How We Define Activity Levels
We rate each trip from Level 1 (Easy) to Level 5 (Challenging)—from fully accessible experiences to adventures best suited for experienced hikers/adventurers.
Whether you prefer a relaxed stroll or a rewarding trek, there’s a pace—and a place—for you.
Interest-Free Payment Plans Available
Trip Highlights
- Explore Havana’s creative heartbeat through music, art, and everyday life in its historic streets, where color spills from balconies, rhythms drift from open doorways, and stories live in every corner.
- Ride bici-taxis through buzzing neighborhoods and share a lively game of dominó with locals, opening the door to conversations that reveal the humor, warmth, and resilience at the heart of Cuban life.
- Connect with artists, musicians, and entrepreneurs who are shaping Cuba’s cultural future, offering candid perspectives on creativity, innovation, and the realities of life on the island today.
- Head west to Viñales, where horseback rides through tobacco fields, farm-fresh meals, and afternoons with local families immerse you in rural traditions that have endured for generations.
- End each day with connection and conversation, whether it’s over a home-cooked meal, a shared song, or a quiet moment in the Cuban countryside—a journey that stays with you long after you leave.
Our Itinerary at a Glance
Day 1: Welcome to Havana
- Arrive in Havana, Cuba’s colorful capital where Spanish colonial façades meet the pulse of Afro-Cuban rhythms and the scent of strong coffee mingles with sea breeze from the Malecón.
- Settle into Casa Vitrales, a beautifully restored guesthouse in the heart of Old Havana, where balconies overlook narrow cobblestone streets and every room blends historic charm with thoughtful, modern touches.
- Kick off your journey with a lively salsa class, learning the basic steps and rhythms that make this dance the heartbeat of Cuban culture, before raising a welcome cocktail with your travel companions.
- End the evening with dinner at one of the city’s most beloved paladares, where warm hospitality, locally sourced ingredients, and creative takes on Cuban classics set the tone for the days ahead.
Day 2: Streets & Sounds of Havana
- Begin the morning with a guided walking and bici-taxi tour through the winding streets of La Habana Vieja, where layers of colonial architecture, political history, and everyday Cuban life unfold around every corner. As you move between bustling plazas and quiet side streets, your guide will share stories that reveal the city’s resilience and creativity.
- Pause midday to join locals for a lively game of dominó over a traditional Cuban lunch—an experience as much about conversation and camaraderie as it is about the food. Then, retreat for a well-earned siesta or a leisurely coffee in a shaded courtyard.
- As night falls, gather for a flavorful dinner before heading to La Fábrica de Arte Cubano, Havana’s dynamic cultural hub. Here, music, art installations, photography, and live performances merge into one electric atmosphere, offering an unforgettable glimpse into Cuba’s modern creative scene.
Day 3: From Shore to Street Art
- Ease into the morning with a relaxed start before heading to Mar Azul, a stretch of sandy coastline just outside Havana where locals come to swim, socialize, and soak up the sea breeze. Spend a few hours enjoying the water, wandering along the shore, or simply settling into the slower rhythm of the Cuban coast.
- In the afternoon, return to Havana for a guided walking tour that explores the city’s vibrant street art scene. As you move through colorful alleyways and open-air galleries, you’ll uncover how murals, graffiti, and installations become powerful tools of cultural expression, reflecting Cuba’s layered history and present-day identity.
- As evening falls, step behind the bar for a hands-on cocktail class, mastering the craft of iconic Cuban drinks before sitting down to a lively dinner with live music. The night closes with an intimate conversation with local artists—a chance to hear firsthand about the challenges, inspirations, and creative visions shaping life on the island today.
Enmanuel, Cuba’s Regional Director
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Where We Stay
At Heart of Travel, we believe your home away from home should feel as authentic as the places you explore. That’s why we seek out premium boutique lodging owned and run by local entrepreneurs whenever possible. Rather than focusing on star ratings, we seek out properties that blend sustainable practices with one-of-a-kind character, heartfelt service, and genuine warmth. From thoughtfully restored heritage houses to eco-minded retreats, each stay is chosen for its ability to tell a story, support small-business communities, and create memorable moments.
