Musically speaking, no two words define summertime quite like Jimmy Buffett. For almost 40 years, the singer-songwriter has been leading concertgoers through hit after hit of sing-alongs (“Margaritaville,” “Cheeseburger in Paradise”) on sold-out tours. This summer is going to be huge for Buffett. Not only is he bare-knee-deep in his Margaritaville resort and casino properties, he’s once again embarking on a North American tour to promote a new album, Welcome to Fin City: Jimmy Buffett Live from Las Vegas.

We caught up with the beach lover at his Florida home and discovered his favorite Caribbean island, the two things he never travels without, and the one song that gets crowds going above all of his classics.

My favorite island in the Caribbean would have to be: St. Barts. I’ve spent the winters on St. Barts for almost 30 years. That’s where I’m based out of … I’ve got a little daysailer and a small plane there. So that’s kind of still my favorite spot to hang from because it’s got the best of everything. I don’t think any island in the Caribbean can beat the food in St. Barts, because it’s Creole, it’s French, and you don’t find the number of great places to eat on other islands like you can on St. Barts.

The Margaritaville properties I have in the works include: There’s one in Hollywood, Florida. We’re kind of in our raising-capital stages, but it’s looking good. We’ve got approval, so we’re doing the financing part of it now. And then we have a casino that will be opening this summer in Biloxi, Mississippi, and there’s one going up in Bossier City, Louisiana, that we’re starting to break ground on.

Two things I never leave home without: I always have my little traveling acoustic guitar with me, and I have my iPad. [Laughs.] I’m a romantic throwback to the days of seaplanes, but I also happen to be a high-tech guy. I think the iPad’s the greatest thing since sliced bread, particularly as a writer. I’ve got GarageBand, I’ve got Photoshop, and I’ve got writing programs. It’s just so convenient.

The one song in my set that gets the crowd going the most is: “Fins.” When you look out at 16,000 people and they are rockin’, and you turn the lights up and everybody does the “fins to the left” and “fins to the right” — that’s an amazing thing. When that moment occurs in the show, I simply never get tired of seeing it … or feeling it.

Someone I haven’t worked with I’d still like to: Guitarist Mark Knopfler [Dire Straits]. I’ve done a couple of his songs and I know Mark, but we’ve never really worked together on a project. I am such a big fan of his writing and his production.

My musical hero growing up was: Gordon Lightfoot, and I was a huge Merle Haggard fan. I had four or five influences, but Gordon was really the biggest influence as a writer, performer, and a style.

When people ask, “When are you going to stop, doesn’t it ever get old up there?” I say: Are you kidding? If you had a job like mine, do you think you’d do it everyday? Yeah, you would. I’ve been lucky enough to figure a fine balance between work and play.