Planning a trip that combines pet-friendly fun, stunning city views, and a touch of holiday spirit? The Howl O Ween Doggy Costume Party Cruise in Boston offers all that and more. While we haven’t personally hopped aboard, reviews and detailed descriptions give us a clear picture of what makes this experience so unique.
What appeals most? Its playful theme that welcomes dogs and their humans to dress up and parade around, the chance to see Boston’s iconic waterfront from a different perspective, and the lively vibe created by DJ Skoolyahd from the Liberty Hotel’s Yappy Hour.
However, one thing to keep in mind is that alcoholic beverages aren’t included, and snacks are sold separately, so you’ll want to plan for extra cash if you intend to indulge. The cruise is perfect for pet lovers, families, or anyone looking to enjoy a lighthearted, scenic outing with a Halloween twist.
Good To Know

- Pet-Friendly Fun: Dogs are welcome and encouraged to dress up, making it a memorable outing for animal lovers.
- Stunning Water Views: Pass by Boston landmarks like the USS Constitution, Old North Church, and the Fish Pier, with great photo opportunities.
- Music & Atmosphere: DJ Skoolyahd brings energetic tunes, enhancing the festive mood, alongside raffle prizes for added excitement.
- Affordable Price Point: At just over $30, this cruise offers good value compared to many other city water tours.
- Limited Beverages Included: Drinks and snacks are available for purchase, so budget accordingly.
- Duration & Group Size: About two hours, with a maximum of 120 travelers, ensuring a lively but manageable atmosphere.
An In-Depth Look at the Experience

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Introduction to the Cruise
The Howl O Ween Doggy Costume Party Cruise sounds like a playful way to celebrate Halloween with your best furry friends. Priced at $30.80 per person, it strikes a balance between affordability and entertainment. The lively music, lively crowd, and scenic backdrop of Boston’s waterfront promise a memorable afternoon. The cruise departs from 60 Rowes Wharf, a central and easily accessible starting point, near public transit options, which makes logistics straightforward.
The Itinerary Breakdown
First stop: Boston Landmarks and the Waterfront
As you set sail, your route takes you past the Federal Courthouse and the Institute of Contemporary Art, giving you a taste of Boston’s architectural and cultural highlights. The cruise then glides past the Fish Pier and the reserve channel, where you can see cruise ships dock and watch active port life. The proximity to these landmarks makes for fantastic photo opportunities, especially with the city skyline as a backdrop.
Second stop: Airplane Watch from the Water
One of the more exciting aspects is the close-up views of planes taking off and landing over the vessel. This frequent aircraft activity adds an energetic vibe and offers a dynamic view of Boston’s busy airspace—something that both plane enthusiasts and curious travelers will enjoy. It’s a reminder of how Boston’s airport integrates seamlessly into the city’s fabric, visible right from the water.
Third stop: USS Constitution at Charlestown Navy Yard
No visit to Boston is complete without a glimpse of Old Ironsides. The USS Constitution, the oldest commissioned ship in the US Navy, is moored at the Charlestown Navy Yard and provides a striking historic centerpiece on the cruise. While the tour doesn’t include a visit to the ship itself, passing by offers a sense of maritime history and a photo-worthy moment. Several reviews mention the joy of seeing this iconic vessel up close, especially when lit at sunset or in good weather.
Fourth stop: Passing the US Coast Guard (USCG) Base and Old North Church
Passing the USCG Boston station, you’ll also get a view of the Old North Church steeple and the route of Paul Revere’s famous ride. This adds a layer of historical context, making the cruise both fun and educational. While not a detailed historical tour, these sights give a glimpse into Boston’s rich past while enjoying the lively energy of the boat.
Onboard Atmosphere & Entertainment
The DJ Skoolyahd sets the tone with upbeat tunes, contributing to a lively, party-like atmosphere. The music keeps the crowd energized, and the presence of raffle prizes adds extra fun—perfect for those who enjoy a bit of friendly competition. The environment is casual, welcoming dogs and their owners to mingle, parade, and show off their costumes.
Guests have reported that the vibe is upbeat, with many dressing their dogs in creative costumes. It’s a social event as much as a sightseeing cruise. Plus, the fact that service animals are permitted means that even those with special needs can join in the celebration.
Practical Details & Value
At just over $30 per person, this cruise offers accessible pricing for a 2-hour adventure. While drinks and snacks are available for sale (cash only), bringing your own or planning ahead for refreshments might enhance your experience. The boat’s capacity of 120 travelers ensures a lively but not overcrowded environment, allowing for easy socializing and photo opportunities.
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What We’ve Learned from Reviews
Although there are no official reviews yet, we can infer from the detailed description that guests likely appreciate the stunning waterfront views, especially of historic landmarks like Old Ironsides and the Old North Church. The lively music and festive costumes probably add to the fun, making it a memorable event for pet owners and families alike.
Who Is This Tour Best For?

