Another nice paddle for intermediate to expert paddlers (depending on wind) is from Maho Beach to Whisling Cay. Whisling Cay is of interest for 2 things: great snorkeling and the old customs / guard house.


The paddle is not far and the level of difficulty depends on the wind. On my carbon raceboard it takes me about 10-15 minutes to get out and 20 minutes to get back on a day with 15-18 knots of wind. It will take longer on an Allround Baoard. On days with little wind (less than 10 knots) this paddle is quite easy, I had athletic students who had a lesson with me and did it on their 3rd day of paddlebaording. On a day with 20-30knots of wind this paddle can be exhausting even for experienced paddlers. Make sure to pack water and some snacks (e.g. energy bars) and take a phone in a waterproof case and ideally a waterproof VHF radio (which you can rent from us). Do not paddle out there alone and always let someone know where you are going and when you expect to be back.


You might also want to take your snorkeling gear if you want to snorkel there. Always check the wind forecast here. We created a custom Windguru spot for Whisling Cay. Do not be fooled by how calm it is inside the bay, like on the picture below it was very peaceful inside the bay but quite windy on the way back. Usually the wind is less in the early morning, then picks up lunchtime / afternoon and dies down again before sunset. The prevailing wind direction is from the East. Sometimes a little SE, sometimes a little NE, NE means you will have headwind coming back. The paddle out will feel easier. Make sure to turn around and test how going back feels somewhere in between. The wind is usually manageable until the last lined of moored boats, after that it will be harder. You need to paddle with the right technique using the weight of your upper body to push the paddle down as opposed to only the arms.

Starting your Paddle at Maho Bay


Take the North Shore Road past Hawksnest, Trunk, Peter Bay, Cinnamon until after some switchbacks the road gets really close to the water. There is roadside parking and a bigger parking lot at the end of the bay. This end is a good place to start your paddle. Looking out to the ocean, Whisling Cay will be right in front of you.


Angle the nose of your board straight onto the cay or slightly further to the right (slightly angled into the wind is easier vs. the wind hitting you fully from the side and keep paddling towards the right end of the cay.

Old Customs / Guard House on Whisling Cay


As you get closer to the cay, you will see the 300 year old house on Whisling Cay which is rumored to have been a customs house. It is said the Danes tried to blow the whistle on smuggling between British islands and the Danish West Indies by maintaining a Customs House on this Cay where the prevailing winds do indeed whistle.

However access to it is not easy, so it could have also been a guard house supplying some shelter for soldiers guarding the passage into the Narrows and the Sir Francis Drake Channel, discouraging escape attempts from slaves (over to Tortola where slavery was abolished in 1840 vs, 1848 on St. John). No matter what the purpose was, you will find some great snorkeling at Whisling Cay too.


To go snorkeling or take a well-deserved break, carry your board onto shore close to the old house being mindful of rocks and coral rubble as you exit. Make sure it is far enough on land that it cannot be swept away by waves.


Snorkeling Whisling Cay

The best snorkeling is on the Western (left side) of the Cay. Looking at this photo, it would be around the corner of the bushes. You can also tie up your board at one of the mooring balls on the West of the Cay. The best snorkeling is close to the big rocks at the Northwestern Point, this is a spot for experienced snorklers and strong swimmers. Be mindful of boat traffic in the passage and also the ocean and current that can be really rough at the back side of the cay.

The proximity to open waters, and the flow of water through the Fungi Passage and the Narrows attracts fish of many shapes, color and sizes: Tarpon, Bar Jacks and many others. The underwater boulders, rock formations, canyons, steep grooves, arches and walls are covered with spectacularly colored corals, sponges  are absolutely fascinating to explore. You can snorkel around the point at Whistling Cay and return through the gap between the cliffs on the cay. On calm days you can snorkel around the whole cay.

Observe the wind and save energy for your paddle back. If the wind goes all crazy while you are there, you can try to hitch a ride back with one of the boats that might be moored there, or you can try to wait the wind out, it usually always drops later in the afternoon….

If the wind is howling from the Northeast when you are ready to leave Whisling, you can also take the wind as a downwinder which brings you straight to the Hawksnest Point Rocks (make a left before the rocks into Hawksnest Beach after the Trunk Bay Swimming Zone buoys)

Paddling back to Maho


The paddle back will most likely feel harder than the paddle out. You will be tempted to paddle further left to the shore of Francis Bay but the headwind there is stronger then if you had straight for the middle of Maho. Try to stay right of the mooring pay station in between Maho and Francis (the further right you are the easier it will be). You can also go to the mooring pay station ponton and take a break there before heading back, or if you get lucky, one of the boats moored there might invite you in for a drink….

Don’t panic when the first bit will feel really hard. It will get easier after you reach the first boats. So just set your goal to reach the first boats and paddle with full power until there. After that you can relax a little, as you get closer to the shore the wind will die down.