Keeping toddlers happy in a non-routine life

Pretty much every parenting book out there advises that Routine is King. In fact, I’m pretty sure it’s the most frequently touted solution to any problem–“just get that baby on a schedule!” No problem. Except, for me, BIG problem! Our only guarantee is that nothing is guaranteed. Our only routine is a general lack thereof. We WANT to be sailing full-time, and then at least the lack of structure comes together in its own sort of routine. But we still have land commitments, so some weeks find us flying and driving between 3 or more locations with kids in tow. So, I try (and try, and try) to create small routines within the chaos that can help keep my little ones on track and all of our lives harmonious.

Magnatiles and fishing…pretty much how these two start every day when we are at the dock!

1. Remember the goal

We don’t live nomadically to test how much fun we can have squeezed together in cramped spaces…we do it to achieve greater access and connection to the big beautiful world outside. Our houses in Vermont and Maine are very small, and are both surrounded by lots of land to explore and play in. Our boat–where we hope to live full time one day, and where we DO live for a good chunk of the year–is of course small, but is without fail surrounded by 360 degrees of outdoor adventures waiting to happen. Kids are happiest outside, so this is where we spend the bulk of our time, whether it is winter in Vermont or summer on the boat. Or better yet, a Caribbean winter on the boat!

These are our front yards!!! If that amount of fresh air isn’t worth a little chaos, then I don’t know what is

2. Bedtime routine

It’s easy as parents to take well-meant advice and run with it- a little too far at times (in my opinion). I know parents who barely do anything fun anymore because they are complete slaves to the ROUTINE. I try to focus on the parts of our day that I can keep consistent no matter where we are. For us this is bedtime, and it’s the only routine that I can be a crazy stickler for. Ever since they were tiny babies, the boys have had “tubby time” no matter where we are. Sometimes this means filling a tub on the aft deck of the boat and letting them splash around. But no matter what is going on, they are in the tub by 7. Then its PJs, lotion (I’ve used the SAME lotion since they were newborns, I swear this scent is part of the routine as well and gets them “in the mood to snooze”!) Then we read, sing a few songs, and its lights out and white noise (I swear by this as well…River was a VERY cranky–ok fine he was all-out colicky baby–and I would blast the white noise and watch his eyes mercifully close).

These collapsible tubs by Stokke go everywhere with us! A bedtime routine lifesaver from age 0 to 4…empty rosé bottle-turned-tub-toy not included

3. Facetime

Of course, keeping in touch via FaceTime is not ideal, but it does provide a way to keep relationships big and small going while we are away. They love talking to family over FaceTime, and we send little pictures and videos all day to other family and friends. They have a few friends they have made that they still keep in touch with, just by sending the occasional silly video message. After talking to someone, we always talk about the things we like to do with those people in real life.

Anytime is a good time to wave hi or shoot a quick “hello” video to send to friends and family

4. Little traditions

No matter where we are, we talk about the little things we like to do in that place. This helps River to identify where we are on his mental map and anchor himself, so to speak. In fact we talk a lot about “our places” wherever we are, so he gets a sense of home even though he is always on the move. We talk about ice-skating in Vermont, and the adventure center at Stowe Mountain. About hiking and our morning ritual of looking for frogs in the pond. We talk about Boston and picking their brother and sister up at school, playing at the local playground, and all the games we play at the nearby park. The boys love to scroll through my pictures and talk about fun memories, where they happened and whom they were with. On my to-do list- making them some small photo books to keep with them. 

Anytime we talk about Vermont, it always starts with their favorite morning routine: catching frogs in their Jammies. Some things aren’t so different whether on the boat, or in the mountains!!


Last but not least is our summer home in Maine. This past summer was our first one there, and we only left once when their baby cousin was born. Otherwise, they enjoyed 3 solid months of consistency. (Well…not counting all the little trips we took on the boat!!) I can tell already that Maine will be a consistent part of every year for them. Even if we are off sailing around the world, I can see us flying back to Maine for at least a month during the summer. I was resistant at first to adding yet another place to our already hectic schedule, but it was well worth it. They will grow up as a part of this amazing small-town island community and I hope they keep returning long after they are grown.

Maine! Home sweet Polly Cove

None of this is perfect. I have loads of mom-guilt and anxiety that I am making them miss crucial social interactions and early learning milestones. River keeps asking to go to school, and I wonder how to make it happen. (Uh does summer camp count?) We will figure it out. (The answer is yes, it totally counts!!) In the meantime, we are doing the best we can. Any suggestions are VERY welcome!!!

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