Simpson Marine Search Yachts
13th September 2018

Explore the Caribbean: a week cruising in the Windwards Islands

Once you have explored Asia with our many yacht charter options, let us take you to the Caribbean for a unique blend of local flavours and total relaxation in one of the most stress-free and easy-going destinations in the world. Welcome to the beautiful palm fringed Windward Islands.

Recently launched and ready for her first charters the luxury catamaran JOY, a Lagoon Seventy 7, is now available to take bookings in the Caribbean. Here is a sample one-week itinerary for from St. Lucia to St. Vincent & the Grenadines, which can be amended or extended depending on your preferences.


Day 0

Fly into St Lucia, either stay in a hotel for the night or check-in directly to the boat if your arrival time to St. Lucia is in the morning.

ST Lucia


Day 1

Check-in to the boat at 12:00 Noon.

Captain CJ will conduct a safety and chart briefing and share the onboard etiquettes about dos and don’ts. JOY will then sail south along the flank of beautiful St. Lucia, passing the broad mouth of Choc Bay and continuing on until the towering Pitons emerge on the horizon. Your first overnight mooring is one of the most beautiful in St. Lucia, with sparkling Pitons Bay basking in the shadow of the island’s two dormant volcanoes. Lounge on the beach or hike into the mountains to discover unmissable views.

Pitons Bay


Day 2

Continue cruising around St. Lucia and visit Marigot Bay. Marigot Bay is one of the most beautiful spots on St. Lucia and, better still, it’s also home to some of the island’s finest restaurants. Nestled in a scenic valley, Marigot Bay is a sinuous inlet of sapphire ocean and emerald palm. Moor here to try some traditional St. Lucian fare, including saltfish and buoyon stew, or hike into the forested hills to the north of the bay for incredible views across the island.

Marigot Bay


Day 3

Set sail to St. Vincent in the early morning after breakfast, arriving around noon and going through immigration clearance. Once everything is settled enjoy a nice downwind sail down to Bequia Island where we will anchor by Price Margaret Beach. Here you have a few options to enjoy a nice late afternoon, spent either visiting the old town of Port Elizabeth or enjoying the pristine beach with the famous Jack’s Beach Bar to mix up a cocktail or two. Dinner can be served onboard or there are a few well known restaurants in town which can be booked.

Bequia Island


Day 4

After breakfast some snorkelling or diving on Devi’s Table Reef, a very well-known dive site in the area with lots of fish life, is on offer. You will then enjoy a nice sail to the other side of Bequia to anchor off of Petite Nevis, a small deserted Island that use to be an old whaling station. This will only be a ‘pit stop’ where lunch will be served followed by some island explorations or a swim. The yacht will then continue to our next stop – Mustique Island. This is a private island where excursions can be organised on golf carts to show the guests the beautiful beaches around the island. There are very well know restaurants or bars to visit. If you ever hoped to meet Mick Jagger or the Queen then this will be the Island for you as they all have houses here.

Mustique Island


Day 5

Set sail straight after breakfast , covering the largest distance of the week, to reach one of the most amazing stops of the trip, the Tobago Cays. The two to three hour sail is well worth it to relax and take in the incredible sights of the Cays, famous for its shallow turquoise water and reefs. Spend the rest of the day exploring this area either by dinghy or snorkelling. There is an marine reserve where you can swim in shallow water up close to green sea turtles, which are rather tame and great to snap a special photo. Lunch will be served onboard followed by a lazy afternoon of either ‘chillaxing’ onboard, snorkeling around the reefs or visiting Petit Tabac Island where the mighty Jack Sparrow was left to die in Pirates of the Caribbean. RUM ISLAND! For dinner the locals offer a lobster beach barbecue on one of the small islands, which we can organise, or they are also more than happy to sell us some fresh lobsters for Chef Desree to prepare.

Tobago Cays


Day 6

The morning will be free and easy to enjoy with only a small distance to cover for the day. Anchor up by 11 to sail to Palm Island resort, which is perfect as a lunch stop, either onboard or at the beach resort. If conditions are right we can anchor close enough for active guests to swim to shore. For the less brave there is also a dock where we can drop off to the island, which is small and with a nice resort. After lunch set sail to our most Southern stop, Petit Saint Vincent, that has a stunning beach and reef that protects it. Anchor near the reef to enjoy the view and do some snorkelling. Closer to sunset we will move into the protected bay on the south of the island. Again there is a lovely little beach bar to enjoy the view of the sun setting behind JOY followed by dinner being served onboard.

Young Island

Day 7

Start the return sail back to St. Vincent through Canouan and Union Island, Mustique, and Bequia; you could visit any of the islands mentioned above but go to different anchorage spots. Other options include cruising around Petite Martinique and Carriacou, before sailing straight back to St. Vincent overnight.

Union Island


Day 8

Enjoy a final brunch, prepared by the crew, before checking out at 12:00 Noon from St. Vincent.

Convinced or wanting more? Let us know at [email protected]


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