The Heart Experience
What makes this journey special isn’t just where we go—it’s how we go. From trusted trip leaders to street musicians, from local artists to farmers in Viñales, every moment is crafted to connect you with Cuba’s soul and reflect our deep commitment to people, culture, and community.
Meet Enmanuel
Cuba’s Regional Director & Senior Trip Leader
Enmanuel co-designed this journey through Viñales and Havana to share the soul of Cuba—felt in the slow rhythm of its tobacco-lined valleys and the creative pulse of its vibrant, ever-evolving capital.
Some of his favorite highlights include:
- Quiet lunches at a community recycling project—where creativity and resilience meet.
- Wandering through hidden corners of Havana as travelers connect with Cuba’s living history.
- Slow, scenic afternoons at Mar Azul—a beloved local beach escape.
- Visiting organic farms in Viñales and sharing the farmers’ pride in growing everything from scratch.
- Ending the day at La Fábrica de Arte Cubano, where art, music, and conversation light up the night.
This is travel with heart—where impact and experience go hand in hand.
How We Define Activity Levels
We rate each trip from Level 1 (Easy) to Level 5 (Challenging)—from fully accessible experiences to adventures best suited for experienced hikers/adventurers.
Whether you prefer a relaxed stroll or a rewarding trek, there’s a pace—and a place—for you.
What is included:
Our prices reflect the true cost of creating regenerative, respectful, and thoughtfully curated travel experiences. That means fair wages for our local guides and partners, carbon-conscious operations, and deep-rooted collaborations with community-based projects.
Interest-Free Payment Plans
We know that meaningful travel is an investment—and we’re here to make it doable. That’s why we offer interest-free payment options designed to work for you—no hidden fees, no credit checks, and no third-party financing.
Pay in Full & Save
Enjoy 5% off when you pay in full up to 180+ before departure.
Starting at
Standard Plan
Pay a larger deposit + two installments, due 210 and 150 days before departure.
Starting at
Interest-Free Plan
Pay a smaller deposit and start making interest-free monthly payments—trip is due in full 91 days before departure.
Starting at
Add Peace of Mind with Heart of Travel Trip Protection
Travel plans can change - and that’s okay. With Heart of Travel Trip Protection, you get the freedom to protect your investment while staying flexible.
See what’s included
Hear What People Are Saying
I knew my trip to Cuba with Heart of Travel would be wonderful, but I wasn’t prepared for how deeply it would touch me. From the moment I arrived in Havana and was greeted by Enmanuel with open arms, I felt instantly at home. Every detail of the itinerary was thoughtfully crafted to offer a perfect balance of history, arts, culture, food, nature, adventure, and most importantly people, without ever feeling rushed.
Some of my most cherished memories came from spontaneous, unscripted moments: lively games of dominoes, salsa dancing with our kind driver Pablo, visiting local farms, and sharing inside jokes that still make me laugh. These experiences, equal parts unplanned and magical, brought an extra layer of joy to the trip; moments that truly must be lived rather than described.
By the end of the journey, my tour guide Leo felt like a brother, and saying goodbye was unexpectedly emotional. But as hard as it was to leave, I’m grateful to have had an experience so meaningful. I know I’ll return to Cuba one day, it’s only a matter of when.
Four of us (two couples) traveled to Havana and Viñales in mid-February with Heart of Travel, and from the very beginning, the experience was seamless. Chelsea, the owner, sent us a detailed itinerary well in advance and was incredibly accommodating at every step. She shared invaluable tips that made our travels smooth and enriched our time in Cuba.
Enmanuel and Patricia, our guides, brought Cuban life to us in its fullest color; from the elegance of the Hotel Nacional de Cuba to the breathtaking landscapes of Viñales Valley and the vibrant energy of Havana’s neighborhoods. They seemed to effortlessly know the best places to go, the most interesting people to meet, and experiences that truly captured the heart of the country. Without exception, everyone we met was welcoming and warm, leaving us with connections we hope will last.
