Trip Overview
Trip Dates: June 5-10 2026
Availability: Spots Available
Deposit: $200
Cuba is a destination like no other. This vibrant island in the Caribbean is alive with music, history, and culture at every corner, from classic cars cruising Havana’s streets to the rhythms of salsa drifting through the night. And in June 2026, we’re giving you the chance to experience it all, UFC style.
We’ll spend 5 unforgettable days in Cuba, immersing ourselves in the country’s rich traditions while directly supporting the Cuban people through every experience. From learning the art of cigar making to cooking authentic dishes with local chefs, every moment is designed to connect you to the heart and soul of Cuba.
But that’s just the beginning. On this journey, you’ll also:
-
Explore Havana’s colorful streets and iconic landmarks
-
Capture stunning moments with a locally owned photographer and vintage car owner
-
Dive into Cuba’s Afro-religious traditions and spiritual heritage
-
Indulge in delicious Cuban food, coffee, and rum
-
Give back to the community by supporting youth and local businesses
-
Create lifelong memories with a global group of travelers
-
Stamp’d In Cuba 2026 isn’t just a trip, it’s an experience, a cultural exchange, and a celebration of resilience and heritage.
Are you ready to get Stamp’d in Cuba?
Read the itinerary below and claim your spot today. Spaces are limited, and you don’t want to miss this unforgettable journey.
Inclusions
English speaking guide
Daily Breakfast
Licensed driver
Hotel accommodation
Dedicated UFC Host
All activities listed
Goodie bag
Group photos
Flight assistance
Exclusions
Visa
Flight
Tipping
Payment Plan
Deposit - $250
Installment 1 - $555 (Nov 1, 2025)
Installment 2 - $555 (Jan 1, 2026)
Installment 3 - $555 (Mar 1, 2026
You will receive email reminders and make manual payments. Payments are not automatic.
Quick FAQ's
Who is this trip for?
This trip is designed for travelers who:
-
Are 21+
-
Appreciate culture, adventure, and the future we’re building
-
Are flexible and open-minded (no complainers!)
-
Can adapt to being outside of America and embrace new environments
-
Carry positive vibes and good energy
-
Are ready to learn, grow, and celebrate differences
-
Want to be part of a global community and a historic experience
If this sounds like you, then you’re exactly who we want to see in Cuba!
What can I expect after I book?
Once you secure your spot, we’ll make sure you’re fully prepared and connected before takeoff. Here’s what you can expect:
-
Email communication with updates, reminders, and everything you need to know to get ready
-
1–2 Zoom calls to virtually meet your fellow travelers and go over important trip details
-
A private Instagram group chat so we can stay connected, share info, and keep the vibes going before and during the trip
What airport do I fly into?
The main airport in Havana, Cuba and the airport code is HAV.
Do I need shots or a visa?
-
Vaccines: There are no mandatory vaccines required for entry into Cuba. (We always recommend checking with your doctor or CDC guidelines for optional travel health precautions.)
-
Visa: Yes, U.S. citizens need a visa to enter Cuba. The cost is $80, and you can easily apply for it online (electronic visa) closer to the trip.
Trip Itinerary
June 5, 2026
Welcome to Cuba, Stampers!
Today you will land in Cuba and head on over to our small privately owned boutique hotel in the heart of Old Havana! Relax, unwind and get familiar with your new home away from home.
Tonight, we kick off our adventure with a warm welcome dinner! Get ready to immerse yourself in Cuban culture while supporting independent entrepreneurs as you enjoy a delicious home-cooked meal. Dress to impress in your themed dressy attire, and let’s toast to new experiences, meaningful connections, and the vibrant flavors of Cuba.
Beyond the food and festivities, this trip offers a powerful connection to Africa through Cuba’s rich African history and culture, deeply rooted in the legacy of slavery. As we explore Cuba, you'll uncover the profound African influences that shaped the island’s music, religion, and traditions linking you to the continent in meaningful ways.
Our stunning property is designed to make your stay unforgettable, offering a range of amenities such as sparkling pools, free WiFi, a chic bar, a restaurant, and so much more. It's more than a cute property, but we are supporting a local property owner!
Here's to an incredible first night together getting STAMP'D IN CUBA!
June 6, 2026
Today, we’ll dive deeper into the island’s spiritual traditions with an Afro-Religion Tour, where you’ll discover the profound influence of African religions like Santería.
This experience offers a rare opportunity to explore the rituals, beliefs, and practices that have been passed down through generations and remain a vibrant part of Cuban life and culture.
As we engage with local practitioners, we’ll gain insight into the significance of these spiritual practices in daily Cuban life, all while supporting a privately owned, locally run business that keeps these traditions alive.
June 7, 2026
Today is all about giving back and making a difference. We’ll visit a local orphanage to spend time with the children and bring joy through school supplies and toys. This day is more than just a visit, it’s a chance to support education, uplift the youth, and leave a positive impact on the community.
Together, we’ll share smiles, laughter, and hope, while showing the kids that they are seen, valued, and supported. This meaningful experience is sure to be one of the most memorable parts of our journey.
June 8, 2026
Today we’ll step into style and culture with a classic car photoshoot in the vibrant heart of Havana! You’ll dress up, pose with Cuba’s world-famous vintage cars, and capture stunning moments you’ll never forget.
This experience is extra special because we’ll be directly supporting a locally owned photographer and classic car owner. In Cuba, it’s essential that our presence uplifts the community, and this photoshoot is a meaningful way to enjoy the culture while giving back to the people who make it possible.
Once the shoot wraps, the rest of the day is yours to explore at your own pace. We’ll happily provide suggestions for unforgettable activities that allow you to continue supporting the Cuban people.
June 9, 2026
Today is all about cigars and culture! We’ll begin with a tour \and educational session of Cuban cigars by a local, where you’ll explore the intricate process of cigar making from leaf to finish.
This hands-on experience directly supports the workers and artisans who keep this proud Cuban tradition alive.
From there, we’ll head to a venue where you’ll master the art of smoking cigars, paired with the rich flavors of Cuban rum and coffee. Whether you’re a seasoned aficionado or a curious newcomer, this is the perfect way to savor Cuba’s heritage while supporting the people behind these world-famous crafts.
Later, we’ll roll up our sleeves for a Cuban cooking class led by locals on the rooftop of their house. As you prepare dishes like savory plantains and Cuban rice and beans, you’ll not only learn authentic recipes passed down through generations, but also directly support local chefs and their culinary businesses.
This day blends tradition, taste, and connection. By joining, you’re not only enjoying an unforgettable experience, you’re also helping to uplift the Cuban people and supporting them.
June 10, 2026
As our unforgettable journey in Cuba comes to a close, it’s time to head home with hearts full of memories, new friendships, and experiences that will last a lifetime.
From cigars and culture to food, music, and giving back, you’ve embraced the spirit of Cuba and supported its incredible people along the way.
You’ve laughed, learned, explored, and connected, and now, you’re officially Stamp’d in Cuba. ❤️🌍
Invest In Yourself NOW
From the moment you land in Cuba to the moment you depart, every detail is taken care of, all you have to do is show up and enjoy. We’ll fully prepare you before the trip with emails, group calls, and a private chat so you feel confident and connected before you even step on the plane.
Once you arrive, expect unforgettable experiences, cultural immersion, and memories that will last a lifetime.
This isn’t just another vacation, it’s history in the making, and YOUR chance to be part of it.
✨ Spots are limited so don’t wait. Secure your place today and get Stamp’d in Cuba! ✨