Cuba Calling: 20 Essential Tips for First-Timers to the Island of Salsa, Cigars, and Colorful Old Cars

Post originally Published January 6, 2024 || Last Updated January 7, 2024

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Cuba Calling: 20 Essential Tips for First-Timers to the Island of Salsa, Cigars, and Colorful Old Cars - Get Your Paperwork in Order Before Booking


Cuba Calling: 20 Essential Tips for First-Timers to the Island of Salsa, Cigars, and Colorful Old Cars

Before you start dreaming of strolling along Havana's Malecon or sipping mojitos at the Hotel Nacional, make sure your paperwork is in order. Visiting Cuba as an American traveler involves clearing a few bureaucratic hurdles that you'll want to sort out well in advance of booking your trip.

To start, Americans need a special license from the US Treasury Department's Office of Foreign Assets Control (OFAC) to legally visit Cuba. The most common types of licenses are "people-to-people educational travel" and "support for the Cuban people." The former requires traveling with a tour group on an itinerary that provides educational experiences involving meaningful interaction with locals. The latter involves less rigid itineraries focused on patronizing private Cuban businesses and learning about Cuban culture.

Figuring out which type of OFAC license best fits your travel plans will dictate how you go about arranging the details. The people-to-people license requires booking through an authorized tour operator who will walk you through the application process. For general support for the Cuban people licenses, you can submit an application yourself directly through OFAC. Just don't expect a speedy turnaround; it can take up to six weeks to receive approval.
In addition to the OFAC paperwork, American travelers to Cuba need a tourist card or visa issued by the Cuban government. Tour operators will include this for you in your package. But if you're traveling independently, you'll need to purchase a tourist card beforehand through an authorized airline or third-party vendor. Prices are around $50-$100.
It's highly recommended to secure all needed paperwork before booking flights and hotels. While OFAC does not authorize or deny specific travel reservations, you'll have greater flexibility and peace of mind knowing your license to travel to Cuba is already cleared. Plus, some airlines and hotels providing services for US citizens traveling to Cuba require you to present a copy of your approval letter before allowing you to complete reservations.

What else is in this post?

  1. Cuba Calling: 20 Essential Tips for First-Timers to the Island of Salsa, Cigars, and Colorful Old Cars - Get Your Paperwork in Order Before Booking
  2. Cuba Calling: 20 Essential Tips for First-Timers to the Island of Salsa, Cigars, and Colorful Old Cars - Brush Up On Your Basic Spanish Phrases
  3. Cuba Calling: 20 Essential Tips for First-Timers to the Island of Salsa, Cigars, and Colorful Old Cars - Experience Havana's Vintage Vibe
  4. Cuba Calling: 20 Essential Tips for First-Timers to the Island of Salsa, Cigars, and Colorful Old Cars - Venture Outside the Capital to See Real Cuba
  5. Cuba Calling: 20 Essential Tips for First-Timers to the Island of Salsa, Cigars, and Colorful Old Cars - Indulge in Authentic Cuban Cuisine
  6. Cuba Calling: 20 Essential Tips for First-Timers to the Island of Salsa, Cigars, and Colorful Old Cars - Puff on a Cuban Cigar - But Bring Them Home!
  7. Cuba Calling: 20 Essential Tips for First-Timers to the Island of Salsa, Cigars, and Colorful Old Cars - Sway to the Rhythms of Salsa and Rumba
  8. Cuba Calling: 20 Essential Tips for First-Timers to the Island of Salsa, Cigars, and Colorful Old Cars - Pack Light and Leave Room for Souvenirs
  9. Cuba Calling: 20 Essential Tips for First-Timers to the Island of Salsa, Cigars, and Colorful Old Cars - Don't Miss a Mojito at Hemingway's Favorite Bars

Cuba Calling: 20 Essential Tips for First-Timers to the Island of Salsa, Cigars, and Colorful Old Cars - Brush Up On Your Basic Spanish Phrases


While Spanish is not necessary for visiting major tourist areas in Cuba, learning some basic phrases will enrich your experience tenfold when interacting with locals. Knowing just a few conversational words and expressions opens doors to forging connections through language.
Start with "hola" and "gracias"—hello and thank you. Two simple words that will carry you a long way in expressing courtesy and appreciation. Building on that foundation, "por favor" (please) allows you to politely request things. Combine it with "donde esta" (where is) to ask helpful questions, like "Donde esta el bano?" (Where is the bathroom?).

