5-Day Havana Itinerary: The Perfect First Trip

Havana packs an incredible amount into a compact destination — frozen-in-time classic cars, crumbling colonial grandeur, and salsa rhythms. Five days gives you enough time to hit the highlights, discover a few secret spots, and still leave room for spontaneous detours.

Here is a tried-and-tested 5-day itinerary that balances must-sees with off-the-beaten-path experiences.

Day 1: Arrival & First Impressions

Morning/Afternoon: Arrive and settle into your accommodation in Habana Vieja — colonial plazas, cathedrals, and restored mansions. Take it easy — grab a coffee, orient yourself, and shake off the jet lag.

Late Afternoon: Head to Old Havana (Habana Vieja) UNESCO district for your first taste of what makes Havana special. The late-afternoon light is ideal for photos and the crowds start to thin.

Evening: Dinner in the Habana Vieja — colonial plazas, cathedrals, and restored mansions area. Try Ropa Vieja — shredded beef in tomato sauce with peppers and onions — it is the quintessential local dish and the perfect way to kick off your trip.

Day 2: The Iconic Highlights

Morning: Start early at Capitolio building. Arriving before 9 AM means fewer tourists and better photo opportunities.

Afternoon: After lunch, make your way to Fusterlandia mosaic village. Budget about 2–3 hours here to fully appreciate the experience.

Evening: Explore the Vedado — 1950s mansions, Hotel Nacional, and Malecón nightlife neighborhood on foot. Street food stalls serve excellent Moros y Cristianos — black beans and rice, the Cuban staple side dish at a fraction of restaurant prices.

Day 3: Deep Dive into Culture

Morning: Visit Malecón seafront boulevard — one of Havana's most culturally significant sites. Hire a local guide for about $9 to get the stories behind the sights.

Afternoon: Wander through the Regla — Afro-Cuban religious culture across the harbor by ferry district. This is where locals shop, eat, and socialize, so the vibe is refreshingly authentic.

Evening: Treat yourself to a mid-range dinner featuring Tostones — twice-fried green plantain discs served with garlic mojo. Expect to spend around $18 per person.

Day 4: Off the Beaten Path

Morning: Today is about discovery. Head to Fusterlandia — neighborhood mosaic art project by José Fuster in Jaimanitas — a spot most tourists overlook entirely.

Afternoon: Check out El Cocinero — rooftop bar in a converted cooking oil factory chimney in Vedado. The Miramar — diplomatic quarter with paladares and quiet avenues area is great for a leisurely walk and a late lunch.

Evening: Experience Havana's nightlife scene — Fábrica de Arte Cubano — art gallery, club, and live performance space.

Day 5: Final Gems & Departure

Morning: Use your last morning to visit Callejón de Hamel — Afro-Cuban street art alley with Sunday rumba performances or revisit a favorite spot from earlier in the trip.

Late Morning: Pick up souvenirs at San José Craft Market — artwork, woodcarvings, and souvenirs on the waterfront — support local artisans and avoid airport markup.

Afternoon: Head to the airport with memories (and a full camera roll) to last a lifetime.

Pro Tips

• Transport: Classic car taxis (almendrones) run along fixed routes cheaply
• Budget: A comfortable mid-range daily budget is about $70 per day including meals, transport, and activities.
• Packing: Bring all personal supplies — toiletries and medications are scarce in Cuba You will average 12,000–15,000 steps per day on this itinerary.
• Etiquette: Ask before photographing people — offer a small tip if they agree
• Safety: Havana is very safe for tourists compared to other Caribbean capitals

Budget Breakdown (Per Person)

Category	Budget	Mid-Range	Luxury
Daily Total	$30	$70	$180
5-Day Total	$150	$350	$900

Final Thoughts

Five days in Havana is enough to fall in love with the place — and to start planning your return trip. This itinerary is a starting point; feel free to swap days around based on weather, energy levels, and serendipitous discoveries.

---

Planning a trip to Havana? Let TripGenie create your perfect itinerary — it's free and takes just 60 seconds.