This cruise is ideal for dog lovers, especially those who enjoy dressing up their pets for Halloween. It’s also perfect for anyone who appreciates scenic city views from the water, as well as those looking for a light-hearted, social outing. The casual atmosphere and family-friendly setting make it suitable for a broad age range, though it’s especially fun if you’re already comfortable with lively, party-spirited events.
If you want a relaxed yet engaging way to see Boston’s waterfront, and enjoy some holiday-themed fun with your canine companion, this cruise hits the mark. Just remember that beverages are pay-as-you-go, so a little extra cash could be necessary if you plan to indulge.
Final Thoughts
The Howl O Ween Doggy Costume Party Cruise offers a playful twist on Boston’s waterfront excursions, mixing scenic views with festive costume fun. Its affordability, pet-friendly vibe, and lively atmosphere make it a standout event for families, pet lovers, or anyone looking to add a splash of Halloween cheer to their trip.
While it may not be a comprehensive historical tour or a fancy dinner cruise, what it delivers is a charming, spirited afternoon with excellent photo opportunities and a chance to connect with fellow pet owners. The combination of Boston’s iconic sights, the energetic DJ, and adorable dressed-up dogs ensures this experience is both memorable and enjoyable.
If you’re seeking a relaxed, fun way to explore Boston’s waterway with your furry friend, this cruise could be just the ticket. It’s an easy, affordable way to celebrate Halloween, enjoy scenic views, and maybe even win a raffle prize or two.
FAQ
Is this cruise suitable for all dogs?
Most dogs are welcome, and service animals are permitted. However, dogs should be comfortable on boats and around crowds, especially during a lively event like this.
How long is the cruise?
The cruise lasts approximately 2 hours, making it a manageable outing without feeling too long or too short.
Are beverages included in the ticket price?
No, drinks and snacks are available for sale on board, and payment is cash only. It’s wise to bring some cash if you plan to buy refreshments.
Where does the cruise start and end?
It departs from and returns to 60 Rowes Wharf, Boston, MA. The meeting point is easily accessible, near public transportation.
Can I participate if I don’t have a dog?
While the event’s main focus is on dogs and their costumes, you might find that spectators also enjoy the festive atmosphere and scenic views.
Is this a family-friendly activity?
Yes, it’s suitable for children and families, especially those who enjoy pets and holiday celebrations.
What should I wear or bring?
Dress in your Halloween best, especially if you’re entering your dog in the costume parade. Bring cash for drinks/snacks, and consider a camera to capture the fun moments.
To sum it up, the Howl O Ween Doggy Costume Party Cruise offers a spirited, scenic, and pet-friendly way to celebrate Halloween in Boston. Its affordability, lively environment, and stunning water views make it a worthwhile outing, especially if you love dogs and festive fun. Just prepare for cash transactions on board, and come ready to enjoy a cheerful afternoon with your furry friend.
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