Holidays afloat aren’t just for Richard Branson and co, finds Aby Dunsby.
Whether it’s a majestic yacht or a modest sailboat, there’s something wonderfully cinematic about watching the sunset on open water, while the breeze plays with your hair and you sip on a mojito.
And, contrary to the stereotypes, holidaying aboard doesn’t have to cost the earth.
“Sailing is actually quite flexible and accessible, meaning it can be just as appealing to families as it is to couples, or complete beginners as it is to pros,” says Sebastian Hirst, UK sales and service manager at specialist operator Sunsail.
With a dreamlike beach around every corner, the sun-splashed islands of the Caribbean are a great place to discover by boat, allowing clients to explore its sparkling waters with access to secret spots that would be difficult to reach by land or on board a cruise ship.
Whether clients want to leave all the hard work to a skipper or learn the ropes themselves, we round up the best sailing holidays in the Caribbean to suit almost any budget.
Save: land and sea
Clients who can’t afford to charter a giant yacht and spend a week swigging champagne on the sun deck can still have fun too on a tighter budget.
Renting a sailing boat means key holiday costs, including food and accommodation, are usually taken care of, so it need not be any more expensive than staying in a hotel –– especially for clients travelling in a group, as costs are split.
Those who don’t fancy spending an entire holiday on the water can plump for a hotel, then dip their toe into sailing with a purse-friendly excursion or two. Barbados hotel Port Ferdinand offers guests the chance to hop aboard its luxury Cool Runnings Lagoon 500 Catamaran for £138 per person for a five-hour cruise, including a premium open bar, a lunch cooked by the onboard chef, and plenty of opportunities to stop off and snorkel.
Guests staying at the St James Club & Villas in Antigua can take a four-hour catamaran tour with Captain Anderson and his crew to Green Island ($92) or, if they can rustle up nine extra mates or family members, they can charter the vessel for the whole day for about £75 each, with a picnic lunch, snacks and fishing tackle included.
A day trip need not revolve entirely around sailing either: for example, clients holidaying in Mexico can team sailing with a cultural excursion to Isla Mujeres. The catamaran crew will stop to allow clients to swim and snorkel in the coral-lined waters, before dropping anchor to explore the island’s colourful streets and boutiques. AMResorts’ in-house excursion provider Amstar has a full-day Isla Mujeres tour, from $82.
For clients seeking the know-how and the freedom to man a boat themselves, there’s Beaches’ new introductory sailing programme, which is available at Beaches’ Turks & Caicos, Negril and Ocho Rios resorts.
The programme has been created with the American Sailing Association and is designed to introduce adults and children above eight years of age to the sport in a fun way, with the skills they pick up contributing towards an ASA Sailing Certification. Clients can take the four two-hour sessions alongside other resort guests for $150, while rustling up a group of four works out cheaper at $500 in total.
Spend: group together
Sailing newbies can learn their port from their starboard at Nonsuch Bay in Antigua, which benefits from ideal sailing conditions, with warm trade winds and two square miles of sheltered waters.
The resort’s sailing school puts on a programme that incorporates group tuition, unlimited use of the sailing dinghies and informal racing for adults and children aged eight and above (the sailing programme starts from £280 per week and can be booked through Carrier).The BodyHoliday in Saint Lucia also offers various courses for uninitiated sailors, including a complimentary Intro to Sailing course, or private two‑hour sailing lessons, for which guests pay a $150 supplement. If they’ve learned the ropes but still need support, clients should consider a flotilla holiday, where they will sail in the day while expert crews guide them to the best locations and are on hand to help with moorings. Sunsail offers one and two-week itineraries to Tortola in the British Virgin Islands, a location often dubbed a sailor’s paradise (from £1,207 excluding flights).
“The beautiful beaches, turquoise waters and sunny skies of the BVI make for the perfect sailing conditions,” says Dave Hunter, sailing operations manager at G Adventures, which also offers a sailing holiday in the islands. “A lot of our BVI travellers tend to be young professionals who are either travelling solo or with a friend or partner but still want to meet like‑minded travellers to sail with.”
The evenings on a BVI flotilla holiday are particularly sociable, as clients will get to chat to others from their fleet over cocktails and food, and make pit stops to party.
Intrepid Travel’s BVI trip is its most popular sailing holiday, and the small‑group format is perfect for those who want to explore somewhere new but don’t have a large enough group of family and friends to fill a yacht themselves.
“The BVI are often thought of as only within reach of the super-wealthy, but sailing is a great-value option,” says Intrepid’s head of business development Daniel Pawlyn.
“Clients can be as active as they want – there are great hiking trails on Gorda Sound and plenty of chances for swimming and snorkelling – or just sit back and bask in the sunshine.”
Intrepid’s BVI Sailing Adventure starts from £1,148, excluding flights.
As with most of the Caribbean, the views under the sea are just as impressive, and clients looking to inject further adventure into their holiday can explore the deep with a diving excursion. Various Caribbean hotels offer this, as does Sunsail, which has teamed up with Sail Caribbean Divers so holidaymakers can be picked up from their boat and guided towards shipwrecks, coral reefs and rainbow-coloured shoals of tropical fish.
Splurge: splash out
If clients are new to sailing and are happy to splash the cash, the Bitter End Yacht Club in the British Virgin Islands offers various programmes to those staying there.
The price of its Level 101 course is included in a seven-night stay, while other certifications require a surcharge, such as the Basic Keelboat course, which is $800 and can be booked through Western & Oriental.
Kids aged 12 and above can also get involved with a junior sailing programme, during which they’ll learn basic boat handling, terminology, rigging and sail trim – and make new friends in the process (from $150 for three hours; runs from April to August).
ITC Luxury Travel recommends Peter Island Resort & Spa, where clients can add a Learn-To-Sail package to their stay. It includes three days of sailing instruction with Swain Sailing School, culminating in clients taking the US Sailing Association’s Basic Keelboat certification exam. Rates for the Learn To Sail package start at $4,700 for seven nights in an Ocean View Room for two.
If learning on holiday sounds too much like hard work, clients can kick back and relax while an experienced skipper does the sailing. Those visiting the Caribbean for the first time will find a skipper is a particularly useful addition as they often double up as tour guide, helping to pick out the best spots and must-visit locations. The resort of Petit St Vincent in The Grenadines offers guests the chance to charter a skippered boat to explore the nearby islands and reefs for a day.
Port Ferdinand also offers day charters on Wicked Wahoo, a 41‑foot luxury fishing boat that can carry 10 people. For clients wanting all‑out extravagance, the boat can be chartered for a week for $7,875.
Lusso offers seven nights at Port Ferdinand Marina & Luxury Residences from £1,585, based on four sharing a two-bedroom Luxury Harbourside Villa on a room-only basis, including flights with Virgin Atlantic and transfers.
Sunsail offers a week’s charter in the British Virgin Islands on a Sunsail 33i two‑cabin monohull yacht from £1,005 per person based on four sharing. Price includes a fully equipped cruising yacht, snorkelling equipment and a tank of fuel. Flights from Heathrow with British Airways and connecting flights cost from £700 including transfers.
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