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Caribbean Cruising: Anchors Away

Updated: Nov 8, 2019

The perfect winter escape, the Caribbean is a piece of paradise tempting yacht owners and charter guests with its lush tropical greenery, beautiful beaches, vibrant festivals or dropping anchor at a quiet bay. Nautical tourism is an economic float for many Caribbean communities, bolstered by the seasonal migration of yachts between the Mediterranean and the US East Coast and Caribbean.

First up, Fort Lauderdale International Boat Show (FLIBS) is a starting point before yachts dive into the heart of the Caribbean season. The show welcomes around 3 billion dollars’ worth of luxury yachts from 30 October to 3 November, which will be displayed along the show's floating quays and iconic waterways. The Antigua Charter Yacht Show is also highly anticipated, bringing the world of yachting to Nelson’s Dockyard in Antigua in December.

The Caribbean islands offer picturesque anchorages with virgin white sand beaches, turquoise waters for diving or snorkelling and colonial towns for day trips ashore. Most of all, it is the Caribbean people who keep charter guests returning – laidback demeanours demonstrating rich and characterful traditions that combine food, crafts and culture.

From romantic retreats to remote coastlines, we explore a few of the places in demand for VIP entertainment at Caribbean’s top yacht charter destinations.


A favourite for sailing boats, Antigua is a popular yacht charter destination for its annual regattas, such as Antigua Sailing Week. Nelson’s Dockyard at English Harbour and Falmouth Harbour pulse with yachting activity, while remnants of colonial times exist including old sugar mills. Natural attractions include Darkwood Beach, Cades Reef, Great Bird Island and the Pillars of Hercules.


Close enough to add onto a US-based yacht charter itinerary, the Bahamas are made up of over 700 islands attracting vessels for a warm year-round climate, luxury resorts, top golf courses, nightlife and for water sports. Don’t miss discovering some highlights of the Exumas, Abacos or Harbour Island – notably, the swimming pigs, the underwater cave system of Thunderball Grotto and Pink Sand Beach.


Visit World Heritage-listed Bridgetown, a well-preserved town with British colonial influences. Swim at Crane Beach, play golf at Sandy Lane or join a subterranean tour of Harrison’s Cave. Don’t miss taking your tender for a decadent meal at The Cliff before returning for a chic yacht party at sunset.


Not technically located in the Caribbean, Bermuda is often classed with Caribbean islands though sits much further north. With over 200 square miles of reef, Bermuda has some stunning places for snorkelling and diving. Intensely colourful, it’s clear to see why people rent a yacht in Bermuda! Once ashore, explore the disused forts, enjoy a waterfront meal in the pastel-coloured colonial buildings in Hamilton or stroll around St George’s Harbour.


St Barths (St Barts) is world-famous as a luxury yacht charter destination with a pleasant mix of high-end shopping, stunning beaches and gourmet restaurants. Savour the menu at the François Plantation restaurant at Villa Marie, go shopping in Gustavia or join the action each year at St Barths Bucket Regatta. Although the weather is warm year-round, the Caribbean primary high season is December to April making St Barths an ideal option for a Christmas or New Year trip, complete with bespoke entertainment and the finest Champagne!


Known for volcanic landscapes, rainforests and a variety of good beaches, St Kitts & Nevis is a wonderful blend of heritage and natural beauty. Sample craft cocktails in the luxury surrounds of Christophe Harbour, explore Brimstone Hill Fortress National Park or enjoy the view at Dieppe Bay where the Caribbean Sea meets the Atlantic Ocean. David Smith, Booking Manager for Tony Steward, affirms that Tony is available to perform close-up magic at events over the Christmas and New Year period in the Caribbean.

“The opportunity to have Tony create something special for a private event in the Caribbean is a unique glimpse into the worldwide allure of magic. Combining Tony’s thirty-plus years of performing to create world-class entertainment in the second most popular yacht charter region is memorable in itself.”


Located in the southern island group of the Lesser Antilles, the Windward Islands, St Lucia is the epitome of a postcard-perfect location with its lush vegetation and beautiful sands set against the dramatic Piton Mountains. Indulge in time ashore at a relaxing spa or sip cocktails with a magical view.

Relaxing on yacht charter should be an important factor, hence why Tony is a full member of Equity, a union of over 45,000 performers and creative practitioners. The cover allows peace of mind against liabilities with specific insurances designed to cover him in his line of work.


From sailing boats to superyachts. St Maarten welcomes visitors with a French and Dutch vibe. The award-winning Yacht Club at Isle de Sol at Simpson Bay is a major marina, and a great introduction to an island with natural and cultural attractions.


With good shopping, nightlife and upscale restaurants, St Thomas is a drawcard for large yachts. Diving is accessible in these waters with caves, tunnels and wrecks home to hundreds of types of fish and coral – Coki Beach and Kennedy Barge being a couple of the best known. There’s plenty to do ashore or continue your charter experience with visits to St John, Tortola or Virgin Gorda.

M/Y Rising Sun in St. Thomas


Ideal for a relaxing yacht charter, St Vincent and the Grenadines have a number of palm-treed lined islands heady with the scent of tropical flowers and delicious cuisine. Roam wild banana plantations, go scuba diving amongst shipwrecks, lounge on the sand at Princess Margaret Beach in Bequia or indulge like a star at coveted Mustique with a private performance by Tony.

No matter what nature throws at it, the Caribbean is the perfect getaway to enjoy cruising, connect with your family or celebrate special occasions. Tony Stewards fee includes a dedicated account manager 24/7 to provide the highest level of customer service whilst yacht owners and guests set their sights on new horizons.



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