Stars at Sea: Celebrities Cruising the Caribbean This Winter
By Publisher Ray Carmen
As winter tightens its grip on Europe and North America, the world’s most famous names are doing what they do best — escaping to the sun-drenched sanctuary of the Caribbean aboard glittering superyachts. From discreet family retreats to headline-grabbing floating palaces, this season’s celebrity yacht traffic confirms one thing: the Caribbean remains the ultimate winter playground for the global elite.
Here’s a look at the stars most closely linked with Caribbean cruising this winter, and the islands drawing them in.
Floyd Mayweather — The High-Octane Showstopper
Never one to do things quietly, Floyd Mayweather is synonymous with megayacht excess. During Caribbean winters, his yachts are frequently spotted around St Barths, Antigua, and Anguilla, hosting champagne-fuelled parties and attracting A-list guests.
Caribbean vibe: Big yachts, bigger energy
Why it works: Privacy, prestige, and ports that welcome spectacle
Shakira — Caribbean Calm with Latin Soul
Shakira has long favoured warm waters and understated elegance. Her winter cruising style leans toward Antigua, St Lucia, and quieter anchorages, blending Caribbean rhythms with family-focused escapes.
Caribbean vibe: Serene bays and cultural depth
Why it works: Low-key luxury far from paparazzi chaos
Lionel Messi — Family First in Paradise
Messi’s yacht is designed for comfort rather than flash, making the British Virgin Islands an ideal base. Calm seas, short island hops, and world-class marinas make the BVI a favourite for football royalty seeking downtime.
Caribbean vibe: Relaxed, exclusive, and intimate
Why it works: Perfect balance of privacy and natural beauty
Madonna — Iconic Style Meets Island Grace
A long-time lover of island life, Madonna is frequently linked with Turks & Caicos, where wide beaches and crystal waters offer space to unwind away from the spotlight.
Caribbean vibe: Effortless glamour
Why it works: Discreet luxury with room to breathe
John Travolta — Classic Hollywood, Caribbean Edition
Known for his love of aviation and travel, Travolta often pairs Caribbean flights with sea escapes. St Martin and Anguilla remain popular stops for a refined, old-school Hollywood retreat.
Caribbean vibe: Timeless and elegant
Why it works: Seamless air-sea connections and relaxed sophistication
The Celebrity Yacht Hotspots This Winter
Across the region, a few destinations continue to dominate the celebrity superyacht map:
St Barths – The undisputed winter capital of megayachts
Antigua – Sailing heritage with modern marina luxury
British Virgin Islands – Island-hopping perfection
St Lucia – Dramatic scenery and privacy
Turks & Caicos – Calm waters, wide beaches, elite discretion
Final Word
From pop icons to sporting legends, the Caribbean’s winter superyacht season proves that luxury here isn’t just about scale — it’s about atmosphere, freedom, and timeless allure. As the yachts glide between turquoise bays and sunset harbours, the region once again earns its crown as the world’s most glamorous winter escape.
Caribbean World Magazine will be watching the waves.
Suggested Feature Images (Saved with the Article)
Hero Image: A sleek superyacht anchored off St Barths at golden hour, champagne on deck
Lifestyle Image: A-list silhouettes relaxing on a yacht sundeck with turquoise Caribbean waters
Destination Image: Aerial shot of yachts moored in the British Virgin Islands
Detail Shot: Close-up of a luxury yacht’s aft deck — sun loungers, crystal glasses, Caribbean light
