The Cuba Experience

Havana + Viñales

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, Viñales and the Fábrica de Arte Cubano 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!

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.

In the evening, gather for an intimate Welcome Dinner, featuring a carefully crafted multi-course meal paired with fine wines and live Cuban music. This culinary experience sets the stage for days filled with history, culture, and unforgettable moments.

Get ready to dive into the heart and soul of Cuba!

Day 2

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

Hop into a vintage classic American convertible car and cruise throughout Havana’s neighborhoods. Then, you’ll discover the Old City and learn about the culture as we visit the Plaza de Armas, El Templete, La Catedral San Cristobal de la Habana, and the Museo de la Revolucion.

Meet with a local Afro-Cuban entrepreneur, learn about their story, and inspirations, and discuss the experience of running a business in Cuba.

Learn salsa with one of our resident dance instructors, and learn about Cuba’s history of supporting social and health movements across Africa from a local expert. Afterward, head to a favorite local spot after dinner in Havana!

Day 3

After breakfast, we’ll head over to Viñales, an enchanting rural haven with dramatic limestone mogotes and lush tobacco farms. This rural gem is a UNESCO World Heritage Site that beckons adventure seekers and nature lovers. Its main street is lined with colorful colonial-era wooden houses.

We will enjoy a Cuban lunch in the Valley, and then 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.

After returning to Havana, we’ll dine at one of Havana’s most beautiful restaurants, an architectural treasure with quintessential Cuban ambiance.

Day 4

Today we’ll immerse ourselves in an Afro-Cuban cultural excursion through the Centro Neighborhood. Discover the legacy of African ancestors in Cuban culture and its influence on daily life through this immersive journey into Guanabacoa, a neighborhood renowned for its connection to Afro-Cuban culture. We’ll also get to have consultations with a Babalao.

After lunch, we’ll delight ourselves with an Afro-Cuban Art Studio Visi, where we’ll learn all about the unique artistic expressions and cultural heritage of Afro-Cuban artists.

For Dinner, we’ll experience a modern eclectic take on Cuban cuisine. Just across the street, we’ll visit the Fábrica de Arte Cubano. This is a gem where art, nightlife, and entertainment meet.

Day 5

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

Because you need to take some Cuban culture home with you, we are going to learn some Afro-Cuban recipes in a one-of-a-kind cooking class.

But there’s more learning! We’ll talk about Afro Cuban Music History with Dj Jigue, internationally recognized for his music, who dedicates himself to playing and teaching Cuban music.

We’ll relax while enjoying a Rum and Cigar Tasting with a professional sommelier.

As the day comes to an end, we’ll have our signature Farewell Dinner at one of Havana’s most beautiful restaurants: an architectural treasure that exudes Cuban ambiance. Of course, there’s live music!

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
  • Vintage Convertible Ride through Havana
  • Salsa Dancing lessons
  • Old Havana Tour
  • Rum, Cigar and Coffee tasting
  • Tobacco Country Cigar Rolling Experience
  • Afro-Cuban Art Studio Visit
  • Fábrica de Arte Cubano VIP Visit
  • Day tour to Viñales
  • Visit to the school
  • Afro-Cuban Cooking Class
  • Afro-Cuban Music History with internationally recognized DJ
  • 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.