cuba itinerary

Custom Travel Itineraries For Cuba

cuba vacation packagesCustom Travel Itineraries For Cuba
vacations to cubaCustom Travel Itineraries For Cuba

Best Tours For Cuba

We are the custom Cuba travel package experts. Cosmopolitours originally began in 2011 as Havana VIP Tours, and Havana VIP has been known as the very best at planning and producing independent travel to Cuba. We have done more than 400 Cuba Trip Itineraries, over 12 years, all custom Cuba travel packages, all filled with our original and authentic Cuba tours and experiences, resulting in a perfect record of 5-Star reviews. Not bragging, just saying.

Check out our about us page for more of our story.

art in cuba cigars and rum in cuba views in cuba dancing in cuba

Top 5 Places to Visit in Cuba

Travel to Havana Cuba

Even the sound of the word Havana has an alluring ring to it.
Located just south of the Tropic of Cancer on Cuba’s northern coast, Havana Cuba, the island’s capital city is a place of mystique and paradox. One of the oldest continuous capitals in the Americas, Havana’s 500-plus year history spans from the Renaissance and the Age of Exploration through a 150 years struggle for independence from colonialism, to the glamor, exploitation, and excess of Meyer Lansky’s casino era, through Castro’s revolution and Cold War gamesmanship. to today’s fascinating city on the brink. On the brink of what? We’ll show you Havana’s history, arts, cuisine, and culture, and let you decide.

Visit Trinidad Cuba: 500 year-old UNESCO World Heritage City

The 500 year-old Spanish colonial city of Trinidad Cuba, a UNESCO World Heritage Site perched at the base of the seaward slope of the Sierra Escambray mountains on Cuba’s southern coast, is one of the best destinations in Cuba. Trinidad is located near the middle of the island in Sancti Spiritus province, about 75 minutes by car east of Cienfuegos, or about five hours drive time from Havana. The historic core of Trinidad is paved with river-stone streets, and is filled with open-air paladares offering some of the best food in Cuba. At night Trinidad Cuba comes alive with live music and dancing under the stars.

Tour Vinales Cuba: Home of the World’s Best Tobacco

Located 3 hours by car southwest of Havana is the Valle de Viñales in Pinar del Rio Province. This verdant green valley with striking red soil is a popular rural side trip. For tobacco aficionados, this 130 square kilometers of the Valle de Viñales in Pinar del Rio Province is a kind of holy land where what have been traditionally regarded as the world’s best cigars are born. The tropical landscape is ranked by many as one of Cuba’s most beautiful vistas where the unique mogotes, unique flat-topped shear walled rock mounts interrupt the valley floor. Cosmopolitours Tobacco Plantation Experience, for those interested either in agriculture or tobacco (or both) is so far off-the-beaten-track that the only way to get there is by horseback, or even ox-cart.

Visit Cienfuegos Cuba: Cuba’s Pearl of The South

Cienfuegos Cuba is one of Cuba’s most popular destinations. The seaside city is set on a beautiful bay on Cuba’s southern coast 4.5 hours’ drive from Havana. Cienfuegos was an important port for the sugar trade in the 19th century, especially after a African slave rebellion in Haiti sent sugar barons of French ancestry fleeing to Cuba where they re-established themselves and Cienfuegos became essentially a French-style city. In the first half of the 20th century, Cienfuegos Cuba became a popular yachting destination as the beauty of its former yacht club, still attests. With the advent of Cruise ship tourism to Cienfuegos, the small city is occasionally over-run, but because Cosmopolitours Experiences are exclusive for our clients, you’ll never feel overwhelmed by tourists even when the big ships are in port.

Travel to Santiago de Cuba: Historic City of Afro-Cuban Culture

Perched on the southeastern coast of the island, Santiago de Cuba, boasts a storied past, evident in its colonial architecture and museums that unveil the country’s fascinating history. Discover the iconic Castillo del Morro, a majestic fortress guarding the entrance to the bay, and delve into the legacy of heroes at the Moncada Barracks. Immerse yourself in the rhythmic beats of traditional Afro-Cuban music that resonate through the streets, capturing the essence of the island’s soul. Witness the passionate performances of local dancers and indulge in the tantalizing flavors of authentic Cuban cuisine.

