Cuba is a tapestry of rhythm and resilience. Built on Indigenous, Spanish, and African foundations, its culture flows from Afro-Cuban beats to Spanish baroque façades, Soviet-era silhouettes, and a fierce pride that fuels its street art and music. Havana’s Malecón seawall and Trinidad’s cobbles tell stories that still feel alive.

Travelers come for the classic cars, but stay for the human warmth, smoky-sweet cigars, and slow-simmered dishes like ropa vieja and lechón. Havana dazzles with galleries, rooftop bars, and the legendary Fábrica de Arte Cubano, while Trinidad’s ochre-tiled roofs and sugar baron mansions open into mountain trails and a gentle Caribbean coast.

Practical notes: Bring plenty of clean USD/EUR in small bills; ATMs and cards (especially U.S.-issued) are unreliable. Expect intermittent internet and occasional power cuts—carry a power bank. U.S. travelers must comply with OFAC’s authorized travel categories. Book key restaurants ahead, and confirm opening days for museums and FAC.

Havana

Havana is Cuba’s heartbeat: baroque squares, Art Deco theaters, 1950s chrome, and rum drinks perfected over a century. Old Havana (Habana Vieja) is a UNESCO site where cathedral bells mix with street percussion, while Vedado and Miramar add mid-century mansions and edgy art spaces.

• Don’t miss: Plaza de la Catedral, Plaza Vieja, El Capitolio, a classic-car cruise, sunset on the Malecón, and late-night creativity at Fábrica de Arte Cubano.
• Flavors to find: Ropa vieja, tostones, fresh lobster, and daiquiris with a Hemingway backstory at El Floridita.
• Where to stay: Boutique casas in Old Havana for character, or Parque Central for a pool and skyline views.

Book stays: Browse apartments and casas on VRBO Havana or hotels via Hotels.com Havana. Specific favorites: Casa Vitrales (Boutique B&B) in Old Havana and Iberostar Parque Central overlooking the grand square.

Getting there: Compare international flights to Havana (HAV) on Trip.com Flights or Kiwi.com. Typical roundtrips: from Miami $150–300, Mexico City $350–600, Europe $700–1,100 (seasonal). Airport taxis to Old Havana run ~$25–35 and take ~30–40 minutes.

Day 1 – Arrival in Havana: Malecón Magic

Afternoon: Land at HAV and taxi into Old Havana. Check into your casa or hotel and take a gentle orientation walk along Obispo Street to Parque Central and the Gran Teatro. Grab a first Cuban coffee at El Dandy (Plaza del Cristo; espresso and cold brew) or El Café (Aguiar 319; sourdough toasts and eggs).

Evening: Sunset on the Malecón as waves slap the wall and musicians gather. Dinner at San Cristóbal Paladar (Barack Obama famously ate here; slow-cooked meats and spiced pumpkin) or rooftop tables at Café Laurent in Vedado (grilled fish, ocean breezes).

Night: Classic cocktail crawl: test a proper daiquiri at El Floridita (touristy but historic), then inventive sips at Sia Kará near the Capitol (vintage décor, Cuban jazz). Turn in early—tomorrow is for cobbles and cameras.

Day 2 – UNESCO Old Havana + Classic Cars

Morning: Fuel up at El Café (banana pancakes, strong cortados). Walk a loop: Plaza de la Catedral (asymmetrical baroque towers), Plaza de Armas (secondhand book market), and Plaza Vieja (restored mansions). Pop into Taller Experimental de la Gráfica to see printmakers at work.

Afternoon: Lunch at Doña Eutimia (homestyle ropa vieja; reserve) or La Moneda Cubana (balcony over the bay; fresh lobster). Then meet a driver for a 1.5-hour classic car tour through Central Havana, Plaza de la Revolución, Miramar’s embassies, and Hotel Nacional gardens for mob-era tales.

Evening: Dinner at La Guarida (iconic paladar in a crumbling mansion; snap the stairwell). Cap the night at Fábrica de Arte Cubano (FAC)—a gallery-turned-night venue with rotating installations, live sets, and multiple bars. Open most Thu–Sun; check hours.

Day 3 – Tobacco Valleys of Viñales (Day Trip)

Depart 7:00 a.m. for a full-day excursion (2.5–3 hours each way) to the Viñales Valley, a karst landscape of emerald mogotes. Hike or horseback 2–3 hours among tobacco plots, stopping at a small farm to see curing barns and try a hand-rolled cigar dipped in honey.

Lunch with a view at Finca Agroecológica El Paraíso (farm-to-table platters, guava juice) and a quick stop at Hotel Los Jazmines lookout for sweeping photos. Return to Havana by early evening.

