Unique Cultural Tours
Unique Cultural Tours
Cuba is an incredible island, the largest in the Caribbean, and it has so much to offer. It is unlike any place in Latin America because of the fusion of vibrant Caribbean culture and music, along with the political influence that has shut it off from U.S. businesses. Want to go somewhere with no Starbucks, no McDonald’s, just local deliciousness with a small group tour? Cuba is your place! Plus, it is extremely safe.
Do you think that you can’t travel there with a U.S. passport? Think again. There are daily flights on American Airlines, United Airlines, and more from the U.S. Concerned about your visa? Rest easy; we’ve got it all covered for you.
Americans looking for legal, meaningful travel to Cuba
Seniors 55 and older seeking safe, guided adventures (although if you’re younger, you can come too!)
Solo travelers, couples, and small groups
Curious minds who want education and experience, not just leisure
Our trusted Cuba tour agency plans every detail. Itineraries are shaped to provide you with unique cultural experiences.
$3,595
April 7-16, 2026 (+3 days for scuba or snorkel option available)
Step into the incredible limestone-covered region of Cuba. The views are breathtaking, and you’ll learn from the farmers of the country’s world-famous tobacco. As you travel east, you’ll have the opportunity to snorkel in the Bay of Pigs or just relax in the sunshine. Classic cars, UNESCO World Heritage sites, exotic fruits, and Cuban friends are built into this specially curated tour! This loop tour starts and ends in Havana.
$4,395
January 20-29, 2026
The Havana International Jazz Festival is a world-renowned event! Enjoy musicians from 9+ countries in the vibrant and historic city of Havana. The tour cost includes VIP tickets to the shows for 3 nights of concerts. This exclusive itinerary also takes you outside the city to experience the countryside in Cuba, making the most of your trip! This loop tour starts and ends in Havana.
Starting at $4,395
November 4-13, 2025 (FRBO tour, only 4 spots left)
January 30-February 8, 2026
Explore Cuba's birding hotspots in the prime migration season! More than 400 bird species have been recorded in Cuba, including 27 endemics of which 18 are considered globally threatened. We’ll meet with local bird specialists in various ecosystems, including interior tropical forests, salt flats, and swamps. Most days, birdwatching activities happen at sunrise and sunset, with free time after lunch. The itinerary will flex as needed to help us find our target birds.
Local culture, arts, and lifestyle will be built in as part of our unique cultural experiences in Cuba!
*Jenny will accompany this tour.
$4,395
April 17-26, 2026
Join this all-inclusive experience with people from the Hershey History Center of Hershey, PA as we connect with Cubans in Hershey, Cuba. Learn about the historical connection of these cities, Milton Hershey’s influence, and more.
This is a comprehensive trip with big cities and small towns, the best of Cuban architecture, food, music, bird watching, and UNESCO World Heritage sites! You’ll cover half the width of the island on this tour from Havana to Camaguey.
*Denotes Jenny (President at Vive Más Tours) will be attending this tour.
You can sense Cuba's pace when you travel with us. At Havana's Buena Vista Social Club, you may dance and take in live salsa music. Do you love jazz? You can join our annual Havana Jazz Festival 10-day tour with three nights of live shows.
Birdwatchers will spot the Cuban tody, trogon, and over 100 other species. Our guides know the best viewing spots. You can also visit tobacco farms, orchid gardens, and learn about Cuban-style organic farming. Bring your snorkel to see the colorful fish in warm Caribbean waters.
History lovers can explore Hershey, Cuba. You can see the remains of Milton Hershey’s sugar town, schools, hotel, and railways that shaped the sugar industry on the island.
Every tour offers authentic culture, music, history, and nature. Let us help you pick the perfect Cuban adventure. People looking for American tours to Cuba choose us for a reason:
Complete regulatory compliance and documentation/visa support
Small group tours for a more personal experience
Flexible itineraries personalized to your interests
Direct flight coordination from major U.S. cities
Transparent pricing with no hidden fees
24/7 support before and during your trip
Local guides for authentic insights
Cultural exchange opportunities
Personalized, responsive customer service—emails, texts, or calls, we respond quickly and directly
When you book your Cuban tour from the U.S. with us, the process is simple.
At Vive Más Tours, we’ve been leading tours to Cuba for more than 10 years. We are proudly based in Colorado. If you require assistance while traveling or if you have a question regarding your reservation, we’re just a phone call away. Our goal is simple: We provide comfortable, safe tours that allow you to experience authentic Cuban culture.
Proven Track Record: We have more than 10 years of experience. We’ve guided countless travelers to Cuba, building trust through our expertise.
Legal & Compliant Travel: We’ve operated through four presidential terms, always keeping tours fully compliant with U.S. regulations and updating clients as rules evolve.
Deep Local Connections: Our network across Cuba runs deep. From artists to restaurant owners, we know locals by name and bring you authentic cultural connections.
Small Group Experience: Every traveler gets personal attention with our small group tours. We customize our tours according to our travelers' needs.
Experienced Guides & Team: Our Cuban tour guides have been there for decades. Jenny, our Vive Más Tours owner, frequently accompanies the tours to ensure the high standards and fun activities of our tours.
Consistent Communication: From registration to departure, you’ll receive clear timelines for flights, payments, and packing. You’re always prepared and stress-free.
