Article by Tyler W.H. Backman
It was just after dawn and the wind was already starting to alternate between dead calm and tiny gusts on a warm spring day at Berkeley Marina. My two year old son Tevian and I had launched our Montgomery 15 the day before, in preparation for his first overnight sailing trip—to Angel Island. A lot has been said about sailing single handed, but I could find almost no information on sailing “half handed,” i.e. sailing while simultaneously caring for young children.
Now you ask “What’s this romantic boy,
Who laments what’s done and gone?”
There was no romance on a cold winter ocean and the gale sang an awful song
But my fathers knew of wind and tide, and my blood is Maritime
And I heard an old song down on Fisherman’s Wharf
Can I sing it just one time
-Stan Rodgers, Fisherman’s Wharf
I’m a fan of engine-less sailing (some might say snob), but the surest way to ruin a new sailor’s experience is to subject them to a windy and wet afternoon sail in the infamous San Francisco bay “slot” between the Golden Gate bridge and Berkeley. So we left at dawn, planning to motor to Angel Island in the usual glassy morning calm on the bay. I let Tevian take the tiller for a while, and he enjoyed steering the boat around in circles. A few minutes out of the harbor the wind started to pick up, and we killed our trusty old 2hp Yamaha. My son got a little upset, because he loves motors and can’t understand why anyone would shut one off! A few minutes without the loud excitement of a 2-stroke, he climbed into the cabin and passed out for a nap with his life jacket on. Just after he fell asleep, a humpback whale surfaced right next to the boat, and I felt bad that he missed it, but caught a cell phone video for him to watch later. As we were crossing the main shipping lane, we entered the wind shadow of the island just as a big freighter came over the horizon. I was a bit relieved to fire up the motor, instead of having to paddle for my life as I would have done engineless! Tevian woke up just in time to bark back at the seals on the dock as we pulled into Ayala Cove on Angel Island. Before we could tie up, someone yelled from the dock that the moorings and dock were closed. So we turned around and headed down to the free anchorage in China Cove, frustrated because we had left our inflatable dinghy at home in hopes of using a public dock.

It was now blowing about 20 knots, along with a strong tidal current through Raccoon Straight, and since we had no dinghy… our only options were to bounce around at anchor all day in the poorly protected cove or try to get ashore. So we beached our little M15 on the outgoing tide, and spent the entire day playing on the island. A few sticks and your own shoes are fun to play with all day long in the sand when you’re two years old! Hanging out on the beach together, I alternated between playing in the sand like a toddler myself, and loudly singing Eagles songs off key to a very non-critical audience. Later we watched the sunset while eating cold boxed soup in the heavily slanted cockpit, as we gradually started to refloat on the flood tide, and anchored out for the night in the (now calm) cove.
The night was peaceful and beautiful, except for the three times freighters came through, sending our little M15 rolling like the inside of a washing machine. My son slept through it all, but I bolted up wide awake each time, or as far up as you can get in an M15 until you hit your head. We had a breakfast of cold instant coffee, shelf stable milk, and oatmeal at dawn, and started motoring back with the flood tide. The wind picked up soon, and we sailed most of the way home. As we pulled into the marina, I contemplated how lucky I am to be raising my son by the sea, and started planning longer trips together.
Trailer launching and recovering
Launching the boat with just the two of us was the scariest part for me, and I delayed doing our first trip for a long time until I was confident I could do this safely. My biggest fear was the chance of the vehicle rolling into the water with him strapped inside. What I ended up doing is putting him in the front passenger seat with his life vest on, and no seatbelt. I then roll all of the windows down, turn the steering wheel full lock, and place a wheel chock behind one wheel in addition to the parking brake and having the transmission in park with the engine off. I remove the key and lock the car, so the power windows won’t work, and he can’t roll them up on himself. If you try this, think through everything that could go wrong, take your time, and don’t rush. With a two year old it took me two hours to launch our M15 from mast up storage with the mainsail already rigged. I can go from driving up with the mast down to sailing off in under 30 minutes when all by myself. If possible, I highly recommend a wet slip, or launching and recovering the day before/after the trip alone, if you have child care options. Launching and rigging is the hardest part of sailing ‘half handed’ with young children.
Safety at sea
Both sailing and watching young children can unexpectedly require your full attention at any, or even the same time. To do this safely, you must have the right onboard equipment and environment so that your toddler will be absolutely safe if you need to focus entirely on the boat for an extended length of time.
Finding high quality toddler offshore sailing safety gear is a real challenge- the market is pretty small. I am mentioning brand names here that I have no affiliation with, because they were really the only options I could find. Anytime we are underway, Tevian is tethered to an anchor with backing plate in the cockpit with a West Marine Child's Safety Harness and tether, in addition to wearing his Mustang Lil Legends life vest. I double the tether up to shorten it so that he cannot exit the cockpit, and can only go as far as peering into the water. The harness attaches from behind unlike an adult harness, but I noticed the newer version moved the attachment back to the front. A critical feature for a toddler life vest is the ability to float an unconscious or non-swimming person face up. The life jacket has a whistle he knows to use if he falls in the water, and a water activated strobe light. At the dock or anchored in a quiet cove he wears the life jacket anytime he is in the cockpit or dock, but can take it off for sleeping in the cabin with the hatch boards in place.
With young kids in a boat with a round bottom and limited ballast like the M15, it’s helpful to keep the boat under-canvassed at all times, to keep things easier and less scary. In windy San Francisco Bay we usually leave the dock with the main double reefed, and sometimes with a storm jib as well. It’s always easier to shake out a reef in light wind than put one in during a blow.
Cooking and provisions
Keep it simple. I bring enough “just add cold water” or “just open the bag” type meals for the entire trip, plus some extra warm meals and a camp stove that are optional if we have the desire to cook. Sometimes you will be too exhausted to cook and need to be able to just eat. Tetra pack soup boxes, freeze dried coffee, instant oatmeal, fruit, and shelf stable UHT pasteurized milk are key staples. You can put ice cubes inside a zip freezer bag inside a thermos to keep milk cold without diluting it, if you don’t have shelf stable milk or a cooler on board.

About the Montgomery 15
The M15 is a uniquely high quality and seaworthy boat for its size.
Cons
Very limited headroom in the cabin- just enough room to lie down, but no sitting headroom, at least for adults
Although very stable under sail, with a rounded bottom and low displacement, the M15 rolls a lot at anchor when larger crew members move around
Pros
At only 750 pounds, the M15 can be towed by even the smallest cars. Our M15s previous owner towed with a 52 horsepower diesel VW Rabbit
With a simple lightweight rig, you can be on the water in under 30 minutes
An excellent performing boat- it points well even in rough conditions
Responsive and fast- it sails almost like a racing dinghy, but much more stable
No through-hulls below the waterline despite having a self bailing cockpit
The arched cabin top with no compression post, gives you a massive bunk rarely found on any boat under 40 feet
Great story, great dad/son time, great advice re tether, food.
Two things I used to do with my son, when he was younger than yours: I had a pack basket that could be secured in the middle of the boat, with a cushion for him. He was also secured with a long enough lead that he could help me steer. We also went to the boat show every year to get his new jacket. They grow fast, don't they.