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# Meet Tyler: A Life Under Sail, a Voice Built on Experience
- URL: https://www.scalingmasts.com/meet-tyler-a-life-under-sail-a-voice-built-on-experience/
- Published: 2026-10-12T16:04:28.000Z
- Updated: 2026-10-12T16:04:28.000Z
- Description: Meet Tyler, Scaling Masts’ newest contributor, sharing firsthand insights on sailing, boat ownership, and the cruising lifestyle, with inspiration to turn your own sailing dreams into an adventure.
- Author: Scott Mayer
- Tags: Voices of Scaling Masts

## Introducing a New Voice to Scaling Masts

Growing up in Southern California, Tyler was essentially born into water sports. He was swimming competitively by age 4, followed by surfing and sailing in his mid-childhood years. In the 1990s, this was standard practice for kids in Newport Beach.

It wasn't until his early 20s, however, that a rock-climbing fall left him with a permanent injury, forcing him to find a new passion. In the summer of 2007, he fell back on his roots, and sailing became the focus of his life. His story from sailing bum to professional captain is a clear example of how dedication and mastery lead us down paths previously unknown to us. 

It was never his intent to sail professionally. In fact, the inspiration came from his sailing hero Bernard Moitessier, who in 1962 started a sailing school as a way to fund a voyage to Polynesia. Tyler realized that his high standards of seamanship had conditioned him quite well to become a sailing instructor.

At age 27, Tyler became a licensed captain and started his own sailing school in Portland, Maine, in the summer of 2012\. In many ways this was the beginning of his sailing experience, not because he hadn't put miles under the keel, but because now there were no more distractions.

![](https://storage.ghost.io/c/0e/d4/0ed438f7-b249-453e-aa5f-cefa1eb4faf8/content/images/2026/10/D85_0777-copy.jpg)

Tyler alongside Captain Dasiel, the new Owner of the sailing school Tyler founded in Maine

Sailing had become life in every way. There was no car, no other job, no wife or kids, only wind, sails, and a compass heading. That course eventually took him south. In 2015, he rounded the lighthouse that marks the entrance to Portland Harbor and steered toward Key West, Florida.

He landed a temporary job with another sailing school to get started. Eventually his talents were recognized, and he was given the opportunity to start his own sailing school with access to all the brand-new boats of a local charter company. These doors led into the heart of the sailing industry itself, and he stood out because he had what everyone else didn't: experience. They had the money, but their time had been spent working land jobs, while Tyler had been at sea.

Talk about being in the right place at the right time. Travel to Cuba had just opened up with the Obama Administration easing travel restrictions for Americans, and Key West was the epicenter. Scores of yachts set sail for Havana each month, and Tyler was among them. Brand-new catamarans and monohulls fresh off the press were tested in the Straits. That meant 25 trips and 50 crossings to Cuba alone, plus the Bahamas and the entire eastern seaboard.

Watch Tyler’s Knot Tying YouTube Series from his time in Key West, Florida

The business changed, but the sailing rolled on. More boats, more clients, more charters, more deliveries, more students, more ports. The experience piled up. He saw where boat buyers did it right and where they got it wrong. He saw through the glamour and into the pocketbook. He saw what broke and what didn't. What started as a passion became an industry of products, buyers, and sellers. Tyler was just a bystander, able to watch and record. His job was to sail, watch, and learn. He listened to customers' stories and took part in repairs and broken dreams. He instructed and guided many sailors to safe haven, both at sea and in decision making.

Now Tyler lives his own dreams, sailing aboard his modest 37-footer in the Caribbean. He is retired from the daily grind of the sailing industry, yet living closer than ever to the heartbeat of the sea.

We’re excited to bring Tyler’s voice to Scaling Masts. His stories will offer an honest look at sailing and boat ownership, along with a little inspiration to turn “someday” into something real. Tyler has helped others find their way onto the water, and we hope his words help you take the next step toward your own adventure.

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