For a little over two years, Americans have been able to visit Cuba—something that hadn’t been possible for about a decade. This September 21st-25th, your tour guide could be none other than Rufus Wainwright, through a Cuba travel package he’s named  “Wainwright Libre!”  With his Canadian-U.S. citizenship, the musician has become intimately familiar with the country, in no small part due to his connections. On his first visit in 2013, he fortuitously ran into the Norwegian ambassador at dinner, who turned out to be a fan. “He and his husband are real socialites in Havana and really knew all the right people,” says Wainwright. “And we’re suddenly plunged into evenings with cousins of the Castros and all the new artists coming up, and all of the expatriate Americans who stayed in Cuba. We got thrown in the deep end, which was fun.”

While carousing with Castro’s kin isn't actually on the agenda this fall, Wainwright  will lend an insider’s perspective for four days and four nights in Havana, including cultural excursions like cigar and rum tastings, salsa dancing, art tours, and, of course, music. Multiple concerts include a solo private concert by Wainwright and a public showcase where he’ll collaborate with renowned Cuban singer-songwriter Carlos Varela. This package is one of a trio coordinated this year by Music & Arts Live, with other trips helmed by musicians Melissa Etheridge and Ben Folds.  We talked to Wainwright about his love for the land and the one thing you should do when visiting Havana.

How did this trip come about?

“My husband and I have been to Cuba a few times. We have friends down there now and we fell in love with the place immediately and have made it a repeat stop. I’d done a little show there just for fun—it was almost like a private thing, just for friends of friends, and then this offer came around and it just made sense for me to keep broadening and deepening my relationship with that wonderful city, with Havana. One of the main perks for me was that [the Cuban people will] still be able to see the shows and still be a part of the experience. We’ll have a nice sort of mix of us bringing people down from the U.S. and all over the world, and going there for the experience with me, but then there’s also room for people in Havana to come to the concerts who might not have had the chance otherwise. So that’s a nice way to kind of bridge the gap there.”

Among others, you’ll be performing with Carlos Varela. 

“He’s an international star at this point. He’s opening for Dave Matthews right now. So he’s bigger than me, and he’s been gracious enough to join me for an evening and we’ll perform some songs together. I’ve met him once and we had an evening of troubadorial trade. Because he doesn’t speak much English and I sadly don’t speak Spanish at all well, we kind of communicated through song, which is always very heightening.”

You’ve said that art appreciation is a hobby of yours and your husband’s. Where would someone go to see art in Havana, beyond private studio visits?

“Well,  La Fabrica is a big place. It’s a gallery that turns into a club. It’s like a complex. That’s kind of the hub of what’s going on. And I guess anything around 23rd Street is kind of like their East Village.”

And how about music? Where would we go?

“There’s a great place to dance salsa which is right on the water, called 1830.”

Do you salsa?

“Yeah, well, I’m sort of flung around by various obliging locals. So there’s that and one of the most amazing places we went to was this fantastic drag show, gay bar. It’s called Cabaret Las Vegas.  That was really amazing because first of all the people were gorgeous, the guys were gorgeous, and women can go too. It’s not solely gay men. But the performers were very unusual drag performances. It was kind of more socially varied. They’re not singing Dolly Parton, they’re not singing Barbra Streisand, they’re singing this Cuban music that has its own subtext that you don’t totally understand, but it’s definitely potent.”

Is there anything that you’re doing this time that you’re looking forward to?

“There’s that restaurant  that a lot of people go to, La Guarida,  where Fresa y Chocolate was filmed. It’s very good. And one of the great things that one should always do when they’re down there on the weekends is to hang out on the Malecón, which is the road on the water, where all the teenagers hang out. And not only teenagers, young people, because they don’t have money to go to bars.  In Cuba you just buy a bottle of rum and hang out outside facing the ocean and it’s very whimsical. It’s something you don’t see a lot anymore in the Western world because everybody’s on their device.”

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