Join us on a vibrant 9-day journey through Cuba, where history, culture, and stunning landscapes come alive! From the bustling streets of Havana to the lush valleys of Viñales, and the charming colonial towns of Cienfuegos and Trinidad, this tour immerses you in the soul of Cuba.
With a perfect balance of culture, nature, and adventure, this tour promises unforgettable memories and the chance to connect with the warmth and hospitality of Cuba’s people. Book today for an experience that’s as rich and colorful as Cuba itself!
Get ready to fall in love with Cuba’s charm, color, and rhythm on this unforgettable adventure. This isn’t just a vacation—it’s a celebration of culture, connection, and joy.
🌆 Step back in time as you take in Havana’s old-world elegance during the iconic cannon-firing ceremony at the fortress by the bay.
🥘 Spice things up with a hands-on Cuban cooking experience surrounded by the stunning scenery of Viñales Valley.
💃 Feel the rhythm during a salsa class at a local dance school—because in Cuba, movement is magic.
🎨 Be inspired as you visit grassroots community art projects that are transforming neighborhoods through creativity.
💦 Chase waterfalls just outside of Trinidad for a refreshing dip in Cuba’s natural beauty.
🌟 Soak in the soul of Cuba’s most vibrant towns—each one filled with stories, flavor, and energy that will steal your heart (but not your happy).
This trip is perfect for curious travelers who crave cultural immersion and care about meaningful impact. If you’ve always wanted to dive into Cuba’s rich traditions—but with all the details taken care of—this is your moment.
Our carefully curated itinerary supports Cuba’s growing private sector, allowing U.S. travelers to comply with the Support for the Cuban People general license. That means you can enjoy an authentic, worry-free journey that’s not only joyful—but purpose-filled too.
Guest House Stays
When you travel with You Can’t Steal My Happy, you’re not just checking into a place to sleep—you’re stepping into the heart of Cuban hospitality. On our small group tours, we primarily stay in charming casas particulares—Cuba’s version of bed-and-breakfasts. These family-run guesthouses offer a uniquely personal, cozy, and culturally rich experience you just won’t find in traditional hotels.
You might hear them called guesthouses, B&Bs, homestays, or casas—they all refer to private homes licensed by the Cuban government to host travelers. Run by local families and often located in residential neighborhoods, these stays are a highlight for many of our guests.
Why? Because they’re more than just a place to rest your head—they’re a doorway to real Cuban life. You’ll have the chance to connect with your hosts, hear their stories, and share a breakfast made with love (and probably a little Cuban coffee magic).
Guesthouse rooms are typically simple, clean, and comfortable—think of them like the Cuban version of a cozy 3-star hotel. What they might lack in square footage, they more than make up for in warmth, charm, and personalized care. Families take great pride in making you feel at home, and you’ll quickly see why travelers often rate casas higher than hotels in terms of experience and hospitality.
Unlike state-run hotels, which can suffer from low morale and spotty service, casas are privately owned, guest-focused, and fueled by passion. Hosts genuinely care about your comfort and rely on traveler word-of-mouth—so they go above and beyond to make your stay special.
All of the guesthouses we use are equipped with air conditioning and hot water for your comfort. However, due to the ongoing power situation in Cuba, there are occasional blackouts that may affect your experience.
While most guesthouses have backup power generators, these typically support only essential appliances. That means during a blackout, only ceiling or standing fans may work—not the air conditioning units, which require more power to operate.
The situation in Havana is generally more stable, with fewer and shorter blackouts. In other provinces, power outages can be more frequent and last longer, so we appreciate your flexibility and understanding.
Despite these occasional challenges, the hospitality, charm, and authentic experiences offered by our local hosts more than make up for any temporary inconvenience. We encourage you to embrace the local rhythm and enjoy the journey!
No two casas are the same, and that’s part of the magic. While each home offers different décor and vibes, all the guesthouses we use meet a high standard of cleanliness, comfort, and friendliness. These accommodations are licensed, regulated, and often more stylish and well-maintained than the average Cuban home.
In Havana and select destinations, we sometimes stay in premium casas particulares. These upscale guesthouses feature modern touches like spacious rooms, designer interiors, cotton linens, and boutique-style flair. They’re truly one-of-a-kind and perfect for those who want an extra splash of comfort and charm.
While pricing for premium stays is higher, the experience is unmatched. Think artful design, heartfelt service, and the kind of spaces that make you pause and say, “Wow, I’m really here.”
Whether it’s a cheerful guesthouse in Viñales or a boutique beauty in Havana, one thing is for sure: you’ll feel the heart of Cuba through the people who welcome you into their homes.
Please be informed that all of our guesthouses feature rooms with private bathrooms, with each room having its own dedicated bathroom inside.
Here’s a peek at the kind of charming, locally-run accommodations you might call home during your Cuban adventure with us.
As a U.S. traveler visiting Cuba, your trip must follow the guidelines set by the U.S. Department of the Treasury’s “Support for the Cuban People” travel category. This means that during your stay, you’ll need to spend your time in ways that directly support the Cuban people—and keep a general record of how you do so.
Don’t worry—it’s easier than it sounds, and most of the activities you’ll be doing already fall within these guidelines! Here are examples of OFAC-compliant activities:
✅ Stay at a private guesthouse (casa particular)
✅ Dine at privately owned restaurants (paladares)
✅ Visit local entrepreneurs, artists, or small business owners
✅ Enjoy drinks at privately owned bars or cafes
✅ Take transportation arranged through private drivers
✅ Join tours led by local private guides
You’ll need to log both group and individual activities—a simple journal or notes in your phone will work just fine. It doesn’t need to be overly detailed, just enough to show that your time supported the Cuban people.
If you’d like to add extra activities before or after your main tour, check out this list of OFAC-compliant day tours in Havana:
👉 Havana Day Tours
All options are fully compliant with U.S. travel rules.
For help with booking day tours, short stay packages, or additional nights in Cuba, please contact Yanet with Cuban Adventures directly:
📧 Reservations – Cuban Adventures
📩 [email protected]
She’ll be happy to assist you with any custom arrangements!
HOW TO GET TO CUBA
While Cuba is a captivating destination for American travelers, it requires some planning due to U.S. travel restrictions. Fortunately, travel is entirely possible under one of 12 authorized categories of travel, such as Support for the Cuban People. This category allows for engaging, culturally immersive experiences, like staying in local guesthouses, dining at private restaurants, and supporting small Cuban businesses.
To get to Cuba, most major U.S. airlines offer direct flights to Havana (Airport Code: HAV), where this trip starts and ends. You'll need a Cuban Tourist Card (visa), which can usually be purchased through your airline or at the airport before departure. Additionally, U.S. travelers must obtain Cuban health insurance, often included in the cost of your airline ticket.
To check for the best value and routes of flights, we suggest using Google Flights. Google Flights compares all of the different airline websites in one place and lets you book with the airlines directly. Never book through a third party and always book through the airline so you have ownership of your ticket. Remember to plan your activities to align with the approved travel category and keep a record of your itinerary and receipts for at least five years as required by U.S. regulations. Following these guidelines, you can enjoy an unforgettable journey exploring Cuba’s vibrant culture and warm hospitality.
Flight Booking Details: Travelers are required to book their own flights to and from Havana (HAV). If you would like assistance with flight booking (for a fee), you can contact Laura Marchese at Travel Central: Laura Marchese at Travel Central.
Key Entry Requirements:
Cuban Tourist Card (Visa): Required for all visitors to Cuba, typically available through your airline or a travel agency.
Cuban Health Insurance: A mandatory requirement for all travelers, often included in your airline ticket or available for purchase at the airport in Cuba.
Valid Passport: Your passport must be valid for at least six months beyond your travel dates.
Travel Itinerary: U.S. travelers must have a travel itinerary that aligns with their declared travel category and must retain records for five years.
Cuban Visa (Tourist Card): The visa is valid for one entry and a stay of up to 90 days, which can be extended. It is essential to keep the visa safe, as it will be collected upon departure.
New eVisa for U.S. Travelers (Effective August 2024): Cuba now offers an electronic visa (eVisa) as an option for U.S. travelers, which replaces the traditional pink or green paper visas. The eVisa is available for purchase through various channels, including the Cuban Government's official eVisa website, and it will be linked to your D'Viajeros customs and immigration forms. The eVisa is more affordable and can be completed entirely online.
The Pink Visa (for U.S. Flights to Cuba): If you're flying directly to Cuba from the U.S. (e.g., Miami, Tampa, Houston), you'll need a pink visa. This visa is available for purchase at the airport from Cuba Travel Services or can be ordered in advance from the airline. The pink visa costs around $50-$100 USD and is typically processed quickly.
The Green Visa (for Non-U.S. Flights to Cuba): If you're flying to Cuba from outside the U.S., you'll need a green visa. This visa is also available through the Cuban embassy or through third-party vendors.
For further visa information and to ensure you’re applying for the correct visa, you can click this link for more details.
Health Insurance: U.S. travelers will need travel health insurance that is valid in Cuba. This is typically included with your flight, but confirm it before departure. You’ll need to present proof of insurance upon arrival.
The first and last nights of your Cuba trip will be spent in guesthouse accommodations, ideally located in Old Havana, Central Havana, or Vedado.
Arrival and Departure Transfers: We’ve got your airport transfers covered! You'll be picked up from the Havana airport (or any other location in Havana if you're already in Cuba) and taken directly to your joining guesthouse.
Late or Early Arrivals/Departures: If you’re arriving late or departing early, don’t worry! We can help arrange for you to catch up with the group or assist with early departure arrangements. Additional transport costs may apply for these adjustments.
Cuba uses the Cuban Peso (CUP). U.S. dollars are not widely accepted, and American credit or debit cards are generally not functional in Cuba. It's advisable to bring enough cash in U.S. dollars or euros, which can be exchanged for Cuban Pesos upon arrival. Euros often receive a better exchange rate than U.S. dollars, which are subject to a conversion fee.
Currency exchange can be done at official CADECA offices, banks, or some hotels. Avoid exchanging money on the street, as this can be risky. For most purchases, you’ll rely on cash, but a few tourist spots may accept euros or dollars directly.
ATMs and Banking: ATMs are scarce, and international cards can be limited in their usability. It's wise to plan ahead and exchange currency before you arrive. Avoid relying on ATMs to withdraw cash once you're there.
We estimate each traveler will need between $450 and $600 USD for local expenses, including meals and optional activities during your time in Cuba.
Cuba uses 110V and 220V electricity, with Type A, B, or C outlets. Many accommodations have dual voltage, but it’s a good idea to check ahead and bring a voltage converter if needed. If you have a three-pronged plug (common in the U.S.), be sure to bring an adapter, as many Cuban outlets are two-pronged.
Wi-Fi in Cuba is limited and generally slower than what you might be used to. Access is available in some hotels, guesthouses, and public Wi-Fi hotspots, but speeds can vary. To use public Wi-Fi, you’ll need an ETECSA Wi-Fi card, which can be purchased in hotels, at ETECSA offices, or from vendors on the street.
Prepare for a slower, more disconnected experience—it’s the perfect opportunity to unplug and immerse yourself in Cuba’s vibrant culture!
Your local guides are already compensated, but it's customary to budget at least $100.00 USD for tips during your trip. This money will be distributed to our hardworking local guides, who help ensure you have an unforgettable experience.
March is one of the best times to visit Cuba. Expect warm, pleasant weather with daytime temperatures between 77°F to 85°F (25°C to 29°C) and cooler evenings around 65°F (18°C). Rain is minimal, making it perfect for exploring the vibrant cities and picturesque landscapes.
Pack lightweight, breathable clothing (cotton or linen) for the day and a light jacket or sweater for cooler evenings. Comfortable walking shoes are essential, especially for exploring the cobblestone streets of Havana and other historic areas. Don’t forget sunscreen, a wide-brimmed hat, and sunglasses to protect against the tropical sun.
Check out recommended travel accessories here to help you prepare for your Cuban adventure!
