainforests, and dramatic coastlines. The UNESCO-listed Nelson’s Dockyard, led by Admiral Horatio Nelson, is a masterfully preserved glimpse into the island’s naval past, while elevated viewpoints reward visitors with panoramic vistas of emerald inlets and rugged cliffs.

St. Thomas, U.S. Virgin Islands- A dramatic island of mountains and sea, St. Thomas rises steeply from turquoise waters into lush, jungle-covered peaks. Charlotte Amalie, the historic capital, cascades toward the harbor with luxury boutiques and colonial charm. Ascend to Paradise Point by Skyride for breathtaking views over the natural amphitheater below or pause at Drake’s Seat for serene panoramas of Magens Bay, where the ocean stretches endlessly in tranquil blues.

Little Bay, Montserrat- Quietly captivating, Little Bay represents Montserrat’s elegant rebirth. Set along the island’s northwest coast, it is poised to become the future capital following the volcanic events of 1995. Known as the “Emerald Isle of the Caribbean,” Montserrat blends lush landscapes with a distinctive Irish heritage. Framed by volcanic peaks and untamed beauty, Little Bay Beach offers one of the region’s most peaceful escapes—raw, restorative, and profoundly beautiful.

Castries, St. Lucia- Bold and breathtaking, St. Lucia is defined by towering mountains, fertile valleys, and dense rainforests. Rising dramatically from the sea, the iconic Pitons—a UNESCO World Heritage Site—stand as the island’s most powerful symbol. Nearby Marigot Bay, famously cinematic, offers sheltered beauty, while Castries Market delivers a vibrant sensory experience, rich with spice, color, and Creole tradition.

Bequia, St. Vincent & the Grenadines- Unspoiled and effortlessly elegant, Bequia invites travelers to slow the pace and savor simplicity. Known as the “Island of the Clouds,” it remains blissfully untouched, with a small local population and an authentic island rhythm. Days unfold on tranquil beaches and in crystalline waters, with Princess Margaret Beach standing out as one of the Caribbean’s finest—an arcing crescent of soft sand and luminous blue sea.

Les Saintes, Guadeloupe – French West Indies- A vision of French-Caribbean refinement, Les Saintes is an intimate archipelago of rare beauty. Only two of its nine islands are inhabited, preserving an atmosphere of exclusivity and calm. Overlooking the bay, Fort Napoléon—once a military stronghold—now houses serene gardens and a cactus park. Timeless, tranquil, and undeniably elegant, Les Saintes is Caribbean luxury at its most understated.