Howl O Ween Doggy Costume Party Cruise

An Unlikely Halloween Adventure in Boston: The Howl O Ween Doggy Costume Party Cruise

Imagine cruising around Boston harbor, your dog dressed in a cute or spooky costume, while a DJ spins lively tunes and everyone gets to parade or dance with their four-legged friends. For just $30.80 per person, this 2-hour event offers a unique way to experience Boston’s stunning waterfront scenery and iconic sights. Led by Massachusetts Bay Lines, this cruise is a playful, lighthearted break from typical sightseeing, especially suited for dog lovers and families looking for a fun, pet-friendly outing.

What we love about this experience is the up-close views of Boston’s landmarks—think of the USS Constitution or the Old North Church—paired with the joyful energy of seeing furry friends dressed up in all their Halloween finery. The live DJ and the chance to participate in a raffle add to the festive vibe, making it more than just a boat ride.

One thing to keep in mind is that alcoholic beverages are not included and available for sale only with cash. Also, the tour’s casual, pet-friendly atmosphere might not be for someone seeking a formal or quiet cruise. But if you’re after a lively, inclusive event with plenty of photo opportunities and city views, this cruise hits the mark.

This experience suits dog owners, families, and anyone who enjoys a lighthearted, community-focused outing. It’s particularly appealing if you want to combine your love for Boston’s harbor with a fun celebration of Halloween — furry friends optional but highly encouraged.

Key Points

• Pet-friendly event that welcomes dogs in costume
• Scenic views of Boston’s historic sites and harbor
• Live DJ and raffle for added fun
• Approximate 2-hour cruise with a lively, festive atmosphere
• Cash-only beverages available for sale, no included alcohol
• Most travelers can participate, service animals allowed

The Experience in Detail

What the Tour Offers

The Howl O Ween Doggy Costume Party Cruise combines Boston’s iconic waterfront sights with a playful Halloween theme. For just over $30, you gain a two-hour journey aboard a boat departing from Rowes Wharf, with a lively DJ—Skoolyahd from the Liberty Hotel Yappy Hour—playing music that encourages dancing and celebration. The event is designed to be casual and inclusive, with most travelers able to participate and service animals allowed.

Itinerary Breakdown

The cruise’s route takes you past some of Boston’s most recognizable sights. You’ll glide by the Federal Courthouse, the Institute of Contemporary Art, and the bustling Fish Pier. These are the spots that define Boston’s waterfront charm, and being on the water offers a different perspective—more scenic and relaxed than on land.

A highlight for many is the close-up views of planes taking off and landing overhead. It’s a sight that’s fascinating and adds an exciting, dynamic element to the cruise. The plane noise is brief, but it’s a unique feature of the Boston harbor experience.

As you pass the USS Constitution at the Charlestown Navy Yard, you get a chance to see the oldest commissioned ship in the US Navy. It’s a reminder of Boston’s long maritime traditions. The captain’s narration or the cruise guide might share some tidbits, but mostly, you’ll enjoy the view and the festive mood.

On the return, you’ll cruise past the US Coast Guard base and catch glimpses of the Old North Church steeple and Paul Revere’s historic ride route. These iconic landmarks add a layer of historical significance to the fun, colorful event.

What Makes It Special

Two specific things stand out. First, the dog costume parade is a highlight. Seeing pups dressed as witches, skeletons, or superheroes adds a delightful, humorous touch that’s perfect for social media sharing. Second, the views of Boston’s skyline and harbor are genuinely stunning, especially with the natural light of late afternoon or early evening.

The DJ, Skoolyahd, keeps the energy lively, and the raffle prizes give everyone a chance to win small, fun giveaways. This element of surprises keeps the event interactive and engaging.

A Few Considerations

While the event is fun and accessible, it’s worth noting that alcoholic drinks are not included and can only be purchased with cash. This might be inconvenient for some, especially if you prefer a full bar experience. Also, since most travelers can participate, it’s quite informal; those seeking a more subdued or formal cruise should look elsewhere.

Plus, the two-hour duration means this is a quick, energetic event—great for a lively afternoon, but perhaps less suited for those seeking a slow, contemplative experience.

Who Should Go?

This cruise is perfect for dog owners wanting to celebrate Halloween with their pets, families looking for a fun outing, or groups of friends eager to enjoy Boston’s waterfront with a twist. It’s especially appealing if you love festive costumes and enjoying scenic views with a lively crowd.

Why This Tour Offers Real Value

For $30.80, you get a distinctive experience blending sightseeing, celebration, and pet-friendly fun. The views of Boston’s harbor, combined with the chance to see historic landmarks like the USS Constitution, make this more than just a costume party—it’s a memorable way to see the city from the water. The live DJ and the casual, festive atmosphere create a sense of community and celebration that’s hard to replicate on land.

This cruise also offers flexibility and simplicity—most of the logistics are handled for you, and the free cancellation policy provides peace of mind. Plus, for dog lovers or families, this is a chance to enjoy Boston’s harbor in a relaxed, friendly environment.

The Bottom Line

If you’re after a unique, lighthearted Halloween experience with chances for photos, music, and stunning views, this cruise is worth considering. It’s especially appealing if you want to combine your love of Boston’s history and scenery with a fun, pet-friendly event. Just remember to bring cash for drinks and be prepared for a lively, informal atmosphere.

Frequently Asked Questions

Is this tour suitable for children?
Yes, most travelers can participate, and families with kids who enjoy fun, festive activities should find it entertaining.

Are dogs allowed on board?
Absolutely. This is a dog-friendly event, and pets in costume are encouraged. Service animals are also permitted.

Do I need to bring my own costume?
While not mandatory, dressing your dog (or yourself) in a Halloween costume is part of the fun and adds to the festive spirit.

What should I bring?
Bring cash for beverages since alcohol isn’t included. A camera or phone for photos is recommended as the views and costumes make for great shots.

Does the cruise operate rain or shine?
The description doesn’t specify, but most outdoor boat tours operate regardless of weather, so dress accordingly.

Can I purchase snacks on board?
Yes, snacks and beverages are available for sale, but they are cash only.

What is the duration of the cruise?
Approximately 2 hours. It’s a quick, lively trip—perfect for a fun afternoon.

Where do I meet the tour?
At 60 Rowes Wharf, Boston, starting at 2:00 pm. The ticket redemption is at the ferry terminal there.

What is the cancellation policy?
You can cancel for free up to 24 hours in advance for a full refund.

Final Thoughts

The Howl O Ween Doggy Costume Party Cruise offers a refreshing take on Boston sightseeing—adding a playful, pet-friendly twist to the city’s harbor views. It’s a straightforward, affordable event that combines scenic splendor with festive fun, making it ideal for dog lovers, families, and anyone looking to enjoy Boston from the water without fuss.

While it’s casual and lively, the experience delivers genuine value through its memorable sights, cheerful atmosphere, and the chance to share a joyful celebration with fellow pet enthusiasts. If you’re in Boston during Halloween and want an event that’s both entertaining and scenic, this cruise should definitely be on your list.