Start Sailing Now: From Beginner to Liveaboard

Meet Philip Steinback. When it comes to sailing, he’s gone from zero to 100 in just a few months’ time.

Thirty-two and single, Phil sailed for the first time earlier this year. Fast forward to October and already Phil had purchased a 1982 C&C Landfall 38 and was sailing weekly. Now he lives aboard and sails often out of Spa Creek in Annapolis.

Tell us about how you got into sailing?
I’ve been on the water since my best friend in high school’s family got a small powerboat. We would fish and tube and just cruise around. Well, this year I met a guy named Michael Brown through a friend who had been living on his sailboat in Fells Point in Baltimore. Mike had just moved to Annapolis and offered to take a few of my friends out sailing on the Bay. We went out and sailed a few times, and I was hooked. I got linked up with a great broker, and within a couple of months I purchased a sailboat of my own.

How did you learn to sail? Who have been teachers or mentors for you?
First, I am still learning, but I’ve read a few books and researched online quite a bit. My friend Mike has definitely helped me out a lot. I have a couple of other liveaboard neighbors who have been very helpful also. One used to teach sailing, one works on boats at the marina, and one works at a local boat store. We try to go out sailing at least once a week. I’ve had no professional classes or lessons, but I plan to take some classes this spring when the season starts again.

What surprised you about the sport?
Sailing for me is more of a lifestyle than a sport. I’ve been very surprised at how many interesting and friendly sailors I have met, online and in real life. It seems as if most are willing to lend a hand or give advice. No matter our age, race, or gender, we all have a common bond. I also quickly found out that there is so much to learn. It’s a constant process of gaining knowledge. It’s not always a quick fix. You need to have patience.

What has been your sailing experience thus far, and what are your future plans?
So far it’s been a very positive experience. I’m still very new at sailing. One of the speakers at a seminar for the Annapolis Sailboat Show stated anyone with under 10 years experience is still considered green. Depending on hours and conditions on the water, that may apply. 

It’s been challenging, especially with some high wind days on the Bay. It’s one of those learning experiences where you can’t wait to learn more. I had some amazing help with choosing the right boat and have not run into too many issues thus far.

My future plan would be to pay off all my debt and cruise down to the Caribbean to start a charter business. I would also love to do some solo cruises up and down the East Coast. More short-term, I would love to crew when the Wednesday night races start again.

What made you think living aboard would be a good idea, and how is it working out?
I wanted to simplify my life. I used to be the guy who spent all his money at the bar, on friends, on cars, on too many materialistic things and frivolous things. Living aboard forces you to live more basic, at least the way I am living. Coming from a fairly large one-bedroom apartment in downtown Annapolis, I had to prioritize my belongings. I do have a storage unit, but future plans are to rid myself of those items also. I am very aware of what is important to me, even more after moving aboard. I love it.