Caribbean Sailing Holidays

Coral Reefs, Island Hideaways & Barefoot Luxury

Introduction

The Caribbean offers a gentler kind of luxury — coral reefs, palm-fringed beaches, colourful harbours and warm island hospitality. From the barefoot elegance of St Vincent & The Grenadines to the easy island rhythm of the British Virgin Islands, Elysian Sailing brings together private crewed catamarans, natural beauty and relaxed cultural discovery.

For guests seeking a more curated journey, each Caribbean itinerary can be shaped around our Elysian Experience of sailing, culture, cuisine and quiet luxury.

Palm-fringed Grenadine anchorage with turquoise water, sailing boats and relaxed island scenery

Barefoot Paradise: St Vincent & The Grenadines

Sail from St Vincent to Bequia, Mustique and the Tobago Cays on a crewed Caribbean catamaran itinerary shaped by turquoise seas, coral reefs, chic island hideaways and authentic Grenadine charm.

Sheltered British Virgin Islands beach with turquoise water, granite rocks and boats beyond

Easy Island Living: The British Virgin Islands

Sail a necklace of emerald islands from Tortola to Virgin Gorda, Anegada and Jost Van Dyke. This relaxed British Virgin Islands itinerary combines coral reefs, barefoot beach bars, sheltered anchorages and iconic Caribbean harbours.

For a broader sense of our sailing style, you can also explore The Elysian Collection — our curated guide to boutique sailing experiences.

Elysian – Sailing Beyond Ordinary