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Timeshare: Same Concept, Totally Different Experience With TradeWinds Cruise Club
January 8, 2009 by Fractional Property Ownership, Timeshare & Luxury Travel Magazine · 3 Comments
The timeshare concept in its barest bones form is relatively simple, you vacation in various resorts in different locations, but one company offers a different experience altogether – a week onboard a private catamaran complete with crew which you can either fill with family and friends or share with other timeshare owners.
A Little Bit Of History
TradeWinds Cruise Club was founded in 1998 by Magnus & Edith Lewin and Joe Costello and Carina Ludvigson, who were all employees of the hospitality brand Pestana Hotels & Resorts at the time working in the TradeWinds charter left from Bobby’s Marina Phillipsburg, St. Martin in January 1999. Later that year Joe and Carina arrived to share and ultimately take over charter responsibilities.

That first year saw TradeWinds operate their one boat in St. Martin between January and April before heading south and chartering in the Grenadines through the summer then returning north again to be ready to charter in St. Martin once more from November.
Ten Years Later
After hearing about this different kind of timeshare experience we decided that Sharon & I (owners of Perspective International Ltd) should check this one out ourselves, so on July 19th we flew to Bequia (pronounced Beck-Way) in the Grenadines to join “Jo”, one of the 19 TradeWinds Catamarans belonging to TradeWinds that sail throughout the Caribbean, Europe and Central America.
Being the insatiable workaholics that we are, at first we liked the idea, but then it dawned on us that a little boat in the middle of the Caribbean Sea probably wouldn’t have Wi-Fi and not being connected for a week would be an experience in itself…and yet we turned up with two laptops, internet anywhere mobile connection service and our BlackBerry’s just in case.
When you first think of cruising the Caribbean you think of a large ship, fine dining, entertainment, shopping and land excursions in locations such as St. Lucia, Sint. Maarten, Antigua and so on. You don’t think of a 10 berth catamaran, your own crew and chef, just eights guests, no fixed itinerary, dinner with the captain every night, swimming with turtles, deserted islands and beaches worthy of films like Pirates of The Caribbean, sleeping under the stars and drinking cocktails in the water as the sun sets These are just a few of the attractions that the TradeWinds experience offers to members and guests.
Getting There
To get to Bequia, the easiest route is to fly into Barbados and take an SVG flight down to the islands, although another way is to fly into St. Vincent and then take a ferry. The SVG flights are an interesting way to travel, operating 8 and 19 passenger aircraft they fly down to The Grenadines area, from Barbados this takes about 40 minutes and then you hop from one main island to the next spending an average of 10 minutes in the air each time and 5 minutes on the ground to drop some passengers off and pick up others. During this latter part of the flight the aircraft flies at just 1,000 feet giving fantastic views of the islands and coral reefs below.
James F Mitchell airport at Bequia is small and quirky, one room for arrivals, another for departures; a single immigration desk and a moving baggage claim belt that despite being only approximately 7 metres long, still delivers your baggage from a hole in the outside wall to the other end for you to collect. Having given our flight details to the TradeWinds customer services department prior to travel there was transport waiting for us and as there are only two flights a day from Barbados, we then found that 75% of our fellow guests on our boat were on our flight too.
After a 15 minute drive to the other side of the island, we arrive at the TradeWinds base and are checked in before relaxing in the bar adjacent to the dock where two of the three catamarans present were being prepared for their imminent voyage. Whilst in the bar there was time to begin to get to know our soon to be fellow cruisers and be sized up and kitted out with masks, snorkels and flippers.
Setting Sail
The week runs from Saturday to Saturday and we set sail shortly after 5pm, but the first night is spent just off dock in the bay which is designed to get you used to being on the water and for you to be introduced gently to the whole experience of being on a catamaran, which is perfect for those who have never travelled like this before.
Onboard Accommodation
We were sailing on a Privilege 51 Catamaran that has just four guest cabins and one crew cabin making a total of only ten people onboard giving a real feeling of space on what essentially is a small sailing vessel. After relaxing onboard with a few cocktails the Captain takes each pair of guests individually and shows them the cabin that will be home for the next seven nights.

There is exceptional use of space – the shower is no smaller than most hotel rooms, there is a separate toilet and washroom and then there is an elevated double bed, dressing table, mirror and wardrobe. After being left to settle in, you then realise that amongst all areas except the shower there are countless storage chests, cupboards and draws and as the couple with the most luggage, even we found space for all of it with room to spare. The bed is comfortable and spacious with an overhead fan and light switches for convenience as well as hatches to the outer deck to benefit from the cool evening breeze. All in all, a very clever use of space made for a comfortable stay onboard.
