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 US$180 (S$251) per person (maximum five people per trip in Phase 2). 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, and takes you around Singapore, including the Southern Islands, Pulau Ubin and Pulau Hantu on a larger catamaran. It's also subject to a maximum of five guests in Phase 2.

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:

The itinerary for our 2D/1N Southern Islands Cruise starts at 5pm at ONE°15 Marina Sentosa Cove, where the boat is docked, and will end back here at 1pm the next day.

Helming our trip today is our skipper, Wei Yong, and two more crew members. With current Covid-19 restrictions, a maximum of five guests (excluding the skipper) is allowed onboard. The yacht is somewhat compact, but has ample room for a group of five. There’s enough space for the entire group to hang out together or have meals at the deck (above).

Need some me-time? Hang out at the front of the boat (above) for the best views and peak Insta-worthy opportunities. The cabins below deck also offer plenty of privacy.

The boat has three private cabins, and each accommodates up to two people. We get the largest of the three, with a double bed, an ensuite bathroom and windows that open up to the deck so you can sleep under the stars, literally, if you wanted to.

The bathroom's interior — and size — is reminiscent of those in Japan hotels. But, hey, it's clean and it serves its purpose.

After we leave the marina, we sail around for a couple of hours. Truth be told, it feels much shorter than that. Unlike a hotel staycay, a sailing holiday proffers ever-changing views. We’re treated to fantastic views of the Marina Bay skyline, and minutes later, of the offshore islands — Sisters’ Island, Kusu Island, St John’s Island and Lazarus Island. We don't realise how little we know about them until Wei Yong regales us with island trivia (and plenty of stories from his sailing trips around the world).

DSA founder and our skipper, Wei Yong

While you're onboard, you’ll also have a chance to learn the ropes, literally. Wei Yong will personally teach you how to maneuver the sails and to steer the boat. We’re happy to report that we did not veer off course… much.

Our itinerary also includes time to go on a hike at St John’s Island, explore Kusu Island or Lazarus Island, or just leisurely swims around the islands. You can opt to do everything or do nothing — it’s entirely up to you. But for now, we’re chasing sunsets.

After over one month of running these cruises, the crew has found the sweetest spot for catching these glorious sunsets. We arrive just in time for golden hour. Phones are whipped out, and countless of photos, Boomerangs and videos are taken.

But we make it a point to put down the phone to truly be in the moment (because experiences, okay?). One of the good things about being on a sailboat is that there is no engine constantly blaring in the background, unlike a power boat, as you have the option to just let the wind coax you along. All we hear are the soothing sounds of the gentle waters lapping away (save for the occasional container ship horn sounding in the distance). It’s so tranquil and laidback, you forget that you’re not actually on a boat trip somewhere off the coast of Phuket.

We arrive at St John’s Island around dinnertime and anchor off at the pier. This is where we’ll be spending the night. There are three other boats in the vicinity, but they soon depart, leaving us the solo boat to stay overnight here.

Yup, it’s us, the sea, the stars and the flickering lights from the city in the distance.

The staycation package includes three meals, all prepared by Wei Yong. The menu is not fixed, and depends on what ingredients he can get for the day. Tonight, the comforting, homely fare includes chicken, pasta, a cheesy baked eggplant, salad and fruits.

Okay, so what happens between dinner and, er, breakfast? To be honest, we’d packed a Kindle and downloaded a ton of shows on Netflix, expecting that there’d be nothing much to do on the boat once the sun sets. Turns out, we didn't even need Netflix, the Kindle or any Internet connection, for that matter (fret not, there's still 4G connection here if you need it).

You’ll be surprised at how quick time passes when you’re just chatting or zoning out (maybe it’s all that pent-up wanderlust from the past few months). The skies are clear enough for a spot of stargazing. At times, St John’s Island’s resident cat sidles over, mewing gently in hopes for supper (they don’t jump onboard). It's a good time to get contemplative, escape the hustle and bustle of city life, WFH, and then some. If you've always wanted to glamp under the stars, this could be it.

It's midnight by the time we retire for the night. Being under deck in the cabin means you feel the movements of the boat a little more, but waters are very calm (we’re not in the open seas, after all). With the windows shut and the aircon turned on, it doesn’t feel much different from sleeping in a hotel room, albeit with the gentle swaying of the vessel. It doesn’t take long for us to drift off to sleep. We’re not prone to seasickness and sleep soundly through the night. But those who do get seasick should bring their own motion sickness medication, just to err on the side of caution.

We wake up bright and early the next morning to Wei Yong preparing breakfast, which came with freshly baked bread and bagels (below), believe it or not.

This is the closest you’ll get to a bona fide vacation these days, without having to travel. You’ll feel like you’re on an island getaway overseas, which technically, ain’t far from the truth. An overnighter on a yacht, though pricier than a stay in a five-star hotel, is a one-of-a-kind experience. The itinerary is pretty flexible — it could be as adventurous as you want, but it could also be the most laidback and Zen staycay you’ll experience.

More info at https://www.facebook.com/discoversailingasia/. Book at https://discover-sailing-asia.myshopify.com/.

Photos: Discover Sailing Asia, Jasmine Teo, Jillian Chang