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The Ultimate Cuba Trip: Itinerary Tips from an Addict

Salsa, Havana, Bachata, Mulata… Cuba speaks to the imagination of almost every traveler who has some Latino vibes on his/her bucket list. I don’t blame you. Having traveled there myself over and over again (guilty as charged, yep) I can ensure that the socialist country keeps surprising and inspiring as you keep traveling on. But as much as I am a dreamer, I am also a realist… So I am going to share my recommendation for your ultimate Cuba trip in 2, 3 to 4 weeks, as we can’t all be so lucky as I was to stay there for months in a row.

You’ll experience the best beach days of your life in Cuba!

3 Weeks in Cuba: The “Surprise Me Special” Trip

If you like to be surprised, discover, love variety and a good combination between natural and city life, then this is the perfect itinerary for you! Maybe the focus here is not as much on culture as it is on adventure, but hey, you can’t have it all!

Day 1: Home – Havana

Welcome to Havana. As soon as you jump out of the plane, change some of your home country’s currency to CUC or CUP and catch a taxi to the city centre. Don’t forget to eat and drink something while you adapt to the tropical heat before you go to bed to deal with your little jet lag.

Day 2: Havana

Enjoy your first Cuban breakfast. Head over to the seaside where you catch a ferry to Casablanca and visit the famous landmark Castillo del Morro from where you have a spectacular view over the old city center. In the afternoon, return to town and sign up for a Free Walking Tour of Havana Vieja or Central Havana. Have dinner in one of the many paladares (local restaurants) and enjoy a salsa night out.

Discover the authentic streets of Centro Havana during a Free City Tour

Day 3: Havana

Today you will get a different view of the larger city surroundings, such as Vedado and Miramar, from a bike. Sign up for a Free Bicycle City Tour (yes, that also exists and is a great way to support local youngster with a well-deserved tip). Have quick lunch in the city before you head over to the other side of town to stretch your legs on one of the splendid near-the-city located beaches in Playa del Este. You can do this cheap by catching a collective taxi from the train station. You deserved this beach day! After heading back to your casa particular (kind of a B&B) for a shower, head towards Casa de la Musica for some Cuban musical vibes.

Day 4: Havana – Las Terrazas

Take a Viazul bus from Havana to Las Terrazas (only 1 hours 30 minutes driving) and discover the beautiful community life in a natural surrounding. Start with a community tour and end your day with a relaxed evening on the porch of your homestay room in the village.

Day 5: Las Terrazas

Today go zip lining and take a hike to one of the nearby hills with spectacular views over East Cuba and get to know more about coffee plantations and local flora and fauna. If you are a birdlover, watch out for the Cuban national bird which you are highly likely to spot somewhere around here. If you feel like you have some energy left, head over towards Soroa where you can take a swim in the natural baths.

In Las Terrazas you will get a glimpse of the Cuban rural community life.

Day 6: Las Terrazas – Vinales

Ready for another Viazul bus ride? Two hours further lies Vinales in the province of Pinar del Rio, it won’t get more rural and authentic than this. I highly recommend you to have a nice lunch in town, visit the botanical gardens and book a Sunset Horseback Riding Tour to enjoy one of the most scenic sunsets you’ve ever experienced. And oh… Of course there will be Mojito to accompany you!

Day 7: Viñales

Get up early to go horseback riding and visit a tobacco plantation. In the afternoon you can visit Cueva de los Indios and take a little boat tour, just so you feel like a real tourist. You know… 😉 In the afternoon, take some rest. You will need it now, you’re almost a week in Cuba! You can go out later to discover the guajiros’ (farmers’) dance moves in town.

Horseback riding through the stunning landscape in Viñales can’t be missed on your trip!

Day 8: Vinales – Cienfuegos

If you have a hangover from yesterday, that’s perfectly fine. You can nap on a long bus ride from Vinales to Cienfuegos, about 7 hours driving further. Upon arrival, drop your bags in your new casa and discover the beautiful university city with historical buildings, climb the staircase of one of them to get great city views. Book a sunset boat tour around the Bahia from the marina dock and enjoy all-you-can-drink rum punch while trying not to get seasick.

Cuban nightlife is unforgettable, so make sure to bring your party shoes and get ready for the sun to set…

Day 9: Cienfuegos

Wake up early to go on an adventure! Today you will discover the Waterfalls of El Nicho, enjoy a creole lunch and go on a jeep safari into the surrounding mountains. Hike around and find your spot for a swim in one of the many natural pools. Make some fun and socialize with the many travelers you will surely meet around here. For diner, head into town and see if you can join a local street concert.

Cuba seems to have it all: fascinating culture and adventurous nature. Explore these waterfalls in El Nicho!

Day 10: Cienfuegos – Trinidad

From one splendid city to another one. Enjoy a full Cuban breakfast on your casa’s rooftop terrace and grab your bags to leave to the busstation where you’ll catch a Viazul bus to Trinidad. This trip might take a while because the buses come from far and usually have some delays on route. Once upon arrival in Trinidad, explore the city center and climb the tower of Convento de San Francisco de Asis for a beautiful panoramic view over the old town. Nightlife is vibrant here, so put on your fancy party shoes and go out tonight.

The old town of Trinidad is simply picture perfect.

