We Went On A Sailing Staycation On A Yacht To The Southern Islands Of Singapore. This Is What It’s Like

Remember how Darren Lim, Evelyn Tan and their brood lived on a yacht for years, sailing the high seas from country to country? Well, now you can do the same, sort of, with a couple of charter boat companies in Singapore now offering staycations at sea.

Since we’re not going anywhere that requires a passport anytime soon, we’re all for experiences in Singapore that make us feel like we’re overseas. A day — and night — out on a yacht around the Southern Islands of Singapore does exactly that.

Which was why when the folks at Discover Sailing Asia (DSA) floated the idea of an overnight staycation on a sail boat, we were onboard. The Hongkong-based company used to primarily operate sailing holidays in Asia around Taiwan, Hongkong and Thailand. But as fate would have it, this boat was passing through Singapore when the circuit breaker happened and borders around the world were closing, and is not able to sail out of the country until travel restrictions ease up.

The company’s Singaporean skipper, Chong Wei Yong, 43, decided to adapt the business to offer local sailing staycations around Singapore’s Southern Islands instead. The company has been running such overnight trips and day outings since July.

Prices for a 2D/1N trip start at $280 per person (maximum eight guests). It includes three meals, drinks (non-alcoholic), a chance to try your hand at sailing, and exploration around the Southern Islands.

There are currently only a handful of companies in Singapore offering overnighters out at sea. Besides DSA, there's Ximula Sail, the charter company where you can book Darren Lim’s yacht for a trip out in the waters. A two-day sailing holiday (from 10am on Day 1 to 6pm on Day 2) starts at $5,000 (maximum six guests), and takes you around Singapore, including the Southern Islands, Pulau Ubin and Pulau Hantu on a larger catamaran.

Admittedly, regardless of which company you book with, a staycation on a boat is pricier than one at a five-star hotel. But, hey, you’re paying for a very different experience. How different? Read on.

What it’s like to go on a sailing staycation in Singapore: