The Cuba Experience

Havana + Matanzas

There aren’t many places in the world where you can pop champagne from a lively rooftop with a new group of friends, learn about the African heritage of a dynamic Caribbean culture, and dive into the sea for a refreshing swim after an incredible day exploring historic towns.

Join us on our 6-day luxury journey through Cuba as we take part in this comprehensive educational program, focusing on Afro-Cuban culture and history while exploring the island and supporting the Cuban economy as we embrace the local sounds and tastes of one of the most vibrant islands in the world.

You can’t call yourself woke until you’ve experienced some of the many faces of this Caribbean island.

Do you hear that? That’s the sound of the salsa bongos and our crew dancing after a fun day exploring the colorful neighborhoods, learning about the island’s musical heritage, and sharing incredible experiences with new friends.

Cubans are part of the same African diaspora in America, and we are heading to the island to share a brother-to-brother, sister-to-sister type of vibe.

And you didn’t come snatched for nothin’! The pics you will snap of your melanin poppin’ as you take a swim in the Caribbean or pose in front of the colorful neighborhood of Fusterlandia will be enough to shut down the ‘Gram. No cap.

Whether you are soaking it in on the rooftops, taking a dip in the sea, exploring the city, or listening to our local guide enlighten us about the Afro-Cuban culture of this Caribbean gem, you’ll feel blessed to be experiencing the beautiful scenery of Cuba.

Priceless moments with your crew, soaking in the incredible views from rooftops bars and unveiling a dynamic and diverse multifaceted culture await you on our homecoming journey to Cuba.

Love the trip but not the dates?



Here's your trip at a glance.



From exploring the cities and natural beauty to embarking on a cultural journey diving in head first as all your senses are tantilized, this trip offers a wide variety of scenery (and selfie) opportunities. You will be able to check must-see sites like Havana's downtown, Matanzas and the Callejon de Hamel off your bucket list.



This trip is your chance to connect with our roots as you embrace the deep cultural connection bursting from every corner of Cuba. From learning about Afro-centric experiences and visiting a local school to donating supplies and enjoy the best fine dining on the island, this insightful journey will open your eyes to everything you thought you knew but didn't know about Cuba.



Our luxury accommodations are off the chain. After a long day exploring the cities, finding the best deals in the market, or hitting the clubs, you will relax in one of Havana's most talked about luxury hotels. A World Heritage icon standing in the city pays true homage to the history of the town whilst affording you unmatched 5-star world-class hospitality. Only the best for Lifers!

Explore the day-by-day itinerary.



Day 1

Welcome to Havana, Cuba!

Arrive in Havana (HAV), Cuba, and meet your new crew and tour leader before getting whisked to our luxurious hotel. The afternoon is yours to make yourself comfortable and relax after the flight.

We’ll start tonight with a drop-top cruise around Havana, followed by an intimate rooftop welcome dinner; a 3-course feast paired with wine, mojito lessons, and salsa dancing to prepare you for the days ahead! 

We’ll head out to a hip Cuban nightclub where you can show off your newly acquired sales skills.

Day 2

After waking up to a magnificent breakfast, we’ll soak up Cuban vibes on a comprehensive day tour of Havana.

It’s time to discover the city and learn about their culture as we visit the Plaza de Armas, El Templete, La Catedral San Cristobal de la Habana, and the Museo de la Revolucion.

Because last night was so lit, we’re off on another drop-top convertible ride. Get your cameras ready, you’re about to shut the Gram down. No cap.

The day ends with a walking tour of Old Havana and rooftop cocktails paired with a sumptuous dinner as we look out across the jaw-dropping views of the city. 

Day 3

After breakfast, we’ll tantalize our taste buds by visiting the Rum, Cigar, and Coffee Factory where you can shop, enjoy a tasting and learn about the production of these world-recognized Caribbean delights.

Today we will visit the Callejon de Hamel to learn about Cuban music, religion, arts, and culture. We will also discover how the locals perform it and enjoy a delicious lunch at the famous El Alijibe restaurant.

After lunch, we will explore the local market with arts and crafts at Cathedral Square. This is the best place to stock up on souvenirs, so come ready to shop!

Dinner tonight is at one of the dopest intimate rooftops in Havana. 

Can you guess which one?

Day 4

Today we’ll hit the road and head East, soaking up the views of the countryside and the local vibes as we travel to Matanzas.

This city is famous for its Afro-Cuban culture and history. Here we will follow the steps of Black culture through the world and the global influence this Caribbean island has had over time.

On this tour, we’ll get a glimpse into the daily life of locals and enjoy the city’s stunning bay, rivers, caves, and alleys.

Once back at the hotel, the night is yours to enjoy. Unleash your new salsa skills at one of the cities hottest clubs or enjoy a night in… the choice is yours.

Day 5

Sadly, today’s our final full day in Cuba.

We are passionate about community empowered, so today we will visit an elementary school and learn about the Cuban school system. This is a great opportunity for you to give back an we highly recommend bringing some much needed school supplies with you to donate.

After, we will visit Fusterlandia, home of the artist Jose Antonio Rodriguez Fuster. Fuster covered his house in mosaics, and ceramic statues and as a result the entire neighborhood became a living piece of art. A fantastic place to take stunning pictures for the ‘Gram and soak in Caribbean culture. During the tour, you will see his studio and the art installations that have taken over the street. 

Tonight, as we say goodbye to beautiful Cuba, we’ll enjoy reflecting on our trip with new friends at our farewell dinner.

Day 6

Enjoy your last morning in the hotel with another scrumptious breakfast, and say your goodbyes to your new friends!

Check out at the hotel and get whisked away by your private transfer to the airport (HAV), where you will head home or onwards to your next adventure.

No matter where you travel, our standards are the same.


Connect with amazing people.

We provide the opportunity to make friendships with people who share your worldview and won't ask why you wear a bonnet to sleep.

Experience attentive
and authentic hospitality.

Not only is the staff of Up in the Air Life dedicated to making sure your trip is flawlessly executed, but we are also intentional about choosing locales and vendors who celebrate Black travelers.

Be pampered with only the best.

There is no need to take a break from your baller lifestyle when you travel with us. Our lodging, excursions, and dining are pure luxury.

Feel safe and secure.

Our experienced American guides and well-maintained local relationships mean that you will have peace of mind when you travel with us.

Say "goodbye" to FOMO.

Our trips are anything but basic. While we make sure you see well-known main attractions, we also develop itineraries that will give you unique stories to share with your friends back home.


The Cuba Experience

What is included:

Our trips get you close to that Beyoncé-on-a-boat lifestyle. Let us handle your travel style glow-up.

  • Up In The Air Life On-site Tour Leader
  • A Bon Voyage Group Video Call to review your trip live with the Up in the Air Life Team
  • Concierge Support before your trip to assist you in Upgrading Your Room and Booking Optional Tours
  • Concierge Support before your trip to book your spa appointments
  • Concierge Support before your trip to book your restaurant reservations
  • Up in the Air Life Private Concierge Chat during your trip for dining/spa reservations and more
  • Local Tour guides in Cuba
  • 5 nights stay at an Upscale Hotel
  • Daily breakfasts, 4 lunches, and 4 dinners
  • Mojito-making and Salsa lessons
  • Havana Tour + Cocktail dinner at the rooftop
  • Rum, Cigar and Coffee tasting
  • Visit to the Callejon de Hamel
  • Visit to the Cathedral Square
  • Day tour to Matanzas
  • Visit to the school
  • Fusterlandia Tour
  • VIP Meet + Greet Private Airport Transfer
  • Personalized Swag Bag

What is not included:

We take care of all the details on your itinerary once you land. If you want to further personalize your experience, go off!

  • Round-trip airfare to and from the destination
  • Travel Medical Insurance Insurance (Please note this is required to attend the trip.)
  • Room Upgrades are available for purchase after booking
  • Optional tours are available for purchase after booking
  • Tips for Tour Leader, Guides and Drivers
  • Passport or Visa Processing Fees
  • Your passport must be valid for at least 6 months from the time of travel with at least 2 free visa pages.
  • Expenses for vaccines that may be required

Can you envision yourself on this trip?

Download "The Cuba Experience" trip brochure and keep it handy as you continue to explore, or take the plunge and book now.