11 South Africa Sailing Tours for the Logbook

1.Cape Town Waterfront and Bay: Sailing Trip

★★★★★★★★★★4.6 · 190 reviews · 1 hour · from $25Our pick

Set out from the V&A Waterfront for a one-hour sailing trip across Table Bay. Depending on wind, you may head toward Milnerton Lighthouse or Robben Island. The crew explains sailing terms, and guides such as Rocky are known for warm service and helpful photos. Calm-weather and harbor routes keep the outing flexible.

“You'll be going out to sea with a bunch of pretty cool personalities, very accommodating and fun friendly”

Check availability →Read our full review

2.Knysna Sunset Sailing Cruise with Light Dinner and Wine

★★★★★★★★★★4.8 · 96 reviews · 2h 30m · from $124

Join an experienced skipper and deck crew aboard the 50-foot Outeniqua for a 2.5-hour sunset sail from Knysna Waterfront. You may cruise through the Knysna Heads into the Indian Ocean if conditions allow, then return for cheeses, fruit, savory snacks, and two glasses of South African Cap Classique. The yacht carries no more than 12 passengers.

“Apart from the attentiveness and friendliness of the crew, we felt like we were in very safe hands with their experienced skipper. The boat is beautiful and very comfortable and it was an awesome experience sailing out of the Knysna Heads before making our way back into the lagoon.”

Check availability →Read our full review

3.Sailing in The Bay by Catamaran (One Hour)

★★★★★★★★★★4.5 · 87 reviews · from $21

Sail Table Bay from Cape Town’s V&A Waterfront aboard Esperance or Serenity One. Your captain chooses the route based on wind, with views toward Robben Island, Milnerton, or Clifton. Expect a one-hour sightseeing cruise, crew commentary, music, chilled refreshments, and a cash bar.

“Very neat, safe and the music is beautiful. Crew is great, such gentlemen and helpful. Over all 120% service.”

Check availability →Read our full review

4.Knysna Sunset Sailing Cruise, Light Dinner & Bubbly

★★★★★★★★★★5.0 · 41 reviews · from $104Top rated

Spend about two and a half hours aboard a small sailing yacht from Knysna Waterfront. Captain Steve and the crew guide you across the lagoon and, sea conditions permitting, through Knysna Heads into the Indian Ocean. Expect two glasses of South African sparkling wine, a Mediterranean-style platter, local stories, possible wildlife sightings, and a maximum of 12 people.

“Excellent way to experience Knysna lagune and open sea beyond the Knysna Heads. Experienced skipper and helpful assistants made the experience even more memorable.”

Check availability →Read our full review

5.Knysna Sunset Sailing Cruise with captain’s steak Braai & Bubbly

★★★★★★★★★★4.5 · 27 reviews · from $97

Spend about two and a half hours aboard Ocean Sailing Charters’ 55-foot LaraBella, sailing from Thesen Island across Knysna Lagoon and, if conditions allow, through the Knysna Heads. You’ll get a welcome glass of bubbly, a braai with steak and salads, and time to watch for dolphins, seals, and sea birds.

“Awesome sunset trip around the lagoon and out the Knysna heads. Staff were super friendly and attentive.”

Check availability →Read our full review

6.Cape Town: 1 Hour Table Bay Sailing Tour

★★★★★★★★★★4.8 · 21 reviews · 1 hour · from $21Best value

Set out on the Spirit of Victoria from Quay 5 for a relaxed one-hour sail across Table Bay. You’ll see Table Mountain, Cape Town, and the waterfront from the water, with a cash bar serving sparkling wine, beer, and soft drinks. The route has no fixed destination and may reach toward Milnerton lighthouse before returning via Granger Bay.

“Even though it was my friend and I they still took us on a tour. It was amazing”

Check availability →Read our full review

7.Knysna: 2.5-Hour Day Sail & Lunch Charter

★★★★★★★★★★4.8 · 9 reviews · 2.5 hours · from $143

Join Captain Nick and the crew aboard Outeniqua, Knysna’s only chartered monohull sailing yacht, for a 2.5-hour cruise from the Waterfront. Expect classic hands-on sailing, views of the estuary and Knysna Heads, a cheese and fruit platter, and a cash bar. Ocean sailing depends on wind and sea conditions.

“Fabulous trip on the yacht perfect sailing conditions and given the opportunity to sail the yacht with my husband (for a short while:)) saw a whale - great captain nick and crew. Highly recommended”

Check availability →Read our full review

8.Knysna: 1.5-Hour Sailing Experience

★★★★★★★★★★4.9 · 5 reviews · 1h 30m · from $95

Join an experienced skipper and deck crew aboard Outeniqua, Knysna’s only chartered monohull sailing yacht. This 90-minute trip carries no more than 12 people through the estuary toward the Knysna Heads, with ocean sailing possible when weather and sea conditions permit. Stephan is named in recent trip feedback, and the onboard cash bar serves drinks.

“Mooie zeiltocht waar we volop van genoten hebben ; vriendelijk personeel en goede service ! Wij komen terug.”

Check availability →Read our full review

9.Knysna Day Sailing Cruise 1.5 hour

★★★★★★★★★★5.0 · 4 reviews · from $79

Set out from Knysna Waterfront for a 90-minute sailing trip with up to 12 people. Cruise the lagoon, attempt the Knysna Heads when sea conditions allow, and possibly reach the Indian Ocean. The crew, including Eric, Easton, and Matilda, provides local commentary. Dolphins and seals may appear, and drinks are available from the onboard cash bar.

Check availability →Read our full review

10.Sailing in Table Bay Cape Town aboard a Classic Schooner

★★★★★★★★★★4.0 · 3 reviews · from $23

Spend about an hour sailing Table Bay aboard a classic twin-masted schooner with a professional crew, including Captain Tinashe and deckhands Keagan and Bruce. Ride the bowsprit, watch for seals, dolphins, or whales, and enjoy changing views of Table Mountain and Cape Town’s Atlantic coast. The route depends on the wind.

“Lovely, helpful crew - deckhands, Keagan and Bruce, were very personable and professional. Also thanks to Captain Tinashe.”

Check availability →Read our full review

11.Knysna Day Sail & Lunch Charter 2.5 Hour

★★★★★★★★★★4.5 · 2 reviews · from $119

Join a skipper-led 2.5-hour sail from Knysna Waterfront through the lagoon toward the Knysna Heads. If sea conditions allow, the yacht enters the Indian Ocean. Expect a small shared group of up to 12, marine-life commentary, a picnic-style lunch of cheeses, fruit, and savoury snacks, plus drinks available from the cash bar.

Check availability →Read our full review