For the past five summers John Cruz has been coming to the Vineyard to sing on the schooner Alabama for three nights in August. The day after one of the cruises this year, John talked about his work, his music, his life and deep connections to the Vineyard. “The two things I love most to do are making music and cooking,” he said while preparing a lunch of striped bass for friends in the ramshackle red farmhouse across from Alley’s General Store in West Tisbury.

Talk about your yearly performances on the Alabama.

“The cruises are a crap shoot. I have to warn musicians who play with me, because sometimes the crowd is mellow and totally into the music and then there are other times when half the crowd is just into being on the boat, drinking, partying and would rather there wasn’t any music at all. Another problem for me is that most of the people I like to play for aren’t on vacation and can’t afford to go on the cruises.

“I make up for it though by coming out in the winter. I rent the Katharine Cornell Theatre, get friends to put posters up around the Island, put an ad in the paper and we come out and we do it. People are less busy, have nowhere else to go after the show and are more able to relax and connect with me and the music. The other thing I do is go to the bars at night after the cruises and play. I can’t actually book and publicize a gig, that would take business away from the Douglases; it just wouldn’t be right.”

Why leave Hawaii for the Vineyard?

“I was a student at the University of Hawaii and like most young people I wanted to get as far away from Hawaii as possible and that turned out to be UMass Amherst. Summers I played the bars on Circuit avenue, like the Lampost for three hours and the Rare Duck for another four hours, and painted houses during the day. So I was born in Hawaii but I grew up here. My blood family is back there but my spiritual and musical families are here. I don’t think I’ve ever said this out loud before but I feel more at home here than in Hawaii. I am close to anonymous here and can be a student of life. New York is even better in some ways — not only am I anonymous but it is an almost even playing field professionally and that helps me to keep an edge. The traveling is easy; I have to fly everywhere I go whether it’s between islands or the West Coast or the East Coast — it’s all the same to me, just longer flights. I only play Hawaii, the West Coast and the East Coast. My life is good but I really miss the bar scene. Sometimes it seems the bigger I get, the further away I get from the things I love about music . . . . Only a 35-minute set — what’s that about? That doesn’t even warm me up. I need the experience of four and five-hour sets, drenching me in the music, lifting me physically to a place where I am aware of nothing else but the music and have the crowd right with me. A perfect night for me is to walk out of a venue after four or five hours of playing music that I love and have the audience be completely happy, not having asked for any of the hits that I’ve sung a million times like, Island Style and Shine On. I live for those nights.”

In Hawaii you’re a rock star.

“Being at home in Hawaii is a complicated thing. It’s not just about being in Hawaii, it’s also about family and celebrity. I’ve finally written a song about that. Some people there think that because I’m famous I know everything. Well, I don’t know everything. I know some things and if that can help someone avoid what I’ve gone through to get here, I’m happy to share those things. Then there is family and I’ve got lots of it. Some of them treat me like the guy they grew up with in the projects and feel as though because I’m a star that I have no time for them. When I get that vibe, and it’s a legitimate one, I have to stop and spend time fixing it. I don’t want anyone feeling like that. I have lots of family from different times in my life, from brothers and sisters to first cousins to the third cousin of my mother’s second husband — they are all family. That’s just the way it is, complicated. When I walk out of my door I am on stage no matter where I go or what I’m doing. I have a hard time dealing with that sometimes.”

There was a 10-year gap between your first and second album.

“Some of that is because I produce my own records. I don’t have a record company pushing me to get more work done. Another part of that was having three kids born during that time and then there was a drug thing. During that time I didn’t write a note. Finally about three years ago I had to do something to break out of that negative place I was in, so I called my friend Mark Herschler [his backup guitar, vocals and co-writer] in Northampton. And I came East to start writing again and get back to the things about music that make life good for me. We struggled for about six or seven days without much result until the last two hours before I had to get on the train. And the floodgates finally opened and have stayed open.

“Something that I‘m dealing with right now, and I always knew it was coming, is that I am getting older and wiser and my community needs leaders. I’ve been looked up to for a long time as a role model but now they are asking me to get involved and I know it’s the right and natural thing to do. It’s time for me to step up. Okay it’s lunchtime. Let’s eat.”

John Cruz is making an album in Nashville to be released soon. His website is