Episode 2: 2,000 Miles at Sea

In this episode of Let’s Go Boating, host Franklin Pillsbury sits down with his nephew Tyler Pillsbury, the fourth generation in a remarkable boating family. Tyler joins us live from aboard the 125-foot Westport Serenity as it makes its way from Maine back to West Palm Beach.

From navigating nearly 2,000 miles on the water, to running a 39-foot Bertram tender through tricky channels, Tyler shares what it means to grow up surrounded by boats, family, and the lessons of the sea. We talk about childhood memories on Lake Minnetonka, long weekends at Doll’s House, the joys of fishing, and even his Texas-style love for brisket on the grill.

Tyler also reflects on how boating has shaped his perspective on life, work, and leadership, and what it means to carry forward a family legacy that spans back to the 1700s in shipbuilding. Packed with stories of adventure, mentorship, and passion for the water, this episode is a must-listen for anyone who believes boating is more than a pastime...it’s a way of life.

Settle in, grab your favorite boating snack, and join us for a conversation that looks not just over the bow, but toward the horizon.

In this episode of Let’s Go Boating, host Franklin Pillsbury sits down with his nephew Tyler Pillsbury, the fourth generation in a remarkable boating family. Tyler joins us live from aboard the 125-foot Westport Serenity as it makes its way from Maine back to West Palm Beach.