The Crew
The Captain and First Mate are the entirety of the crew onboard and are typically husband and wife who live full time on the boat. Our crew were Geoff and Anna, an early 30s / late 20s married couple who worked together seamlessly throughout the week. Captain Geoff from Scotland and First Mate Anna from USA have worked and travelled extensively gaining superb knowledge of many sailing destinations, sailing and with Geoff being a naturalist he could also name almost any fish or bird just by the description we would give after briefly seeing something fly above the boat or whilst snorkelling in the sea.
Tailor-Made Itinerary
After being shown around our rooms on the first evening it was back on deck for drinks and evening meal. Then Geoff began to ask everyone if there was anything in particular anyone wanted to do during the week, such as diving, snorkelling, hiking etc… and continued to explain that apart from a couple of main stops, the rest of the itinerary can be altered to cater for guests’ preferences, changes in weather, specific places of interest and so on, but with a boat full of people who had never been to the Grenadines before we left it up to the Captain to just show us the best places.
Later in the week as we learned more about membership with TradeWinds we were told that a popular trend is for members to charter the whole catamaran and take friends or family onboard. This can be done in a new location of course, but many return to where they first experienced the TradeWinds Cruise and do it again, but with their own itinerary and schedule in mind, visiting different islands and customizing the experience to their preferred pastimes whatever they may be.
All-Inclusive
The First Mate Anna was responsible for all of the culinary delights onboard which covered breakfast, lunch and dinner and Captain Geoff was the barman. The first evening set the standard for the week with a scrumptious Caribbean style King Prawn Curry with roasted Pineapple as dessert, plus wine, beer or anything else you wanted from the very well stocked onboard bar.
Throughout the week breakfasts were a combination of cereals, fresh fruit, toast, bagels, cheeses, bacon, juices, tea and coffee. Lunches were a mixture of hot and cold dishes including meats, fish, salads and more, but the evening meals were the real feasts. Each day surprised us with yet another impressive restaurant worthy dish made onboard by the First Mate in the spatially challenged galley or cooked on the grill / BBQ by the Captain, especially when it’s the catch of the day. All dietary requirements are also catered for by notifying customer services in advance.
Alcoholic drinks, soft drinks and water were always available to just help yourself to and sunset was usually celebrated with a different cocktail each day made by the Captain, served either onboard, on the beach or even in the water depending on where we were.
Also included are a some water sports (depending on location), all snorkelling gear, an ocean kayak, swimming aids and more, with scuba equipment also available for hire by certified divers at $75 per dive. TradeWinds Members dive free.
On two evenings there is the opportunity to eat in restaurants onshore to soak up some of the local atmosphere. This is not included in the all-inclusive package but is great fun!
Idylic Islands
Unlike the larger tourist driven islands of the Caribbean, most of what you see in the Grenadines is unspoilt paradise and as we travelled from day to day each spot was unique and offered a different twist on Caribbean life, keeping the whole journey interesting and inspiring. Some of the islands we visited were as follows:
Bequia
The largest of St Vincent’s Grenadines, this island is just seven square miles. Isolated enough to remain unspoilt and yet lively enough to be entertaining it offers a unique blend of old and new. TradeWinds’ base lies in Admiralty Bay at the town of Port Elizabeth which has numerous bars, restaurants and shops to explore before and after the cruise.
When sailing out of Admiralty Bay and we saw the Moonhole. The Moonhole is a collection of prehistoric looking homes carved from the living rock by the late Tom Johnson. He began his stone-age venture in 1961. The original one was built for himself in the natural arch called the Moonhole. He then continued to build for his family and friends and now there are over 20 homes. They have no electricity and only cushions and rattans. Whalebones from Petit Nevis have been used as decorative motifs.
Each room only has 3 walls so that lizards and birds can travel freely through – just another person’s take on paradise in the Caribbean.
Mustique
Mustique is the second largest of St Vincent’s Grenadines being 3 miles long and 2 miles wide. It was given its name by the French who found it swarming with mosquitoes – Moustique. Today it is a privately owned island that has been developed as an area for holiday homes for the wealthy. There are only about 90 homes on the island plus one hotel and a guest house. Each house lies in its own spacious grounds either nestled in the rolling grassy hills or on secluded beaches.

