‘It’s not just sunsets and cocktails:’ They sold their home in Colorado to live on a sailboat

Charly Oliver and Michelle Denton spent over 30 years saving to retire early and buy a sailboat. (Charly Oliver via CNN Newsource)

Not long after Charly Oliver and Michelle Denton met in the 1990s, they found they had the same dream — to live on a sailboat and explore the world.

It took many years for that goal to be realized, but the couple were finally able to sell their home in Boulder, Colorado, a decade ago and buy a sailboat named “Rascal.”

Since then, they’ve spent November through April each year sailing across the clear waters of the Bahamas, admiring striking sunsets and tropical shores from their 41-foot (12.5-metre) floating winter house.

The summer months are spent globetrotting — the couple have so far visited 36 countries across Europe, Asia, Africa and the Americas.

Freeing lifestyle

“What pretty much sums up the sailing lifestyle is the freedom and just working and living with nature,” says Denton, who couldn’t be happier to be living the life she first imagined when she learned to sail as a child.

Their lifestyle at sea didn’t come easily. Back when she was a law student, Denton had put together a 40-year plan that involved living frugally and saving as much as possible so that she could retire early.

When she and Oliver married in 2004, Denton laid out her plan to him and found he was willing to pursue it with her.

“For me, retirement has always been about travelling and doing the things I want to do like climbing, motorcycling, sailing,” he says. “Settling down in one place and not going anywhere is not in the cards for me.”

Life on land felt fast-moving and uninspiring at times, adds Denton, who explains that they’d travelled all around the U.S., visiting most of their bucket-list places, and the prospect of exploring new shores and hard-to-reach spots was hugely appealing to both of them.

After 33 years of saving they were finally able to retire in 2016, three years earlier than they’d initially projected.

That same year, they took their first sea trip, from Galveston Bay in Texas, where they bought the vessel, along the Gulf Coast to Florida and then from the Florida Keys to the Bahamas.

For the past 10 years, their winters have been spent exploring the more than 700 islands of the Bahamas, such as the Abacos, the Berry Islands (a 30-island chain), Conception Island, and Mayaguana, its most remote isle.

Challenging times

During the summer months, they usually leave the vessel behind to continue their travels on land.

While they say there are many pros to life at sea — such as the freedom, the affordability, and the boating community — there are also many cons.

“It’s not just sunsets and cocktails,” says Oliver, who previously worked in the industrial safety sector.

Maintaining a sailboat can be hard work and constantly being at the mercy of sea conditions requires a lot of preparation, forward planning and patience, they say. Anything that goes wrong with the boat, they have to fix themselves.

“You don’t go anywhere fast,” says Oliver. “Dealing with weather can be problematic both at sea and when anchored.”

The couple have had many challenging days at sea, including a bad-weather crossing of the Gulf Stream, an ocean current that flows through the Straits of Florida and up the eastern coastline of the United States.

They live simply onboard. The kitchen contains only a small oven and all digital comms are via a limited satellite internet link. However, they say they embrace a slow-paced routine and don’t miss modern comforts.

The cost of living on a sailboat is also much lower than on land, they say. While boat insurance is comparable to house insurance, Rascal is fitted with solar panels, which generate all the energy they need. They also avoid luxuries such as eating out.

“We don’t spend very much money out on restaurants because there just aren’t very many restaurants around. We also don’t spend much time in marinas as we prefer to be anchored out,” says Denton.

In 2023, they decided to buy a home near the Cascade Mountains in the city of Cle Elum, Washington, so that they had a base on land between trips.

The couple recently bought a new 34-foot (10.4-metre) motor yacht, which means they are less reliant on seasonal winds, and can sail toward cooler, northern destinations in America and Canada during summer rather than having to wait for winter.

Their new vessel, which will be named “Motoryacht Rascal,” is smaller, with more restricted living quarters, but it can be transported using a trailer.

They’re looking forward to sailing to Desolation Sound and the Gulf Islands in British Columbia, as well as Alaska’s Prince William Sound and the San Juan Islands, an archipelago in Washington State.

The couple also plan to head to Maine and Nova Scotia in the near future.

Looking back on her past life as a lawyer, Denton remembers barely having two weeks off work each year, feeling rushed during vacations and struggling to plan dinners with friends because their schedules never aligned.

Over the past 10 years, the couple have become part of a tight-knit community of “boaters,” making lifelong friends, whom they meet up with for beach yoga, dances and folklore festivals.

When anchored, they often meet up with friends and enjoy open-water swimming or playing bocce ball on the beach.

Denton, now 57, feels that the couple’s lifestyle keeps them young, quoting the famous line from veteran actor Clint Eastwood, “I don’t let the old man in.”

By Silvia Marchetti, CNN