A Drinking Ship With a Sailing Problem

Windjammer Barefoot Cruises has long been known for its fun-loving ways. But is the party finally over?

The Clipper en route to Union Island

"Do not ask me when we're going to get there!" bellowed Captain Julian. "This is the Caribbean! We live in la-la land 90 percent of the time! If there's food and booze, we don't give a damn!"

A Windjammer cruise isn't for control freaks or prudes. You gotta expect a little chaos. That has always been the case--there's a reason for that "No Whiners" sign above the ship's bar.

On our cruise, the chaos was consistent. Flights in and out of Grenada were delayed or cancelled and luggage was lost (none of which was Windjammer's fault), and airport pickups and drop-offs never materialized, causing last-minute scrambles for cabs (which was totally Windjammer's fault). Once we made it on board, we learned that the itineraries on the company's website are more like...possibilities. We visited just five of the seven ports of call listed for our St. Vincent and the Grenadines trip--Grenada, St. Vincent, Bequia, Union Island, and Mayreau.

Just go with the flow, mon.

And yet, we had way better flow than Windjammer passengers who sailed a month after we did. In August, passengers booked on three of the line's ships were stranded in Aruba, Costa Rica, and Panama. Crews reportedly hadn't been paid for months. (So that's why our crew nudged us to leave tips in cash.)

Clearly there's a sea change of some kind ahead for Windjammer. The company was started in 1947 by Captain Mike Burke, who says he awoke from a bender to find himself the owner of the 19-foot boat on which he had passed out. (It was floating in the Bahamas. He'd begun drinking in Miami.) Burke christened it Hangover, using a half-empty bottle of Scotch, and soon began leading tours on it. Thus was born an empire. His children ran the company for years, amid stories of sibling squabbles, drug abuse, and accusations of embezzlement.

But as of this writing, a group of investors has agreed to take a controlling interest in the company, perhaps ending the financial turmoil (and reimbursing those stranded passengers for their out-of-pocket expenses). One hopes any new owners can also retain the qualities that make Windjammer an affordable, attitudinal antidote to oversize, homogenous cruise ships.

WHEN WE BOARDED the ship, my husband, Jonathan, and I were ready to party. We hadn't had a kid-free vacation since our older child was born almost six years ago, and Jonathan had just finished a round of cancer treatment. Bring on the rum!

Like Windjammer's other three ships, the Yankee Clipper is a repurposed, reconditioned old sailing yacht small enough to slip into harbors that the big ships have to skip. Built in Germany in 1927, it was one of the few armor-plated private yachts in the world, and was later owned by the Vanderbilt family. It's ravishing, a 197-foot, 64-passenger vessel with teak and mahogany finishes, swooping carved railings, and brass accents. Yes, the deck could use refinishing and the masts are showing their age, but those flaws only give the ship character, like a glamorous old-time movie star.

Windjammer's rabid fans agree. More than half the folks on our ship had sailed with the line before: Some were on their 14th Windjammer cruise. Several were starting their second week on the ship. Our 60 fellow passengers were a diverse crew--a cop, a high-school math teacher, a lounge singer, a travel agent, a radiologist, an equity analyst, a biker dude with a giant moustache, a young female soldier who ran a mobile military hospital in Iraq, a retired flight attendant, a farmer. We ranged in age from 16 to 70. There were a couple of families with teenagers. Officially, kids 6 and older are welcome on Windjammer cruises, but I wouldn't recommend the trips for kids younger than 15, unless they were weaned on rum.

Though outnumbered, we newbies quickly picked up the lingo: Veterans are "Jammers," the captain's daily briefing is "story­time," and the rum drinks pounded every afternoon are "Swizzles." (They--as well as early morning Bloody Marys and wine at dinner--are included in the cost of the cruise. To buy other drinks, you use "doubloons," round punch cards you buy for $20.) Oh, and the Yankee Clipper is not a boat. "Can you stand in the middle and pee off the side?" Babu, one of the stewards, sputtered in outrage after I used the b-word. "If you can, it's a boat. If you can't, it's a ship!"

I goofed again later, in front of Captain Julian. He clutched his heart in mock agony and wailed, "Calling my ship a boat is like telling a man that his penis is small!"

Penis, penis, penis. There was so much below-the-belt sniggering that it often felt like we were cruising with the cast of Superbad. At the buffet lunch on our first afternoon, the centerpiece was a massive cucumber resting on two apples. At the towel-folding seminar one evening, we learned to make a giant towel penis. (Every day, the crew left adorable towel sculptures on our beds--butterflies, swans, elephants, and monkeys, all with Hershey's Kisses for eyes. There was no Hershey's Kiss in the penis.) And unlike storytime at home, the captain's spiels always ended with an off-color joke.

Get Inspired with more from BudgetTravel.com


Note:This story was accurate when it was published. Please be sure to confirm all rates and details directly with the companies in question before planning your trip.
 

Budget Travel Real Deals


  • From $1,399

See more deals »

Video


Our newsletter delivers vacation inspiration straight to your inbox.

Check Prices