“She loved the sea. She liked the sharp salty smell of the air, and the vastness of the horizons bounded only by a vault of azure sky above. It made her feel small, but free as well.” George R.R. Martin, A Storm of Swords

This is Chaos. She is the lead vessel among a small fleet of sailboats owned and operated by live-aboard cruisers from around the world. With each new Pirate Jam a new fleet will assemble, take aboard developers, and sail from Krabi Boat Lagoon to beautiful destinations around the Andaman Sea.

If you’ve never been on a sailboat, please read this section carefully. Sailing is a sport, and as with other sports there are risks involved. Somewhat unique to sailing is the huge impact weather and environment can have on the comfort and safety of the activity. Sailboats, and thus sailors, are at the mercy of the sea.

Let’s get all of the scary things out of the way first.

The scary

Rough conditions

Big seas, heavy winds, flying water. We could be sailing in 20kts of winds with 3~4m seas (this is considered uncomfortable to mildly terrifying, depending on your level of experience) for 5+ hours without the possibility of stopping for a break or jumping off for a rest on a nearby island. Sailing sometimes involves long slogs in difficult conditions in order to get from point A to point B. We’ll try our best to avoid this sort of thing, but weather and related conditions aren’t 100% predictable.

If you aren’t prepared to accept the potential difficulty and discomfort, please search out a more comfortable game jam.


Often described as one of the worst forms of motion sickness, seasickness can strike in rough conditions, or while drifting along in a moderate ocean swell. Many articles have been written on how to prevent and treat seasickness, such as this one. It’s important to understand that seasickness can (and will) happen, and that if it strikes while we’re under sail between destinations you’ll just have to ride it out.

Keeping an eye on the horizon will prevent sickness in most people. For those in need, there are seasick pills aboard (they will make you drowsy), and must be taken before you get sick. The chance of seasickness decreases with each day spent aboard. By the 2nd or 3rd day most people have gained their “sea legs” and no longer need to fear seasickness.

Not going anywhere fast

5kts equals 6mph/9.5kph (the speed of a very fast walk or jog) and is the average speed we’ll achieve in ideal sailing conditions. Speeds can easily drop below 3kts average, meaning we’re moving slower than a fast walk. We’ll try to sail as much as possible, but when becalmed we’ll use the motor, which will push us along at 4~5kts. This means some days will find us sailing (or motoring) for 3~4 hours, depending on our destination. During this time it’ll be difficult (if not impossible) to look at a laptop for more than a few minutes without getting sick. We usually occupy these hours with silent contemplation, fishing, social-political discussions, and sailing lessons. Be warned that once we’re under way and heading towards our destination, it can be hours before you’re able to get off the boat onto land.

Tropical Heat

Thailand is in the tropics and the tropics are hot. Some like it hot. If you don’t like being hot, you might check out Splash Jam, which takes place on a cruise ship up near the arctic circle. Brrrrr.

The Sublime

Still want to be a pirate? With all the scary stuff stuff out of the way…

Beautiful sailing

More often than not we’ll experience smooth seas and moderate winds, under clear blue skies. When the wind is up we’ll raise the sails and hop between island anchorages.

Deserted anchorages

On a sailboat you can really get away from it all. No tourist, no traffic, and no trouble as we leave behind the mainland and crowded beaches for secluded islands only accessible by boat.

Stunning scenery and sunsets

One word best describes the natural environment of Thailand: Stunning. A sailboat is the perfect platform from which to commune with nature in the marine environment. And once the sun goes down? The stars come out!

So Far, So Good (knock on wood)

Sailors are loath to trumpet their good fortune for fear the gods may punish their hubris. So we’ll say this in a low whisper: Dozens of pirates have enjoyed three years of Pirate Jam without incident. The weather has always cooperated fantastically. And no one has ever suffered sea sickness!

Check out video episodes from Pirate Jam 2019 and you'll see just how amazing these trips can be!

The plan

We’ll sail mornings, making quick hops between anchorages not more than 20nm (average of 4 hours sailing at 5kts) between each other. One hop per day maximum. When we find a nice, comfortable anchorage where everyone’s happy, we may decide to settle in for a few days of development, diving, fishing, and other activities. Our goal with sailing is not miles under the keel, but smiles and good feels.

CRITICAL NOTE: It is possible, though unlikely, that a Pirate Jam is scheduled, everyone flies to Thailand, and weather conditions make it unsafe to leave the marina. In this event, the Pirate Jam will take place at the marina, with sailing occurring only when/if conditions improve. (Note from American: In many years of sailing around Thailand during all seasons, I have never had to cancel or postpone a sailing trip due to weather. That being said, there have been severe storms that, had I been in Thailand when they happened, would have forced me to stay in the marina).

Learning under sail

Sailing is easy and fun. While we’re out on the water you will have an opportunity to experience and learn all aspects of sailing. By the end of the trip, depending on your level of interest, you will know how to operate a sailing vessel under sail and power; raise and lower sails; drop and weigh anchor; perform basic navigation tasks; and tie some basic sailing knots. You’ll also learn about day to day life aboard a sailboat while we cook meals, wash clothes, and go fishing.

Which brings us to our next topic: Fishing!