When you stumble through the language, don't forget "lo siento" (I'm sorry) to smooth over any linguistic faux pas. And patch up minor misunderstandings with "no hablo español muy bien" (I don't speak Spanish very well).
Beyond essential niceties, learn phrases that invite conversation. "Como estas?" (How are you?) opens the door for local Cubans to express how they're doing. Take interest in their responses before sharing "muy bien, gracias” (very good, thank you).

And leverage the universally beloved topic of family to find common ground. Ask "tienes familia en Cuba?" (do you have family in Cuba?) to discover connections. Share about your own family back home with "tengo dos hermanos" (I have two siblings).
Food offers another portal into Cuban culture through language. At restaurants, read the menu aloud to pick up new vocabulary. Try out words and phrases like "quiero el ropa vieja" (I want the shredded beef) or "no quiero picante” (I don’t want spicy food). Your efforts will be appreciated.
Beyond mealtimes, seize opportunities for simple exchanges. Compliment an artisan’s handiwork by saying “que bonito” (how beautiful). And if you're enjoying live music, tell the performer "¡qué buena música!” (what great music!).

Cuba Calling: 20 Essential Tips for First-Timers to the Island of Salsa, Cigars, and Colorful Old Cars - Experience Havana's Vintage Vibe


With its cobblestone streets and colorful classic cars, Havana oozes nostalgic charm. From historic hotels and nightclubs to faded mansions and bustling markets, the city provides a portal into Cuba’s storied past. Wandering Old Havana feels like walking onto a movie set with the backdrop of vintage architecture and automobiles transporting you back in time.

One of the best ways to soak up the vintage ambiance is strolling the Malecon waterfront promenade. The century-old seawall hugging Havana harbor teems with locals and tourists mingling, fishing, and watching the fiery Caribbean sunsets. Gaze out across the water to see relics of Havana’s colonial era, like the 15th century fortress Castillo de la Real Fuerza and the baroque Catedral de San Cristóbal. Then join the crowds along the Malecon surviving the salty sea spray as waves crash against the barrier.
Vintage cars putter along the Malecon, but to fully experience Havana’s iconic classic car culture, go for a ride. Colorful 1950s Dodges, Chevrolets, and Cadillacs form part of Havana’s taxi fleet. Negotiate a fare with one of the drivers to be transported in style to your next destination. Glide through the city’s historic streets in the backseat of a pink 1957 Chevy convertible and it will feel like time travel.

For a dose of mid-century modern style, unwind with a mojito at Hotel Nacional. The 1930s art deco icon has hosted the likes of Marlon Brando and Fred Astaire. Sip your drink in the lush gardens or on the terrace with sweeping harbor views and imagine the decadent historic scenes that unfolded. Nearby, the newly renovated Hotel Manzana harbors more nostalgic vibes with its grandiose colonial facade and abundance of Spanish tilework.
After dark, enjoy live mambo and salsa music with a culturally authentic flair. Cafe Cantante is a popular option set in a stadium that once hosted Cuba’s biggest stars. Now, vibrant dance shows recapture the glitz and glam of the 1950s heyday. Similarly, the historic Cabaret Parisien duplicates the iconic nightclub's original show encapsulating the spirit of Old Havana.

Cuba Calling: 20 Essential Tips for First-Timers to the Island of Salsa, Cigars, and Colorful Old Cars - Venture Outside the Capital to See Real Cuba


Beyond the brightly-colored facades of Old Havana lies the vibrant heart and soul of the real Cuba. Venturing beyond the capital introduces you to Cuba's rich cultural tapestry woven together by art, music, people, and landscapes waiting to be discovered inland and along the coasts.

Trinidad on Cuba's southern shores provides a lively glimpse of colonial history merged with small-town charm. Founded in 1514, the remarkably well-preserved UNESCO World Heritage city exemplifies Spanish colonial architecture with its pastel buildings, cobblestone streets, and grand churches framed by the Sierra del Escambray mountains. Wander plazas dotted with 18th-century mansions and soak up the easygoing atmosphere over coffee at Plaza Mayor. Then head to clifftop La Vigia for a different perspective gazing out on the terracotta-roofed cityscape and Caribbean beyond.
Further inland, Santa Clara illuminates Cuba's pivotal revolutionary history. Che Guevara memorials and museums honor the revolutionary icon who led the decisive 1958 Battle of Santa Clara. See the famous derailed armored train marking the battle's significance along with a mausoleum housing Che's remains. History buffs could spend days poring over exhibits showcasing artifacts, letters, photos and more immortalizing Cuba's revolutionary struggle.

