Hello, friends..

Welcome to The Travelling Tribe.



Hawaii is always a good idea. I mean, what's not to love about palm-tree lined shores, miles of beaches, lush mountains dropping into the sea and those laidback folk who excude health and happiness. Winona Bailey is one of those people. The mum, wife and traveller is originally from Vancouver Island but is currently based on the beautiful Hawaiian island of Kaua'i with her man Jason and twin boys, Cass and Marlow. We first spotted Winona working in The Barn 808 at Hanalei during our own family holiday on Kaua'i and had to chat to her about her idyllic life on the Garden Isle. 

"I’ve had so many moments where I stop and try to soak in this incredible feeling of gratefulness that hits me that I get to spend some of my life here," she tells The Travelling Tribe. "It’s funny as humans, and especially as young parents, the days kinda blur by and it’s easy to feel too busy or tired to take in your surroundings. Being in a place as stunningly beautiful as Kaua'i makes it a bit easier to stop and soak in the mountains, the ocean, the rain, the birds and flowers and trees. Most of my surreal moments happen when I’m waiting for a wave on my surfboard and I turn to look at the mountains and valleys and all the waterfalls streaming down to the ocean and I’m like, ‘Whoa. Thank you! Thank you, thank you."

Here, Winona shares her local haunts with The Travelling Tribe.

Tell us a bit about your background?

I grew up mostly in Victoria on Vancouver Island BC but was born further north in Campbell River. Before having kiddos, I travelled as much as possible. I did massage, taught yoga and occasionally worked with my Pops doing construction to save up for my next trip.

How did your tribe end up on Kaua'i?

We were living in Sayulita, Mexico, the winter we got pregnant and our intention was to spend half of the year there after the boys came. When I was three months pregnant, we drove our truck and camper north through the desert and back to Vancouver Island where the boys were born. When they were about three months old, we went back to Sayulita for a couple of months and realised that Hanalei would be a better fit for us to raise the boys. We ended up finding the perfect place in Hanalei and - after a year of living in Bellingham, WA, a summer in Denver, Colorado, and a few little trips to Pennsylvania, Seattle, Tucson and our wedding on Hornby Island BC - we moved here. It's been pure magic. Once we had the boys, it was important to both Jason and I to be somewhere where we could be outside as much as possible and where we could surf. We wanted to be close to the beach and a town so we didn't have to drive and somewhere that felt like a safe, thriving community to raise the boys. Hanalei felt that way to us even before Jason and I met and it's just getting better and better.

What does an average day look like on Kauai?

We get up with the sun - thanks to our early risers - make coffee and breakfast, get the kids out the door and on our cargo bike and ride to pre-school. They only go for four hours in the morning but it's so amazing to have that little bit of time now. Jason and I usually go surf if we can or do a beach walk. After running errands and eating lunch, we pick up the boys, they nap for a bit at home and when they wake up, we go to the beach. They love the water, boogie boards, surf boards, floaty vests or being naked in the waves - they love it all. No matter how the day has gone, every single time I see them in the water and watch how their little faces light up and they are a bubble of complete joy, I know we are in the right place.

Can you share any local haunts for must-dos for families visiting Kauai?

If you're coming to Kaua'i, you have got to check out this company that rents Westfalias all camperised out for you - such a great way to cruise and camp. You also have to check out all of the food trucks that have popped up in the past year - Fresh Bite, Cafe Tumeric in Hanalei and Scorpacciata in Kapaa. If you feel like a break from the beach, check out The Barn 808 and then grab an Acai bowl and a cold brew coffee with macadamia nut milk at Wishing Well. The biggest tip? Slow yourselves down! Enjoy the waits, the one-lane bridges, the low speed limits; it's all part of life on Kaua'i.

Where do you and Jason go on a date night?

Hmmm, what's a date? Haha! Baracuda is a great restaurant, good food, yummy cocktails and an awesome atmosphere. Palate in Kilauea is super lovely, too. My favourite date, though, is a bottle of wine and some snacks at the beach - quiet, mellow, beautiful and an amazing time to truly connect with my love.

You live in paradise but have travel in your blood. No doubt you have some adventures planned?

We will forever be travelling, some years more than others but we have so many future dreams for our family like living on a boat and sailing around the Caribbean, homeschooling in Mexico, half a year in Italy, house swaps in Australia to name a few.

We'll go back to BC every summer and spend a month or two on the Gulf Island where I grew up. It's so amazing there that time of year and gives us a chance to connect with friends and family. We'll spend the next Christmas holidays in Colorado and get the kids on some skis. We're also planning a little kid free surfing trip to Sayulita after that! But we plan to have Hanalei as our base for many years. We're open to adventures and can't wait to see where we end up as our little guys grow.

Thank you for your beautiful words and time, Winona. If anyone has any questions about Kauai, we also visited in 2016 so feel free to ask any questions.

Images of Kaua'i and family provided by Winona.
Cafe Tumeric, via Pinterest.
Wishing Well Shave Ice images, via @wishingwellshaveice.