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insightCuba

InsightCuba is a single destination tour operator specializing solely in legal travel to Cuba for Americans.
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Since 2000, we've brought tens of thousands of Americans to this fascinating island country - making us one of the most experienced providers. InsightCuba is a tour operator specializing solely in legal people-to-people travel to Cuba for Americans. We offer in-country knowledge and expertise that is unmatched in the industry, providing travelers with once-in-a-lifetime experiences.

05/06/2024

NEW TOUR ALERT 🇨🇺

Experience the vibrant and diverse island of Cuba on our Scenic Cuba tour, a seven-day journey that takes you from the bustling streets of Havana to the serene beauty of Viñales National Park.

Whether walking through lush to***co fields or enjoying a home-cooked meal with locals, Scenic Cuba promises an enriching adventure that highlights the essence of Cuban life and culture.
https://ow.ly/ILGe50S9Hym

31/05/2024

⭐⭐⭐⭐⭐
"A visit to Havana has been on my wish list for over ten years, and it lived up to my best expectations. Our accommodations were just as we had hoped... comfortable rooms, bottomless cups of hot coffee and nutritious breakfasts each morning, and always someone to greet us when we returned from our adventures. We were located right in the heart of Havana and felt very safe. We could not have been better cared for, thanks to the entire insightCUBA team!" - Molly

15/05/2024

Introducing: Havana Jazz Festival 2025 🇨🇺🎷

Our meticulously curated 2025 departure offers an insider's itinerary for jazz aficionados, featuring admission to daily Jazz Festival events and concerts plus intimate meet-and-greets with contemporary jazz musicians. In addition to amazing music, each day is filled with enriching experiences, from cooking alongside locals to meeting emerging Cuban artists and exploring inspiring community initiatives. Every moment of this unique program promises an unparalleled journey to the heart and soul of Cuba.
https://ow.ly/nN0f50RHqiH

09/04/2024

Immerse yourself in Cuba's rich culture, vibrant history, and stunning landscapes for an unforgettable adventure. 🇨🇺

Join us on one of our small group tours and discover this once-forbidden island's traditions!

03/04/2024

Our Spring into Savings Travel Sale ends tonight, so don’t miss this chance to book your trip! Save up to $200 per person on our immersive packages to Cuba! 🇨🇺
https://ow.ly/WwrK50R4s3G

30/03/2024

This exciting, 8-day journey to Cuba's most famous cities will add the brushstrokes to the unfinished canvas of your vision of Cuba. Your experience begins in the bustling harbor city of Havana and continues on through Playa Larga and Playa Girón before settling into the artistic enclaves and colonial treasures of Trinidad and Cienfuegos, known as "the pearl of the South."

From now - April 3, save on all 2024 departures!
https://ow.ly/nmkR50R4ma9

28/03/2024

🗓️2019
Global tour operator Friendly Planet Travel acquired insightCuba. The new association between the companies is designed to bring a unified voice to the certainty of legal travel to Cuba by Americans and increased demand for the destination. 🇨🇺

According to Friendly Planet Travel Founder and President Peggy Goldman, the decision to acquire insightCuba comes from a shared philosophy about the indisputable role of travel to improve lives through economic development and true human connection; and the burgeoning demand for travel to Cuba, which has been estimated at 1 million U.S. travelers annually.

26/03/2024

Experience the vibrant rhythm of Havana, Cuba, in just one weekend. From the colorful streets of Old Havana, where classic cars line cobblestone streets, to the lively beats of salsa echoing from every corner, the city offers a captivating blend of history, culture, and passion.

From now through April 3, save on all 2024 departures!
https://ow.ly/vCnL50R2pQM

22/03/2024

🗓️2019
Condé Nast Traveler names insightCuba the world's top Cuba Travel Specialist for fifth consecutive year.

The White House amends Cuba travel regulations prohibiting cruise ships originating from the United States to sail to Cuba. Administration also consolidates People to People and Support for the Cuban People, the two most popular travel categories, into Support for the Cuban People. Any American can still legally travel to Cuba under this category.

20/03/2024

Ready to delve into the vibrant culture and rich history of Cuba? Take advantage of limited-time savings on all 2024 departures during our Spring into Savings Travel Sale!

