The rhythm of absolute autonomy

Your dedicated hosts

Jason at the helm, navigating the journey, and Erin bringing together the details that make every day aboard unforgettable. Together, your hosts create a sailing experience that feels effortless, personal, and entirely your own.

For us, an unforgettable sailing vacation is about much more than simply getting from one island to the next.

As your dedicated skippers and hosts, Jason & Erin bring extensive sailing experience and internationally recognized sailing certifications to every voyage. We know how to handle the wind, navigate unfamiliar waters, and maneuver a catamaran into a Mediterranean harbor—but we also know that some of the best moments happen after the sails come down.

We’ll seek out the secluded coves, quiet anchorages, waterfront villages, and local favorites that most tourists never experience. Whether we’re dropping anchor in a hidden Caribbean bay or backing into a historic Mediterranean harbor, our goal is to make the journey itself one of the best parts of your vacation.

And then there’s Erin...

An accomplished sailor in her own right, Erin shares the same international sailing certifications as Jason—and she absolutely loves to cook. From breakfast overlooking a quiet anchorage to appetizers and dinner aboard after a day on the water, food and hospitality are an important part of the STL Skippers experience.

We’re not simply here to sail the boat. We’re here to share the kind of sailing vacation we love ourselves.

Come aboard as our guests. Explore the world with us. Leave as friends.

A menu shaped by sea and culture.

From sunrise breakfasts of tropical fruits the galley operates entirely on your schedule.

Uncompromised crewed freedom

Escape the crowded tourist tracks. Step aboard a private sanctuary where every detail is tailored and the horizon is yours to command.