The crew gets ready for a sail.

David Liscio photo

When and If can carry 32 passengers during daysails or accommodate six guest for extended cruises. Most days, Salzmann said he embraces his pirate’s life as a charter boat skipper, understanding it’s a ticket to a much greater adventure. His two sons, Ollie, 3, and Arlo, who turns 2 after Christmas,  join the two-hour trips when not at daycare or attending the local pre-school. Jenny said there’s lots to consider when it comes to bringing kids along on a global circumnavigation. There are logistical hurdles like home schooling, emergency medical treatment, health care, socialization, and safety amid foul weather. 

When the boys near the open companionway, mom is there to block them. But they can be quick as mercury and already Ollie wants to join Salzmann at the helm.

In addition to running Sunset Sail Salem and Sunset Sail Key West aboard When and If, Salzmann and his brother, Dylan, are co-skippers of the 141-foot steel-hull tall ship Columbia, which they sail in the Caribbean. 

“We’re both active captains of Columbia. If Dylan’s not there, I am,” Salzmann said. “It’s the whole thing, the boat, the sea,
the adventure.”

There’s no 9 to 5.