Now-April 3, save up to $200/person 🇨🇺

From the bustling city life to the tranquil beauty of the countryside, Cuba offers an authentic and enriching experience that will leave you with memories to last a lifetime.
https://ow.ly/HR8150QXEXR

14/03/2024

🗓️2018
Condé Nast Traveler names insightCuba the world's top Cuba Travel Specialist for fourth consecutive year. Cuba achieves record breaking 4.75 million travelers.

12/03/2024

🗓️2017
Condé Nast Traveler names insightCuba the world's top Cuba Travel Specialist for third straight year.

President Donald Trump repeals people-to-people travel for individual U.S. citizens, which President Obama authorized the year before. However, the White House leaves many of the Obama travel provisions which increased U.S. travel to the island, intact.

insightCuba and acclaimed world music record label, Putumayo World Music, collaborate on a series of tours to Cuba and beyond.

10/03/2024

🗓️2016
Condé Nast Traveler names insightCuba the world's top Cuba Travel Specialist.

People-to-people travel for individual U.S. citizens is authorized. President Obama travels to Cuba, marking the first time an American President has visit Cuba since Calvin Coolidge in 1928.

08/03/2024

Celebrating the strength, resilience, and spirit of Cuban women on International Women's Day ❤️💙

¡Feliz Día Internacional de la Mujer desde Cuba!

06/03/2024

🗓️2015
InsightCuba celebrates its 15th year of providing licensed travel to Cuba for Americans.

On January 16, new travel regulations are issued to make it easier for Americans to travel to Cuba, namely on people-to-people tours. By year's end, Cuba was ranked the hottest destination for U.S. travelers by various travel publications.

Cuban Embassy in Washington, DC opens and insightCuba is present for the opening ceremony.

U.S. mobile phone carriers began roaming service in Cuba.

04/03/2024

🗓️2014
InsightCuba receives authorization from the U.S. Department of the Treasury to offer an ocean cruise around Cuba, and the first authorized cruise for Americans since 1963.

InsightCuba receives the first amateur sports license allowing Americans to participate in the Marabana Havana Marathon. Only 156 runners are allowed to go.

December 17, President Obama announces efforts to normalize relations with Cuba. The first such overture since 1959, these efforts are to include establishing diplomatic relations with Cuba, establishing banking relations between the US and Cuba, and facilitating an expansion of travel under general licenses for the 12 existing categories of travel to Cuba authorized by law. While the US Embargo Against Cuba and the ensuing travel restrictions remain in place, the announcement represents a new era in U.S.-Cuba relations and travel to the island nation.

02/03/2024

🗓️2013
On June 30, insightCuba receives its sixth people-to-people license and launches new tours.

29/02/2024

🗓️2012
In April, insightCuba sends its 6,000th American to Cuba legally.

On September 28th, insightCuba receives its fifth people-to-people license to legally send Americans to Cuba.

27/02/2024

🗓️2011
On January 28, people-to-people travel to Cuba is restored by President Obama. InsightCuba submits its license application that very same day. On June 28, insightCuba is granted its fourth license authorizing, licensed people-to-people travel to Cuba. On August 11, insightCuba is the first organization in eight years to send Americans to Cuba legally under the new people-to-people regulations, and relaunches with six signature Cuba tours.

25/02/2024

🗓️2010
In August, insightCuba receives word that the loosening of travel regulations to Cuba is pending. Preparations begin immediately to relaunch insightCuba, and resume its Cuba tours in anticipation of the restoration of people-to-people travel by the Obama administration.

23/02/2024

🗓️2004 - 2010
InsightCuba continues to strengthen partnerships and friendships in Cuba while travel programs are suspended by the Office of Foreign Assets Control. Hope remains steadfast that travel to Cuba will soon resume.

21/02/2024

🗓️2004
InsightCuba receives the Hospitality, Sales and Marketing Association International (HSMAI) Adrian Award for its efforts in the travel and hospitality industry. Considered the benchmark for the industry, this is the most prestigious travel marketing competition globally.

