Private Cuba Tours

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Art & Architecture Tour

7 Days / 6 Nights

  • Havana
  • Cienfuegos
  • Trinidad

Like a stroke of fresh paint, Cuba’s most famous cities prevue the long desired Cuban fantasy of rhythm and dance, color and time – victoriously so, the forbidden fruit no more. Defiant to a decades-old dwindling economy, Cuba’s soul is pounding stronger than ever with thriving arts and culture, bursts of color, and visions of architectural allure. 

Beginning with Havana, Cuba’s cultural epicenter, onwards to Cienfuegos, the “Pearl of the South” and then to Trinidad, the enclave of colonial architecture - the one-off triangle of excellence comes bursting with steady doses of culture. Throughout the seven-day tour, together with your local Cuban guide and insightCuba leader, follow along the architectural trail of these three cities, each a mesmerizing UNESCO World Heritage site of its own.

As you journey along the capital’s prestigious landmarks and distinctive Cuban villas, learn about Old Havana’s diligent restoration efforts, visit fine art museums and institutions promoting modern architecture and urban planning.

To follow, visits to the National Association of Writers and Artists (UNEAC) and outings by the bay in Cienfuegos shower more insight. In Trinidad, the far-flung sugar cane fields of Sugar Mill Valley play hide and seek with rambling colonial mansions, prevalent throughout town and documented in the grand Museum of Colonial Architecture. To top it off, imagine your life as an aristocratic in the old palace of Count Brunet, more memorably known today as the the Romantic Museum.

This is cultural infusion at its very best. Beyond Cuba’s undisputed cultural riches, its people remain solid as its biggest wealth. Their joy of life and welcoming embrace – your lasting memento as you journey back home. 

Havana Cuba Miami Vintage Car
Day 1

Arrival at José Martí International Airport in Havana. Upon clearing customs and immigration, a scenic bus-tour through Havana awaits.

After hotel check-in, you’ll meet your insightCuba tour leader and local Cuban guide throughout the trip, during a brief information meeting.

Your first evening on Cuban soil commences with a welcome dinner at a local restaurant. To follow, a stroll trailing Old Havana’s sea breeze is the best way to press start on your Cuban venture.

havana cuba el morro
Day 2

The day begins at the Headquarters of the Cuban Institute for Friendship with the Peoples (ICAP), an NGO fostering “friendship” ties with other countries, while imparting the Cuban culture abroad. During your visit, enjoy a guided tour around the ICAP venue and the Friendship House - both considered heritage sites of Havana. A presentation of AMISTUR Cuba S.A. follows, the Institute’s official travel agency and your host in Cuba.

Following lunch at Casa de la Amistad (Friendship House), we’ll 
head to Jose Martí Memorial, honoring Cuba’s national hero, crowning the sprawling Revolution Square. At the Christopher Columbus Cemetery, a gem of world architecture reveals sumptuous tombs and mausoleums, goodly and imposing.

For the evening, we’ll make it across the bay from Old Havana to the Morro-Cabaña Park, an expansive complex of fortifications comprising the city’s former colonial defense system. Enjoy the Cannon blast ceremony, followed by dinner on premise.

Old Havana Cuba famous plaza
Day 3

For today’s city discoveries, meet with specialists from the City Historian’s Office at the City Museum for insight into restoration and development efforts of Havana’s Historical Center.

Following lunch at a local restaurant, we’ll set about a walking tour of Old Havana, a UNESCO World Heritage site since 1982. Walking through history of revived colonial splendor, feast your eyes to a wealth of architectural styles: baroque, art deco, Moorish, neo-classical and more. Stops on today’s tour include: Plaza de Armas, Plaza de San Francisco, Plaza Vieja, Plaza de la Catedral; and Bodeguita del Medio - a symbol in Havana. We’ll then break with a return to the hotel.

As the day comes to an end, we’ll visit the Almacenes de San José Cultural Project, for an example of the current Cuban economic model. 

Art in Cuba Havana Cienfuegos
Havana / Cienfuegos
Day 4

On today’s agenda, we swap the bustle of Cuba’s capital for a jaunt down South. Known as the “Pearl of the South,” the city of Cienfuegos – founded by French settlers in 1819 – awes with splendid architectural sites and urban designs. Observe the beauty of the UNESCO World Heritage site on this morning’s bus tour.

Then, meet with members of the City Historian's Office in Cienfuegos and with the local delegation of the Cuban Institute for Friendship with the Peoples (ICAP).

After lunch, we’ll stop by the esteemed National Association of Writers and Artists (UNEAC), followed by the Tomás Terry Theater, an architectural landmark and one of the most important theaters in the country. Next, meet with artists of a cultural project.

Following hotel check-in and dinner at the hotel, the evening concludes with the members of a Committee for the Defense of the Revolution (CDR).

Trinidad Cuba streets.
Cienfuegos / Trinidad / Havana
Day 5

Continuing along the Southern coast, next stop on Cuba’s cultural trail is Trinidad, in the Sancti Spíritus province.

To start, we’ll visit an arts school. Next, we’ll set forth the Historical Center of Trinidad, another UNESCO World Heritage site that Cuba boasts. Today’s journey through the island’s colonial mecca will include visits at the Museum of Colonial Architecture, the Romantic Museum housed in the old palace of Count Brunet, and Santander’s’ Potters workshop.

After lunch, Sugar Mills Valley follows, a living museum and testament of Cuba’s sugar production. Learn about the realities of the sugar industry today at the ruins of a sugar mill.

On our way back to Havana, explore your options for the evening back in the bustling capital. 

fine arts havana cuba musicians
Day 6

Back in Havana, the day begins in Miramar with a visit to the Green Roof Tiles House, a striking mansion unique of its kind for being the sole example of the American Queen Anne style - now a center promoting modern and contemporary architecture, urban planning and interior design. Prepare to debate on the topic of modern Havana with an architect. Then, a visit to the Higher Institute of Arts ensues.

Soon after lunch in town, an overview of Cuban Visual Arts awaits at the Fine Arts Museum.

For your final night in Cuba, all bets are off. What surprised and baffled you most? Let it sink in as you enjoy a joyous farewell dinner, musicians and mojitos in place.

Havana Cuba Miami Vintage Car
Day 7

After breakfast and hotel check out, depart for Jose Martí International Airport. 

Twitter Feed

  1. Before you embark on your insightCuba experience, get to know our team! Jessica Lebowitz:
  2. Bike riding in the beautiful countryside of Pinar del Rio! Visit on our Legendary Cuba tour:
  3. Learn why icons like Hemingway, Churchill, and Sinatra felt an affinity for this rare place:
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TRAVEL UPDATE: Cuba has recovered from Irma and remains one of the safest destinations for travel. Tours and cruises are currently operating across the country.