A Sample Journey
A Sample Day-by-Day
This is a private trip, planned around your dates and your people, so every day below is a starting point rather than a schedule. Book a call and we will make it yours.
Day 01DinnerBienvenidos—Havana Is Ready for You!
Bienvenidos! Touch down at José Martí International Airport where Cuba's legendary energy wraps around you from the moment you land. Transfer to the Voya Boutique Hotel—your stylish home base in the heart of Havana. Tonight, we kick things off right at one of Havana's hottest rooftop venues, where locals mingle with travelers, live music fills the air, and the mojitos flow freely. This is the Cuba introduction you deserve.
- Airport transfer
- Voya Boutique Hotel check-in
- Rooftop welcome dinner with live music
Day 02Breakfast · Lunch · DinnerOld Havana Magic & Classic Car Dreams
Old Havana is a UNESCO World Heritage site, and today you'll understand why. Walk cobblestone streets that have witnessed centuries of history, from Spanish colonial grandeur to revolutionary fervor. Visit the four legendary plazas while your expert guide drops knowledge that goes way deeper than any guidebook. Lunch on a trendy Old Havana rooftop comes before the main event: cruising Havana in a restored 1950s classic convertible as the sunset paints everything gold. Dinner at a colonial-era paladar caps the magic.
- Old Havana walking tour
- Plaza visits and UNESCO sites
- Rooftop lunch in Old Havana
- Sunset classic car tour
- Nacional Hotel views
Day 03Breakfast · Lunch · DinnerViñales Valley—Cigars, Caves & Pure Magic
Leave Havana behind for the stunning Viñales Valley—a UNESCO World Heritage site where dramatic limestone formations rise from tobacco fields that produce the world's finest cigars. Watch skilled craftsmen demonstrate the art of hand-rolling, then explore the mystical Cueva del Indio cave via underground river boat. The Mural de la Prehistoria is massive and mind-blowing. Lunch at a local paladar, sunset at Los Jazmines viewpoint, and dinner at an acclaimed family-run paladar back in Havana. Today delivers.
- Viñales Valley UNESCO site
- Cigar making experience
- Cueva del Indio cave tour
- Los Jazmines viewpoint
Day 04Breakfast · Lunch · DinnerAfro-Cuban Soul—Spirituality & Nightlife
Today we go deep into the African soul of Cuba. Visit Centro de las Raíces, Cuba's premier cultural center celebrating Afro-Cuban identity, then journey to Guanabacoa—the cradle of Afro-Cuban culture. A Babalawo (Santeria priest) performs a traditional cleansing ceremony that'll move you in ways you didn't expect. Feast on authentic Afro-Cuban cuisine beneath a sacred Ceiba tree with live music and dance. Conclude at a pioneering Afro-Cuban style shop. Evening brings dinner in a converted cooking-oil factory followed by VIP access to Havana's must-see center of art, music, and nightlife, set in the same converted factory.
- Afro-Cuban cultural center
- Babalawo spiritual experience
- Traditional lunch under Ceiba tree
- VIP night at Havana's art and music center
Day 05Breakfast · Lunch · DinnerArt, Rumba & Farewell Feast
Your chariot awaits—a meticulously restored 1950s classic car that's as stunning as you are. First stop: Fusterlandia, where artist José Fuster transformed an entire neighborhood into a mesmerizing mosaic wonderland comparable to Gaudí's Barcelona. Callejón de Hamel pulses with the rhythms of rumba and celebrates Afro-Cuban heritage through vibrant murals. The Christ of Havana statue delivers panoramic city views. Lunch at a neighbourhood café, then gather for a farewell dinner at a landmark rooftop paladar—one of Havana's most beautiful restaurants, in an architectural treasure, with live music. This is how legends say goodbye to Cuba.
- Fusterlandia mosaic neighborhood
- Callejón de Hamel rumba experience
- Christ of Havana statue
- Farewell dinner at a landmark rooftop paladar
Day 06BreakfastNo Goodbyes, Just See You Soon!
One final breakfast at Voya, one final moment to soak in what just happened. Your private transfer takes you to José Martí International Airport carrying memories of vintage cars, live music, spiritual encounters, and the authentic Cuban spirit. You came as a traveler and leave as someone who truly felt Cuba. Until next time, mi amor.
- Final breakfast
- Private airport transfer
- Departure
Words From Our Travelers
What travelers say about Caviar in the Air
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"I have been on trips before with other groups. This was the most professional and best put together of all of them. I learned a lot about wine, travel, life abroad, and myself on this trip. All those things combined made it so worth every penny."
Heather Hunter
Luxury Travel
"I've traveled to many destinations before - some of which I have revisited. But, I always experience something new & exciting, and see things through a different lens. It's exactly the kind of luxury and FABULOUSNESS that every discriminating traveler deserves - delivered SEAMLESSLY - EVERY TIME!"
Lana Fountain
Luxury Travel
"I am a happy member of this tribe and always eager to support Claire and her team! I love them all! The mere fact that clearly they are committed to ensuring that every detail of our travel experience is on point is always evident."
Deborah Renee Smith
Luxury Travel
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