Cuba Cities to Visit
CubaIt's a cosmopolitan getaway...back in time. If you're looking for a high-end vacation with all of the modern amenities, check out some of Anywhere's other exciting destinations. If you want a return to elegance and simplicity then a Cuban cities vacation may be just what you're seeking. It's easy to unplug and enjoy a fine rum when technology isn't everywhere you turn. Explore the shops of the Vedado Neighborhood or the charm of Central Cuba's Santa Clara.
Cuban cities wear their hearts on their sleeves. You’ll see crumbling yet grand architecture, and watch classic cars rumble down cobblestone streets. While you’re in Cuba's cities of interest, you'll rediscover that live music beats even the best mixes on shuffle. Dance with the locals, who are especially fond of salsa and son. Satisfy your academic side as you explore the art galleries and museums showing off the country's considerable talent — Cuba's cities are full of colourful works...which you'll see reflected in street art as well.
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 DestinationVedado Neighborhood
Vedado is a pocket of moderate prosperity in modern Havana, and you can find lots of shops in this area. 20th-century mansions in Vedado have neoclassical, art deco, and beaux-arts architecture. Walk down Calle 17 to see some of the area’s most impressive buildings.
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 DestinationCentral Havana Neighborhood
Central Havana’s real estate is mostly residential – streets are lined with apartment buildings. Some have fallen into disrepair, but they still reflect Havana's eclectic architecture. This neighborhood has one of the densest populations in all of Havana.
Explore DestinationMiramar Neighborhood
Miramar is best known for its embassies, which line Quinta Avenue (or “Fifth Avenue” in English). With its distinctive tower, the Russian Embassy is one of the most striking. Along Quinta Avenue you’ll also find interesting landmarks like the mansion called Casa de la Tejas Verdes (House of the Green Tiles), and Reloj de Quinta Avenida, a large clock.
Explore DestinationNuevo Vedado
Nuevo Vedado is one of Havana’s middle-class residential neighborhoods. Houses here have interesting, retro looks — they're the result of a building boom that took place in the 1950s. See these houses on a stroll after you visit the Plaza de la Revolución, or stay in one of the casas particulares in the area.
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 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 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 DestinationPlaya Neighborhood
Playa is the northernmost municipality in Havana. “Playa” means beach in Spanish, and along the waterfront you can still find designated swimming areas. These are called balnearios, and they are located on the seaside Primera Avenida (First Avenue).
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 Destination10 de Octubre
This is a municipality in southern Havana, and has the same name as the neighborhood’s main avenue. October 10th commemorates the anniversary of Cuba’s independence from Spain.
Explore DestinationSiboney
Siboney is a small village with a beach, and it’s located just to the east of Santiago de Cuba. This beach is quite popular with locals due to its proximity to the city.
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.
More Cuba Cities to Visit
There's always more to discover in Cuba. From off-the-beaten-path gems to well-loved classics, these destinations are worth adding to your itinerary.
Havana
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.
Matanzas
Matanzas has a distinguished history as a cultural center in Cuba. Its heyday lasted from the late 19th century to the early 20th century.
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.
