The Chaser and her sister aboard the Red Witch
The Chaser (right) and her sister, aboard the cocktail cruise

You’ve seen the Windy. It’s that many-masted vessel docked at Navy Pier that looks like a playground for fanny-pack wearing families from Iowa hoping to live out their Pirates of the Caribbean fantasies.

Or at least that’s what I was thinking yesterday as my sister Liv and I prepared to venture aboard a skyline cocktail cruise on the Red Witch, a smaller boat operated by the same company. But as temperatures continued to fall and I found myself packing extra sweatshirts and then gloves (gloves!) for the excursion, I began to suspect we weren’t in for a breezy pleasure cruise.

The Pianissimo
The sleek Pianissimo, docked in Burnham Harbor

Unlike the Windy, the Red Witch and the newest member of its sibling fleet, a sleek 2011 Beneteau Oceanis 50 called the Pianissimo, both leave from Burnham Harbor, which gives the outing more of a local feel, as most of the other boats docked there are personal crafts. Also ranking low on the tourist scale: The group cruises are small, about six passengers max on the Pianissimo and 49 on the Red Witch versus the Windy’s 150. Oh, and one other thing new this year: booze.

Once I laid eyes on the Pianissimo, I wished it was our vessel for the trip. The Red Witch is interesting in an old-timey kind of way, but the new boat just looks fast (you shell out for speed: $244 per person for Pianissimo cruises; $95 per person for the two-hour cocktail sail on the Red Witch). But as we grabbed seats on the Red Witch’s varnished deck and clinked our plastic glasses filled with tart Sparrow Mojitos (two drinks—from a list with names like the Pearadise on the Horizon and the Red Witch Royale—are included in the cruise price; passengers may BYO canned beer for no extra charge), I was glad just to be getting out on the water—even if fog was beginning to envelop the skyline. Liv and I tightened our hoodie drawstrings as the wind whipped our hair into our eyes, thanking our lucky stars for those gloves.

Our fellow passengers, a group of office workers from the burbs who all knew one another, seemed apprehensive about the conditions. “We’ve got a few novice sailors onboard,” said one of crew as the engine chugged to reverse us out of the slip. “It’s gonna be pretty rough out there.”

The Red Witch
The Red Witch on a calmer, balmier day

Right before we motored out of the harbor and onto the lake, a crewmate named Andrew with shoulder-length curly hair and a Jack Sparrowesque beard (not to mention a skull ring; he totally looked the part) dug his heels into the deck in front of us, toward the bow. “You’ll thank me in a minute,” he said. When we crashed into a swell and a spray of chilly water hurtled toward us, Andrew blocked it, but when the captain steered into a slight turn, nothing could have stopped the wave that broke over the side of the boat and soaked our backs, head to tail.

“Oooh!” we squealed as the Red Witch pitched. Surprised to find ourselves sliding off of our wooden seats and reaching for any steady thing to grip, we had to decline mojito refills until we reached calmer waters.

That wasn’t to be. After few minutes at sea, the office dwellers on board insisted we turn back. The cocktail cruise was over for the day, thwarted by high winds and whitecaps just 24 hours after we’d all been sweltering in sauna city. Chicago weather. What can you say?

If it were up to me, we would have taken on that chop, Lieutenant Dan–style. Instead, we’ll try again another day—a real summer day—and I’ll bring that pirate a thank-you brew.