Famous home owners on the island include Mick Jagger, David Bowie, Beyonce, Raquel Welch, Brian Adams, Tommy Hilfiger and Shania Twain. On Britannia Bay you will find the most famous bar in the Caribbean, Basil’s Beach Bar, built on stilts off the beach with the water lapping underneath. Everyone gathers here to watch the sunset and sip cocktails like Rum Punch and listen to the house band. The Cotton House is the only hotel on the island and was constructed from the ruins of an 18th century coral warehouse and sugar mill. There is also an abundance of wild turtles on the island and a giant monument to celebrate their love of breeding on their own paradise island.
Tobago Cays
Tobago Cays are made up of a small group of deserted islands protected from the sea by a Horseshoe reef. Here you will find some of the most pristine waters in the Caribbean. The reef and water are a kaleidoscope of colours – blue, turquoise, gold and green. Because of its beauty it was purchased by St Vincent in 1988 and designated a National Marine Park. The deserted islands that make up the Tobago Cays are Petit Rameau, Petit Bateau, Barabel, Petit Tobac and Jamesby. The Horseshoe Reef is made up of coral walls ranging from 30-65 feet. Visibility of approx 100 feet make it an amazing place to snorkel and scuba dive. Petit Tobac was chosen for the scene in The Pirates of the Caribbean where Johnny Depp’s rum stash goes up in flames.
Palm Island
This island was originally called Prune Island and was a mosquito infested swamp. It was a 135 acre site with four low hills and surrounded by white sandy beaches and a coral reef. It was leased in 1966 by John and Mary Caldwell who fell in love with it and changed its name to Palm Island. They built a small hotel and planted lots of palm trees. The hotel was bought and upgraded and today is a first class resort with many lovely thatched roof villas and rooms.
Union Island
Union Island stands out from a long way off due to its mountainous outline. The main harbour is Clifton, which is protected by a reef. The water around the reef is a brilliant turquoise-green. Clifton is vibrant, cosmopolitan and full of local character.
Union has become the party centre of the Grenadines due to the selection of entertainment and great restaurants. One of the most famous is The West Indies Restaurant which is on the waterfront. The
atmosphere is elegant / casual and the cuisine a blend of French and Creole.
Petit St Vincent
PSV is approx 113 acres in size, surrounded by 2 miles of sandy beaches, and is the most southerly of the Grenadines. In the late 50s Haze Richardson and Doug Terman quit the Air Force and chartered a yacht to the Caribbean. One of their clients onboard the charter, Willis Nichols thought it would be fun to buy an Island and build a hotel so he did. Haze and Richard built and started the hotel which we now know as Petit St Vincent Resort. Haze tried to find a manager once it was finished but was unable to so he ended up staying and now owns the resort. It is a very quiet and exclusive resort with each guest staying in a secluded stone cottage. When a guest needs something like room service a flag is raised up the flagpole and a mini-moke arrives to attend to his needs.
Mayreau
Mayreau is approx 700 acres and is the smallest inhabited island of the Grenadines with a population of only 200 inhabitants. Salt Whistle Bay is a beautiful half-moon shaped beach and the Salt Whistle Bay Resort is tucked away hidden behind it in the trees. It is a great place to have dinner. Each dining table is built in the woodland and the resort is made of stone with a thatched roof. A steep road runs from Salt Whistle Bay to the Old Wall Village at the top of the hill. Once you reach the top there is an ancient church, a school and a communications building. It offers amazing views of neighbouring islands.
Mopion
The perfect destination for a picnic. It is a sandbar surrounded by coral reef with a solitary thatched umbrella in the middle. A classic photographic opportunity.
Happy Island
Is a tiny island big enough only for a small bar that sits in the outer harbour of Clifton, Union Island. It was built by a local man who built the island on the reef by sailing out and dropping thousands of conch shells. Once the island was finished he built his bar and then declared independence!
Marine Life
The Grenadines is arguably the best snorkelling location we’ve been to, with the Tobago Cays topping the bill for colourful coral and vibrant marine life which included Parrot Fish, Surgeon Fish, Trigger Fish, Porcupine Fish, Trunk Fish, Butterfly Fish, Angel Fish, Trumpet Fish, Grouper, Squid and Octopus.