Cuban cuisine is a vibrant fusion of Spanish, African, and Caribbean influences. Dishes like ropa vieja (shredded beef), arroz con pollo (chicken and rice), and tostones (fried plantains) offer a true taste of the island. You’ll find meals at paladares (private restaurants) and casas particulares (guesthouses) where home-cooked meals feature fresh local ingredients.
Don't miss out on the delicious street food, including empanadas and sugarcane juice. Pair these with a refreshing mojito, guarapo, or a rich Cuban coffee.
Carnival in Santiago de Cuba: While Havana's carnival is later in the year, Santiago de Cuba (on the southeastern side of the island) celebrates a vibrant carnival in March. If you're interested in experiencing Cuban culture and lively street parades, consider visiting this part of Cuba.
Music and Arts: March also features various music and arts events in Havana. Cuba is known for its jazz and classical music, so you might find performances at places like the National Theatre or cultural centers in Havana.
Local Transportation: While public transportation in Cuba is available, it can be unreliable. Taxis and private car rentals are widely available but may be more expensive than you expect. Consider using a private driver for more comfort and flexibility.
Bicycles and Walking: Havana and many Cuban cities are relatively small and walkable, so renting a bike or simply walking around can be a great way to explore.
Cuba is one of the safest countries in Latin America, with violent crime being rare. However, petty theft can happen, so be cautious and keep your belongings secure, especially in crowded areas. Stick to official taxis and avoid unlicensed ones.
Local Customs: Cubans are friendly and welcoming to tourists. Be respectful of local traditions, especially regarding politics. Avoid discussing sensitive political topics, as these can be considered controversial.
Cuba is the largest island in the Caribbean, known for its vibrant culture, colonial architecture, classic cars, and rhythmic music. With a rich history shaped by Spanish and African influences, it offers travelers a unique blend of tradition and natural beauty.
Cuba's history is fascinating, from its indigenous roots to Spanish colonization, and the Cuban Revolution of 1959. Today, the island’s colonial cities and revolutionary monuments tell the story of Cuba's resilient identity.
Cuba's geography is diverse, with beaches, lush valleys, and tobacco fields. Must-visit spots include Viñales Valley, the Sierra Maestra mountains, and historic cities like Havana, Trinidad, and Santiago de Cuba. With its tropical climate, Cuba is a year-round destination for nature lovers and beachgoers alike!
Travel insurance is strongly recommended to protect against unforeseen circumstances that could impact your trip, such as cancellations, medical emergencies, or lost luggage. We advise all travelers to purchase a comprehensive travel insurance policy that covers both medical expenses and trip interruptions. For more information on travel insurance options, you can check out You Can't Steal My Happy's Travel Insurance Page.
Before booking your trip, please review the terms and conditions associated with this trip. By participating, you acknowledge that you understand and agree to these terms. For full details, please refer to You Can't Steal My Happy's Terms and Conditions.
As part of your journey, we encourage you to embrace the values and principles that ensure a positive and enriching travel experience. These guiding principles are designed to help you make the most out of your adventure. Please review and embrace the 10 Commandments of You Can't Steal My Happy.
Robert Hearn
My name is Robert, and I am one happy dude! Having travelled to 90 plus countries I discovered long ago that a smile is the same in every language. My brand, You Can’t Steal My Happy, was conceived in 2011 when I was visiting in the US Virgin Islands. While waiting to catch a ferry from St John to St. Thomas, I was treated to some island drama. A local had just been evicted from his home and he decided to let everyone know just how he felt about it. Using a black can of spray paint, he graffitied “You Can Steal My House, But You Can’t Steal My Happy” on the building. I certainly don’t condone this behavior, but his message struck me as very powerful. I decided at that moment, I would remind everyone that they have 100% control over their happy- no person, situation, or thing can steal it!
The images on my apparel will hopefully inspire you to get out in play in this world that I call my playground. If you are up for some adventure then join us on a life changing happy tour to one of our exciting destinations. I hope you will join the “You Can’t Steal My Happy” movement by showing the world your smile.
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