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Travel Blog

Blog post December 3, 2018
Bill Hare, 73, on the aft deck of Wind Surf during his 99th Windstar cruise in March. He's been sailing on the small-ship cruise line since the mid-1990s.

JD Lasica / Special to Cruiseable

Bill Hare, 73, on the aft deck of Wind Surf during his 99th Windstar cruise in March. He's been sailing on the small-ship cruise line since the mid-1990s.

99 cruises and counting for this diehard Windstar fan

You hear stories about cruise passengers who travel so frequently on a particular vessel that it becomes a second home.

If you’re sailing on Wind Surf, the flagship of Windstar Cruises, you’re likely to meet one of those diehard fans.

Bill Hare, 73, of Dallas, will embark June 8 on his 100th Windstar cruise — a Mediterranean itinerary, Barcelona to Lisbon, that’s one of his favorites. With his tousled white hair and gregarious manner, he’s easy to find (“I hide out on the port side”), a pleasure to meet and proud that the yacht’s tight-knit crew considers him family, and vice versa.

Cruiseable caught up with “Mr. Bill,” as he’s known to staff, on a Classic Caribbean itinerary in late March — his 99th Windstar sailing — and wanted to know: Why Windstar, and why Wind Surf in particular?

Windstar as home base for deep diving

Bill and his wife were smitten with Windstar since 1994, when they watched Wind Spirit sail out of Venice like a waterborne poem

Turns out that Bill and his late wife, Mary Catherine, were smitten with Windstar Cruises from the time in 1994 when they watched Wind Spirit, sails billowing, glide out of Venice like a waterborne poem. The “sail away” vision held considerable appeal for an adventurous couple who had ditched the corporate world, earned masters’ degrees in religious studies and embarked on second careers. They were living at the time in Rome, where Bill was studying canon law and Cath was deep-diving into scripture. Snorkeling and scuba diving had been a passion since their first trip to the Caribbean in 1976, and it wasn’t long before Windstar began transporting them to some of the best dive spots in the world.

The couple tried other cruise lines over the years but kept coming back to Windstar’s three original sailing yachts, which offered intimate ambience, personalized service and robust dive programs to match. After moving to Dallas, where Bill continues to serve as canon lawyer for the bishop of the local Catholic diocese, the couple organized their work lives to allow for three or four back-to-back cruises each year. They experienced every itinerary the line offered, and Windstar’s vessels became their vacation homes.

Wind Surf anchored off Pigeon Island, St. Lucia, during Mr. Bill's 99th Windstar cruise.
JD Lasica / Special to CruiseableWind Surf anchored off Pigeon Island, St. Lucia, during Mr. Bill's 99th Windstar cruise.

Then Cath was diagnosed with cancer. “At that point, we began traveling exclusively on Wind Surf, in large part because it’s the only one of the sailing yachts with elevators, which became essential as Cath’s health declined,” Bill says. “She was tough as nails … for three years, she insisted on coming straight from chemo to the ship.”

On their last cruise together, Cath took Bill aside for a heart-to-heart talk. “’When I die, I know it will be difficult for you,’ she told, me. ‘But I expect you to get it together, move forward and be back on this ship sooner rather than later.’”

Wind Surf crew as Bill's extended family

Four months after Cath’s death in 2014, after 48 years of marriage, a grieving Bill was back on Wind Surf, surrounded and supported by his second family. “I’d been out here 68 times, and from the minute we stepped on the gangway for all those years, it was the same happy experience: an engaged crew who knows who you are. They all knew Cath and they all wanted to remember her, so they hung her photo downstairs in their quarters, as a kind of memorial. It’s still there.”

Bill Hare is attracted to the history of European ports from April to October and Caribbean itineraries during winter.
Janet Fullwood / Special to CruiseableBill Hare is lured by Caribbean itineraries during winter and by the rich history of European ports from April to October.

These days, Bill serves as an informal tour guide for parishioners and friends who join him in various parts of the world. He’s happy to dispense tips to new acquaintances — advising, for example, that the yacht’s alternative restaurants, Stella and Candles, can be booked more than once per cruise just by asking. He doesn’t dive anymore (“the doc said no to that”) but never tires of the yacht’s ports of call or of the excursions arranged either independently or through the ship. He's also a fan of the large aft deck on Wind Surf. 

As for those itineraries: “I like them all,” he says. “In July and August I’m doing Copenhagen to Stockholm. I also like Venice to Rome down the Croatian coast. When I go to Europe, I love the history.”

That said, Bill knows that Windstar isn’t for everyone, particularly families with young children. He recently took his grandkids on a Disney cruise, an experience he describes as “an absolute beating” in comparison to the small-ship experience. “They were marketing and selling ‘a la carte everything’; it drove me crazy,” he recalls. 

Windstar, on the other hand, “maintains a much more authentic feel, and that’s due in large part to the staff. It’s a great lifestyle for them and they can make more money than on bigger ships with a better all-around experience. There’s nothing to complain about here.

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Janet Fullwood
Janet Fullwood is an editor, writer and photographer-at-large specializing in travel and hospitality topics.