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CUBA

Introduction

The largest Caribbean island frozen in time, Cuba is a sensory explosion of 1950s American cars, pulsating salsa rhythms, hand-rolled cigars, and revolutionary spirit. From the faded grandeur of Havana to the emerald tobacco valleys of Viñales and the perfectly preserved colonial jewel of Trinidad, Cuba delivers raw authenticity and some of the warmest people on earth.

Top Cities/Regions to Explore

Havana

Vibrant capital with classic cars, colonial architecture in Old Havana (UNESCO), and lively Malecón promenade.

Viñales Valley

UNESCO-listed tobacco fields, mogotes (limestone hills), and rural charm—perfect for horseback rides.

Trinidad

Colorful colonial town (UNESCO) with cobblestone streets, live music, and nearby Valle de los Ingenios.

Varadero

20km of powdery white beaches and turquoise waters, ideal for relaxation and water sports.

Santiago de Cuba

Birthplace of son and rumba music; vibrant carnival culture and revolutionary history.

Key Cultural and Historical Highlights

Cultural Practices

Cubans are incredibly hospitable—accept offers of coffee or conversation graciously. Greet with “¡Hola!” or a cheek kiss. Tipping (propina) is appreciated but modest; Music and dance are life—join in!

Major Festival

  • Carnival in Santiago (July)—elaborate costumes, conga drums.

  • Las Parrandas (Remedios, Dec)—UNESCO-listed fireworks and floats.

  • Havana Jazz Festival (Jan).

Seasonal Connection

Dry season brings outdoor son music evenings; rainy afternoons perfect for indoor rumba or dominoes. Christmas (Noche Buena) features lechón feasts.

UNESCO Sites

Old Havana, Viñales Valley, Trinidad & Valley de los Ingenios, Cienfuegos, Santiago’s San Pedro de la Roca, Camagüey, Coffee Plantations.

Unique Experiences

Vintage Car Tour in Havana

Cruise in a restored 1950s convertible through historic streets.

Horse Riding in Viñales

Trot through tobacco plantations and dramatic karst landscapes.

Cigar Rolling & Tasting

Learn to hand-roll a puro at a plantation, paired with aged rum.

Mojito Making Class

Craft the perfect Cuban cocktail with fresh mint and Havana Club rum.

Signature Food

¥500–1,000

Ropa Vieja

Shredded beef stew with tomatoes, peppers, and rice.

¥500–1,000

Lechón Asado

Slow-roasted pork with garlic and mojo sauce.

¥500–1,000

Mojito

Rum, mint, lime, sugar—Cuba’s iconic refreshment.

¥500–1,000

Ajiaco

Hearty stew of meats, root vegetables, and corn.

¥500–1,000

Moros y Cristianos

Black beans and rice, a daily staple.

Sample Itineraries

1-Day Highlights of Havana: Old Town & Iconic Sights

Embark on a whirlwind journey through Havana’s vibrant heart, capturing the essence of this unique city in just one day. 

  • Stroll the Malecón waterfront at dawn.
  • Explore Habana Vieja’s cobbled streets, plazas, and colonial landmarks like the Catedral de San Cristobál.
  • Visit the Museo de la Revolución for a dive into Cuban history.
  • Snap photos at Plaza de la Revolución and relax at the historic Hotel Nacional.
  • Enjoy sunset from Edificio Focsa and live jazz in Vedado.
  • Savor cocktails at La Bodeguita del Medio and inventive cuisine at trendy spots.
View Full Itinerary

7 am:

  • Wake up early and head to the Malecón to observe locals, fishermen, and musicians.
  • Breakfast at Café Bohemia in Plaza Vieja, then explore Habana Vieja’s lanes, including Plaza de San Francisco de Asís, Plaza de Armas, and Plaza de la Catedral.
  • Visit key sights: Iglesia y Monasterio de San Francisco de Asís, Catedral de San Cristobál de la Habana, Castillo de la Real Fuerza, Palacio de los Capitanes Generales museum, and Museo del Ron.
  • Stop at La Bodeguita del Medio for a cocktail.