Day 11: Trinidad

Wake up early to make an excursion to the Valle de los Ingenios, a rural valley in the surroundings of Trinidad. Take the (very touristic but fun) steam train at 9h30 from the train station and travel back in time. On the way you will visit one of Cuba’s famous sugar factories, interesting as Cuba is famous for its sugar trade (and it is an import ingredient for mojito). The train makes various stops, also at the Guachinango Farm where you can find the Manaca Iznaga tower, where you can enjoy a lookout point at 45m height.

In the afternoon, so still have time to go unwind at Playa Ancon. There are public buses or taxis, take whatever works for you. Enjoy your lunch at a beach bar, dive into the ocean and read a book while you work on your tan. Don’t forget to stay until sunset, not only for Happy Hour but also for spectacular views.

Wherever you are, the beach is never far away. Zip from a cocktail while watching sunset at Playa Ancon.

Day 12: Trinidad – Sancti Spiritus

Feel like something different? Head over to the nearby village Sancti Spiritus and get to know the less-touristic Cuba. Visit the library and the church, chat with the locals (if you speak some Spanish), cross the Yayabo bridge and relax by the Yayabo river, like the locals do.

Day 13: Sancti Spiritus – Cayo Santa Maria

You can’t leave Cuba without having enjoyed one of its pristine beach resorts. If you travel by public transportation, your choices will be limited to Varadero and Cayo Santa Maria (accessible by Viazul). This last one is a bit more exclusive and beautiful in my opinion. More relaxed. A large portion of your travel budget will go to your 2-night stay here but it is worth it to enjoy a couple of all inclusive pampered days.

There is no place closer to paradise than Cayo Santa Maria where you have endless beaches (almost) for yourself.

Day 14: Cayo Santa Maria

Today you have the ultimate free day on your trip. Eat, sleep, relax, swim, drink cocktails and join some animation activities in the hotel if you feel like. If you feel like doing something fun, go for one of the many watersport activities such as kayaking, sailing or diving. Personally, I love long walks along the endless beach. Sometimes it’s simple things that bring us joy.

Day 15: Cayo Santa Maria – Santa Clara

Today the Viazul bus will conveniently pick you up from your hotel (therefore it is important to make a reservation) to bring you to Santa Clara, about 3 hours driving. Santa Clara is a nice student city known for its vibrant nightlife and everyday hustle and bustle. A recommendation here is Club Mejunje, there is a famous travesty show on Saturdays, so if your timing is right, you might be lucky!

Day 16: Santa Clara – Havana

In the morning you can explore the city center of Santa Clara and the monument and museum of Che Guevara, one of Cuba’s famous revolutionaries which is located a bit out of the center. It also has many paladares where you can enjoy a local Cuban lunch. Then you head back to Havana in the afternoon. I bet you will be happy to spend the night in Havana-na-na-na.

When visiting Cuba you’ll get to know historical landmarks and symbols of its Revolution, such as Che Guevara.

Day 17: Havana

After a good night of sleep (did it become late yesterday? 😉 ) you will take the ferry to Regla. Remember I promised you to see Something Special… The ‘launch’ boat costs only 10 Cuban pesos nationals and takes you to the other side of the city where you find a village famous for Afrocuban religion practices. If you dare, you can not just visit the spiritual museum but also get a Santera consultation (something we would know as a tarot card reading). Or just buy some beautiful souvenirs. Once back in Havana, remember this is your last night in Cuba, so better make it memorable.

Did you know that Cuba has its own religion, shaped by a mix of African and Catholic beliefs? It’s called Santeria!

Day 18: Havana – Home

Tonight you will take a long flight back to your home country, so you can either take it easy today and explore the city of Havana, or you can take an oldtimer taxi and go somewhere special again, like to Fusterlandia. This is a neighborhood in Jaimanitas which has gone through a transformation because of the artist José Fuster (AKA the Cuban Antoni Gaudi) who made a masterpiece of this area.

Day 19: Home

Due to the differences in time zones and long flights with possible stopovers, you are likely arrive on a day +1 in your home country with all your luggage and a suitcase full of beautiful memories of an unforgettable trip.

I bet your greatest moments will be lived on the Malecon in Havana where everyone gathers for drinks and plays music.

LESS: Sad… Only 2 weeks in Cuba

If you only have 2 weeks, I almost feel sorry for you. You won’t have enough time to see all the beauty. On a positive note, call this the “You Can’t Skip This” itinerary which will show you all the highlights.

  • What You Can’t Skip: Havana, Viñales, Cienfuegos, Trinidad, Cayo Santa Maria
  • What You Can Skip: Las Terrazas, Santa Clara, Sancti Spiritus

MORE: Yes… A Full Month in Cuba

Are you planning to stay longer in Cuba? YES! You are going to make the most out of your tourist visa (which allows you to stay up to a month). As you have some extra time left, I would definitely recommend you to travel all the way to the Eastern side of the island where you can visit Holguin, Santiago de Cuba and Baracao. Cubans call this La Tierra Caliente, the birth place of Cuban music and where you find generally a more black population and much more. Absolutely beautiful and worth to extend your holiday!

On Eastern side of the island, in the province of Guantanamo, you’ll find an unspoiled paradise called Baracoa.

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