I’m jealous. It’s snowing in Birmingham and Matt Nathanson is speaking by phone from Miami. The singer/songwriter is departing shortly for the “Rock Boat Cruise” – an annual event featuring live music on the high seas. Nathanson – along with Marc Broussard, Brett Dennen and Toad The Wet Sprocket among others – will travel to Jamaica and the Cayman Islands on this year’s cruise. Before the ship sails, Boston native and current San Francisco resident Nathanson takes time to catch up with the Weekly.

Weekly: You must be looking forward to spending time with other artists in a relaxed setting like the “Rock Boat Cruise.”

Nathanson: Totally – we talked about that at breakfast this morning. On tour, you want to hang out with the people you tour with, but it never really works where you get quality time. Now, we’re getting hyper-quality time. Everybody gets to play with everyone else and you get to hang out. I think it’s going to be really neat.

Weekly: If you will, talk about your latest album on Vanguard Records, Some Mad Hope. Did the songs to come to you in a creative burst or did the material evolve over time?

Nathanson: The record was a lot of trial and error. The songs went through a couple of different recorded incarnations. I’ve made a bunch of records before this one, but this is the first one where I was determined to not cut corners. Everytime I made a record before, I would think, ”It’s good enough” or ”We ran out of money,” but I was never 100 percent happy with what was going on. On this record, I figured out what I wanted it to be through writing a bunch of songs and woodshedding. The record took two and a half to three years – I would go in and record a couple of songs and take them out on tour and reassess. Then we’d record one or two of those songs again – it was this evolving process. The song ”Come On Get Higher” went through three or four recorded versions and the song really benefited from it. It was like going to school, actually.

Weekly: With the emergence of technology’s role in music – namely the Internet, iTunes and satellite radio – how do you view the climate as an artist?

Nathanson: I feel like the internet is incredibly potent and effective for spreading the word about touring. The discovery aspect of the Internet is great in that respect. The part that’s a bummer is how quickly music can be discovered and discarded – it cheapens music. The way a connection happens is when people take the time to go out and discover you physically. Whether it’s buying a record or interacting at a show, that human contact is crucial to building a rapport with people. There’s something to be said for physicality and making a commitment to the music.

Weekly: How does material remain fresh when you’ve played some songs literally 1,000 times already?

Nathanson: It has a lot to do with the reaction of the crowd – there’s that cycle of energy. The songs are the songs, but what makes the show great is a connection with the audience. The song is a vehicle and when you get that cycle from the audience it becomes brand new. That’s the moment of lift-off. That’s the moment you yearn for.

Matt Nathanson will perform at Workplay on Sunday, January 27. Ingrid Michaelson will open the 8 p.m. show. Tickets can be purchased at www.workplay.com or by calling 380-4082.