- Starting at ground zero? Try a sailing school or volunteer as part of a sailing crew first.
- Budget for more than you think: Boat upkeep, repairs to plumbing and sails are expected.
- Don't forget to insure your floating home.
Geoff Thomas, 58 years old, still fondly remembers when he and his wife, Laurie, went from being sailing hobbyists to "liveaboards."
"We knew we wanted to take off, see the world a little bit, live on board and sail for a couple of years," he said.
At the time, he was 33 and an executive at a shipping container company, and his then-31-year-old wife was a medical editor.
The Thomases were living out of a marina in Norfolk, Virginia, aboard Saturnalia, a Cuthbertson & Cassian 35 sailboat.
"I would dress in the marina's bathroom and go to work in my wingtips," Geoff said. "Then I'd shuck the suit later and get back into cutoffs."
They enjoyed marine life enough that they decided to set a date, save aggressively and part ways with their jobs so that they could sail Saturnalia to Bermuda in 1993. The couple kicked off a two-year jaunt that eventually brought them up and down the East Coast and into the Caribbean.
But the going was far from easy. "We had difficulty getting health insurance, said Laurie. "We came back after two years with our bank accounts depleted, got our jobs back, and have had employer-based insurance since then."
Here's where to begin if you'd like to take a shot at living aboard a boat.
Geoff Thomas worked in marinas through high school and college, and then spent much of his time as an adult sailing during his free time.
Meanwhile, Behan, 48, and Jaime Gifford, 51, who are in their 10th year of living aboard Totem, a Stevens 47, logged decades of sailing experience prior to setting off on their journey in 2008.
Roll up your sleeves.
"You can buy a small boat that you can make mistakes on without expensive consequences and work your way up," said Geoff Thomas. "Or you can go to a sailing school and get your experience there."
If you're really looking for an adventure, try volunteering as crew for someone else's yacht. Depending on the arrangement, a boat owner might cover your onboard and travel costs.
Expect to work: Duties could include watch standing, cooking, manning the helm and pretty much anything that arises.
If you're ready to commit to a boat, watch your expenses. Both the Thomases and Giffords used older boats for their trips: Saturnalia was built in 1973 and Totem in 1982.
"You'll have your boat goal and your provisions goal," said Ryan Dignum, a financial planner with Dignum Financial Partners in Fort Worth. "You always have to build in cushions in case it's a little more expensive."
Expect to spend time and money maintaining your vessel – and know that you'll have to do a good deal of work yourself.
"After taking the boat around the world, it requires quite a bit of maintenance," said Behan Gifford. "You have to replace the wiring and the rig to know it's good and strong."
Plumbing and sewage were the most burdensome maintenance items for the Thomases.
Those are just two items on a long list of boat care responsibilities, including caring for your sails, preventing corrosion of metal equipment and more.
Don't forget the financial side of boat care: Even if you only sail on the weekends, you need to insure your vessel. If you're living aboard, however, you'll need to notify your insurer and add coverage.
"The island people of the Pacific are so warm and welcoming, and I don't feel I'm in danger there," she said. "Things get riskier in southeast Asia."
Behan Gifford also makes a point of steering clear of areas in the Indian Ocean and South China Sea. "It's not safe to go into the northwest Indian Ocean," she said. "We're very conservative and risk averse."
The Giffords had socked away money for 10 years with a goal of hitting $200,000 before setting off on a five-year sabbatical to sail around the world with their three kids.
They had less than half that amount by the time they sailed out of the Puget Sound in 2008.
Behan and Jaime cover their expenses on with some rental income from a house they own on Bainbridge Island, Washington, along with additional income from Behan's writing, Jaime's sail-making and rigging work, plus personal coaching for other prospective cruisers.
Currently, the family of five resides on Totem in Banderas Bay, Mexico.
"There are a lot of people here who've taken the FIRE approach — financial independence, retire early," Behan said.
"Most people out here have bits of trickle income in addition to their retirement plan; it's not the conventional 'I saved and live off of my savings,'" she said.
Among Dignum's clients is a married couple who are about to retire and have recently sprung for a customized Hallberg-Rassy 48 MKII. They are planning on sailing in the Mediterranean and eventually making their way back to the U.S. on a transatlantic trip.
The two did extensive research in order to determine how much they can expect to spend while living on the boat.
"They had done multiple-week sails in the Mediterranean before, and they kept records and calculated how much it cost," said Dignum. "In port, everything is a little more expensive."
Marina expenses can vary wildly, depending on where you keep your boat: Expect to be charged based on the size of your boat, plus potential extra fees for electric service and other amenities.
"If you're coming into a marina every night, you can't do this unless you have a great deal of money," said Geoff Thomas. He had budgeted for daily expenses of about $25.
To keep a cap on costs, anchor out and take an inflatable boat to shore for local food and interaction.
It's also the best opportunity for exploration. "I look back at the kids' childhood and the experience they have swimming with whales in Papua New Guinea," said Behan.
"Be aware that there may be hot spots when you're traveling," she said, "but it's beautiful, friendly, safe, and the food is amazing."