Sierra Maestra Photography Expedition
Three days chasing golden hour with a Cuban photographer who knows every ridgeline by name.
Hidden gems, insider experiences, and unforgettable moments with the most interesting locals on the island. Your real Cuban Bucket List starts here.
We started as a newsletter to share Cuba’s true hidden gems and introduce you to our network of remarkable locals — photographers, chefs, scuba instructors, mountain guides, mechanics who can rebuild a ’57 Chevy with a butter knife. Every story we publish, and every vote you cast, helps us build exactly what you want to experience — before anyone turns it into a brochure.
Max group sizes of 3–12. Often just you and the local.
Locals get paid first, paid fairly. That’s the whole moat.
No Varadero, no cigar-rolling photo ops. The other Cuba.
A handful of the moments locals have let us in on. Tap one to tell us you’d love to live it — your interest decides what we build first.
← swipe through the album →
Three days chasing golden hour with a Cuban photographer who knows every ridgeline by name.
Cook a four-course Cuban supper in a Centro Habana home. Music, rum, real conversation.
A dive with the man who taught most of the divers on the island. Reefs the boats never reach.
Trek to falls that don’t appear on maps. Lunch with the family who keeps them secret.
Drop your email to vote on the experiences you want us to turn into real packages. Top voted ideas get launched first — and voters get early access + special perks.
Drop your email to start voting ↓
We won’t email you unless you ask us to. Just used to make sure each vote is a real human.
← swipe to see them all →
Three days chasing golden hour with a Cuban photographer who knows every ridgeline by name.
add your email to vote ↑
Cook a four-course Cuban supper in a Centro Habana home. Music, rum, real conversation.
add your email to vote ↑
A dive with the man who taught most of the divers on the island. Reefs the boats never reach.
add your email to vote ↑
Trek to falls that don’t appear on maps. Lunch with the family who keeps them secret.
add your email to vote ↑
A ’57 Chevy, a route through the Escambray, and a mechanic who can fix it with a butter knife.
add your email to vote ↑
A live septet, a rooftop most Cubans don’t know exists, and lessons that work even on you.
add your email to vote ↑
Voted experiences hit their goal in front of you. The first to reach 500 gets built — and voters get the first dibs.
Stories, hidden gems, and dispatches from the people who let us into their corner of the island.
On the eastern tip of the island, where the road runs out, we spent a morning with Reinaldo and his grandson.
Three hours up a mule track outside Santiago is a finca where the beans dry on the porch and the rocking chairs are always free.
She builds tres guitars in a converted bedroom. The waiting list is now eighteen months long.
Photographers, chefs, divers, mechanics, mountain guides. Most have been doing this their whole lives. We just opened the door.
+ 38 more locals across 11 provinces
vetted personally · paid fairly · always credited
Cuban Bucket List is in its early days — and we’re looking for the right people to help shape it. Whether you’re a local with a story worth telling, someone who knows Cuba deeply, or a professional with skills that fit, we’d love to hear from you.
a personal note ↓
We read every message, by hand.
Usually within a few days. Sometimes longer. We promise it will be a real human writing back — never a template.
— Cuban Bucket List
Not a single cigar-rolling photo op. Every experience starts in someone’s home, workshop, or boat — never a tour bus.
Fair, transparent splits with the photographers, chefs, and guides who make the moments. That’s the moat — and the right thing.
You will come back with a phone full of moments, a name in your contacts, and one story your friends actually want to hear twice.