On Cuba's southern coast, Cienfuegos and Trinidad unveil the island's French influences with 19th-century architecture lending European flair. Wander the historic city centers’ pastel neoclassical buildings that earned Cienfuegos UNESCO distinction. In Trinidad, highlights include Plaza Mayor, the former wealth center surrounded by museums inhabiting colonial mansions and Cuba's oldest church, Iglesia Parroquial de la Santísima.

Nature beckons inland at Topes de Collantes Nature Reserve in the Escambray Mountains blanketing Cuba’s interior. Outdoor enthusiasts hike through valleys, waterfalls, and limestone caves. Spend the night after adventures immersed in nature at one of the reserve’s scenic campgrounds or ecolodges. Cooler temperatures offer relief from the heat of Havana and beach destinations.
Venturing east, Baracoa unveils a whole different side of Cuba's topography as the island's oldest settlement hemmed in by mountains and rainforests. Explore colonial highlights like Castillo de Seboruco Fort built in the 1600s to fend off pirates. But Baracoa's real treasures are natural, including Bahia de Taco Bay's boat-lined beaches, indigenous flora, and scenic viewpoints like El Yunque mountain.

Cuba Calling: 20 Essential Tips for First-Timers to the Island of Salsa, Cigars, and Colorful Old Cars - Indulge in Authentic Cuban Cuisine


When it comes to experiential travel, few things immerse you in a destination's culture like its food scene. Cuban cuisine represents a melting pot of Spanish, African, and Caribbean influences that has evolved over centuries into the mouthwatering flavors celebrated on the island today. Indulging in the country's quintessential dishes and libations offers a tasty window into Cuban heritage.

For a classic sampling, order the “CUBA Libre” cocktail blending rum and cola with a squeeze of lime. Rum production has deep roots on the island, so sipping Cuban rum will introduce you to the smooth aged varieties coveted worldwide. Pair your drink with ropa vieja showcasing tender shredded beef stewed in a tomato-based criollo sauce. The iconic entrée encapsulates the essence of Cuban comfort food.

Seafood stars prominently in Cuban fare given the island's extensive coastlines. Recognizable options like lobster tails, shrimp, and grouper frequent menus. But also keep an eye out for more obscure species relished locally like biajaíbos, a small brown fish fried whole to crispy perfection with eyes still intact. Habaneros, meanwhile, are tiny lobster-like crustaceans loved for their briny ocean flavor.
Cuban sandwiches hold their own claim to fame beyond the island’s shores. A taste transports you with layers of ham, roasted pork, Swiss cheese, pickles, and mustard pressed between crusty Cuban bread. You can find classic iterations at local hole-in-the-wall spots all over Havana and other Cuban towns. For a sit-down experience, gastro pubs like Habana 61 put a gourmet spin on the iconic snack with added touches like house-made mojo sauce.
Venture further into Cuban cuisine’s African roots with yuca con mojo. The starchy vegetable grows in abundance on the island and is prepared by boiling then sautéing with olive oil, garlic, onion, cumin, and citrus juice. It makes a delicious side, along with black beans and rice, another staple combination known as moros y cristianos (or “Moors and Christians”). Both provide glimpses into the impact of African culture permeating Cuban culinary traditions.
When it comes to beverages, don't overlook Cuban coffee either. Locals love the sugary brew served strong and small as a concentrated espresso shot. You can find Cuban coffee all over the country, but atmospheric spots like El Escorial in Havana let you sip surrounded by historic ambiance. Finish your cup then request a cafecito to experience the sweet saturated jolt again.
Beyond classic fare, Cuba puts its own spin on international influences as economic shifts continue opening the island’s culinary landscape. Creative fusions include Cuban-style tapas, Italian flatbreads with tropical twists, and Chinese-inspired vegetarian options. With more restaurants privately owned by aspiring chefs, the possibilities keep evolving.

Cuba Calling: 20 Essential Tips for First-Timers to the Island of Salsa, Cigars, and Colorful Old Cars - Puff on a Cuban Cigar - But Bring Them Home!


Among Cuba's most iconic exports, a cigar in one hand completes the quintessential Hemingway image of Cuba. Yet while cigars may seem ubiquitous across the island, Americans face significant restrictions transporting Cuba's coveted tobacco products back home. This presents a confusing conundrum for US travelers eager to partake in one of Cuba's legendary pastimes.

Unlike rum or coffee, the US trade embargo prohibits Americans from returning from Cuba with alcohol or tobacco products—including the famed cigars and cigarettes. The Obama administration relaxed restrictions, but limits remain allowing just $100 worth of authorized purchases. Essentially, this translates to two boxes containing 10-25 cigars each at most.

