The reluctant sailor’s ICW guide

Sailing Scared: Maine to Florida 2014-15
by Karlene Osborne; Custom Communications, Inc., 2019; 128 pp.; $16.95.

Book review by Randy Randall

Reading “Sailing Scared,” Karlene Osborne’s new book about a cruise from Maine to Florida via the Intracoastal Waterway (ICW), one realizes early on how entirely appropriate the title is. Because the author readily admits that – at least out on the water – she’s scared of almost everything! It doesn’t matter that she’s sailed with her husband Tom for nearly 40 years, on four different boats. Her stomach still does flip-flops when the boat heels, and she’s never learned to swim – a fact that terrifies her. Truth be told, she doesn’t really enjoy boating that much. Because everything is so . . . scary!

And yet, when husband Tom decides he wants to take Nest Egg, their 40’ O’Day, down the ICW, Karlene, with little hesitation, signs on as first mate. Karlene is tough. She’s a breast cancer survivor, and used to overcoming fear and rising above calamity. A trip down the ICW?

She’s got this.

Here’s a partial list of the things – her fears – Karlene must conquer: She doesn’t like sailing out of sight of land or sailing in the dark; she’s afraid of going through canals or locks and sometimes hides below when Nest Egg passes under a bridge; she worries about mechanical failures and about running out of fuel, food or water; she worries about being able to find a doctor, should they need one; she worries when they lose cell phone reception, or the AIS system drops its signal; she worries that they’ll run out of toilet paper.

It’s a lot for one person to have on her plate. But Karlene tackles these issues and more head-on. The inability to swim? How about rigging netting around the entire boat to prevent slipping over the side, and always wearing a pfd? The toilet paper issue? Make sure there’s a lot of toilet paper. She gives the whole endeavor her best shot by overcoming the obstacles placed before her with a mix of persistence, resilience and self-confidence.

Karlene’s writing style is straightforward and factual. She’s a keen observer of waterfront activities, of the people they meet, and a sharp critic of some of the places they visit. She’s keen to point out which docks are sailboat-friendly and which towns can be passed by. She’s an uncompromising judge of marina showers and laundry facilities – information every southbound cruiser needs.

Aboard Nest Egg they run aground a lot, probably too many times to count, and gradually they learn how to expertly extricate themselves. They have problems deciphering the ICW buoyage system. They spend seven months confined together in a small space. She worries that their 46-year marriage can survive the ordeal. But then they fall in with other boats – over 1,500 head south each year via the ICW – moving in the same direction and become fast friends with other cruising couples. Some of it is hard, and some of it is highly rewarding. The trick, of course, is striking a balance.

“Sailing Scared” is a valuable read on several fronts, the first being that it’s a wonderful example for sailors who dream of making a long cruise but harbor real anxiety about doing so. No one is more scared than Karlene, but she shows how fear can be faced and overcome with detailed planning and a healthy sense of humor.

The second is that her day-by-day account of their trip – where they went, where they stopped and what they saw – provides an excellent real-life guide for others navigating the waterway. Ultimately, though, her story is one of personal growth and the unending love between her and her husband.

Saco, Maine, resident Randy Randall is a friend of the magazine and a waterman of the highest order. Karlene and Tom Osborne are longtime members of Centerboard Yacht Club in South Portland, Maine. To order a copy of the book, email them at