Night (light): Casual bites at Jíbaro (bowls and tapas, local craft cocktails) or a cone at Helad’oro (passion fruit gelato). Rest up for the transfer day.

Day 4 – Havana to Trinidad (Colonial Dreams)

Morning (travel): Depart around 8:00 a.m. for Trinidad. Options: Viazul bus (~6–7 hours, ~$20–30 per person) or private taxi/collectivo (~4–5 hours, ~$180–220 per car). Optional 1-hour stop in Cienfuegos for lunch and a glance at Moorish Palacio de Valle.

Afternoon: Check into your Trinidad casa and wander the cobbles around Plaza Mayor: pastel façades, the Romantic Museum, and craft stalls. Coffee at leafy Café Don Pepe (iced coffee with cinnamon) or a cold guarapo (fresh cane juice) from a street press.

Evening: Dinner at Taberna La Botija (24/7; tapas, seafood, live troubadours) or Restaurante San José (reliable steaks, lobster, big portions). Dance under the stars at Casa de la Música—live salsa on the steps, lessons often available.

Trinidad

Frozen in the sugar boom of the 1700s–1800s, Trinidad is a living museum with a laid-back soul. Between museum mansions and terracotta roofs, you’re a short ride from waterfalls in Topes de Collantes and the palm-fringed sands of Playa Ancón.

• Top sights: Plaza Mayor, Museo Romántico, Valle de los Ingenios lookout, Playa Ancón, and Topes de Collantes hikes to Caburní or Vegas Grandes.
• Sounds & sips: Nightly son and timba around town; try the local canchánchara—honey, lime, and aguardiente—at its namesake tavern.
• Local crafts: Seek the Santander family’s pottery and handwoven textiles in backstreet talleres.

Book stays: Compare casas and small hotels on VRBO Trinidad or Hotels.com Trinidad. Look for restored colonial homes around Plaza Mayor for atmosphere and rooftop breakfasts.

Day 5 – Colonial Core + Beach Time

Morning: Breakfast on your patio, then visit Museo Romántico (period furniture and city views) and Museo de Arquitectura (how these houses “breathe” in the tropics). Pause for churros or coconuts in the square.

Afternoon: Taxi 15 minutes to Playa Ancón for white sand and calm water. Lunch beachside—grilled fish and tostones—then swim or rent bikes for a coastal pedal. Return via La Boca fishing village for sunset photos.

Evening: Pre-dinner at La Canchánchara (the signature honey-lime cocktail in clay cups). Dinner at Vista Gourmet (rooftop views, tasting menus) or Sol Ananda (colonial dining room, curried shrimp). Nightcap with live trova at a small casa de la trova nearby.

Day 6 – Topes de Collantes Waterfalls

Full-day nature escape into the Escambray Mountains. Take a jeep or taxi (45–60 minutes) to Parque Natural Topes de Collantes and hike to Salto del Caburní or Vegas Grandes (moderate, allow 3–4 hours roundtrip). Swim in jade pools beneath towering ferns and watch for endemic birds.

Pack snacks; otherwise stop for a hearty farm lunch at a mountain paladar (grilled pork, malanga fritters, coffee grown on site). Return to town for a siesta.

Evening: Dinner at Guitarra Mía (fresh pastas, guitar sets) or back to San José if you crave crowd-pleasers. If energy remains, venture to Disco Ayala, a quirky cave club outside town, for a late-night dance session.

Day 7 – Ingenios History + Departure

Morning: Taxi into the Valle de los Ingenios (20–25 minutes). Climb the Manaca Iznaga tower for panoramas and a sobering view of the former sugar empire. Shop for linens and lace at roadside stalls.

Midday/Afternoon (travel): Begin your return to Havana for your flight. Private transfer from Trinidad to HAV takes ~4.5–5.5 hours; Viazul bus adds time and requires a Havana taxi (~30–40 minutes) to the airport. Aim to check in 3 hours early; reconfirm flights on Trip.com Flights or Kiwi.com if schedules shift.

Notes on costs: Expect private car Trinidad–Havana at ~$180–220 per vehicle; buses ~$20–30 per person. Bring snacks and water for the road.

Extra tips: Reserve La Guarida and FAC days ahead; carry copies of your passport; tip musicians and guides in small bills; and download offline maps before arrival. Coffee standouts: El Dandy and El Café (Havana), Café Don Pepe (Trinidad). For souvenirs, seek cigars from reputable farms in Viñales or La Casa del Habano shops in Havana.

In seven days, you’ll glide from Havana’s big-city swagger to Trinidad’s time-stilled grace, with tobacco-scented countryside and Caribbean surf in between. Cuba rewards curiosity—listen for the drumbeat, follow the scent of garlic and lime, and let its stories carry you home.