Ahoy there! If you’re anything like me, you’re always looking for the perfect Boston adventure, something that shows off our city’s charm in a fresh way. As your Cambridge host, let me tell you about the secret I discovered to shake off the winter chill: setting sail with the Charles Riverboat Company for their legendary Cookies & Carols Cruise.

We’re talking about warming up with sweet treats, singing along with live carolers, and watching the holiday skyline glide by. In this piece, I’ll share everything I learned from Captain Sam about why this cruise is a must-do and how you can plan your own escape on the water.

According to Captain Sam of the Charles Riverboat Company, the secret is to get on the water. In this article, we break down what makes their special Cookies & Carols Cruise a must-do winter activity and answer the question many are asking: What’s the best way to see Boston from the Charles?

The Charles Riverboat Company operates a fleet of seven vessels, offering everything from public sightseeing tours to private events. Their seasonal approach means there’s always something new to experience, from summer history tours to festive holiday outings.

Holiday cruises offer a unique, cozy vibe. While summer tours are the classic choice, the holiday-themed cruises provide a special atmosphere. As Captain Sam explains, the Cookies & Carols Cruise features a festive playlist, live carolers coming aboard, and “a whole giant array of sweets” laid out for guests. It’s an hour-long, non-narrated journey perfect for relaxing and taking in the glittering city lights.

“Boston's beauty isn't limited to sunny days. A cruise on the Charles offers a fresh perspective in every season.”

The sightseeing is world-class, year-round. The route offers stunning, uninterrupted views you can’t get on land. The cruise passes major landmarks, including the entire Boston skyline, the Charles River bridges, and numerous universities. Captain Sam notes they typically go “a little past Boston University,” ensuring a comprehensive vista.

Captains double as expert local guides. The captains, like Sam, often have years of experience as tour guides. They love pointing out unique sights that have emerged during their time on the river. Sam’s personal favorite is Boston University’s Center for Computing and Data Sciences, nicknamed the “Jenga Building” for its striking, stacked design. He also highlights the historic Charles Street Jail, now the luxurious Liberty Hotel, as a point of beautiful irony and Boston history.

Operations are seasonal and diverse. Understanding their schedule is key to planning your trip. The season begins with private events on April 1st. Public sightseeing tours (their “bread and butter”) launch on Memorial Day Weekend and run strong through September. Fall and winter bring intermittent public cruises and specialty voyages, such as the holiday event, offering reasons to visit year-round.

Booking is simple and direct. For those inspired to set sail, the process is straightforward. All public cruises can be booked directly online at charlesriverboat.com. The site also provides contact information for planning private events. As Sam assures, the team is available during standard business hours (9-5 on weekdays) and often on weekends during the active season to answer calls and help plan your outing.

This is an essential Boston experience that combines scenery, history, and local flavor. It’s a reminder of the world-class attractions in our own backyard and a fantastic option for hosting out-of-town guests or a unique date night. The diverse fleet and private booking options offer a memorable venue for any group occasion.

Boston’s beauty isn’t limited to sunny days. A cruise on the Charles River offers a fresh perspective in every season, especially when wrapped in the festive cheer of holiday cookies and carols.

If you’re thinking about booking a cruise for sightseeing, a private event, or a special holiday outing, visit charlesriverboat.com for schedules and tickets. For local Cambridge real estate insights and how to live your best life near the river, you can always reach out to me at (857) 210-9925, email Lou@c21revolution.com, or visit my website at https://louis.c21revolution.com/.

Now, who’s ready to come aboard?

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