Planning a trip to Boston and looking for a unique, lighthearted way to see the city? The Howl O Ween Doggy Costume Party Cruise might just be the quirky experience you’re after. It’s a two-hour water-based event where furry friends and their humans get to parade around in costumes, dance to a DJ, and enjoy some of the city’s best views—all from the water.
What makes this cruise worth considering? First, the fun atmosphere—with dogs dressed up and a DJ spinning tunes, it’s a lively, lighthearted scene. Second, the stunning vantage points of Boston’s landmarks you get from the water are pretty hard to beat. The possible downside? If you’re not into crowds or dogs in costume, this might not be your scene. It’s best suited for those who love a bit of whimsy and want a casual, social experience rather than a deeply historic tour.
Whether you’re a dog lover, a family looking for something different, or just someone who enjoys city views on the water, this cruise could add a memorable twist to your Boston trip. Let’s walk through what you can expect and what’s worth knowing before booking.
Key Points

- Cost-effective at just over $30 per person for a 2-hour experience
- Great for dog lovers and those who enjoy lively, casual events
- Offers beautiful views of Boston’s iconic landmarks from the water
- Includes a DJ and raffle prizes for added fun
- Cash-only beverages and snacks might be a small inconvenience
- Service animals are allowed, making it accessible for more guests
What is the Howl O Ween Doggy Costume Party Cruise?

This is a themed cruise celebrating Halloween with a pup-friendly twist. For two hours, you and your four-legged friends can enjoy Boston’s skyline while dressed up in costumes. It’s not a typical sightseeing tour—think of it more as a social, festive gathering on the water, where the focus is on fun, costumes, and good vibes.
The cruise is run by Massachusetts Bay Lines, a reputable company that offers various boat experiences around Boston. For $30.80, you get a lively atmosphere, the chance to showcase your pet’s costume, and lots of chances to mingle.
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The Itinerary and Key Stops
Although this isn’t a traditional sightseeing tour with multiple stops, the cruise does pass by several notable sights, giving you a feel for Boston’s waterfront and historic sites. Here’s what you can expect:
Passing by the Federal Courthouse and Institute of Contemporary Art
As the boat begins, you’ll cruise past the Federal Courthouse and the Institute of Contemporary Art. Both are interesting in their own right—the courthouse with its classical architecture and the ICA with its modern design—giving you a glimpse of Boston’s blend of old and new.
Fish Pier and the Reserve Channel
Next, the boat glides by the Fish Pier and the reserve channel where large cruise ships dock. This area is bustling with maritime activity, adding a lively backdrop to the cruise.
Up Close Views of Planes Taking Off and Landing
One of the fun aspects of this cruise is the chance to watch planes taking off and landing right over the vessel. It’s a bit unexpected and adds an energetic, dynamic element to the experience.
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Passing the USS Constitution
You will also pass by Old Ironsides, the USS Constitution, docked at the Charlestown Navy Yard. This historic ship is a symbol of Boston and U.S. naval history, and from the water, you get a good side view.
US Coast Guard and Old North Church
As the boat continues, you’ll see the US Coast Guard base and the Steeple of Old North Church, linked to Paul Revere’s famous ride. These are iconic sights that add a layer of historical context to your water tour.
The Atmosphere Onboard

The vibe is what really sets this experience apart. With DJ Skoolyahd from the Liberty Hotel Yappy Hour spinning tunes, the mood is energetic and playful. Expect a crowd of fellow dog lovers, costume enthusiasts, and curious Bostonians. There’s also a raffle, which can add a bit of excitement, especially if you win a prize.
Most reviews or feedback (though sparse) mention how much fun people have dressing up their pets and seeing the city from a different perspective. It’s a casual event rather than a polished, formal cruise, so bring your sense of humor and enjoy the party.
Food and Drinks
Beverages and snacks are available for purchase, but keep in mind cash only on the boat. Alcoholic beverages aren’t included, so if you want a drink, you’ll need to buy it there. Considering the price of the ticket, you might find it a bit of an extra cost if you plan on drinks or snacks.
This setup might be a downside for some, especially if you prefer all-inclusive experiences or bring your own snacks. But on the bright side, it keeps the ticket price reasonable and the atmosphere informal.
Group Size, Duration, and Practical Details

The cruise accommodates up to 120 travelers, making it a fairly lively but not overcrowded event. The duration of about 2 hours is perfect for a relaxed, fun outing without feeling like a long commitment.
Meeting at 60 Rowes Wharf at 2:00 pm ensures you have plenty of time to arrive, check in, and settle in before the cruise departs. The activity ends back at the same point, so no worries about complicated transfers.
If you’re local or staying nearby, the location is accessible via public transportation, which makes logistics easier. Service animals are permitted, so pet owners with service animals can comfortably join.
Is It Worth the Price?

