Colorful Cuba 13

Sam Says Series

Sam grew up roaming the green meadows and river valleys of Vermont. Iit was there that she gleaned an appreciation—and a curiosity—for the small towns of America, and later, for farther corners of the world. She has a deep-rooted penchant for exploring the connection between people and place. As a writer, Sam has focused on food, travel and lifestyle storytelling. 

Pack your bags, power down the phone, break out the map and prepare for a travel experience like no other: Once your plane touches down in Cuba, you’ll be amazed, perplexed and delighted. Cuba is a paradox; it’s vibrantly beautiful, a disarming time warp, both bucolic bliss and urban grit, an old-school kind of cool derived from economic isolation and a rich, enduring cultural backbone. Cuba can leave you inspired and incensed in the same moment. It’s a place that is misunderstood and deeply entrenched in its sense of place.

As ease of travel improves, tourism has brought a sweep of visitors that populate the white-sand beaches of Varadero, the cobbled streets of colonial Trinidad and the sprawling, music-filled cafes of colorful Havana. Cuba—all 42,000 square miles of it—is a sight to see. A lesson in poverty, happiness, beauty, simplicity. If you’re lucky, you’ll be able to visit the diverse range of landscapes in its entirety.

On a recent trip there, I homed in on two locations in the western region of the country: Havana and Viñales, a small valley town nestled in the mountains of the Pinar del Río. Here are some best practices—a collection of things to know before you make your own trek to the Pearl of the Antilles.

Getting There & When to Go

You can generally expect warmer weather (and more tourists) in the dry season between November and April. If rain doesn’t put you off, May through October is the rainy season. Travelers might want to avoid September and October when the threat of hurricanes is at its highest. Although most organized tour trips now arrange chartered flights directly from the United States, we booked flights to Cancún and worked with a Canadian travel agent to book our Cancún to Havana leg, all without a hitch.


A feast for the senses, an untamed energy, a place of contradictions. The steady beat of horse hooves and salsa music. Havana is a place that emanates spirit, even in the face of neglect, and survival through its people and its multitude of awe-inspiring architectural treasures. Explore the sun-washed streets, sip a rum at an open-air bar, share an ice cream walking the leafy promenades of Vedado—it holds a beauty and contagious state of mind that is all its own.

Where to Stay

Keep an open mind: skip the hotels and explore the local casas particulares, a private homestay similar to a bed and breakfast. Knock on the door of any building with the tell-tale white and blue symbol to check nightly availability. If you’d like to plan farther in advance, Airbnb has a growing roster of casa owners who list properties.

What to See

The Malecón is a quintessential eight kilometer stretch of road that flanks the sea. Walk it, and you’ll see the culture of Cuba: fisherman, 1950s-era automobiles, rowdy teenagers and a host of street food vendors. The road snakes up into the leafy Vedado neighborhood, site of the Hotel Nacional de Cuba and streets evocative of aging grandeur.

Getting Around

Let your feet take you where they will. Get lost. The best way to learn about Havana is to explore the crowded neighborhoods, quiet back streets and sunlit squares. If you’re heading somewhere that requires a taxi, you can grab one easily near hotels and plazas; most rides are equivalent to five U.S. dollars or less.

What to Expect

Havana can be overwhelming, but if you’re there for longer than a day you’ll settle into the mindset and movement of the city. The same things—same contradictions—that can inspire confusion (or even anger) are also what make the city so soulful.


A lush, rolling expanse of jade fields, sprawling tobacco crops and thatched tobacco-drying houses. A valley cradled by towering mogotes and rugged hills. In the quiet of the valley, you’ll find endless opportunity for hiking, rock climbing, cave exploring and swimming hole-hopping. The spirited, cigar-smoke laced village is easygoing; travelers kick-off their shoes (or lace them up) to trek the landscape, seek out dramatic vistas and take in the countryside bliss of the simple life on a porch swing.

Where to Stay

If you go the casa particulares route, opt for a room in a house on Viñales’ main drag; most have inviting porches for taking in the activity of the town or relaxing with a book. There are two hotels that can provide the definitive Cuban experience: La Ermita and the class Hotel Los Jazmines; both offer stunning panoramic views of the valley. Rates start at $61 CUC.

What to See

Viñales is a Unesco World Heritage site, meaning you’ll want to take in the traditional agriculture at the tobacco farms and take advantage of the otherworldly natural surroundings. Yoan and Yarelis Reyes can guide you on a trek through the Valle de Silencio, a gentle, unexplored stretch of valley, where the majority of the municipality’s tobacco is grown. They’ll take you through fields dotted with oxen and ploughs, as well as the Finca Raul Reyes, the family farm where you can sample hand-rolled cigars and a dose of local rum.

Getting Around

To get to Viñales from Havana, we arranged a taxi collectivo (or shared taxi) with several other travelers. Our casa host was happy to help us with this, but you can ask any taxi driver if they know of groups that are leaving and have extra space. Once you get there, Viñales is entirely walkable, but there are plenty of taxis available by the town plaza for longer trips to nearby caves or national parks.

What to Expect

Viñales is simple: you’ll find a slow, relaxed pace here—a far cry from the frenetic energy of Havana, and a welcome measure of peace and quiet—a pint-sized agricultural settlement situated in one of Cuba’s most beautiful natural corners.