Caribbean Sailing: From Martinique to the Tobago Cays

Our sailing instructor Maren Christoffer takes us along on an all-women sailing adventure through the Caribbean. In this personal travelogue, she shares memorable moments at sea, wonderful encounters with locals and practical tips from her own experience – from navigating the waters between the islands to choosing the best places to anchor.

Fourteen days of sailing under the Caribbean sun. In spring 2026, a dream came true for our crew. Aboard a spacious catamaran, we set sail south from Martinique, snorkelled alongside sea turtles, discovered beautiful islands and met some truly unforgettable people.

From Martinique to St Lucia: Our First Days at Sea

Our journey began at Le Marin Marina in Martinique. From there, our first leg took us via Sainte-Anne in Martinique and Rodney Bay in St Lucia, before reaching the small village of Laborie.

Once we had left the shelter of Martinique behind, we experienced our first taste of the characteristic ocean swell between the Caribbean islands. With glorious sunshine and moderate winds, the women on board had the perfect opportunity to get comfortable handling a sailing catamaran.

Laborie, on the southern coast of St Lucia, was a lovely surprise, with its beautiful sandy beach and charming little streets.

Still a little sleepy, we set off again the following morning.

Bequia and Mustique: Exploring the Grenadines

Our next passage was a long one, taking us past St Vincent to Bequia, before continuing on to Mustique.

Known as the playground of the rich and famous, Mustique was the perfect place for a little exploring. The women headed off on a jeep tour around the island, admired its impressive villas and rounded off the day with a rum punch at the famous Basil's Bar.

Tobago Cays: Reaching Our Caribbean Paradise

The following day, we finally reached the destination we'd all been looking forward to: the Tobago Cays. The women had been particularly keen to go snorkelling, and we were determined to make that happen.

We sailed west of Canouan towards the Tobago Cays. With one crew member stationed at the bow, keeping a constant lookout into the water, we carefully made our way through the reefs, inch by inch.

We dropped anchor just west of Horseshoe Reef in around two metres of water. We'd barely finished the manoeuvre when a small boat approached us.

It was Willy, a local resident of Union Island, who had been watching us arrive and wanted to share a few useful tips.

We took his advice. That afternoon, we headed closer to Horseshoe Reef in the dinghy and spent some wonderful hours exploring the incredible underwater world.

Just before sunset, we moved our catamaran to a more sheltered anchorage behind the little island of Baradal. Willy had told us it was an excellent place to spot sea turtles the following day. That suited us perfectly, as we'd already planned to spend two nights in the Tobago Cays.

Sea Turtles, Snorkelling and an Unforgettable Evening

Willy's advice turned out to be spot on. We spent a peaceful night at anchor, with the catamaran barely swinging, while we could see the waves breaking over the reef and rolling into the bay beyond.

The next morning, Willy stopped by to check how we'd slept. He also invited us to a beach barbecue that evening, an invitation we were more than happy to accept.

We spent the day snorkelling, reading and enjoying good conversations in the glorious sunshine. Some of the women spotted not only the sea turtles Willy had promised, but also a few small sharks, which they wisely admired from a safe distance.

Afterwards, Willy brought us safely back to our catamaran. Tired but happy, we climbed into our bunks for a well-earned night's sleep.

We would happily have stayed in the Tobago Cays a little longer, but the following morning it was time to begin our journey north.

Wallilabou Bay: Following in the Footsteps of Pirates of the Caribbean

Our northbound route took us to Wallilabou Bay on St Vincent. The bay is famous as a filming location for Pirates of the Caribbean, particularly the memorable scene in which Jack Sparrow steps off the mast of his sinking boat and onto the jetty.

With the boat secured to a mooring buoy and an additional stern line tied ashore to the trees, we could finally relax and enjoy the evening.

Some of the women went for a walk to a nearby waterfall and enjoyed a refreshing swim. Afterwards, we all met at the bar to watch the sunset.

St Lucia: The Pitons, Rum and Local Encounters

From there, we continued north, making our way back to Rodney Bay in St Lucia, just as we had on the outward journey.

This time, we spent two nights in the bay, which is also the finishing point of the Atlantic Rally for Cruisers (ARC), and took the opportunity to explore more of the island.

We set off on a taxi tour, visiting local art workshops, admiring the famous Pitons, discovering traditional St Lucian cuisine and enjoying a tour of a rum distillery.

Our taxi driver, Eddie, was wonderful. He took his time showing us around, shared fascinating stories about his home island and made sure we had a truly memorable day. That evening, he drove us back to Rodney Bay.

Back to Martinique: Memories That Stay with Us

The following day, we returned our catamaran to the marina in Le Marin.

Looking back on our two weeks together, we'll certainly remember the beautiful places we visited. But more than anything, it's the wonderful people we met along the way, especially Willy, who made this trip so special.

More than six months later, we're still in touch with him. When he heard about the unusually hot summer in Germany, he even got in touch from Union Island to check how we were doing.

It's an encounter we'll never forget. ☺