Howl O Ween Doggy Costume Party Cruise

A Fun-Filled Halloween Water Adventure for Dogs and Their Humans in Boston

Whether you’re a dog owner looking to combine your love for your pet with a scenic outing, or just someone eager for a quirky, festive cruise, the Howl O Ween Doggy Costume Party Cruise offers a unique way to enjoy Boston from the water. This two-hour event promises a lively atmosphere, adorable costumes, and some of the most iconic city sights—all with a playful twist.

What makes this experience stand out? First, the chance to parade or dance alongside dogs dressed in creative costumes—something that promises plenty of photo-worthy moments. Second, the scenic views of Boston’s historic skyline and landmarks, from the USS Constitution to the Old North Church. Third, the lively DJ spinning tunes from the Liberty Hotel Yappy Hour, adding a fun, party vibe. The only potential drawback? It’s a CASH-only bar, so you’ll want to come prepared for refreshments.

This cruise is best suited for dog lovers, families, or groups seeking a lighthearted, festive outing that combines sightseeing with a lively social scene. If you’re after a memorable, pet-friendly experience that blends city views, costume fun, and a relaxed atmosphere, this cruise deserves a spot on your Boston to-do list.

Good To Know

• Dog-friendly and festive: Perfect for pet owners wanting to celebrate Halloween with their furry friends.
• Iconic Boston sights: Pass by the Federal Courthouse, Institute of Contemporary Art, and the USS Constitution.
• Scenic views and close encounters: See planes taking off and land overhead, and enjoy up-close views of historic landmarks.
• Entertainment and prizes: DJ Skoolyahd keeps the energy high, with raffle prizes adding to the excitement.
• Affordable fun: At $30.80, it offers a lively experience without a hefty price tag.
• Cash bar: Be prepared for drinks and snacks available for sale, cash only.

Exploring the Itinerary in Detail

Starting Point at Rowes Wharf

The cruise launches from 60 Rowes Wharf at 2:00 pm, a central spot easily accessible via public transportation. The boarding process is straightforward, and the crew is friendly and welcoming, setting the tone for a relaxed, enjoyable afternoon. The proximity to Boston’s bustling downtown means you’re close to many other sights and activities, making this a convenient addition to your day.

Passing Iconic Landmarks

As the boat departs, you’ll quickly pass by key landmarks like the Federal Courthouse and the Institute of Contemporary Art. These are impressive sights from the water, offering perspectives you wouldn’t get from land. The vessel glides smoothly past the Fish Pier and the reserve channel where cruise ships dock, giving a sense of Boston’s busy maritime activity.

Up Close with the USS Constitution

One of the highlights is a close-up view of the USS Constitution, the oldest commissioned ship in the US Navy. Docked at the Charlestown Navy Yard, this historic ship acts as a tangible link to America’s maritime past. We loved the way the boat’s perspective provided a different angle—one that really emphasizes the ship’s grandeur and its significance. It’s an unmissable photo opportunity for history buffs or anyone who appreciates classic naval architecture.

Watching Planes and Historic Boston

Another fun element is observing planes take off and land directly over the vessel. This adds an exciting, almost cinematic element to the cruise—imagine watching aircraft zoom just meters above your head while you’re sipping a beverage or snapping pictures.

The boat also glides past the US Coast Guard base and the Old North Church, famous for Paul Revere’s legendary ride. Watching these landmarks from the water adds a nostalgic, patriotic layer to the experience, especially during Halloween when the festive atmosphere enhances the sense of community.

The Entertainment and Social Aspects

DJ Skoolyahd from the Liberty Hotel’s Yappy Hour keeps the mood lively, spinning tunes that encourage dancing or just relaxed mingling. The inclusion of raffle prizes gives a fun competitive edge; you might just go home with a little extra holiday cheer.

Refreshments and Additional Details

While alcoholic beverages aren’t included, the boat offers snacks and drinks for sale—cash only, so come prepared. The relaxed, social setting makes it easy to chat with fellow dog lovers or watch your pup strut in their costume. Service animals are welcome, which is a thoughtful touch for those traveling with dogs.

Duration, Group Size, and Practicalities

At around two hours, this cruise strikes a nice balance—long enough to soak in the sights and enjoy the festivities without feeling rushed. The maximum group size is 120, maintaining an intimate enough environment for everyone to enjoy the event comfortably. Confirmed bookings ensure a smooth process, and the tour is suitable for most travelers, including those with service animals.

Why This Cruise is a Great Value

At just $30.80 per ticket, this event offers a surprisingly rich experience. For that price, you get a scenic voyage, lively entertainment, and ample photo opportunities—all while celebrating Halloween with your furry friend. The cruise captures Boston’s spirit beautifully, blending iconic sights with a festive, pet-friendly vibe. It’s particularly good for dog owners, families, or groups looking to enjoy a relaxed yet lively outing.

The two-hour length is ideal for those wanting a fun diversion without a full-day commitment. Plus, the opportunity to see historic landmarks from the water provides context and beauty that land-based tours might miss.

Who Should Consider This Experience?

This cruise is perfect for pet owners who want to involve their dogs in holiday festivities, and for anyone who enjoys a casual, scenic boat ride. Families and friends looking for a light-hearted, memorable activity in Boston will find this a charming choice. It’s also a good pick for those interested in local sights with a playful, festive twist.

If you’re after a fun, affordable way to see Boston from the water, and don’t mind cash-only beverages, this cruise hits the right notes. It’s ideal for those seeking a lively, social atmosphere with a touch of Halloween flair.

FAQs

Is this tour suitable for children?
Yes, most travelers can participate, and it’s a family-friendly event, especially if kids enjoy costumes and scenic views.

Are service animals allowed?
Yes, service animals are permitted on the cruise, making it accessible for guests with special needs.

What should I bring?
Bring cash for snacks and drinks, and consider wearing comfortable clothing. If your dog has a costume, be sure it’s secure and suitable for outdoor conditions.

Does the cruise operate rain or shine?
While the data doesn’t specify, most water tours in Boston operate in various weather conditions, so check ahead if rain is forecast.

How long is the cruise?
Approximately two hours, making it an easy, manageable outing for most.

What landmarks will I see?
You’ll pass by the Federal Courthouse, Institute of Contemporary Art, Fish Pier, USS Constitution, Old North Church, and US Coast Guard base, among others.

To sum it up, the Howl O Ween Doggy Costume Party Cruise in Boston offers a lively, scenic, and pet-friendly way to celebrate Halloween. The combination of city views, historic landmarks, and playful atmosphere makes it a memorable outing—especially for dog lovers or those wanting to add a splash of fun to their visit. With affordable pricing and a relaxed vibe, it’s an experience that balances entertainment with a genuine sense of connection to Boston’s maritime charm. If you’re seeking a unique, festive way to see the city from the water, this cruise is definitely worth considering.