Heart of Travel delivered exactly what we were looking for: an authentic, eye-opening journey filled with culture, beauty, and genuine human connection. Chelsea’s attention to detail and the expertise of her team made all the difference. We’re already dreaming about our next trip to Cuba; and when the time comes, we’ll be booking with Heart of Travel again without hesitation.
Our mother emigrated from Havana to the United States in 1953 at just 17 years old, so visiting Cuba was always going to be an emotional journey for me. Chelsea at Heart of Travel created a fantastic custom itinerary for our private family tour, from welcome day activities that brought Habana Vieja’s history to life and salsa dancing lessons, to an excursion through the UNESCO-listed Viñales Valley and a final evening of rum and cigar tasting. We truly felt immersed in Cuban culture.
We were impressed by Heart of Travel’s commitment to supporting local communities. Bringing along hard-to-find goods like over-the-counter medicines and personal care items felt meaningful, and staying in casa particulares, dining in paladares, and joining locally-led cultural experiences made it feel like our visit could have a positive impact.
The highlight, however, was the people; especially our wonderful tour leaders, Enmanuel and Patricia. Their flexibility, warmth, and knowledge made every day special, and by the end of the week, they felt like family. We’re so grateful to Chelsea and the Heart of Travel team for creating a trip that was both personal and unforgettable.
Had an amazing and unforgettable time in Cuba with Heart of Travel. Heart of Travel is well named as they truly put their heart into this trip. The love they share for Cuba and the Cuban community is evident and infectious- they genuinely care about positively impacting the community and supporting locals.
I was continually impressed by the team's professionalism, knowledge, and enthusiasm. I particularly loved that Heart of Travel's itinerary included several opportunities to interact with locals and experience Cuba through a local lens. This is what sets Heart of Travel apart from other organized tours and makes for a memorable and unique experience. I'm so glad I had the opportunity to visit Cuba with Heart of Travel. This was an experience I would not have been able to replicate if I traveled to Cuba on my own. I can't recommend this group enough and hope to be a repeat customer.
What to expect when booking!
Reserve Your Spot
Lock in your adventure with a deposit and a few quick details about who’s traveling. Choose the payment plan that fits your life—pay in full, split it in three installments, or spread it out monthly—and start counting down the days for your next adventure!
Get Trip-Ready
As we get closer to departure, we’ll drop a Welcome Packet in your inbox loaded with need-to-knows: packing lists, weather tips, local customs, currency info, and any visa or entry forms you might need. You’ll also get steady pre-departure emails and the option to attend a pre-trip Zoom call with your Tour Leader to answer questions big or small—so you can show up confident and stress-free. Call recordings will be made available to all trip participants.
Travel & Connect
A few weeks before our departure, you’ll be invited to a private WhatsApp group and PhotoCircle where fellow travelers, Heart of Travel Tour Leaders, and local guides start swapping intros, answering last-minute questions, and sharing playlists. Once on the ground, the Whatsapp group becomes your real-time hub for insider tips, updates, and reminders, and sharing the moments that make each trip unforgettable.
Keep the Journey Going
We keep every trip’s WhatsApp thread open long after the farewell hugs—because the stories, photos, and friendships shouldn’t end when the plane lands. Drop your best shots into our PhotoCircle, stay in the loop for alumni perks, and (coming later this year) join our online community designed to keep travelers and local partners connected between adventures.
How We Define Activity Levels
We rate each trip from Level 1 (Easy) to Level 5 (Challenging)—from fully accessible experiences to adventures best suited for experienced hikers/adventurers.
Whether you prefer a relaxed stroll or a rewarding trek, there’s a pace—and a place—for you.
Interest-Free Payment Plans Available
Trip Protection Available
Have more questions?
We’re here to help. Whether you’re unsure about flights, packing, affordability or picking the right trip—just reach out.
No question is too small!