Club Dos+ Loyalty Program: Many travelers return for more adventures, so we created Club Dos+ to celebrate repeat guests. It’s proof that people love coming back to travel with us.
Want to talk with someone who has traveled with us? Many of our customers have offered to provide referrals, so you can get the truth, without having to worry if it’s a sales pitch.
Your money goes directly to local families when you travel with us. Each experience is made to celebrate Cuban culture and support the community in real, lasting ways.
Planning a trip to Cuba from the U.S. can feel overwhelming, but we make it easy. At Vive Más Tours, every detail is handled for you from visas to flights.
Visa & Documentation Support: Your Cuban visa is included in the cost of your tour. No extra paperwork, no hassle—we take care of the process so you can travel worry-free.
Flights from Major U.S. Cities: Most travelers fly to Cuba through Miami or Tampa, with simple round-trip booking online or with our team’s assistance. We guide you step by step to ensure a smooth trip.
Stress-Free Travel Planning: We provide a full itinerary, packing checklist, and ongoing support. Two to four weeks before departure, you’ll join a live Zoom orientation where we cover weather, activities, and what to expect.
Unique Cultural Experiences: Our specialty is taking U.S. travelers to Cuba for once-in-a-lifetime cultural immersion. Choose from 10-day tours starting at $3,595. You can enjoy music, history, art, and local connections you won’t find anywhere else.
At Vive Más Tours, we operate under the Support for the Cuban People category, making your trip 100% legal. We understand the regulations inside and out as a U.S.-based company. We stay up to date on policy changes, so your experience remains safe, compliant, and stress-free.
We know the rules, and we make travel easy. Our tours are carefully prepared, entirely legal, and intended for US citizens. We are trusted by everyone for our tours, including small groups, retired couples, and single travelers. Our staff takes care of every detail—so you can focus on enjoying the true Cuba.
At Vive Más Tours, you’ll be guided by experts who know Cuba inside and out.
Jenny Desmond, our President & CEO, brings her background in Spanish and nonprofit leadership to design meaningful, cultural travel experiences. She customizes the itineraries for smooth travel experiences.
Roger has been guiding for more than 20 years. He is a former high school teacher, a birder, and a photographer. His storytelling skills are a highlight, and he is deeply knowledgeable and friendly. Together, this team guarantees that each journey is genuine, enlightening, and remarkable. Read more on the Team Page.
Traveling to Cuba is easier when you know what to expect. From packing light to how much money to bring, the right tips make your trip smooth. Our step-by-step guide to Cuban customs explains the arrival process clearly so you feel confident before you even board your flight.
Cuba’s charm lies in its culture, flavors, and stories. Milton Hershey was a trailblazer in both the U.S. and Cuba. Learn more about this sweet side of Cuban life in A Sweet Connection, and get inspired to explore the island beyond the usual tourist paths.
When you travel with experts, you see the real Cuba. Every moment feels authentic, from lively music in Havana to peaceful countryside villages. Cuba has a lot of obstacles for the independent traveler. Exploring Cuba on a Tour will help you understand how a guided tour is the way to go in Cuba.
Packing smart makes your Cuban trip easy. Bring light clothes to stay cool. Comfortable shoes are most important for walking. Add sunscreen and a good hat for sunny days. A small daypack works well for excursions and carrying your essentials.
For more tips, check out our Cuba packing list. It covers currency exchange, cultural outings, and outdoor adventures. With the right items, you’ll enjoy every moment in Cuba.
We provide you with your visa to Cuba! Our tours are in compliance with Support for the Cuban People licenses. If you are not traveling with Vive Más Tours, you can find more information here: § 515.560 Travel-related transactions to, from, and within Cuba by persons subject to U.S. jurisdiction.
You can trust that we remain in full compliance with both U.S. and Cuban regulations, so you can travel with ease. Tourism is not legal in Cuba under U.S. regulations, but traveling in Support of the Cuban people and supporting small private businesses in Cuba is legal!
A: Cuban Bed & Breakfasts, or casa particulares, are not like a homestay. You get the privacy and comfort of a hotel room with your own bathroom, yet welcoming hospitality that surpasses Cuban-run hotels. We are often divided into smaller lodgings, most with 2+ guest rooms. The B&Bs are located near each other, so it’s easy to walk from one to another. If you are a single traveler, we will be sure you are not the only guest staying at a B&B.
Yes! We are a licensed Cuba tour operator, and all our trips follow U.S. travel rules under the “Support for the Cuban People” category. We handle the required documents for you, including the Cuban Tourist Card (visa) and the travel affidavit.
Our Cuba tour packages include
Accommodations in Casa Particulares
Private, air-conditioned transportation (including city tour in vintage American cars)
Activities, most meals, and entry to attractions
Experienced, English-speaking local guides
We plan each itinerary to directly benefit local communities in Cuba. You will dine at privately owned restaurants (paladares), stay in family-run bed-and-breakfasts. You will also meet artisans, musicians, and farmers face-to-face.
Our top choices include
Mountains & Snorkel Tour
Havana International Jazz Festival Tour,
Birdwatching Tour in Cuba
Hershey History Center Tour
Yes, we highly recommend it. We provide guidance on purchasing coverage with our partner, Allianz Travel Insurance.
Our packages are all-inclusive trips to Cuba from the USA. They cover accommodations, ground transportation, activities, most meals, and all guided experiences. Free time is built in for personal exploration.
