The best way to enjoy your trip to Cuba is to embrace both the cities in Cuba and the rural experiences.
Start in Havana but don’t stop there!
It is also good to get off the beaten track to explore the incredible scenery and culture of the entire island. Each place in Cuba offers a completely new and unique experience.
Here are my top five best places to visit in Cuba (cities) listed in order of most favored to least.
These Cuba cities are sure to leave an imprint on your heart.
5 Cities in Cuba to visit
1. Trinidad De Cuba
Trinidad De Cuba cannot be missed!
As one of the most preserved colonial cities in the Caribbean it is to be admired for its preservation, cleanliness and culture.
Lined with cobblestone streets, you walk around in awe of the pastel and bright coloured buildings and the well-kept grounds and gardens.
There are so many photo opportunities to be had in one of the best cities to visit in Cuba!
Cars are not allowed in the centre so it is nice to meander around to the various markets, artesian shops, and art studios.
Enjoy a meal in a colonial home restaurant with 19th century antique furniture and come out to find a band playing tunes on a cobblestone corner.
Trinidad is a UNESCO World Heritage Site and museums are plenty.
Take a visit to the Museo Histrico Municipal and venture up to the tower with a panoramic view of the city.
The town center is about 20 km from the beach but an escape from the sweaty city in a Collectivo is well worth the refreshing swim in the Caribbean Sea.
This city presents its soul at night.
Plaza Mayor, the main square comes alive with both locals and tourists coming together to watch and listen to the Salsa band or join in on the dancing.
Others take to walking the streets to enjoy the bars with their cocktails in plastic cups. The partygoers take a walk down a dirt track for about 4kms to the “Rave in the Cave”.
This is a nightclub in an underground cave playing mostly Salsa and Reggaeton music.
We partied until dawn, raving in a cave. If you dare to risk walking the dirt track, in return you will get one of the best nights of your life!
Hotels to stay in Trinidad De Cuba:
- Book homestays in Trinidad through Airbnb
- Book hotels in Trinidad directly on Booking.com
- Read reviews of hotels in Trinidad on Trip Advisor
Havana will be your first stop on your group tour to Cuba. But be sure not to get stuck here.
It is easy to forget the rest of the island because you won’t want to leave this cosmopolitan side of Cuba!
Whilst it has a spectacular nightlife, the days are just as charming and fun.
It is a city of many faces and places.
Walk the streets in La Habana Vieja or the Old Town for the many different sights. Be drawn to the preserved Colonial architecture & structures, whilst the run down, derelict buildings also draw you in for their mysterious feel and photographic appeal.
Take a tour of the Museo de la Revolucion to gain an appreciation for Cuban history and culture.
Stroll along the Malecon; the seawall right along the coast.
And a stop at Hotel Nacional for a sunset drink is a good way to enjoy the sea views.
If you want to step back in time for old-fashioned flair, El Floridita is a beautiful historic hotel with great live music and dancing.
For more sizzling nightlife action, the basement discotheque at El Café Cantante is the place to bump and grind!
Havana will ignite your fire and give you an unforgettable experience.
Be sure to get in a salsa dance lesson (one of the top things to do in Cuba), a trip to the cigar factory and a ride in a vintage car and if you are there in season, a seat at the baseball game to chew the local tobacco.
Hotels to stay in Havana:
- Book homestays in Havana through Airbnb
- Book hotels in Havana directly on Booking.com
- Read reviews of hotels in Havana on Trip Advisor
Baracoa is the hidden gem of Cuba!
Isolated from the rest of the country in the Guantanamo Province, the isolation has kept Baracoa authentic and untouched.
It is small, relaxing and a lot quieter than the other cities.
It offers a place to chill with the beach, mountainous surrounds and tropical rains. You soon become intimate with the locals seeing the same faces everywhere you go.
Known as the “First City” for being the first capital of Cuba, founded in the early 16th century by Explorer Diego Velazquez and for retaining much of its colonial architecture.
Well at least when I was there in Feb 2017. Sadly in Sep 2017 Hurricane Irma swept through and left a trail of destruction to homes and buildings.
Take a visit to El Yunque, a mountain overlooking the city where you can hike and explore the lush green environment near my favourite Cuban beach, Playa Maguana.
Enjoy a delicious seafood lunch here at the Maguana Beach Bar Restaurant.
Have a mojito in a coconut on a beach chair and even dance salsa with the chef during lunch service! Nowhere else but Cuba!
Another highlight was the visit to the Cacao Plantation. Cacao was one of the early agricultural pursuits in Baracoa and the city is dripping in chocolate.
It is on sale everywhere and there are many different versions of it.
The tour of the Rancho Toa plantation was about $2 CUC and we were shown step-by-step how the local farmer makes the chocolate from the cacao beans which are grown from fruit trees.
Taste a cup of Chorote, the local chocolate drink made from ground cacao and locally made coconut milk.
Rumbumba is the daring version of Chorote, the difference being the addition of local rum!
Hotels to stay in Baracoa:
4. Santiago de Cuba
The heart of the second largest of the cities in Cuba is the main square, Parque Cespedes, where the architecture is beautiful and all the action happens.
The best spot to be in all of Santiago is sitting above the square at the rooftop bar of Hotel Casa Granda looking at a stone angel on top of the cathedral across the street with the sun setting through the harbor and mountains behind.
As the major cities in Cuba, both Havana and Santiago have a rich heritage of music and dance and they have a rivalry over which scene is best.
They are both vibrant cities in cultural and musical life so it is hard to compare.
Even though Santiago is the birthplace of Salsa, Havana still gets my vote.
Take a trip to the coastline and explore the Castillo de San Pedro de la Roca, a 17th century fortress overlooking the bay.
The history is fascinating with breathtaking scenery and offers a cool breeze away from the scorching hot city.
Hotels to stay in Santiago de Cuba:
- Book homestays in Santiago through Airbnb
- Book hotels in Santiago directly on Booking.com
- Read reviews of hotels in Santiago on Trip Advisor
Cienfuegos became a trading place for sugar cane, tobacco and coffee when the French founded it. The French Influence is why it has a unique feel and a lot of wealth.
Known as La Perla del Sur, or the Pearl of the South, it has a relaxed and breezy vibe that sets it apart from the other places to visit in Cuba.
The city center is Pueblo Nuevo, where you can explore the history museums, dine at an outdoor cafe, or purchase some local hand made goods from the markets.
Here, the Casa Particulares are quite a few notches above the rest in Cuba.
Our casa had French provincial décor and a newly renovated bathroom with marble! It was actually quite a shock to experience this unusual sort of wealth in Cuba given the communist situation.
Hotels to stay in Cienfuegos:
- Book homestays in Cienfuegos through Airbnb
- Book hotels in Cienfuegos directly on Booking.com
- Read reviews of hotels in Cienfuegos on Trip Advisor
Book your Tour to Cuba
Below are the tour companies we trust and support.
Intrepid Travel has a tour specific to the Cuban people category for Americans traveling to Cuba.
Intrepid Travel Tours:
- See all tours here
- Grand Cuba Westbound – 21 days
- Hola Cuba – People to People for US Citizens
- Cuba Family tour
G Adventures also offer:
Independent Cuba Tours:
Need More Tips for Cuba?
- 27 things to know before you visit Cuba
- Traveling to Cuba – 10 changes you should know about
- The pros and cons of Cuba travel (+ concerns and logistics)