On his light, escapist approach to travel…
“One of the plans this year is to disappear. To find some small town in Southern
Spain where we can rent a room on the cheap, drink wine in the only bar in town
and drink coffee there in the morning…and have to walk somewhere to find an
internet connection. For a trip like this, you bring next to nothing—just a small
bag. You don’t need more than a pair of swim trunks during the day anyway.”

On the importance of being prepared…
“I knew an older photographer who told me, ‘Always have a clean white shirt in
your bag, because you never know who is going to invite you for dinner.’ I’m
taking that up a notch and packing a suit jacket this time.”

What else he always travels with (aside from his cameras, a well-worn
map pouch, his knife, and a nice watch)…
“I’ve been wearing this little Saint Christopher charm a friend of mine had picked
up in Jamaica when he traveled there back in the ’80s and passed on to me.
I’ve worn it every day now for seven years.”

On what a Polaroid guy shoots when there’s no more Polaroid film (it’s
practically extinct)…
“I’ve got 20-plus packs of really fresh Polaroid film and then another 30 to 40 of
expired film that still does some interesting things when you shoot it. I’m looking
forward to the end… Everything ends—that’s the point. That’s what gives things
their value. I’ll just put that camera down and do something else.”

To shop all of Kennedy’s J.Crew picks, click here.