Monday Minute: Matthew Calabretta of Float On Travel Co.

The Monday Minute is a weekly feature in PAX that highlights the movers, shakers, leaders and rule breakers of Canada's travel advisor community. Wanna be profiled? Wanna nominate someone? Email newsroom@paxglobalmedia.com!

Name: Matthew Calabretta

Business: Float On Travel Co. (Trevello Travel Group)

Where do you live? Toronto, ON

How long have you been a travel advisor?

I’m brand new to the industry, having officially started in August 2025.

What is your specialty?

Ocean, river, and expedition cruises—curated for all travellers, with a proud focus on LGBTQ+ travel.

What inspired you to become a travel advisor?

I’ve always been the planner in my friend group, organizing everything from group trips with a dozen friends staying in beautiful Puerto Vallarta villas, to all-inclusive resorts, Montreal long-weekends and Eurotrips. I wanted to combine my strengths in research, planning, and organization with the flexibility to work remotely—ideally from warmer destinations for part of the year

In January 2025, I was lucky enough to be invited as a plus-one on the Virgin Voyages Top 100 First Mates celebration voyage. Connecting with so many incredible travel advisors, learning from their experiences, and seeing the industry up close made me realize that an idea I’d been considering for over a year could truly become a reality. The Virgin Voyages experience was so great I went on my second cruise a month later! Starting part-time felt like the perfect next step.

What’s the first trip you ever took?

My parents made a point of travelling every year as a family. The first trip I actually remember – confirmed with them – was to Florida when I was about two or three years old.

Of all the bookings you’ve made, which itinerary are you most proud of?

I’m currently planning a celebration getaway this December for my sister and her fiancé. They’re having a small wedding ceremony in Toronto, followed by a large group celebration at a resort in Mexico's Riviera Maya. With 40-plus travellers, it will be my first major group booking—and one I’m especially excited about.

What’s the most memorable trip you ever took?

Spending a month travelling solo through Europe in 2015 was truly transformative. I visited London, Paris, Nice, Milan, Florence, Venice, Dubrovnik, plus a day trip into Montenegro. I stayed mostly in hostels, met people from all over the world, practiced my French and non-existent Italian, and focused on experiencing each place like a local. It completely changed how I travel and how I see the world

Where do you see your business one year from now?

My goal is to become a go-to travel advisor for Canadian LGBTQ+ travellers, particularly those seeking luxury and adults-only ocean, river, and expedition cruise experiences.

What’s one new skill you’ve acquired recently?

I’ve been diving deep into group bookings with cruise lines. I’m currently working on a very fun, well-known drag-queen-hosted Virgin Voyages sailing for 2027 that I can’t wait to share. I’ve also spent what feels like a hundred hours building my website (FloatOnTravel.ca) and creating a workflow with Travefy. I’m a big fan of the service so far.

What is your motto?

Attitude is everything.

Where are you travelling next?

I just returned from my third Virgin Voyages cruise. I convinced nine friends to join me, including a few first-time cruisers. Next month I’m checking out Sicily for a week, with a three-night stop in Malta on the way in and the same with Dublin on the way out. I’m learning that flying into other cities and taking connectors with multi-day layovers can sometimes be cheaper than direct flights, plus you have the added benefit of time in another destination.

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