Less than 100 miles from the coast of Florida, Cuba is an enigmatic country that has been frozen in time and a sought-after destination for adventure travelers. Near, yet seemingly unreachable, foreign, yet familiar, this small island nation finally opens its doors to inquisitive American tourists after over half a century. Politics aside, visitors can't help but fall in love with the magic and spirit of Cuba's ramshackle glory. From the cobbled streets of Old Havana to the colorful colonial buildings of Trinidad to the rolling hills of Viñales, this unique Caribbean country entices us like the beat of the drums in the “casa de la musica.”

Spanning thousands of miles, the island's landscape is as varied as its heritage. You can loosely divide the country into a few main regions, leading you from bustling cities to tranquil farming towns, forested trails to pristine beaches and back again. In the west, discover Havana, the crown jewel of Cuba, which is steeped in 1950's charm, chockfull with classic cars and the rich scent of fine cigars. Here you can amble along city streets, soaking in the architectural splendor of startling intact Spanish colonial mansions alongside crumbling buildings. Even the facade flaking mustard colored paint chips has a quality all its own. The city (and country)’s magic is the intoxicating mix of contradictions that quickly win you over.

On the far western side of the island lies Viñales Valley, a stunning national park encircled by mountains, where age-old farming techniques produce tobacco for making the best cigars in the world. Here you can lose yourself in a different world altogether, a world comprised of natural wonders without the sprawl of urban life or modernization, peppered with small villages across acres of fertile green fields. Make your way east into the center of the island to Cienfuegos and Trinidad. If classic charm (a little rough around the edges) is your style, Trinidad is not to be missed. With less revitalization than Havana, Trinidad can seem worse for wear, but it simply serves to enhance the spirit of this lively city. Merging sugar plantations and vast forests with a smaller city atmosphere, Trinidad delights with a similar authenticity to Havana without the hustle and bustle of the bigger city. Cienfuegos is more laid-back with idyllic views of the bay and surrounding mountains. Here you can spend a half day enjoying more cultural pursuits like visiting the university, botanical gardens or theatre, or simply people-watch at the local “coffee shop” with iced coffee in hand.

Now is the time to visit Cuba.

Secrets and Tips

  • From Trinidad, boat down the Río Mamoré for a unique adventure on the water.
  • Take a tour of a local artist's studio in Havana. 
  • Get moving with salsa classes and dance the night away in true local fashion. 

Good To Know

Spanish is the official language - Currency in Pesos - Expect a subtropical climate

Frequently Asked Questions

What are your favorite areas in Cuba?

While there's a TON to experience in Cuba, the highlights are mostly condensed into one half of the island. We love exploring the central and western areas, where you can really dig into the cultural heritage of cities like Havana and Trinidad but also mix in the beauty of the countryside and mountainscapes within just a few hours of leaving the city. While Havana is the biggest tourist draw, we highly recommend exploring the farther reaches of the island to get a thorough flavor of local living and the vibrant arts and historical scene. 

Outside Havana, the scenery of Viñales Valley is spectacular. As wilderness buffs, we love the vast tracts of natural beauty without the hustle and bustle of city life. While not the kind of wilderness you'll find in Africa, the gentle valleys here definitely pull at our heartstrings and are perfect for a quiet escape and to see the diversity of the island. If you do want more outdoor adventure, we recommend heading toward Trinidad. That area is home to forests and rivers with great trekking options before or after the beach!

Who would like Cuba?

Cuba makes an excellent destination for travelers who want a mixture of city life, history and idyllic settings close to beaches and outdoor activities. For many of us, city-hopping becomes stale after too many years of sightseeing but cities like Havana and Trinidad offer a unique perspective even for the most seasoned traveler. Still in the process of catching up from the past 50 years, exploring the island is much like stepping back in time and gives otherwise mundane city sights an exhilarating twist. It's not only the architecture and history that we love so much; urban life is rich in the arts, flavorful cuisines and rumba! If you love experiencing local culture and vibrant cities but think you've seen it all, Cuba will definitely spice things up for you with its quirky and, at times, ramshackle charms.

Who wouldn't like Cuba?

If you're looking for wildlife and wilderness, Cuba may not be your first choice. While the landscapes are spectacular and scenic, the island's outdoor activities are limited compared to other destinations, and animal-viewing is hard to come by. For some travelers the timeworn nature of Cuba may not be a good fit either. If you want 5* accommodations, then Cuba isn't the place for you. Finally, if you are a diehard foodie, then you may struggle with the limited fare: pork, fish, rice and beans. However, accommodations and restaurants are privatized and rapidly changing. 

When is the best time to go?

Like most destinations approaching the equator, Cuba has a tropical climate with a two season calendar: wet and dry. To make the most of milder temperatures and sunny skies, the dry season from November to April is your best option. Temperatures typically hover around 70°F during this time, making it comfortable for sightseeing or venturing into the countryside. 

Is there a time you should avoid going?

While Cuba can be a year round destination, June begins the wet season with high humidity and temperatures rising close to 80°F, with rain as an unpredictable contender. August through October is typically the least popular time to visit due to increased risk for tropical and otherwise inclement weather that might derail travel plans and activities. 

How much should you budget for a trip to Cuba?

While Cuba offers numerous budget options, we set a high bar to ensure our travelers have the best experience possible. With our preferred boutique hotels that offer the best in comfort, location and local flavor, along with uniquely customized experiences so you get the most from your visit, our guests can expect to plan around $4,000 per person for a one week trip. 

What are some of the ways you can experience Cuba?

Due to its varied regions, there are quite a few options for exploring Cuba. In cities with so many buildings of architectural significance, even a simple stroll can be an experience. For starters, we recommend focusing on people-to-people exchanges like meeting artists in their homes and studios, bargaining with merchants on Obispo Street and touring the city with a resident historian. A salsa lesson is a fun and immersive experience. Then show off your salsa skills at the “casa de la musica,” where tourists meet locals and integrate into the cultural fabric of the country in a more informal way. 

If you're eager to get out of doors, try trekking through the forests and waterfalls of the national parks or hit the beaches for snorkeling in the turquoise Caribbean waters. If you'd rather let someone else do the walking, marvel at lush acres of farmland on horseback or jump onto a cargo boat to drift down the Río Mamoré near Trinidad.

Regions in Cuba

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Lara Ray