The Many Ways to Explore Cuba: A Guide to Vacation Options in Cuba
Cuba is a place like no other. Every moment spent exploring here is filled with music, movement, and an energy that’s hard to describe. We’ve been crafting immersive Cuba vacations since 2015, connecting travelers with this incredible island through authentic experiences. We know that one of the first questions people ask is, “Can Americans travel to Cuba?” The answer is yes, Americans can travel to Cuba. American citizens can still legally travel to Cuba under the “Support for the Cuban People” license category, and all of our Cuba trips are fully compliant with U.S. travel regulations.
Whether you’re drawn to the culture, stunning landscapes, or rich history, there’s a Cuba trip that’s right for you. Our adventures go beyond the typical tourist route, and if you’re looking for something more personalized, we can adjust existing itineraries or work with you to design a fully custom experience tailored to your goals. Here's a look at the best ways to experience Cuba.
Uncovering One of Cuba’s Hidden Gems: Sea Kayaking
Sea kayaking in Cuba is one of the most immersive, unexpected, and rewarding ways to experience the island’s natural beauty. Cuba is a paddling paradise with more than 3,500 miles of coastline, clear waters, hidden beaches, and protected marine areas.
Choosing to kayak here means you’ll spend days gliding past mangrove forests, floating in clear blue waters, and taking your kayak to remote beaches that feel like your own private island. Along the way, you’re likely to spot flamingos, iguanas, and so much more.
But sea kayaking in Cuba isn’t just about the water. It’s about connection. You’ll meet local fishermen on quiet shores, paddle into small rivers that lead to small villages, and experience Cuba in a peaceful yet adventurous way.
We’ve spent years scouting Cuba’s most remarkable places to paddle. From the wild coasts of the east to the serene southern bays near Trinidad and Cienfuegos, our small-group guided tours explore regions that many travelers never reach.
No previous kayaking experience? No problem. Our trips are designed to be accessible and meaningful for all levels, and they combine paddling with cultural exchanges, walking tours, and locally guided encounters that support and celebrate the Cuban people.
Biking Tours: Ride Through Cuba’s History and Heartland
We tend to think that Cuba is best seen slowly, and what better way than from the seat of a bicycle? Our Cuba Cycling Tour offers a unique way to take in the island’s natural beauty and historic landmarks. Biking thought Cuba takes you on a journey that brings you face-to-face with the island’s people, past, and present.
We have a couple of different biking options and finding the one that’s right for you depends on your desired destinations and overall goals. Our Central Cuba Bike Tour takes you through the heart of the island. You’ll start in Santa Clara and end in Havana with days packed with scenic views, learning about the history of Cuba, and interacting with the locals. Alternatively our Western Cuba Cycling Tour takes you into a less traveled part of Cuba. You’ll be met with incredible landscapes, discover areas that you’ve never heard of before, and still get to explore iconic Havana with our local guides.
No matter what part of Cuba you want to explore on your vacation, our biking tours each offer you a glimpse into everyday life and views seen on two wheels that you’ll be dreaming of for years to come.
Hiking Tours in Cuba
For travelers who prefer to explore on foot, we offer two unforgettable ways to experience Cuba’s culture and spectacular landscapes.
Whether you're climbing to the summit of Pico Turquino, Cuba’s highest peak, or strolling through UNESCO-listed towns and national parks, our Cuba hiking and walking tours offer unique paths designed to immerse you in the island. The Pico Turquino trek is a challenging journey through the rugged Sierra Maestra, where you hike past revolutionary hideouts and dense jungle, then get to take in panoramic summit views at the end of the trail. Prefer something a little different? Our 8-day Cuba Walking Tour blends 3–8 miles of daily walking with immersive experiences, including exploring the wetlands and mountains in rural Cuba or Havana’s backstreets and Viñales' tobacco fields.
Led by local guides, these tours are ideal for the culturally curious. Whether you’re summiting Pico Turquino or strolling through the island’s most captivating landscapes, our Cuba hiking and walking tours deliver the kind of travel stories you’ll tell for a lifetime.
Explore Hiking and Walking Trips
Cultural Immersion
Connection is at the heart of all of our Cuba journeys. Connection to the people, the stories, and the rhythms that shape this extraordinary island. Our tours go beyond surface-level sightseeing, and instead offer rich opportunities to engage with local Cubans from all walks of life. Whether you're sharing a meal in a casa particular, exploring a family-run farm, or dancing to live salsa in a town square, cultural exchange is woven into every day.
For those seeking a deeper dive, our Afro-Cuban Heritage Tour offers a powerful and personal exploration of Cuba’s African roots. This tour takes you from the cobbled streets of Old Havana to sacred Santería sites and remote communities where Afro-Cuban traditions continue to thrive.
Every one of our tours is designed to build bridges between cultures, perspectives, and people. No matter what you’d like to see we recommend you come curious and ready to learn about a new way of life.
Havana Deep Dive
If you're drawn to Cuba’s capital, we offer a variety of immersive ways to experience Havana’s energy, culture, and charm. Both as a standalone adventure or a tour to add on to a longer journey in Cuba. From wandering the pastel streets of Old Havana to discovering the city’s thriving art scene, live music, historic landmarks, and culinary creativity, our Havana experiences are packed with the best experiences in this incredible city.
One of our most popular options, the Ultimate Havana Getaway, is a five-day city escape that blends food, art, and local life. You might take a hands-on cooking class, sip Hemingway’s favorite cocktails, visit contemporary art collectives, or dine in hidden-away paladares after shopping at neighborhood markets.
Whether you're visiting Cuba for the first time or returning to explore more deeply, our Havana-based trips offer a window into Cuban life, with plenty of opportunities for cultural exchange and unforgettable moments.
Custom & Private Tours in Cuba
If you have a different idea for how you’d like to spend your time in Cuba, we’re happy to help bring it to life. In addition to our scheduled small-group tours, we offer custom and private trips designed around your interests, pace, and priorities. Whether that means adjusting an existing itinerary or building a journey from the ground up, our team works closely with you and our local partners to create an experience that reflects how you want to explore Cuba.
Why We Love Cuba as a Travel Destination
There’s a reason Cuba captivates people. It’s a country that reveals itself slowly and rewards travelers. Traveling to Cuba somehow feels like peeling back history, when really you’re just stepping into the rhythm of daily life.
We don’t just offer Cuba guided tours, we offer experiences that change you. Our trips support the Cuban people directly, prioritize authentic exchanges, and are fully licensed under U.S. travel regulations. So whether you’re kayaking in Holguín, cycling through the Escambray, hiking up Pico Turquino, or dancing in Havana, you’re not just seeing Cuba. You’re engaging with it and supporting its people.
