Cuba Historic Destinations
CubaCuba has a long and storied history. The following destinations played an important role in the development of the country, and are home to some of the oldest and most important historical sites on the island. In Havana, you can explore Havana Vieja to see exquisite Spanish architecture and well-preserved cathedrals. Visit Trinidad for the colorful houses and cobblestone streets that were shaped by the colonial and industrial eras.
Who can forget Cuba’s tumultuous history in the 20th century? Not you! You'll be learning all about Cuba's historical events at destinations like Santiago de Cuba, which witnessed the birth of the Revolution, and Santa Clara, the location of Che Guevara’s memorial. History occurs at every moment — become a part of the past and indulge your mind on a vacation exploring Cuba's historical sites.
Cuba Highlights
A curated look at the best Cuba has to offer. These are the destinations that consistently stand out — places with real character, great experiences, and something worth going out of your way for.
Old Havana (Havana Vieja)
Spanish conquistadors started building Havana in 1519. The city became an important port in the second half of the 16th century. Over the years the old section of Havana has become an important showcase of Moorish, baroque, neoclassical, and art nouveau architecture. Each plaza and neighborhood of Old Havana has a distinct look and personality.
Explore DestinationTrinidad
Trinidad is a charming, colonial city in central Cuba. Its cobblestone streets, historic houses, and lively atmosphere help make it a top destination in Cuba.
Explore DestinationCamaguey
Camagüey, the third-largest city in Cuba, is known as the “City of Squares” for its many pleasant plazas. Strolling around the historic core of this city will give you insight into the culture of Cuba and the lifestyle of its citizens.
Explore DestinationHolguín
Holguín is Cuba’s fourth-largest city. Located along the Carretera Central in eastern Cuba, Holguín is home to several pleasant plazas.
Explore DestinationSanta Clara
Santa Clara is a midsized town in central Cuba. It’s best known for its massive Che memorial, but the city is also a good place to soak up unfiltered Cuban culture.
Explore DestinationBayamo
The town of Bayamo played an important role in the Ten Years War. It’s not very touristy, and will appeal to travelers with a keen interest in history.
Explore DestinationCienfuegos
Cienfuegos is a midsized town set along the south-central coast of Cuba. It has a pleasant colonial center, and French-styled boulevards that are perfect for strolling.
Explore DestinationSantiago de Cuba
Santiago is unlike anywhere else in Cuba. It’s home to the country’s largest Afro-Cuban population and was the birthplace of the Revolution. Its isolated, eastern setting helped influence its distinct cultural character and significant historical context. It’s a lively, fast-paced city that is older than Havana. Needless to say, it’s a fascinating place to visit.
Explore DestinationHavana
Havana is a beautiful and captivating city. It’s home to the country’s most thriving cultural, culinary, and artistic scenes, and is a fascinating intersection between Spanish colonialism and Cuban Communism. The people here are friendly and welcoming, and it’s easy to spend an entire week strolling its streets, visiting museums, and listening to live music.
Explore DestinationBay of Pigs
Known for the failed CIA military invasion of 1961, the Bay of Pigs is an attractive and interesting area that’s a few hours southeast of Havana. It’s home to the most important wetland in Cuba, contained within the Ciénaga de Zapata National Park, as well as some excellent dive sites.
Explore DestinationSanto Domingo
The small town of Santo Domingo lies amidst the forested Sierra Maestra in eastern Cuba. The setting – with tall mountains, lush forests, and clear streams – is lovely, and the area is home to Fidel’s rebel headquarters at La Comandancia de la Plata.
Explore DestinationFeatured Cuba Trips
Browse our handpicked selection of Cuba itineraries, each crafted by local experts who know the country inside out. Whether you're after adventure, relaxation, or cultural immersion, we have a trip tailored for you.
Cuba's Culture, Charm, and...Rum
Your guidance, personal touches and attention to detail make these trips to Cuba an experience we will continue to do with Anywhere.com. Thanks for a great experience that has gotten better with each trip to Cuba we have done through you!!!!!
History, Culture, and Exploring Nature
Having Anywhere coordinate our trip to Cuba was amazing! We didn't have to worry about anything and always felt very safe and educated!
Tailored to Our Family
Our family was looking for a balance of beach fun, exotic nature, and experiencing the classical culture of Cuba for our two young adults. Anywhere delivered a tailor-made experience on this trip.
Pure Cuba: An Island Nation Essence
What if you could only visit Cuba for a limited time. What must you do? Why, explore Havana and Varadero Beach, of course. If you can distill an experience, this is it.
Our Cuban Getaway
I like the balance between learning from guides and having free time to explore. Daniel meeting us upon our arrival at Casa Prado Colonial was helpful. Giving us a . phone was a nice touch and made us feel cared for by Anywhere. We didn't feel completely on our won.
Our Journey from Havana to Trinidad
Our hosts in Cuba went out of their way to make us feel welcome, as if we were staying in our own home.
Discovering Cuba Together
It’s time to enjoy some quality time as a family. This vacation, unplug in Cuba — a colorful nation with a history still being written, and where time stood still.
Charming Cuba—History and Nature
The people that hosted us and the transportation was great — always on time. Appreciated the Viñales experience and learning not only about agriculture, but also tobacco and meeting locals along the route.
A Quick Havana Getaway
Havana was wonderful. Our 5-day quick getaway includes a thorough introduction to Cuba’s architecture and culture. We also loved the trip to Varadero to experience the beautiful coastline!
Romance 101: Essentials of Cuba
Need a romantic overview of Cuba? Then this Signature Trip is for you. Assembled by Local Experts, this getaway is guaranteed to give you the ideal Cuban experience.
Real Voices, Real Benefits
We believe travel is more than ticking destinations off a list – it's about discovering new places deeply, feeling connected wherever you go, and knowing you have a trusted team of local experts behind you every step of the way.
