Top 10 Tips for traveling to Cuba!

You’re a seasoned traveler. You’re always up for an adventure and you return with fantastic stories. You’ve got your sights set on traveling to Cuba and you want a unique, off-the-beaten-path experience. 

However, it can be difficult to put together your own authentic experience, and you may be unsure if the trip you’d like to take is even legal. (Hint: with us, it is!) 

Below, you’ll find our Top Ten Tips to help you discover the best of Cuba!

  1. Allow Yourself To Step Back In Time

You’ve seen the photos, and now it’s time to experience it for yourself! Zip through narrow streets and down tree-lined boulevards in a classic car to see the colorful and architecturally stunning neighborhoods of Havana. 

You’ll get to ask – how do Cubans keep these 1950s American convertibles in such pristine condition? There’s no better way to see for yourself than paying a visit to a bodyshop where they share their creative ways of keeping these amazing cars going. 


  1. Get a Taste for Cuba’s Unique Restaurants

In Cuba you won’t find any McDonald’s or Starbucks. Instead, you’ll visit unique, privately-run restaurants (called paladares). Until recently there were only government-run restaurants with minimal variety and little incentive to excel. But now paladares are all the rage! 

Private Cuban citizens operate these restaurants out of their residences, and they are nothing if not creative. You will find a wide assortment of brilliantly renovated spaces with the most delicious local and international cuisines and farm to table ingredients. With the likes of President Obama, Jay-Z and stars of all kinds stopping in, make sure you make a reservation well in advance! 

  1. For Lodging, Go Royal or Rustic

But, for a truly Cuban experience, try a casa particular and stay in the home of a Cuban? This is a great way to stimulate the local economy while experiencing the best of true Cuban culture! You’ll bask in the attentive care of a Cuban host and get a sense for what it’s like to live in an authentic neighborhood. Hosts take great pride in their homes and exceptional care of their guests. Opt for breakfast and enjoy seasonal tropical fruits, Cuban coffee, and fresh juices- healthy, delicious and prepared just for you!

If you prefer hotels there are amazing boutique hotels that are privately owned. Either way, we are here to find the perfect one for you.


  1. Immerse Yourself in Cuba’s Art, Music & Dance 

In Havana, the arts are prized above all else. Artists welcome you into their private studios where you can watch as they create a one-of-a-kind masterpiece. Young Jazz musicians featured at NYC’s Lincoln Center give private performances at the famous Abdala recording studios. The fierce women of Havana Compás Dance leave viewers breathless with their rhythmic dancing and drumming. These types of experiences and more could be part of your unique exchanges in Havana. Find the true heart of Havana: her flourishing arts culture. 

  1. Learn About Cuba’s Rich History

Havana is renowned for its beautiful architecture and fascinating political history. Don’t wander through the plazas solo, trying to figure out who built what building, and in what year. When you have an expert local guide to lead you, you will have a much richer experience and the opportunity to discover these hidden treasures for yourself. 

For even more variety, take the time to travel to Trinidad (about 4 hours from Havana by bus or car), an unspoiled colonial town founded in the 1500s. Trinidad is a UNESCO World Heritage site where you can explore the city’s preserved nooks and crannies, mysterious alleys and colorful doorways. Trinidad is steeped in dramatic history. Learn about the sugar plantations that built the city and attracted wealth, pirates, immigrants, and drove the slave trade. Enjoy the unique ambiance of cobblestone streets, riders on horseback and ancient architecture. 

  1. Party Like a Local

It’s no secret that Havana is known for its nightlife! Make sure not to miss one of the most exciting new venues in the world: the Cuban Art Factory. This converted warehouse will keep you busy as you wander through its colorful spaces; at once a bar, club, music venue, and transnational art space; you won’t leave disappointed! 

Looking to go dancing? There are so many options for every taste. Or even if you just want to sit on the Malecon and people watch at night, you are sure to encounter a colorful local scene.


  1. Keep Your Eyes and Ears Open For Cuban Idiosyncrasies

There’s a reason Cubans can easily tell who is Cuban and who is a foreigner! The way Cubans move, speak, dress, and act is all unique to the island nation. Be on the lookout for the expressive ways that Cubans communicate with their hands, or even hail a cab. Certain gestures have specific meanings that might be missed by the untrained eye!

