Anyone who has followed this blog for a while knows I have a thing for trains. Overnight sleepers, rattling third class, border crossings at strange hours. I’ve taken the slow way out of Singapore more times than I can count.
So this one feels a little like a confession.
This time, I left Singapore by sea. No platform, no shuttle to Johor Bahru, no queuing at Woodlands with a backpack. Just a gangway, a ship and the Strait of Malacca.
And honestly? I’m still not sure how I feel about enjoying it this much.
Why Leave The Rails (Just This Once)?
Part of it was timing. The new Johor Bahru to Singapore RTS Link was supposed to make the first stretch north painless. Instead, its passenger service is now expected in February 2027. So the border crossing remains, well, the border crossing.
Part of it was curiosity. The West Coast Line runs roughly parallel to one of the most important waterways on the planet. For years, I’ve watched the Strait from train windows without ever actually being on it.
And it’s a busy one. The Strait of Malacca carried 23.2 million barrels of oil a day in the first half of 2025, about 29% of all maritime oil flows. From the deck, you see it. Tankers, container ships and car carriers, lined up to the horizon like traffic on Sukhumvit.
That alone made the trip worth it.
Doing The Math On An All-Inclusive Fare
Here’s where I need to be honest. Cruises were never really on my radar. In my head, they were floating buffets with expensive extras at every turn.
That’s true of some ships. It isn’t true of all of them.
When I started comparing the best all inclusive cruise lines, the difference came down to what the all-inclusive fare actually covers. Silversea’s version was the one that made me rethink things. On its classic voyages, the fare includes:
- Butler service for every suite
- Unlimited champagne, spirits and wines from the ship’s cellar
- An in-suite bar stocked with the drinks you choose
- Several dining options, plus 24-hour in-suite dining
- Onboard gratuities, port taxes and fees
- Wi-Fi
Shore excursions are extra, which suited me fine. I prefer wandering a port on foot to following a flag anyway. Flights and hotels can be added, but they aren’t automatically included.
The real surprise was the mental math, or rather the lack of it. On a train trip, I’m constantly counting Baht and Ringgit. Here, I didn’t sign for a single drink. For someone who usually travels on a budget, that felt almost suspicious.
Boarding At The Cruise Terminal (Not Woodlands)
Leaving Singapore by ship is a very different experience from leaving by rail.
There’s no scramble for the shuttle train. No double immigration in a crowded checkpoint. You check in at the cruise terminal, hand over the bags and walk on board. That’s it.
The view on the way out is spectacular, too. The city skyline slides past, then the anchorages, then the open water. It’s the Singapore skyline in reverse, and it’s a lot more photogenic than the Causeway.
My one train-guy complaint? You don’t get that slow, rattling sense of the landscape changing outside the window. At sea, the change happens overnight, while you sleep.
The Strait From The Top Deck
The Strait of Malacca has been a trade route for centuries, and the towns along it show it.
Melaka and George Town are both on UNESCO’s list, recognized for 500 years of trading between East and West. I’ve visited both by train and bus before, but arriving by water makes far more sense. These were port cities first. The streets, the clan jetties and the old shophouses all face the sea for a reason.
Penang, in particular, felt different this way. The waterfront came first, not the bus station. A little humbling for someone who has always arrived through the back door.
The sea days in between were the real revelation, though. I expected to be bored. Instead, I spent hours on deck with a coffee, counting tankers and watching fishing boats weave between them. It’s the same slow, staring-out-the-window pleasure I get from a long train ride. Just with a lot more horizon.
There’s also something to be said for unpacking once. No hauling bags between guesthouses, no early checkouts. The room simply moves with you.
Eating My Way Around The Ship
You know I had to cover the food. It’s the main reason I travel.
I’ll admit, I went on board fully expecting to miss Malaysian street food. And I did, a bit. No ship kitchen will ever replace a plastic stool and a plate of char kway teow in Penang.
But the onboard dining was genuinely good. Proper fine dining in the evenings, lighter options at lunch, and room service whenever I wanted it. The bonus of an all-inclusive setup is that you can try everything without second-guessing the bill.
My compromise was simple. Eat well on board, then eat even better in port.
When To Sail Out Of Singapore
Weather matters on water much more than on rails.
Singapore’s Northeast Monsoon runs from December to early March. The early weeks can bring long spells of heavy rain, while late January to early March is windier but much drier.
If you want dry decks, the later part of that window is the sweet spot, though pack a layer for the breeze. The inter-monsoon months can bring afternoon thunderstorms, so plan your outdoor time for the mornings.
Will I Go Back To The Trains?
Of course I will. I’m far too attached to my overnight sleepers to give them up.
But I get it now. A ship out of Singapore isn’t really the opposite of rail travel. It’s the same journey, seen from the other side. The trains show you the land. The ship shows you the reason those towns were built in the first place.
Next time, I might even do both. Train up the peninsula to Penang, ship back down the Strait.
Now that would be a proper life less ordinary.