Are you ready for a Luxury Sailing Adventure?

Unforgettable Journeys and Amazing Sunsets

Ocean Sailing Charters and Boat Trips is a family owned and operated business, with a team of passionate people who have brought together our love for travel, fun, sailing, good food and wine! From the vantage point aboard one of our luxury catamaran cruises, you’ll be able to experience the natural beauty of the magnificent Garden Route. 

All our catamaran cruises depart from the jetty in front  of Sirocco restaurant on Thesen Island. We then venture out for a magical sail on the Knysna Lagoon, navigate the famous Knysna Heads and then head out to sea to explore the spectacular marine and bird life of the Indian Ocean. Being joined by pods of dolphins or a friendly seal is a magnificent experience.

We have a variety of cruise options. Enjoy an exhilarating day cruise, sunset cruise or private charter aboard one of our luxury catamarans, or on our leisure boat, Serendipity with ample time for lazing in the sun, swimming, snorkelling and delicious snacks with bubbly, wine and beer. There is nothing that makes you feel more alive than breathing in the fresh ocean air while gazing out over the blue horizon with the sun on your skin.  

Luxury Sunset Cruise

Watch an exquisite sunset onboard a luxury catamaran while you take in the magnificent ocean views and enjoy an ice cold glass of bubbly. A magical sail on the Knysna Lagoon, and through the famous Knysna Heads and out onto the open ocean. Look out for pods of dolphins and other beautiful creatures. On the way back we will treat you to delicious light snacks.

Romantic Sunset Cruise

2 HR 30 MIN – R 5 900
There is no better setting for a romantic evening with your special person. This intimate cruise at the golden hour of the day gives your panoramic views of Knysna framed by the Outeniqua mountains. Sail on the lagoon and out the Knysna heads to explore the Indian Ocean and coastline. We will treat you to light snacks and bubbly on the way. There's also a cash bar onboard if you fancy something different.

Our Catamaran Fleet

Scenic Day Cruise

R790 per Adult
R640 Children under 12yrs
An amazing way to explore the natural beauty the Knysna lagoon has on offer, with magical bays and coves. We navigate through the famous Knysna Heads out into the open Indian Ocean, abundant with a diversity of marine and birdlife. Spend some time relaxing, sunbathing and sightseeing.

Private Romantic

1 HR 40 MIN – R 4 900

There's no better way to create magic memories with your partner, than with a romantic cruise in Knysna. Make those special moments unforgettable. Let us in on the plan and where we can help make it unique.

Onboard your cruise you can choose to be as entertained as you wish…try your hand at fishing, dive straight off the boat and enjoy swimming in the clear water, or just simply sit back, relax and enjoy every moment.  Speak to our crew to customise a cruise to your liking. We offer variety of charter options to suit the particular preferences of each unique guest.
On our private charters we can create an exciting journey – Hire a musician, a DJ, a private chef, a mixologist for those exquisite cocktails, or photographer, we can make it all happen. The value, luxury, comfort, space and fun which we offer is unmatched by any operator in the area. Our two Catamarans and lagoon lounger can take up to 12 guests per boat exclusively.

Private 1h40


Take in epic views, snap photos of loved ones and listen to relaxing music while you sip on ice cold drinks. Book a private cruise for 12 at a discounted rate, and we can tailor the cruise to your preference.
01h40 - R 7 000
*snacks or oysters available on pre-order

Private Sunset


We have two Catamarans which take 12 guests exclusively. Book a sunset cruise for 12 at a discounted rate, speak to our professional team to create a unique event. The possibilities are endless.
02h30 - R9 000
*snacks or oysters available on pre-order

Private 3h40


Book a private cruise for 12 at a discounted rate, and we can tailor the cruise to your preference. The perfect platform for something special.
3h40 - R 12 000
• snacks available on pre-order

Private Sunset 4h30

Perfect for a family or corporate outing, photo shoot, marriage proposal, or any other special occasion you may have.

This unforgettable experience is your private charter for up to 12 guests. Speak to our team to customise your cruise event. 04h30 - R14 000
*We can arrange a private chef for a gourmet experience.

Serendipity Leisure Lagoon Boat Cruises

Enjoy an exhilarating cruise aboard our luxury lagoon cruiser Serendipity.  Enjoy the sunshine whilst we treat you to delicious snacks (pre-order) and a glass of ice-cold bubbly. Unwind, relax and discover the vibrant Knysna Estuary in style or take a swim in the clear water! We depart daily from Sirocco restaurant on Thesen Island, bookings are essential. 

You can book per person, or hire the boats exclusively for the ultimate function, or celebration.

As owner operators we can offer a service that is uniquely tailored to each customer and the flexibility for you to also tailor your own cruises according to your needs.  We know the yachts and the sailing waters intimately, and it gives us great joy and happiness to give all our customers the best possible time on our yachts.

Overnight Charters

R 15 540 Per night

Words cannot describe the magic of a night on the water. Join us for an unforgettable night or two on the Knysna Estuary.
Excludes: Cleaning fee R1500 Chef and meals
Beach towels
Includes: Skipper Fuel Insurance Bedding & Bath towels

Sailing Holidays

It’s not about the destination, it’s about the journey… that’s what we believe. A sailing holiday is an unforgettable experience, it will awaken all your senses and evoke a sense of immersive exploration.

For those looking for a holiday that exceeds all others, a holiday on board is the ultimate getaway. Explore the destination of your choice in comfort and style with an expert crew that will take care of your every need and ensure you have the holiday of a lifetime. We have lots of local knowledge and can help you to make the most of your time on the unforgettable waters of the Garden Route. 

What you can expect:

• Custom holiday tailored to your exact needs.

• For guests of all levels of sailing experience..

• Friendly knowledgeable expert crew that will unlock the Garden Routes secrets : )

• A tailored custom menu with an expert chef

• Choose to embark or disembark from either our bases in Plettenberg Bay or Knysna

• High specification, safe and comfortable Catamaran Yachts