At $30.80 per person, this cruise offers a lot of entertainment for a small price tag. The combination of city views, a lively crowd, and the novelty of a dog costume party makes it a budget-friendly option for a fun break from traditional sightseeing.
While it’s not a tour packed with historical commentary or luxury amenities, the value lies in the lively atmosphere and unique perspective of Boston from the water. If you enjoy casual events with a whimsical touch, it’s likely worth it.
What Do Past Participants Say?
Though there aren’t many reviews yet, those who have attended mention the stunning views as a highlight. The chance to see Boston from the water, combined with the festive costumes and music, creates a memorable vibe. The mix of historic sights and lively entertainment seems to hit the right note for many.
Some note that the crowd can get lively, and the fact that snacks and drinks are cash only might be a minor inconvenience. But overall, the mood appears cheerful and fun, with many appreciating the unique experience.
The Sum Up
The Howl O Ween Doggy Costume Party Cruise is a playful, social way to experience Boston’s waterfront. It’s perfect for dog lovers, groups of friends, or anyone seeking a lighthearted, informal outing. The stunning views of the city’s landmarks from the water, coupled with music and costumes, make for a memorable afternoon.
If you’re someone who enjoys celebrating with furry friends, or just looking for a different way to see Boston, this cruise offers good value and a cheerful atmosphere. It’s less about history and more about fun—so go in with a sense of humor and an openness to mingling and dressing up.
For those who appreciate great cityscapes, lively crowds, and a touch of canine whimsy, this experience will likely be a highlight of your trip. Just remember to bring cash for snacks and drinks, and prepare for a spirited, festive ride.
Howl O Ween Doggy Costume Party Cruise
FAQ
Is this a family-friendly activity?
Yes, it’s suitable for all travelers, especially those who enjoy playful, social events. Service animals are permitted too, making it accessible for guests with disabilities.
How long is the cruise?
It lasts approximately 2 hours, making it a relaxed, manageable outing without feeling too long.
Where do I meet for the cruise?
The meeting point is at 60 Rowes Wharf in Boston, arriving around 2:00 pm for check-in.
Are beverages included?
No, drinks and snacks are available for purchase on the boat, with cash only.
What sights will I see during the cruise?
You’ll pass by Boston landmarks like the Federal Courthouse, ICA, Fish Pier, USS Constitution, Old North Church, and see planes taking off or landing overhead.
Is the tour suitable for children?
While not specifically geared toward children, families with a sense of fun and dog-loving kids should enjoy the lively, festive atmosphere.
Can I participate with my dog?
Absolutely. It’s a dog costume party, and service animals are allowed. Just make sure your pet is comfortable in a lively environment.
What’s the atmosphere like?
It’s a fun, energetic, party vibe with music, costumes, and a friendly crowd. Expect a casual, lively scene.
Can I cancel if I change my mind?
Yes, the ticket is refundable if you cancel at least 24 hours in advance. Cancellations made less than 24 hours before won’t be refunded.
If you enjoy quirky events, scenic water views, and celebrating with furry friends, this cruise could add a fun, memorable touch to your Boston visit. Happy sailing and dressing up!
More Boat Tours & Cruises in Boston
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- Boston: Charles River Fall Foliage Sightseeing Cruise
- Boston Old Town Walking Tour & Harbor Cruise Tickets
- Boston: Charles Riverboat Cookies & Carols Cruise
- Boston: City Cruises Sunset Skyline Cruise with Commentary
- Boston: Dog-Friendly Halloween Costume & Sightseeing Cruise
More Tour Reviews in Boston
- Lexington & Concord Legends: Revolution & Reflection Private Tour
- Fishing or Cruising Boston Harbor on Private Yacht Trinacria
- Boston: Votes for Women History Tour of Back Bay
- Tour-in-Four — A Private four hour walking & driving city tour
- Cambridge, Lexington and Concord Private Half-Day Tour by Car
- French-American Guided Tour of the Freedom Trail, Boston
More Boston experiences we've covered
- Lexington & Concord Legends: Revolution & Reflection Private Tour
- Fishing or Cruising Boston Harbor on Private Yacht Trinacria
- Boston: Votes for Women History Tour of Back Bay
- Tour-in-Four — A Private four hour walking & driving city tour
- Cambridge, Lexington and Concord Private Half-Day Tour by Car
- Howl O Ween Doggy Costume Party Cruise
- French-American Guided Tour of the Freedom Trail, Boston
- The Best of Boston: Private Half-Day Highlights Driving Tour
- Bostons Freedom Trail: Private Tour including Paul Revere House
- Boston: Private Driving Tour with a Local Guide
- Private 4-hour Walking Tour in Boston with official tour guide
- Boston: Fun Pasta Making Class With Local Chef