12:30 pm:

  • Lunch at O’Reilly 304, then tour Museo de la Revolución and its exhibits on Cuban history.
  • Taxi to Plaza de la Revolución for photos, passing the Capitolio.
  • Stroll the Hotel Nacional’s gardens for coffee with sea views.

6:30 pm:

  • Ascend Edificio Focsa for panoramic sunset views and dinner at La Torre.
  • Evening in Vedado: Dinner and jazz at Jazz Café or other live music venues, then taxi back in a classic car.

4-Day Highlights of Havana: Cultural Immersion & Creative Vibes

Dive into Havana’s thriving scene over four days, connecting with artists, entrepreneurs, and chefs shaping Cuba’s future. From Old Havana’s historic streets to Vedado’s markets and private performances, savor the art, flavors, and rhythms of this dynamic capital.

  • Meet up-and-coming graphic designers and artists.
  • Enjoy a private dance show and live salsa or jazz.
  • Participate in a hands-on cooking class with future chefs.
  • Discuss US-Cuban relations with a university professor.
  • Explore Old Havana’s entrepreneurs and silk screening workshops.
  • Visit local markets to learn about Cuba’s changing ration system.
View Full Itinerary

Day 1: Arrival in Havana

  • Arrive and enjoy a traditional lunch of black beans, rice, roast pork, and seafood.
  • Visit artist Jose Fuster’s creative home in Jaimanitas.
  • Stop at Beatriz’s studio for recycled metal and ceramic art.
  • Check into accommodations.
  • Welcome mojito at Hotel Nacional’s terrace.
  • Dinner at a paladar with upscale Cuban home cooking.

Day 2: Exploring Havana

  • Discussion on US-Cuban relations with a University of Havana professor.
  • Walking tour of Old Havana, meeting new entrepreneurs.
  • Visit a traditional silk screening workshop and a graphic designer’s studio.
  • Lunch at a colonial-style paladar with old photos and memorabilia.
  • Free afternoon to explore the city independently.

Day 3: Vedado

  • Visit a farmer’s market and ration store in Vedado to understand daily shopping and changes in Cuba.
  • Hands-on cooking class at a culinary school with aspiring private restaurant chefs.
  • Private contemporary dance performance by a top troupe.
  • Farewell dinner at a paladar with live salsa or jazz music.

Day 4: Departure

  • Morning at leisure: Explore markets or chat with locals.
  • Transfer to the airport for departure.

8-Day Highlights of Cuba: Western Circuit & Countryside

Experience a fast-paced taste of western Cuba over eight days, from Havana’s iconic streets to the lush Vinales Valley and colonial gems like Trinidad and Cienfuegos. Blend urban exploration, UNESCO sites, revolutionary history, and scenic drives in this tailored island adventure.

  • Guided walking tour of Old Havana’s UNESCO plazas and colonial architecture.
  • Vintage American car tour of New Havana’s landmarks like Revolution Square.
  • Day trip to Vinales Valley for tobacco plantations and cave boat rides.
  • Explore Cienfuegos’ French-influenced squares and Punta Gorda peninsula.
  • Walking tour of Trinidad’s sugar-era historic town.
  • Visit Valley of the Sugar Mills and laid-back Sancti Spiritus.
  • Tour Santa Clara’s Che Guevara sites and revolutionary museums.
View Full Itinerary

Day 1: Arrival in Havana

  • Airport transfer to Havana.
  • Relax at your casa particular for the remainder of the day.

Day 2: Havana

  • Guided walking tour of Old Havana, including Plaza de Armas, Plaza San Francisco, Plaza Vieja, and Plaza de la Catedral.
  • Vintage American car tour of New Havana: Capitol Building, Revolution Square, University of Havana, Hotel Nacional, and former Presidential Palace.
  • Afternoon at leisure for museums or wandering.