Check-out these and many more of Cuba’s best places to visit on a custom Cuba Travel Itinerary personalized just for you by Cosmopolitours.

Explore Some of Our Recommended Locations in Cuba


Can Americans Travel to Cuba Legally?

U.S. Persons can still travel to Cuba 100% legally. Cosmopolitours custom Cuba travel packages are 100% compliant with U.S. regulations governing travel to Cuba, and always will be. We’re so confident in our compliance, that we’ll guarantee it.

Legal independent Cuba travel by U.S. Persons is subject to the Cuban Asset Control Regulations (CACR) issued by the U.S. Department of The Treasury, Office of Foreign Asset Control (OFAC). Under the Obama Administration. Those regulations define 11 categories of authorized travel for U.S. Persons who must be engaged in a full-time itinerary of activities pertinent to their reason for travel. The most commonly used reason for travel to Cuba by U.S. Persons is the “Support of the Cuban People” category. At Cosmopolitours, many of our Cuba Travel clients travel legally to Cuba under the “Informational Materials Exchange” category which allows travel to Cuba for collecting fine art.

So, don’t put-off your travel to Cuba any longer. Contact us today to start arranging your 100% legal trip to Cuba – guaranteed.

A Customized Cuba Trip Will Fascinate Every Traveler


Cosmopolitours builds every Cuba trip itinerary by filling it with our own original Cuba tours and experiences that are not available from any other agency. The Havana Mob Tour: invented it. Visit the practice rooms of the Cuban National Ballet (not the rehearsal, the practice rooms): exclusive to us. Tours of the private studios of the best Cuban artists: we wrote the definitive guidebook on Cuban contemporary art, Cutting Edge Art in Havana, and the companion book to the Havana Biennial of Fine Art. If you ask the curators and specialists from the Havana Biennial who they recommend to plan your vacation to Cuba, they say us.

Why Get a Custom Cuba Vacation Package From Cosmopolitours?

Because we are the independent travel to Cuba experts. We are the Cuba travel pros, the Cuba trip insiders who know:

The best places for live music in Havana
Havana nightlife secrets
The best restaurants in Trinidad de Cuba
The best places to stay in Havana
& So much more

We are custom-independent Cuba travel itinerary creators and originators. We come from the worlds of Cuban Arts, Food, Fashion, Design, and Music. Lots of travel planners like to call themselves “travel curators”, but unlike them, we have actual Cuban fine arts curators on our team. We combine our insider cultural knowledge with our IATA-accredited travel professional know-how to plan flawless vacations with:

Efficient Logistics to minimize wasted time
Safe reliable transportation
Vetted English-speaking hosts and guides
Special access and event bookings
Dining recommendations and reservations
Trip-defining museum, monument & gallery tours
Best lodgings for your budget, with great location and service
& So much more

Cosmopolitours is a boutique agency owned and operated by family and friends. Our motto is that we are exclusive, but not elitist. Meaning that because we are a small agency, we take on only a limited number of clients every month (exclusive), but for every client, we take on we put in the same level of effort regardless of budget (not elitist).

As your custom Cuba travel pros, we keep every essential convenience, cost, and quality-of-life amenity top-of-mind, resulting in custom Havana, Cuba travel packages that connect you with the enriching unique experiences you are hoping to find.



Visit the Best Destinations in Cuba

Ready to plan a trip of a lifetime to Cuba? Contact us. We will gladly outline an amazing handcrafted Cuba itinerary, whether for a long weekend in Havana or a multi-week immersive trip through Cuba’s most off-the-tourist-track destinations. We can discuss different destinations, and must-see monuments, highlight our favorite historic regions or help you organize a lifestyle Cuba trip that revolves around food, art, rum, and Salsa. What’s not to love?

Wherever our travel packages take you, with Cosmopolitours, everything begins with our commitment to excellence in every detail and our sharing spirit as great hosts. To learn more about our expertise or for our Havana, Cuba travel itineraries, contact us for an informative Cuba travel consultation and start planning your custom trip to Cuba today!

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