• TT&W Team

Sailing through the Knysna Heads

Updated: 6 days ago


Sailing out through the Knysna Heads - eastern head in the background
Sailing out through the Knysna Heads - eastern head in the background

Our time in Knysna happened to coincide with Valentine’s Day. Chipp, ever the romantic one, completely deferred to Jenna’s planning for the day’s activities. Result? We spent the afternoon on a chartered trip sailing through the Knysna Heads.


What are the Knysna Heads?


Knysna itself doesn’t sit directly on the Indian Ocean. Instead, the city’s tucked into a protected harbor - more of a lagoon - with a narrow gap connecting to the open ocean.

Sailing directly into the Knysna Heads - Indian Ocean on the far side
Sailing directly into the Knysna Heads - Indian Ocean on the far side

Prior to getting to town, people had told us about the Knysna Heads towering over this harbor. In our ignorance, we both had mental pictures of Easter Island-esque sculptures - not massive geographic features.


In reality, the heads are huge cliffs standing on both sides of the narrow gap heading out to the ocean. Standing tall on both sides, the heads give the Knysna waters a Lord of the Rings or Nordic fjord feel. Leaving the harbor, it seems like you’re sailing directly into a hidden valley - not the turbulent waters of the Indian Ocean.


A Not-As-Romantic-As-Expected Sail


And, these turbulent waters gave us a bit more than we bargained for in terms of a “leisure” cruise. After our sunset cruise in Zanzibar, we had visions of this sail as a fairly relaxed, enjoy-a-gin-and-tonic-while-meandering-along experience. We didn’t know it before the trip, but the Indian Ocean waters stretching from Durban down the southern tip of Africa are some of the windiest and roughest in the world.

Enjoying the calm waters in Knysna's protected harbor
Enjoying the calm waters in Knysna's protected harbor

The skipper and first mate were a father/son duo who chartered the 44-footer we took out and a couple other boats. Similar to New England fishing families, you could tell immediately that they’d spent their entire lives on and near the water. Salt water just seemed to ooze from their pores. So, for these guys, looking at a somewhat stormy weather forecast was just another “day in the office” - no need to worry.

Knysna Heads in the background
Knysna Heads in the background

For us sailing neophytes (Chipp, Jenna, and another couple celebrating Valentine’s Day on the water), we were a little more skeptical looking out at dark clouds over the Knysna Heads. But, the protected harbor has a way of lulling you into a false sense of complacency. For the first 20ish minutes under sail, we enjoyed the sheltered protection of the harbor - focusing more on our gin and tonics than the weather.

Sailing through the Knysna Heads
Sailing through the Knysna Heads

Passing through the towering heads into the open ocean, this relaxed atmosphere changed on a dime. With strong winds and rolling swells, we picked up speed immediately, launching our way out into the open ocean. And, that was just the steady-state weather. Looking out to the west, we watched as a squall made its way across the surface of the water towards us. A few minutes later, ripping gusts of winds and a wall of sideways rain slammed into us, putting the boat on a solid 45 degree tilt.


Jenna, yelling over the wind: “How sure are we that this won’t tip?”

Chipp: “If the skipper’s not worried, we should be fine…”


Romantic? Not so much. Absolute blast? You bet!


“At Sea, We Call the Left Port…”


After the squall passed, the weather turned - relatively - calm. We still had strong winds coming in, but they were steady, and the rain had stopped. Reversing course and heading back to port, the skipper asked if anyone else wanted to take the helm.

Captain Chipp Sparrow
Captain Chipp Sparrow

About 15 years ago, Chipp spent two weeks sailing during summer training at the Naval Academy. Could he take a sailboat out by himself today without crashing? Nope. But, of the four guests, he was the only one with some level of experience. Seeing no one else jumping at the offer, he volunteered to take the helm.


Skipper: “Just keep the bow aimed back towards the heads.”

Skipper’s son to Chipp: “Any experience sailing?”

Chipp: “Well, years ago I did a little, but I definitely need some pointers.”

Skipper’s son: “Okay, well the first thing is that, at sea, we call the left port and the right -”

Chipp, cutting the skipper’s son off mid-sentence: “Yeah man, I’m good up to that point… I meant some pointers about actually sailing the boat.

"Just aim the boat that way..."
"Just aim the boat that way..."

For the next 20ish minutes, we had that initially-envisioned, leisurely sail - sun broke through the clouds, bottle-nosed dolphins swam and jumped beside the boat, and Chipp didn’t get anyone killed. Fortunately, though, the skipper took over to navigate back through the Knysna Heads - would’ve been a coin flip whether or not Chipp could have successfully done that at the helm!


Champagne in Harbor and the Romantic Part


When we tied up back in Knysna Harbor, we did - finally - get the romantic Valentine’s Day experience. With the sails lowered, the father/son team guided the four of us belowdecks, opened a couple bottles of champagne, and laid out a delicious spread of local meats, cheeses, and fruits.


The next hour or so, we sipped champagne, snacked, and chatted with this other couple. In a great coincidence, they’d driven over from Plettenberg Bay - 30 minutes down the road and the next stop on our travels. It’s always good getting local knowledge, and they gave us plenty of solid recommendations.


Finally dry post-squall, we hopped off the boat. Stuffed and in a nice, champagne-induced merry state, it felt good to be back on dry land. Different Valentine’s Day than we first imagined? Yeah, but still a blast!


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