I’ll let you in on a secret: prior to this year, we didn’t have any New York City holiday traditions. Typically, Mr. Five O’Clock and I spend the last two weeks of December in California (and the first two rushing around wrapping up last-minute assignments and purchasing zany holiday gifts), so the festive air and holiday cheer tends to pass us by.

Not so this year. Our fabulous, NYC-savvy friends Lynn and Justin of Mad Hatters NYC invited us to carol the night away on Classic Harbor Line’s Cocoa and Carols cruise, and it was a true holiday offer we couldn’t refuse. Here’s why the Cocoa and Carols cruise is the perfect New York City activity for the holidays.

Prelude to a Holiday Cruise: Or, Definitely Eat Dinner Before You Go & Don’t Be Late!

Classic Harbor Line’s Cocoa and Carols cruise includes a complimentary beverage, cookies, and treats during the 90-minute holiday experience. Because it’s near impossible to make a meal solely out of cookies and hot chocolate (trust me, I’ve tried), a proper dinner was in order for our group prior to our 9 PM cruise.

Our group dined at Death Ave, which was selected based on its proximity to the cruise’s departure point (Pier 62) as well as its excellent reputation. The souvlaki chicken tacos were juicy and succulent, and the beer — made in house! — hit the spot.

It was a true miracle on 34th Street (er, 22nd Street, technically) as we hightailed it over to Chelsea Piers and made it onto the boat with literally two minutes to spare. We New Yorkers are serious experts at power walking on a full stomach if there’s a time crunch!

All Aboard the NYC Cocoa & Carols Cruise!

My initial resistance to a December holiday cruise? I was convinced that it would be uncomfortably freezing out on the water. Not so, it turned out: I breathed a sigh of relief once I realized that we’d be in an enclosed, heated solarium during our holiday seafaring voyage.

As we stepped on board, the super friendly staff directed us to our assigned tables. There were tables for two and plenty of tables for large groups — the cruise was filled with couples and friend groups alike.

Once we left the pier, live music filled the room as we ordered our drinks. We soon realized that this wasn’t just any old song — the band actually sang the pre-departure safety rules to us to the tune of “Carol of the Bells.” This comical warmup song set the jolly, cheerful tone for the evening.

With the festive mood permeating the air and our glasses of champagne in hand, we were ready to begin cruising and caroling!

It’s The Cruise with ALL the Views

The views you’ll see during the Cocoa and Carols cruise are worth the price of admission alone, in my opinion. Throughout our 90-minute journey, we passed by a variety of landmarks — including Governor’s Island, Ellis Island, Battery Park, and Brooklyn Bridge — which are absolutely spectacular at night. My favorite sighting was Lady Liberty herself, looking resplendent and serene lit up in the dark.

Some brave souls stayed outside taking pictures for a very, very long time. (Though I was not one of them, Mr. Five O’Clock turned out to be!) Props to them for withstanding colder temperatures — or maybe they simply dressed more warmly than we did.

If you want to stay inside for your Statue of Liberty view, that’s cool too. Hey, it’s much, much warmer inside the boat — and that’s also where the bar is where you can purchase additional drinks. #Priorities, right? In addition to regular and spiked cocoa, you’ll find specialty cocktails, beer, wine, and cider alongside non-alcoholic options.

It’s A Wonderful (Caroling) Life

Back inside, the interactive portion of our Cocoa and Carols cruise began. The saxophone player suspiciously started handing out tambourines, and we instantly knew that something sneaky was afoot.

The lead singer soon passed around lyrics sheets for the “Sing Along” portion of the cruise. Participation isn’t mandatory, obviously — they’re not the Caroling Grinch here, after all — but most of our fellow cruisers got into the singing spirit.

The carols we sang while carousing ranged from the classic “Let It Snow” to perennial favorite “Jingle Bells.” The best was saved for last, of course, as we all joined in to sing a fabulous boat-wide rendition of “12 Days of Christmas.” Each table was assigned a portion to sing (we were “three French hens”), and the folks who bellowed out “five gold rings” stole the show every round.

In between carols, we noshed on a tray of cookies and treats (which didn’t go far with a group of our size, but that’s OK as more food is available for purchase). Luckily, we were still full from dinner, so the treats made a nice dessert course.

The best part of the night, however, is bonding with your friends and seeing just how much fun they’re (secretly) having while belting out an endearing rendition of “Rudolph The Red Nosed Reindeer.” And, perhaps, attempting to capture said friends’ laughter and amusing them in the process. (Sorry, Mad Hatters!)

Overall Impressions

I’ll admit that cruising around New York harbor wasn’t my first idea for a holiday activity, but by the end of the night, I was sold. Between the toasty warmth of the boat and the hilarious musical antics of the band, we’d seriously consider making this a new New York City holiday tradition. Cheers!

PS: Check out our fellow bloggers’ take on the night, including Mad Hatters NYC, Mary in Manhattan, Rendezvous En New York, Girl in Gotham City, Tea with B Blog, and Musings and Adventures.

Cocoa and Carols Cruise: Practical Info

• Address: Chelsea Piers (Pier 62) at West 22nd and Hudson River in Manhattan, NY. (Exact meeting location details are provided instantly upon purchase of tickets.)
• Website: https://www.classicharborline.com/nyc
• Hours: Several times to choose from in the afternoon. Cruise lasts 1.5 hours.
• Cost: $64 for adults; $36 for children ages 3 to 14. Be sure to verify current information on Classic Harbor Line’s website.

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Thanks to Classic Harbor Line for partnering on this post. As always, our opinions are always our own. Not even some (very) spiked cocoa can change that.