Exceeding the cap—even just one extra cigar—can trigger confiscations, fines up to $55,000, and even criminal charges for smuggling. Penalties apply to purchases from stores, unofficial vendors, and gifts received on the island. And customs officials in the US take inventory seriously, unwrapping boxes to count sticks.

For cigar enthusiasts, the restrictions sting. Many travelers intent on savoring Cuba's tobacco while on the island also want to relish prized stogies back home. But until Cuban sanctions ease further, visitors must carefully adhere to the two-box maximum or risk being, well, smoked by serious penalties.

Ardent cigar aficionados share tips for staying within the cap while still enjoying Cuba's cigar culture. First, strategically purchase singles at cigar shops and hotels for smoking during your trip. Patronizing these official retailers provides peace of mind the products are legitimate, not counterfeits lurking around some street stands. Between purchases, keep receipts with box totals to tally against your $100 allowance.

Next, reserve your two box quota for transporting home care of expert shop recommendations like Havana's La Casa del Habano. Stock up at official outlets your last day to avoid storage issues. Ask to seal boxes so customs knows purchases were untouched in transit. Carry on to keep close supervision through US customs.

If gifted cigars from hosts or new Cuban friends, accept them graciously. But regretfully decline taking them home yourself to avoid crossing the gray lines of personal use exemptions. Instead, leave them for fellow travelers not facing return restrictions to enjoy. Or explore options your hotel may offer for shipping legally acquired cigars for delivery stateside after your return.

Cuba Calling: 20 Essential Tips for First-Timers to the Island of Salsa, Cigars, and Colorful Old Cars - Sway to the Rhythms of Salsa and Rumba


Immerse yourself in Cuba’s lively music and dance traditions for an interactive cultural experience that will have you swaying your hips and tapping your toes. Salsa and rumba rhythms pulse through the island, tracing their African roots. Attending a high-energy show or simply stumbling upon street performers lets you connect with Cuba’s captivating musical heritage.

Few experiences capture the soul of Cuban culture like salsa. The upbeat partner dances blend rhythms across Africa and the Caribbean that coalesced in eastern Cuba. Elements of mambo, cha-cha-cha, and son montuno all shaped salsa's familiar driving beat. Grasping those rhythmic foundations will ease you into traditional salsa's fluid footwork and twirls.

Taking a beginner salsa lesson introduces you to those basic steps so you can feel the beat. Instructors break down the leader and follower roles. Gentlemen act as guides while ladies respond through synchronized hip sways and spins. An hour-long group introductory class at a dance school like Havana’s La Casa del Son centers around nailing the timing and footwork. Then you can infuse freestyle flair.
Bar La Esencia in Trinidad hosts salsa nights, so you can practice new moves after a lesson. Dance beside locals who’ll appreciate your willingness to step outside your comfort zone. Even clumsily finding the rhythm helps you appreciate salsa music’s origins. Soy Cuba in Havana also dazzles with live bands in a glamorous cabaret setting. Its Saturday night salsa soirée packs the dancefloor until the wee hours.

Rumba’s roots delve even deeper into African heritage. Hundreds of thousands of African slaves were shipped through Matanzas, lending rich influences seen in rumba dance traditions centered around percussive rhythm. The mesmerizing polyrhythms transport dancers into almost trance-like states through repetitive drum patterns and call-and-response singing.
Witnessing street performances lets you experience improvised rumba dancing as artistic self-expression. Check out Callejón de Hamel in Havana’s Vedado neighborhood. Murals colored with Santería imagery surround drummers drawn to jam sessions in the alley on Sundays. Even without formal training, you’ll instinctively clap along and absorb the hypnotic ambiance.
Matanzas itself provides an immersive rumba backdrop every summer during International Rumba Festivities and Symposium. The electric atmosphere as generations perform offers perspective on rumba’s evolution and preservation. Talks delve into traditions’ significance alongside pulsing drums and chants exuding spiritual energy to sway even observers.
Fusing rumba with other styles, Havana Rakatan takes place weekly at Dance Studio 26. More formal than impromptu street jam sessions, the performances express Afro-Cuban culture through highly choreographed dances. Yet audiences still holler encouragement and move to the driving beats. Arrive early to snag seats for the rumba-focused first half.

