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About Us

Man steering sailboat with another sailboat in the background.

CAPTAIN STEVE & ANDREW — TWO GENERATIONS ON THE WATER

A FAMILY BUSINESS SINCE 1998

A new name. The same family tradition.

SAIL MDI is a new name for a family sailing tradition that began in Southwest Harbor in 1998.

For more than a quarter century, my father Andrew and I have shared our love of sailing with families, couples, and friends from all over the world, exploring the beautiful waters around Mount Desert Island.

Over the years, the boats have changed and the business has evolved, but our philosophy has remained the same: make sailing safe, fun, and personal.

Today, that tradition continues aboard Swan, our Catalina 38. When you sail with us, you're not joining a crowded tour boat. You're spending a few hours aboard a private sailboat with someone who genuinely loves being out on the water.

The boat has changed. The name has changed. The philosophy hasn't.

Take people sailing. Keep it safe. Keep it personal. Give them a day on the water they'll remember..

Man and dog relaxing on a boat.

How I Found Southwest Harbor

I first came to Maine to visit a friend from the Coast Guard. I had no idea that trip would change the course of my life.

I fell in love with Southwest Harbor, the boats, the people, and the incredible sailing around Mount Desert Island. I started working aboard the schooner Rachel B. Jackson, taking guests sailing out of Southwest Harbor. I also spent time running weeklong sailing charters in the Caribbean, but there was something about the coast of Maine that kept drawing me back.

Eventually, my family and I purchased the Rachel B. Jackson—the very schooner where my sailing career in Southwest Harbor had begun. What started as a job aboard someone else's boat became our own family sailing business in 1998.

For more than a quarter century, we've been sharing the waters around Mount Desert Island with visitors from all over the world. Along the way, I've worked as a boatbuilder, restoring wooden boats and building traditional wooden spars. Today, when I'm not sailing Swan, I teach marine service technology and boatbuilding at Mount Desert Island High School.

After 28 years as a licensed Coast Guard captain, I still love taking people sailing as much as I did when I started.

Southwest Harbor became my home, sailing became my life's work, and sharing it with others never gets old.

Our Vessels, Past and Present

Rachel B. Jackson

Rachel B. Jackson

Rachel B. Jackson

The 67 foot coastal schooner that started it all

SURPRISE

Rachel B. Jackson

Rachel B. Jackson

A Friendship Sloop built in 1964

SWAN

Rachel B. Jackson

SWAN

Catalina 38 "classic plastic"

I LOVE CAP'n STEVE

He is the  best charter boat captain I have ever married!!

I love him thiiiis much ———————>


SAIL MDI
Private Sailing • Southwest Harbor, Maine
Captain Steve Keblinsky
(207) 542-2776
admin@sailmdi.com

Departing from Beal’s Lobster Pier Souwest Harbor

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