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Key West Paddle Classic 2026: “Second wind rising” – East Coast legacy meets paddle sports evolution | Raul Ruiz Interview

The Key West Paddle Classic – the longest-running paddleboarding and paddle sport event on the U.S. East Coast – returns for its 29th edition, continuing to prove the power and pull of a true waterman race, drawing athletes from across disciplines.

Kicking off on 9 May, this 12-mile, multi-sport challenge remains one of the region’s premier events and a favourite destination on the calendar. It brings together one of the most diverse race line-ups in the U.S., spanning SUP (including 3-person relay, 14’ and U-14’), prone, OC-1, OC-2, surfski, and sea kayak divisions.

This year also sees a meaningful mash up, with the Crossing for Cystic Fibrosis crew linking up with the event to connect with paddlers and amplify their mission.

At its core, the Classic is about community. We caught up with Raul Ruiz – local waterman and racer deeply involved in the Key West paddle scene – who, true to form, keeps the focus on the community, humbly noting: “I’m always the guy behind the scenes.”

Hi Raul, great to catch up with you! Last time we spoke, you were in Miami working for a major watersports shop. What have you been up to since then?

Well we moved from Miami to the Florida Keys. I was given the opportunity to help build something from the ground up. I am still managing a watersports store (Saloon Surf Shoppe), a paddleboard and kite school (FKWC) and now a Wake/Adventure Park (The Lagoon).

I also helped establish the Florida Keys Watermans Company and continued throwing the best events our watersports communities have ever seen! Events like Downwindapalooza and The Key West Paddle Classic. It is great to do what I love and to play such an important role in the community.

Raul Ruiz

You’ve got a long history in watersports, especially in SUP. Can you remind our readers how it all started for you and how your journey has evolved over the years?

My wife Lizi and I were totally addicted to SUP from the first time we rented recreational boards 15 years ago. Once we found out you can actually race these things, forget about it! We went on a search looking for the best looking, most efficient and superior construction boards available.

This journey brought us to Delfos Almagro, the creative mind behind INDIGO SUP. At the time, we made history as the only full-custom paddleboard company on the East Coast of the United States. The saturated market combined with being forced to move and rebuild for a third time caused us to abandon this labor of love.

By then we had deep roots in the community and picked up other watersports hobbies like OC1, OC2, OC6. With the experience gained, I started working for Pryde Group Americas. They were distributors for JP Australia, Imagine Paddleboards, Cabrina Kites, Neil Pryde windsurf and for a short time SIC Maui. It was there that I was introduced to wind sports.

From distribution I moved to Adventure Sports, the retail side of the business, where I oversaw four retail stores and a kite school. I am very grateful for the time spent there, the knowledge gained and the ability to organize and throw epic parties and events!

You’re now organizing the upcoming Key West Paddle Classic. How did you step into that role, and what motivated you to take it on?

Shortly after the move to the Keys, we got word that 2024 was going to be the last year for the Key West Paddle Classic. The organizer at the time, Sue Cooper and the Lazy Dogs wished to concentrate on other ventures. She guided us as Florida Keys Watermans Company every step of the way and made sure the transition went smoothly.

As we all know, overall participation to SUP events have been on a decline the last couple of years. All of the major races have thrown in the towel. Key West Paddle Classic is a race that is very dear and near to our hearts and the thought of it going away didn’t sit well. This was my wife’s and my first paddleboard race back in 2012.

We signed up for the short race and the conditions were so challenging, that neither of us completed it. But the event was so amazing that we kept coming back year after year. This event kicked started my path into the watersports industry.

I probably wouldn’t be where I am today if it wasn’t for this race. I feel like it has come full circle and I want to be able to continue running it for as long as we can. We made connections with like-minded individuals and friendships to last a lifetime.

The Key West Paddle Classic has a rich legacy, and not so long ago it was attracting some of the world’s top SUP racers. Can you walk us through the history of the event and its evolution?

This is the 29th annual Key West Paddle Classic. The longest running paddle event. People might think, SUP hasn’t been around for that long? SUP hasn’t, but paddleboards have. This race originally focused on prone paddling and kayaks, the event evolved to feature stand-up paddleboarding in 2010 and is now open to any paddle craft on water! This race has always been on everyone’s bucket list.

Many of the world’s top racers were already in the States for the Carolina Cup and made sure to make Key West Paddle Classic the next destination race on their tour. As the industry changed, big races disappeared, brands became more conservative and world racers followed suit.

I feel a change coming, a second wind if you will. We have the support of our community and I feel everyone wants to get back to it. We have to give them what they want. And that is a big race and a really good time!

One of the unique aspects of the event is its openness to multiple craft. Who is the Key West Paddle Classic really for, and what kind of participants are you hoping to attract?

The Key West Paddle Classic is a vibe! We welcome all water paddle crafts to participate. We want to respect the long history and tradition of this event while also accepting change and the evolution of paddle sports. To open a new division, we require at least five participants; otherwise, the craft can register under the “Other” category. Many of our follow paddlers have moved from SUP to OC or Surfski.

We get it, it is less taxing on the body and more efficient but watching a Prone paddler complete this course is so mesmerizing. We really want the Key West Paddle Classic to be the GO TO destination race for everyone to enjoy.

At Florida Keys Watermans Company we are working on specific events for different disciplines. Some of the upcoming events we are planning include a two-day SUP event, an OC single craft and OC6 event and of course our Kite event, to which we will be adding a wing foiling portion.

Can you give us a detailed overview of the race courses? What formats, distances, and conditions can competitors expect this year?

This year we are offering 3 options:

  • Long course- 12 miles rounding
  • 3 Person relay- 12 Miles rounding (1st Leg 4.68 Miles, 2nd Leg 3 miles, 3rd Leg 4.61 Miles)
  • Short course- 4 Miles

Key West Paddle Classic has a history of being a challenging race, especially on the ocean side. Since you are rounding an island, expect everything from head wind, side chop and hopefully a little downwind for a break. As of now, the weather is looking great! It will be a warm, so bring your sun block and plenty of hydration.

For those who have never been to Key West, how do you get there, and what makes it such a special destination? Any must-see spots or experiences for visiting paddlers?

The two closest airports are Key West and Miami. Miami is often less expensive and you get to experience the scenic three and a half hour drive. Key West is a very unique place with lots to do and see on and off the water. The sunsets are incredible and the pub crawls are unforgettable or very forgettable, depending on how you pace yourself. There are also plenty of places to eat and explore.

This year’s event is shaping up to be incredible, and we’re taking important steps to make next year’s milestone 30th anniversary even bigger and better.

We’re proud to have partnered with the Crossing for Cystic Fibrosis and look forward to supporting this outstanding organization for years to come. Additionally, we’re discussing creating a series of events with other race directors to boost participation. We are also exploring adding a corporate component to the race. We hope to regain international support and are actively connecting with leading industry brands for their backing.

Registrations are now open via PaddleGuru and Webscorer, with the same winning formula: an accessible entry, a challenging course and stories that last long after the finish.

Follow Key West Paddle Classic on Facebook and Instagram

*Images courtesy of Key West Paddle Classic

About the Author

Anna Nadolna

Anna is the Founder of SUPer Whale, a Cambridge(UK!)-based emerging watersports brand and a stand-up paddleboarding community. She is a certified SUP Flat Water Instructor accredited by International Surfing Association (ISA). Anna is also a digital marketing, storytelling aficionado and a growth hacking enthusiast.

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