Gems of the Leeward Islands
Oct 28, 2026 — Nov 8, 2026
Starting from $7,314 Displayed pricing is based off of double occupancy per person. Pricing subject to change based on occupancy and cabin selection.
See more routes around CaribbeanSAN JUAN → SAN JUAN
11 Nights in Star Pride
On your Caribbean voyage to the Leeward Islands, everywhere you look is another cover shot image. Dazzling white sand turns the shallows mesmerizing shades of peacock and mermaid, weathered fortresses point canons at long-vanished schooners, natural pools warm gently under the mid-day sun. On your private yacht, you’re equally at home in exclusive harbors and anchored off barefoot beaches, so you can see it all. Snorkel or dive on vibrant coral reefs. Follow your siren inland to rainforest adventures or delightful boutiques. Thank your lucky Star Pride for bringing you here.
Popular Highlights
Delve into the history of pirates and colonists in San Juan.
On Antigua, explore Nelson’s Dockyard, the only Georgian dockyard in the world.
Absorb the distinctive French charm of enchanting Les Saintes.
Enjoy your day on Jost Van Dyke and let the azure waters wash your cares away.
Sail past the stunning emerald Pitons on St. Lucia, a UNESCO World Heritage Site.
Mingle with the glitterati in St. Barts.
Discover the culinary delights of both the Signature Beach Party and the Signature Onboard Barbecue.
Sail, swim and kayak from your yacht’s Marina Platform.
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.
Affectionately known as St. Barts, the Caribbean's most chic island adds a French flair to Riviera-like beaches and duty-free boutiques. Walk past gingerbread cottages in search of celebrities, shop for designer fashions, or sip the island's signature ti punch as kite surfers fly by.
With Georgian architecture situated against an irresistible backdrop of emerald green hills, Basseterre is one of the loveliest of the Caribbean's small capitals. Beyond town, more than a quarter of St. Kitts has been set aside as Brimstone Hill Fortress national Park, a UNESCO World Heritage Site.
It's said that Antigua has 365 beaches - one for every day of the year. See how many you can discover as our stay in port stretches into the evening to accommodate them all. Watch the stars come out as darkness falls and imagine how residents of Andromeda must envy you.
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.
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.
