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Caribbean Flotilla Holidays

Whether you want to set sail on a romantic adventure with a loved one, or are looking for an action-packed break with friends or family, Sunsail has the perfect flotilla sailing holiday for you. With plentiful Mediterranean destinations, plus Flotilla bases in The Solent and the Caribbean, we have flotilla sailing holidays designed to suit every level of ability. Tell us whether you want easy sailing or more of a challenge, history and culture or excellent swimming and snorkelling, exciting nightlife or laid-back bars and restaurants - or a bit of everything! - and we’ll come up with your ideal flotilla sailing holiday.

The Caribbean offers sailing at its best on a St Lucia or British Virgin Islands Flotilla.

St. Lucia is suitable for advanced sailors on a Caribbean Flotilla, who will enjoy exhilarating blue water passages in warm, steady winds, while the protected waters and short hops of the British Virgin Islands (BVI) are better suited to intermediate level sailors.

And whether the priority is chilling out on fabulous deserted white sandy beaches, bird-spotting or getting in some serious socialising, Sunsail has the perfect Caribbean flotilla sailing holiday for everyone from couples looking for a romantic getaway to groups of friends and family.

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  • BVI One Week Flotilla

    Perfect for all levels of sailor, our one-week flotilla gives you a taste of all that this world-renowned cruising area has to offer. Admire the unique rock formations at Virgin Gorda; enjoy the myriad of watersports, restaurants and bars available at Cane Garden Bay or the superb snorkelling at The Caves on ‘Treasure Islands’ Norman Island.

    • Suitable for all levels of sailor
    • Line-of-sight navigation
    • Consistent trade winds
    • Fantastic island restaurants and bars
    • Island-hopping
    • Family Flotilla
  • BVI Two Week Flotilla

    Sail among spectacular anchorages, hidden sandy coves and endless palm fringed beaches on this tropical adventure where you will find the crystal clear warm waters for snorkelling, swimming and kayaking. A two week flotilla here really allows you to explore this destination and reach the further a field spots that you would miss on the one week.

    • Beautiful beaches
    • Excellent sailing conditions
    • Caribbean relaxed lifestyle
  • St Lucia Flotilla

    This exhilarating 2 week Flotilla explores the majority of the southern Windward Islands. Starting from the exquisite St Lucia, you will journey south exploring Bequia and the underwater paradise that is the Tobago Cays, before journeying on to Union Island, Mayrou, Canouan, Mustique and St Vincent. This Flotilla will provide an outstanding Caribbean adventure for more experienced sailors.

    • Amazing snorkelling spots
    • Sublime white sandy beaches
    • SoufriĆ©re Volcano & Pitons
    • Unspoilt Caribbean
    • Exhilirating Sailing Conditions
    • Stay & Sail choice