Cuba Calling: 20 Essential Tips for First-Timers to the Island of Salsa, Cigars, and Colorful Old Cars - Pack Light and Leave Room for Souvenirs


When traveling to Cuba, packing light and leaving room in your luggage for souvenirs is crucial. With baggage weight limits and potential checked bag fees, you'll want to be judicious about what you bring while still having space for those signature Cuban keepsakes you'll eagerly want to bring home. This takes strategy and discipline, but it pays off by preventing reactive purchases of additional suitcases as others have learned the hard way.
First, stick to carry-on size luggage - this keeps weight low since most airlines max carry-ons around 40 pounds. Prioritize versatile, lightweight clothing like convertible pants, skirts, shirts and dresses that can be mixed and matched and worn in layers. Limit footwear to supportive walking shoes plus a nicer pair for evenings out. Toiletries should meet TSA size limits; consider solid shampoo bars and mini sunscreens to save space and weight.

When you do check a bag, weigh it empty first so you know how much leeway you have to stay under 50 pounds before incurring overweight fees. Pack heavy items like shoes at the bottom to keep the center of gravity low and balance contents. Compress using packing cubes, vacuum seal bags, and rolled clothing to maximize space.
Once in Cuba, you'll encounter endless temptations to bring home keepsakes like art, handmade crafts, cigars, coffee, and rum. Keep a running tally of purchased souvenirs and their sizes. Ship larger, fragile, heavy items through reputable services like FedEx post-trip to avoid airline baggage limits. Distribute smaller goods like jewelry, art prints, and trinkets throughout your bags to prevent bulges. Stuff small empty spaces with cigar boxes and pouches.

Soft-sided duffel bags can come in handy for overages. But gauge if paying extra baggage fees makes sense versus mailing excess items separately. Some travelers even wear a travel vest with multiple pockets on the flight home to creatively hold keepsakes.
When parting with pieces you picked out with excitement stings, remember experiences outweigh things. Photograph special souvenirs left behind to reminisce over their memories. Future Cuban trips may always bring new treasures, but overpacking today risks detracting from current immersive moments. Travel light, then selectively take sentimental, portable mementos reflecting connections formed.

Cuba Calling: 20 Essential Tips for First-Timers to the Island of Salsa, Cigars, and Colorful Old Cars - Don't Miss a Mojito at Hemingway's Favorite Bars


Among the endless draws luring travelers to Cuba—vintage cars, salsa dancing, cigars—literary legend Ernest Hemingway’s larger-than-life legacy looms large. The Nobel Prize-winning author lived outside Havana for over 20 years, and traces of his presence today enrich any Cuban trip for Hemingway fans. Beyond touring his preserved home Finca Vigía, visiting his favorite Havana watering holes offers stirring glimpses into his bustling life on the island while also sampling the mojitos that flowed freely.
No Hemingway homage is complete without raising a glass at El Floridita. Under swaying palms in Old Havana, the bar has scarcely changed since Hemingway frequented it in the 1930s and 40s. His outsize personality still echoes through the wood-paneled rooms where Papa penned classics, enthralling drinkers with tales of deep sea fishing. Bartenders now mix the “Hemingway Daiquiri” he popularized—rum, lime, grapefruit juice, Maraschino liqueur—near a bronze statue of the author leaning on his favored corner bar spot. Savoring the tart concoction amid period décor recaptures the ambiance that inspired him.
For a more raucous Hemingway scene, head to La Bodeguita del Medio. Scrawled with celebrities’ signatures covering nearly every inch of wall space, it brims with legends who stopped in, lured by the house drink: the mojito. In fact, Hemingway himself famously suggested the bar’s name origins came from boasting of having the best mojito in Havana. While disputed, the claim rings true sipping the crisp rum, lime and mint cocktail Hemingway adored in the jam-packed, graffiti-strewn tavern.
Beyond those twin pillars, other establishments Hemingway frequented still serve up spirited inspiration. El Dandy Bar attracted Hemingway with its eclectic mix of European expats and aficionados of the arts. Marked by art deco touches like its checkerboard floor, the bar maintains its worldly, cultured ambiance. Easy banter flows between regulars bellied up enjoying drinks like the Papa Doble daiquiri crafted specially for Hemingway with less sugar to accommodate his diabetes. Places like El Dandy offer glimpses of the diverse social circles the gregarious author relished.

Smaller settings like La Zaragozana also count Hemingway as a onetime regular. Touting its role in chapters of Islands in the Stream, the no-frills joint is an unassuming dive bar frozen in time. Here, simple snacks and bottles of cold beer pair perfectly with tales of Hemingway mingling with locals, perhaps jotting notes for his next vivid passage. In quintessential Cuban style, you may even catch impromptu musicians jamming while regulars play dominos out front.

Beyond the Havana institutions he frequented, Literary Pub Crawl walking tours provide context strolling between establishments. Guides share stories beind Hemingway haunts while pausing for drinks at his favorites spots. The evening excursions channel his adventurous, booze-filled spirit in a mobile bar-hopping quest.

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