Day 3: Havana (Vinales Day Trip)

  • Drive to Vinales with stops at a tobacco plantation and Pinar del Rio cigar factory.
  • Explore Vinales town, Dos Hermanas Valley, and underground boat trip at Cueva del Indio.
  • Lunch at a local restaurant.
  • Return to Havana in the late afternoon.

Day 4: Havana to Cienfuegos

  • 3-4 hour road transfer to Cienfuegos.
  • Guided tour: Plaza Jose Marti, Teatro Tomas Terry, Punta Gorda with mansions, Cienfuegos Club, and Palacio de Valle.

Day 5: Cienfuegos to Trinidad

  • 1-hour drive along the Caribbean coast to Trinidad.
  • Guided walking tour of the historic town.
  • Afternoon at leisure, optional visit to Museo Romantico.

Day 6: Trinidad (Day Trip to Valley of the Sugar Mills & Sancti Spiritus)

  • Visit Manaca Iznaga hacienda and slave tower in the Valley of the Sugar Mills.
  • Walking tour of Sancti Spiritus: Parque Serafin Sanchez, Casa de la Guayabera, Parroquial Mayor church, Casa de la Trova, Ruben Martinez Villena library, and Puente Yayabo.
  • Lunch at a local restaurant.
  • Return to Trinidad.

Day 7: Trinidad to Santa Clara

  • Scenic drive through Escambray Mountains to Santa Clara.
  • Tour: Tren Blindado museum, Che Guevara Monument & Mausoleum, Parque Vidal, La Caridad theatre, and Museum of the Fine Arts.

Day 8: Santa Clara to Home

  • 3-hour transfer to Havana airport for departure.

Day Trips and Nearby Attractions

CHECK MAPS

Hakone

~1.5 hours by train

Kamakura

~1 hours by train

Yokohama

~30 minutes by train

Best Time to Visits by Activities

September to November (Hurricane Season)

Hot, occasional rain; budget-friendly, fewer tourists. Highlight: Cultural events in Santiago; affordable cigars.

December to April (Dry Season)

Sunny, mild weather; ideal for beaches, hiking Viñales, city exploration. Highlight: Fewer crowds in January; perfect for Havana walks.

May to August (Wet Season Start)

Warm with short showers; lush greenery, lower prices. Highlight: Whale watching in Samaná (if combining trips); vibrant festivals.

Summary Notes

December–March best for combining beaches and culture; avoid September–October for storm risk.

Travel Practicalities

Visa and Entry Requirements

  • Tourist card (visa) required for most

  • E-visa online or via airline.

  • US citizens: OFAC license needed (e.g., “support for Cuban people”).

  • Passport valid 6+ months.

Currency

  • Official Currency: Cuban Peso (CUP)
  • Bring USD/EUR cash; 
  • Exchange at CADECA
  • ATM: No US cards work reliably

Language

  • Spanish: Official language

  • English is more common in tourist hubs.

Local Transportation

Domestic Flight

Long-Distance Bus (Viazul)

Classic taxis or Private transfers

Coco Taxi

Car Rental

Local Tips and Culture

Internet: Buy ETECSA SIM or use hotel Wi-Fi; limited outside cities.

Scams: Friendly “hustlers” (jineteros) may overcharge—politely decline. Use official taxis.

Cats & Strays: Stray cats and dogs common—avoid feeding to prevent issues.

Safety and Practical Tips

Safe to explore

Generally very safe for tourists; low violent crime. Stick to lit areas at night; Keep your belongings secure, especially in crowded areas.

Health Precautions

Travelers should use insect repellent, drink bottled water, avoid traveling alone at night, and ensure travel insurance includes medical evacuation. Pharmacies well-stocked.

Emergency

All Emergencies: Police (106); Fire Department (105); Ambulance (104).