Also, if you listen closely, you might catch how Cubans drop their S’s and leave out the ends of words when they speak. People from Havana, habaneros, are especially famous for speaking lightning fast. If you travel outside Havana, you might notice Cubanos in other provinces speak slower and sweetly, almost like a song. 

Looking to use some local lingo? Try asking a young Cuban what’s up: “¿Que bola?


  1. Escape the City

We’ve all seen those wooden cigar boxes, the ones from Cuba that were so prized by our fathers and grandfathers. The smell of them calls to mind a place in the world where the craftsmanship of a good cigar is still highly prized. Get out of Havana and into one of the world’s most scenic countryside areas, Viñales Valley (in fact, the New York Times named this area one of the top 10 places to visit in 2016). Visit a local tobacco farm in Viñales and watch the plant go from root to roll, and then take home a few fresh Cuban cigars for yourself. 

While there, don’t miss the heart-warming world of artist, Mario Pelegrin, who has transformed his own property into a community hub for art, music, gardening, pottery and more. Teachers from around the world donate their services to further advance this unique project. I guarantee you have never seen anything like it and you will leave changed (and probably with some incredible, original, inexpensive art too).



  1. Give Back to the Cuban People

Cubans truly appreciate anything visitors bring as gifts. It could be something as small as chocolates, or school supplies for the kids. A bottle of bubbles can keep them laughing for hours in the town squares! And vitamins. Tipping helps too. Those in the tourism industry might support their whole extended families on their tips.

  1. The Big Question: How do I Travel to Cuba Legally?

Let us take care of all your paperwork and preparations (Cuban visa, Certificate of Travel, and official itinerary, restaurant and nightlife reservations) so you can focus on what really matters: getting to Cuba and seeing it all for yourself!

When you let CIT plan your trip to Cuba, you will have the trip of a lifetime with off-the-beaten-path adventures and refined cultural experiences. You’ll have insider access to the island’s artists and musicians, the best culinary experiences, and the most exclusive hotels and B&Bs. We will answer your questions and help with currency and anything that can be confusing about Cuba. 

Hear what our past clients have to say: 

I have always consciously avoided any kind of organized tour — but Cultural Island Travel literally handed me the country of Cuba. Our guide, Patricia, designed an intimate week just for us that absolutely dazzled my family. I have been gushing about Cultural Island Travel’s tour of Havana since we returned two months ago. They showed me the Cuba I had only dreamt existed.


         Mitchell A.“Mitch” Glazer, American movie producer, writer, and actor, NYC


Traveling with you to Cuba wasn’t just amazing, it was a life changing experience. We are already looking forward to our next adventure with Cultural Island Travel and even making excuses up so we can go back to Cuba soon. 


         Maria Cristina Marrero, Author of Las Imperfectas & Editorial VP at Hola! USA, NYC


My daughter and I were very hesitant to travel to Cuba by ourselves and researched many travel companies to find the one that fit our plans. Cultural Island Travel helped us plan an itinerary that suited us and the travel restrictions placed on US citizens. Our tour guide, Laura, was sensational. She is a Cuban national and a very educated woman. She gave us so much history of the country and gave us so much more than our tour book did. Our drivers, Carlos and Pedro, were very conscientious and safe drivers. I can’t thank them enough for making us feel comfortable and safe. This trip was so much more than we expected. I am very grateful to Cultural Island Travel for all they did to make our trip exceptional!


         Sandy and Megan, Lake Havasu, AZ


Email or call us at 800-494-1945 to book your own custom tour today, we will answer any questions you have about Cuba! 


Havana is the most romantic city in the world-Book your own Cuba photo session with us!


July, 2o22 

Habana is the most romantic city in the world! 

Between the gorgeous architecture, the vast sea, the passionate people and all of the COLOR! No place is more romantic for a couple to visit. Book a Cuba trip today and request a photo session with our very own Ebony O’ Reilly! Thank you to Susan and Daryl for trusting us with your Cuba adventure!

Email or call us at 800-494-1945 to book your own custom tour today! 

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