Classic 1957 Chevrolet in coral pink catching afternoon light on Havana's Malecón seawall
Weathered colonial building facade in Old Havana with peeling ochre paint and ornate iron balcony
Snorkeler's silhouette suspended above a vivid turquoise Caribbean coral reef shelf
Lush green tobacco leaves drying inside a dark wooden barn in Viñales valley

Cuba doesn't wait —
neither should you

Next departure: March 14, 2026·3 seats left
Explore tours
Private Beach Access
Casa Particular Stays
Vintage Cars Included
Local Guides Only
8–12 Travelers Max
Son Cubano Nights
Phosphorescent Reef Dives
Tobacco Farm Visits
Havana Rooftop Sessions
Santiago Street Food
Private Beach Access
Casa Particular Stays
Vintage Cars Included
Local Guides Only
8–12 Travelers Max
Son Cubano Nights
Phosphorescent Reef Dives
Tobacco Farm Visits
Havana Rooftop Sessions
Santiago Street Food
Curated Collection

Choose your Cuba

Havana street at dusk with neon bar signs reflecting on wet cobblestones and a classic car passing
Havana
Limited· 3 left
7 days

The Havana Deep Cut

Seven days inside the city most tourists never find — azotea rehearsals, 3am bolero bars, and a crumbling bookshop that only opens when it feels like it.

$1,890pp
View itinerary
Next: March 14, 2026
Lush Sierra Maestra mountain range covered in dense tropical forest with mist in the valleys
Musical
Available· 8 left
10 days

The Wild East

Santiago to Baracoa through the Sierra Maestra — the Cuba that built the revolution and still carries its music in its bones.

$2,450pp
View itinerary
Next: April 2, 2026
Tobacco farmer hand-rolling cigars in a wooden drying barn in Viñales with golden light streaming through slats
Rural
Limited· 2 left
8 days

The Tobacco Trail

Viñales valley, dawn mist, and a veguero who's been rolling the same marca since 1979 — the slowest, most beautiful week in Cuba.

$2,090pp
View itinerary
Next: March 28, 2026
Diver silhouette above a pristine Caribbean coral reef with shafts of turquoise light from above
Coastal
Available· 6 left
9 days

The Coastal Run

María la Gorda to Trinidad — Caribbean shelf snorkeling, empty beaches that don't appear on Google Maps, and a colonial city frozen in 1850.

$2,280pp
View itinerary
Next: April 18, 2026
Cuban musicians playing live son cubano in a warmly lit Havana bar with brass instruments gleaming
Musical
Sold Out
8 days

The Musical Circuit

From Buena Vista to changüí to jazz — three cities, five genres, and a trumpet player in Trinidad who learned from a man who learned from Benny Moré.

$1,980pp
View itinerary
Next: SOLD OUT — Join Waitlist
View across Havana's pastel rooftops toward the Caribbean at sunset with the Capitol building silhouette
Havana
Available· 9 left
6 days

Havana to Trinidad

Cuba's two most beautiful cities connected by the open road — with everything worth stopping for in between.

$1,590pp
View itinerary
Next: May 9, 2026
Why Travesía

Designed for
recovery.

Every decision we make — the casa, the car, the guide, the timing — is designed to get you further inside Cuba than you'd get on your own.

See all tours

8–12 Travelers

Small enough to get into places tour buses can't. Large enough to split a vintage car seven ways.

Casa Particulares

Cuban family homes, not hotels. Breakfast is homemade, the conversations are real, and your host knows everyone in town.

Cars That Actually Run

We've driven every vintage car in Havana and kept a list of the ones that make it to Viñales. You get those cars.

Local Guides Only

Every guide was born in the region they're showing you. No outsiders explaining Cuba from a script.

2019
First tour ran
47
Tours completed
4.96
Average rating
520+
Travelers placed
"I've done Southeast Asia, Morocco, the Balkans. This was the first trip where I genuinely had no idea what was coming next — and that was entirely by design. Ernesto let us roll a cigar at 6am, then wouldn't tell us where we were going for lunch. We ended up in someone's kitchen. It was the best meal of my life."
Aoife BrennanThe Tobacco Trail · November 2025

Cuba doesn't wait.

Browse the collection

Can't choose?

Tell us what you love