Snorkelling became the favourite pastime of all the guests with most of us spending at least an hour each day in the water, enjoying every different location visited. Our personal favourite for fish was snorkelling off Petit Tabac but the highlight was swimming with Green, Hawksbill and Loggerhead Turtles and Spotted Eagle Rays and Southern Sting Rays at 6am as they ate near the shore of a small island before heading out to sea. Starting at daybreak ensured we were the only group in the water which made the experience even more special.
On The Boat
When not in the water, on a beach or in a boutique shop, there was plenty of time to relax on the boat When moving from one location to another, guests could choose to sunbathe or get involved with the sailing of the boat, including turns at the helm, raising and lowering the sails and learning how to anchor the boat close to shore without damaging the reefs. On some nights a few guests also chose to take advantage of the clear skies and low light pollution and experience sleeping on deck under a blanket of stars.
Island Shopping
There are no shopping malls on this trip, but Mustique and Palm Island have a boutique shop in each resort to browse in and Union Island where the boat takes on more supplies has a small harbour town to explore. Some beaches also have local trinkets and t-shirts to buy, plus on a couple of mornings you’ll get a speedboat will arrive at the back of the catamaran which will be selling either jewellery or artwork and crafts which are nice for souvenirs and presents.
Comments From Some Of Our Fellow Guests:
Mary – The excitement of the sea when riding in the pulpit in the bow of the boat with swells of 8-10 feet. It is the best seat in the house. Every day is an awesome adventure, exploring an island paradise. Meeting the local island children was a delightful experience and food and dear new friends.
Steve – Wind in your sails and wind in your hair (Well maybe not the hair thing) Snorkeling got better and better. Experiencing remote and fascinating islands. Great friends to share with make adventures wonderful.
Jana & David – Anna (1st Mate) and Geoff (captain) their enthusiasm, knowledge and professionalism have made this an experience beyond expectation. The Grenadines and Cays are absolutely as beautiful as my travel guide, book or postcard illustrate. I so enjoyed Geoff’s knowledge of the sea, the boat, wildlife, fish, coral etc… Anna’s gracious ways, her wonderful meals and amazing presentation left me in awe on a daily basis. This is the first time we have ever taken this kind of a vacation and hope that it won’t be the last – it’s an experience of a lifetime. I cannot say enough positive things about TradeWinds and thank two amazing people.
Judy & Jim – We came to experience living on board a boat and to enjoy the sea, wildlife and islands. We also bought because we love love love it and want to spend many more days at sea.
Our Opinion
One of the most relaxing and active holidays we’ve ever had all rolled into one. Simply the best type of holiday for workaholics – our laptops never saw the light of day.
The unique experience offered by TradeWinds is testament to the diversity of the timeshare product, where members don’t just get to “stay” they get to “interact” with their ownership, whether it be simply deciding on the itinerary or participating in the sailing of the boat. Now with several worldwide locations to choose from we would wholly recommend anyone that has enjoyed reading this article to consider experiencing it themselves in the very near future.
We also look forward to bringing you more information on yet more locations soon to be added into the TradeWinds Cruise Club such as Brazil which will be a combined cruise and land stay destination, cruises in the South Pacific and new locations in the Greek Islands.
TradeWinds Membership
Owning at TradeWinds differs slightly from typical timeshare properties in the sense that membership is for 12 years (based on the luxury life expectancy of a catamaran) and in the number of weeks / cabins you expect to use within that time period. Then you could use one week to join a cruise with other owners or use 4 weeks at the same time and take all four cabins for a private charter for them, their family and friends.
There are varying levels of membership too catering for the occasional cruiser up to the cruise addict. But it doesn’t stop at cruises – there’s TradeWinds by the Sea, a little boutique resort above the marina in Bequia where members can stay before or after their cruise and Belize Villas in Placencia, right on the water.
In addition TradeWinds Cruise Club, Bequia is an RCI Gold Crown resort and offers exchange opportunities to more than 3,700 other resorts around the world.
Plus there is TradeWinds Associates; a collection of carefully selected resorts throughout Europe, South America, Asia and the Indian sub-continent which have direct associations with TradeWinds for its members to exchange to, including high quality resorts that are not affiliated to any other exchange company, but all selected and sampled by TradeWinds before being offered to members.
More Information
For more information on membership with TradeWinds Cruise Club or the opportunity to experience one of their cruises contact:
info@tradewindscruiseclub.com
RCI Members – you can also contact your RCI representative for details on how to exchange into TradeWinds Cruise Club.
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