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Come be a part of the culture, the mystery, and the beauty

Welcome to Santiago de Cuba

At Out-Of-The-Box Tours, we are firm believers that to say that you’ve been somewhere, you need to experience everything it has to offer.

That’s why our tours focus on the natural beauty, history and the magic of the true Cuban experience.

But more importantly, we offer tours that are 100% customizable, both before you fly, and on the fly.  Want to add elements from different tours together? Feel free.  See something you want to explore more deeply while you’re on the road? We’ll detour.

Below, we’ve outlined a couple sample tours.  As we mentioned, these can be changed any way you like, including where we pick you up, how many people you’ll have in your party, where we go, and what we do along the way.

Come be a part of the true Cuban culture.  You won’t regret it.

Bird’s Eye View Of Santiago

The Streets Of Santiago

Experience Cuba With One Of Our Tours

Below, we’ve listed a few of the sample tours to give you an idea of your options. These tours are completely customizable, add or remove any elements you wish, and we’ll create a fully immersive experience for you.
(All sample pricing is per person, in Cuban Convertible Pesos)

Natural Wonders

Discover and taste the natural beauty of Santiago de Cuba in the protected area of Gran Piedra-Baconao in the mountain range around Santiago de Cuba. Enjoy a ride up to the protected area Gran Piedra-Baconao in a comfortable car prepared for the mountain ride. You will see a unique view of the Caribbean Sea, the city of Santiago de Cuba and the Bay of Guantanamo. You will have the chance to explore the history of French influence in the culture of Santiago de Cuba and observe and taste traditional Cuban coffee processing in the country side.


Castillo del Morro

A fortress with a colourful history!

Built at the entrance to Santiago Bay as a defence against raiding pirates corsairs, it has seen attacks from English freebooters, French, Antilles filibusters and lastly by Americans in 1898. In the mid-1700’s, part of the fortress was converted into a prison for political prisoners. Discover the hidden secrets on your own! A must-see World Heritage site!


Explore The City

Discover the story behind the history of Santiago de Cuba and its people. Find out what defines this as the most interesting city in Cuba.

Visit the most important spots in the city- old and new Santiago- and the places that defined the identity of its people. Based on your interests, you can choose the main focus of your excursion:

Architecture, traditions and folklore, local stories and legends, 500 years of rich history, or music!


Music Of Cuba

Santiago is well known for being the seat of the Cuban revolution. Lesser known, it is also the cultural center of the country. In the evening the streets are filled with music: both classical and progressive. Take a casual stroll with us in the warm evening and immerse yourself in the sounds of live bands. Our guides know where the best of the best are. Go inside to watch them play. Have drinks and dinner, or just watch and absorb the rich sounds!


Adventures & Experiences

Think outside the box and live outside the box! Don’t just stick to the basics, you want to come to Cuba to try all we have to offer. If you have a different idea, we will make it happen! Our services also include, but are not limited to:
  • Multiday tours
  • Travel packages & transport
  • Experiences
  • Art tours
  • Dancing and Percussion classes
  • Bicycle tours
  • Watersports (Paragliding & Scuba)

Custom Tours & Special Requirements

Looking to combine the best aspects of some of our tours?

See some things you like, but others you’d rather avoid? Want to bring a large group? Interested in exploring a specific area in greater depth? Add or subtract any element you choose for any of our tours, before you fly or on the fly!

We are able to accommodate a wide variety of special requirements (mobility, accessiblity, dietary, etc.).  Please contact us discuss your particular requests.

When you think of touring with us, think out of the box!

Our Team is Lead By…

Yoe (Joe) Moreno

Originally a language professor, Yoe decided to share his passion
for his home with its visitors. After a number of years working in
traditional tour companies, Yoe realized something was missing…he was
tired of delivering the “traditional” content to guests.

Yoe vowed that he would create a customer-first tour experience, where you are fully in control of where you go, what you see, and how you experience it.

Our team can deliver tours in English, French, German, Italian, and of course, Spanish. We can’t wait to host you.

We were awarded TripAdvisor’s 2019 Certificate of Excellence! Want to read our reviews?


*Note that we are OFAC compliant and fall under the category “Support for the Cuban people”, which you should check in the Affidavit for travel to Cuba.  We can provide a compliance letter should you be required to by OFAC. For that we only need the agreed program and the full names and passports of all the travelers.

Contact Us

Connect with our Canadian-based partners, or our local Cuban team to create your custom tour.




+53 58947745