- With no sailing experience, this couple moved their family of five to live on a boat in 2019.
- They reassessed what was important to them and now homeschool their children while sailing.
- They love exploring the world from their 2-bedroom boat even though they’ve faced difficulties.
- Visit Insider’s homepage for more stories.
Many people dream of selling their possessions and traveling the world, but this family of five is actually doing it.
Samantha Kalil, 28, and her husband, Aaron, 31, had spent years chasing the American dream. They were pursuing successful careers, saving up for a house, and dreaming about expensive cars.
But the couple hit a crossroads when they had to decide whether they wanted to continue living in downtown Boston or move to the suburbs.
“We weren’t excited about either prospect and that got us thinking – whose dream are we actually living?” Aaron told Insider. “Are we pursuing the things we want or are we just doing what society expects of us?”
He said he tossed around the idea of living on a boat, but never expected it to result in a full-time move.
It didn’t take the couple long to decide to move onto a boat
Samantha didn’t initially jump at the suggestion.
“When Aaron threw out the idea of living full-time on a sailboat, my first reaction was ‘absolutely not!’ Somehow he convinced me, and two weeks later we were looking for our forever boat,” she said.
Although the couple had some savings, they decided to sublet their apartment and move in with family for eight months to help save up for the adventure.
Soon enough the couple and their three children – Quinton, 9, Camryn, 5, and Beau, 3 – were boarding their vessel in June 2019.
With no sailing experience behind them, the couple took a leap of faith
You may think that Samantha and her husband had years of boating experience, but the couple had never even been sailing before.
They didn’t let this stop them from chasing their dreams and they taught themselves how to sail during summer 2019.
The first few months onboard was spent learning how to get off the dock and sailing while the sun was up.
Fast-forward to today, and the family has managed to sail from Boston up to Maine, where they stayed in the Acadia National Park area for the summer.
“It was magical and filled with other boats filled with kids,” Samantha said.
Their next goal was to make their way down the East Coast to the Bahamas just in time for Christmas, which they achieved.
The family has also been to Freeport, the Berry Islands, and Andros Island.
Although it isn’t big, the boat has everything they need
Before moving, the family downsized and reassessed what was important to them.
Their 12.80m sailboat has two bedrooms, one bathroom, a galley, and two settees around a table.
The limited space meant they had to cut the kids’ toys down to the necessities. Indoor toys, like blocks and dolls, were replaced with outdoor ones – snorkeling gear, fishing rods, and paddleboards.
“We’ve also learned to utilize space better. In such small quarters, you don’t want any wasted space,” Samantha added.
“Our favorite space on the boat is our cockpit, a.k.a our outdoor patio/living room. This is where coffee is sipped in the morning and sundowners are drunk in the evening with new friends,” Samantha told Insider.
Although the space is small, they’ve added some personal touches, like flowers and paintings, to the boat to help it feel like home. Next they want to add some jellyfish wallpaper to the kitchen.
To make this experience work, the parents are homeschooling their children
Out on the ocean, no day is the same since the family’s daily experiences depend on where they are.
But Samantha and Aaron still try to keep a light schedule to provide their children with structure.
The kids are currently being homeschooled, which Samantha said has been “interesting.” She told Insider she’s been able to do six hours’ worth of schoolwork in about three hours.
She also said she’s had to get creative to deal with the challenges of homeschooling since her kids vary in age and it’s difficult to keep them all focused at once. Still, for her, the freedom has been worth it.
“We love having the freedom to take our kids out exploring, hiking, fishing, and sailing during the week,” she said.
Samantha said that those considering having their children homeschooled should free themselves from all preconceived notions.
“We certainly don’t have it all figured out in this department but the best advice we got from another cruising family was to figure out what interests your child and work their schooling around that,” she added.
The couple also decided to make some career changes
To make this experience work, Samantha stopped working once they started cruising. Aaron has a wealth-management practice that doesn’t require him to be in one place.
“Originally, we had planned to spend six months in the Bahamas and while there I’d work remotely the best I could,” Aaron told Insider.
When the global pandemic hit, his plans changed and he now intends to work remotely indefinitely while he travels with his family.
Their journey hasn’t always been sunshine and rainbows
Although the last year and a half has been a dream for the couple, it hasn’t been without difficulties.
The pandemic hit seven months into their big adventure, and the family has had to navigate it at every town they visit.
Although their goal is to explore each new destination as much as possible, they’re also trying to be responsible.
“Things in Nassau are pretty devastated from COVID. Almost all businesses and restaurants we’ve seen are shut down, and there are basically no tourists on the island except other boaters,” Samantha explained.
“We plan on staying in Exuma for a few months to isolate with other boaters while we ride out this COVID madness,” she added. “It’s during times like these that we miss friends and family back home.”
They’ve also faced challenges at sea.
In one incident, their anchor dragged in high winds at 1 a.m., forcing Samantha and Aaron to get out of bed and relocate in the middle of Hurricane Isaias. With the help of another cruising family, they were able to grab a mooring in the dark.
And they’ve had their wind generator snap off while fighting 1.52m-tall waves. Samantha was able to free climb the mizzen mast – while holding on for dear life – and secure it before it caused any more damage.
The family also got caught in a lobster trap in rough seas and spent four hours freeing themselves from it.
But Samantha said that these challenges have helped her family build confidence at sea.
“It’s not always beaches and margaritas,” she added. “Some days it rains, stuff breaks, and things go wrong but every day begins and ends together as a family.”
The family’s life has completely changed – and they couldn’t be happier
Although there have been highs and lows, making the decision to drop everything and hit the high seas has completely changed the family’s life.
Even though they don’t always have access to things most people take for granted – including grocery stores, laundromats, and Wi-Fi – it has taught them to be prepared for whatever may come.
“My favorite part is the freedom we have to go and explore the world. While we’ve only sailed around the East Coast of the US, we often talk about all the places we’ll visit over the years,” Aaron said.
Their best advice for anyone else who dreams of following in their footsteps and living on a boat full-time is to just dive in.
“Don’t wait. There are a million excuses why you can’t do it – money, lack of experience, kids’ ages, schooling, family. Just jump in headfirst and everything will sort itself out,” Samantha told Insider.