Cubaoutings

Description

Cubaoutings in Havana, Cuba, has this curious way of wrapping travelers up in a day that feels less like a tour and more like living an entire chapter of Cuban life. It’s not just another walking tour or sightseeing stop along Paseo de Martí; it’s an experience designed to peel back the island’s layers and show travelers what pulses beneath the postcard image. Over the years, many visitors have called it one of the best experiences they’ve had in Cuba—and honestly, that sentiment makes sense once you see how much thought goes into each itinerary. There’s a blend of knowledgeable guides, local musicians, and small group settings that make each outing feel intimate and personalized.

Known for their music and culture focus, Cubaoutings takes guests well beyond the glossy surface of Havana’s colonial architecture. The guides—most of whom are native Habaneros—share stories of Cuba’s history with warmth and often a pinch of humor. Whether it’s wandering down the cobbled streets of Old Havana, hearing professional musicians tune up for an impromptu rumba session, or learning about the way life still moves at its own deliberate rhythm, this outing feels honest. It’s real Cuba—colorful, imperfect, beautiful, and deeply human. And perhaps that’s what sets it apart: its ability to make the traveler feel connected, not just entertained.

Key Features

• Expert-guided experiences: Every Cubaoutings tour is led by certified local guides with deep knowledge of Cuban history, art, and daily culture.
• Small group tours: Guests enjoy a more personal touch, usually with small groups allowing conversation and interaction with guides and locals alike.
• Live music and cultural immersion: Expect to meet musicians, dancers, and artists who share their craft with authenticity and joy.
• Flexible itineraries: Each tour can be adapted to fit personal interests—whether that’s history, food, art, or the rhythm of Havana’s nightlife.
• Family-friendly experiences: The tours are suitable for children, offering educational and engaging elements without being exhausting.
• Local partnerships: Many excursions include visits to small family businesses, helping support Havana’s local economy in meaningful ways.
• Photography opportunities: The scenic Paseo de Martí area and colonial landmarks make it ideal for travelers who love capturing photos of authentic Cuba.

One thing I really appreciate is how Cubaoutings feels handcrafted rather than corporate. The tour guides often add quirky side stories—like the one about a café owner who played in a salsa band during the 1980s or the painter whose studio doubles as a makeshift classroom for neighborhood kids. It’s these spontaneous moments that remind you travel isn’t just about seeing places—it’s about meeting people and collecting moments that don’t fit into brochures.

Best Time to Visit

If you ask me, the best time to book a Cubaoutings Havana tour is in the dry season—roughly from November to April. The air is pleasant, the humidity manageable, and the old town streets of La Habana feel especially alive with travelers and locals mingling. These months also line up with some of Cuba’s biggest festivals, meaning you might unexpectedly find yourself walking into a parade, a concert, or a street food fair. If music is your thing (and let’s face it, in Cuba it’s practically unavoidable), the Havana International Jazz Festival in January is phenomenal—Cubaoutings often creates itineraries around it, which is a smart move if you love live music.

That said, there’s a case for visiting during the so-called slower months too. May and June can be humid and occasionally stormy, but they also let you experience a quieter, more local feeling Havana—fewer tour buses, less rush, and more space to take in the city’s colonial character. I once went in June and ended up staying longer than planned because I stumbled into a tiny open-air salsa dancing event near Parque Central. It wasn’t part of any itinerary, just local life happening right there at sunset. That’s Cuba for you—it catches you off guard in the best way.

How to Get There

Cubaoutings operates mainly around Paseo de Martí, a central boulevard that cuts through some of Havana’s most recognizable districts. If you’re staying in Old Havana, it’s often just a short walk. The route is lined with restored colonial buildings, palm-shaded benches, and vintage American cars that honestly look like they’ve driven straight out of another century. If you’re staying elsewhere in the city—say, in Vedado or Miramar—your best bet is to take a taxi or classic car service. Some hotels even partner with Cubaoutings to arrange direct pick-ups for their guests, which makes things smoother if you’re new in town.

Travelers arriving in Havana by air will land at José Martí International Airport, about a 30–40 minute drive from Paseo de Martí depending on traffic. While public buses are available, most visitors prefer private transfers for convenience. And if you’re the adventurous kind, walking from nearby landmarks like El Capitolio or La Plaza del Carmen is a treat—you’ll see small galleries, street performers, and those old casas particulares that make Havana’s streets so photogenic. There’s always something happening on the sidewalks; even a short walk can turn into a mini adventure.

Tips for Visiting

First things first—book your Cubaoutings tour ahead of time. Yes, some spots might offer on-the-day bookings, but because the groups are intentionally small, availability can become tricky, especially during festival season. Getting your spot secured means less stress once you arrive, and more time to wander freely. I learned that the hard way when I tried to snag a same-day tour on a Saturday and ended up waiting until Sunday morning. Lesson learned.

Bring comfortable walking shoes. Streets in Old Havana can be uneven, and you’ll likely walk more than you think (trust me, you’ll want to because every block reveals another detail worth stopping for). A hat and a refillable water bottle are also smart moves—the Cuban sun has no mercy, particularly around midday. If you’re into photography, mornings are magical for light; the colonial facades glow golden, and the streets are calm enough to capture shots without too many cars or people blocking your frame.

Another thing: don’t be shy about chatting with the guides. They love questions—about history, politics, food, even daily Cuban life. Many have lived in Havana their entire lives and can give you honest insider details you won’t find in guidebooks. Some share local restaurant recommendations—tiny paladares (family-run eateries) where you can dive into dishes like ropa vieja or fresh seafood from the Bay of Pigs area. These tips often become trip highlights in themselves.

It’s also good practice to carry some small local currency for gratuities and spontaneous purchases. Since Cubaoutings supports many small craftspeople, you might spot handmade jewelry or artwork during a stopover. Buying directly supports those communities and, honestly, makes for meaningful souvenirs beyond standard magnets or postcards.

Families traveling with children can rest easy—Cubaoutings tours are kid-friendly. Kids often love the music and open-air dancing displays, and the guides naturally include interactive moments. Parents I’ve met on these tours said even their normally restless toddlers were happily clapping along by the end. There’s something about Cuban rhythm—it seeps into every generation.

And finally, keep an open mind. Traveling in Havana, especially through experiences like Cubaoutings, invites a bit of spontaneity. Things might not always go exactly as planned—a street might close suddenly for a local parade, or a musician might invite the group to join in a song. But those unpredictable moments are often the ones that make the trip unforgettable. I still talk about the day a guide took a detour through a local art cooperative in Central Havana; it wasn’t on the itinerary, but it ended up being the single most interesting hour of my whole stay.

To sum up, Cubaoutings isn’t about ticking boxes off a travel list—it’s about connection. Connection with Havana’s heartbeat, with its history poured into the walls of old buildings, and with the people whose laughter echoes through Paseo de Martí every evening. Whether it’s your first time in Havana or your tenth, this experience gives you a new way to see an old city—with music, movement, and that unspoken island magic that Cuba does best.

Location

Places to Stay Near Cubaoutings

Find and Book a Tour

Explore More Travel Guides