A Timeless Weekend in Havana
Classic Cars, Colonial Charm & Caribbean Soul
Trip Overview
Experience the essence of Cuba's captivating capital in this carefully crafted weekend escape. This itinerary balances Havana's UNESCO-listed colonial architecture with its vibrant cultural scene, from the cobblestoned streets of Old Havana to the iconic Malecón seafront. You'll explore historic fortresses guarding the harbor, wander through atmospheric plazas filled with live music, and discover colorful street art that tells Cuba's story. The pace allows for leisurely exploration with time to soak in the city's unique rhythm, enjoy live son cubano performances, and savor traditional cuisine. This weekend captures Havana's romantic nostalgia while revealing its contemporary creative energy, offering an authentic glimpse into Cuban life that will leave you enchanted and eager to return.
Day-by-Day Itinerary
Colonial Havana & Harbor Fortresses
Where to Stay Tonight
Old Havana (Habana Vieja) (Casa particular (private homestay) in a restored colonial building)
Staying in the historic center puts you within walking distance of major attractions and allows you to experience authentic Cuban hospitality while supporting local families
Art, Culture & Hemingway's Havana
Where to Stay Tonight
Vedado neighborhood (Mid-century casa particular near cultural venues)
Vedado offers a more residential atmosphere with proximity to nightlife, cultural centers, and easier access to the airport for departure
Practical Information
Getting Around
Havana is best explored using a combination of walking (Old Havana is very walkable), classic car taxis for atmosphere and medium distances ($5-15 per ride), and official yellow taxis for longer trips. Many casas particulares can arrange private drivers. Avoid unlicensed taxis. The hop-on-hop-off tourist bus is useful for reaching Fusterlandia and other outer neighborhoods. Most attractions are concentrated enough that a rental car is unnecessary and parking is challenging.
Book Ahead
Book casa particular accommodation 2-3 weeks ahead through trusted platforms. Reserve Grand Theater performances online if available. Most attractions don't require advance tickets, but arriving early is recommended.
Packing Essentials
Comfortable walking shoes, sun protection, light breathable clothing, modest outfit for religious sites, small bills in CUC/USD, offline maps, basic Spanish phrases, any medications, and a reusable water bottle
Total Budget
$175-245 for 2 days (excluding flights and accommodation)
Customize Your Trip
Budget Version
Stay in shared casa particular rooms ($15-25/night), eat at local cafeterias and street food stands ($3-5 per meal), use collective taxis and local buses, focus on free walking tours of plazas and neighborhoods, skip paid performances for free street music at Central Park and Old Town Square, and visit John Lennon Park and Cristóbal Colón Cemetery which are free to explore.
Luxury Upgrade
Book a restored colonial boutique hotel in Old Havana ($150-250/night), hire a private classic convertible car with driver for the entire weekend ($80-120/day), enjoy upscale paladares with wine pairings, arrange VIP seats at Grand Theater performances, take a private sunset cruise from the harbor, and book a private art tour with visits to artists' studios and galleries beyond the standard tourist circuit.
Family-Friendly
Add Torreon de la Chorrera for kids to explore a smaller fortress with cannons, spend more time at Fusterlandia where children love the colorful mosaics and playful atmosphere, visit John Lennon Park for photo opportunities, choose casual restaurants with outdoor seating, break up walking with classic car rides that kids find exciting, and stay in spacious casa particular apartments with family rooms and home-cooked meals.
Book Activities for Your Trip
Tours, tickets, and experiences in Havana