19/02/2024

⭐⭐⭐⭐⭐

"insightCuba is an awesome and reputable company who knows Cuba like no other mainstream tour provider. I had the great privilege of going on a hosted tour about a decade ago to check out their services and I was greatly impressed by the activities and the depth of their experience, knowledge and local connections. Truly memorable." -Michele

08/02/2024

🗓️ 2003
InsightCuba is issued a third license authorizing people-to-people travel to Cuba. By year's end, insightCuba is featured in over 120 nationwide news outlets, including New York Times, Los Angeles Times, and Newsweek. With established on-island ties and carefully fostered relationships, the organization sent over 3,000 Americans to Cuba since travel restrictions were loosened in 1999. Under the Bush administration, the regulations governing travel to Cuba are tightened, and all people-to-people educational travel programs are suspended at the end of the year. The last groups of Americans traveling to Cuba legally under the people-to-people license return home with insightCuba on December 31, 2003.

06/02/2024

🗓️ 2002
InsightCuba is issued a second license authorizing legal, licensed people-to-people travel to Cuba. Shortly after, a partnership between JazzTimes magazine and insightCuba brings hundreds of Americans to the Havana International Jazz Festival. The pulsating, Latin experience draws big names in global jazz. Past performers include Dizzy Gillespie, Charlie Haden, Max Roach and Chucho Valdés.

04/02/2024

🗓️ 2001
Inspired by Cuba’s infectious rhythm and vibrant art scene, insightCuba launches a themed Cuban Music program, offering participants the chance to immerse themselves in Cuban music, dance, art and the people behind it all.

02/02/2024

🗓️2000
InsightCuba is granted a two-year specific license from the U.S. Department of the Treasury's, Office of Foreign Assets Control, authorizing legal, licensed people-to-people travel to Cuba. InsightCuba is the first organization to take Americans on people-to-people Cuba tours.

31/01/2024

Journey through the history of legal travel to Cuba 🇨🇺

🗓️1999
Forty years after the Cuban Revolution, the Clinton administration announces measures to increase people-to-people exchanges between Americans and Cubans. InsightCuba, a division of Cross-Cultural Solutions, sends in its first license application to the U.S. Department of the Treasury's, Office of Foreign Assets Control, wanting to help Americans travel to Cuba legally and to build close relationships with the Cuban people.

17/01/2024

Join us for a weekend in Havana 🇨🇺

An immersive discovery where you’ll witness Cuba's incredible people, budding entrepreneurial scene, and dynamic rhythm and color.
https://ow.ly/q7Qc50QrPsL

13/01/2024

"Havana, for all its smells, sweat, crumbling walls, isolation, and difficult history, is the most romantic city in the world." -Mark Kurlansky

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Opening Hours

Monday	09:00 - 18:00
Tuesday	09:00 - 18:00
Wednesday	09:00 - 18:00
Thursday	09:00 - 18:00
Friday	09:00 - 18:00

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https://insightcuba.com/travel-info/coronavirus-covid-19-update

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Classic Cuba

Our seven-day Classic Cuba tour highlights Cuba's most famous cities, beginning in the boisterous harbor city of Havana and continuing on through Playa Larga and Playa Girón before settling into the artistic enclave of Trinidad and Cienfuegos, known as "the pearl of the South." Treat yourself to this incredible journey and book your trip with us today 🇨🇺

insightCuba's Classic Cuba Tour

'Making it in Cuba' Documentary

insightCuba's 2019 Havana Marathon Package

insightCuba Havana Marathon Package

insightCuba Tours

insightCuba's Undiscovered Cuba Tour

insightCuba Classic Cuba Tour

insightCuba_Weekend in Havana Tour

2019 Havana Marathon

insightCuba_Weekend in Havana Signature Tour

insightCuba Jazz in Havana Tour

insightCuba Undiscovered Cuba Tour

insightCuba Classic Cuba Tour

Set Sail with insightCuba!

Marabana Havana Marathon

Classic Cuba Tour

Legendary Cuba Tour_insightCuba

insightCuba: Undiscovered Cuba Tour

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Our Story

InsightCuba is a single destination tour operator specializing solely in legal travel to Cuba for Americans. Since 2000, we've brought tens of thousands of Americans to this fascinating island country - making us one of the most experienced providers of legal Cuba travel in the industry. Our in-country knowledge and expertise is unmatched in the industry, allowing us to provide travelers with unique access to people and places the average person rarely sees. Simply said, we do Cuba better than anyone else.

Our success is built on nearly 20-years of detailed research, extensive exploration, and our long-established relationships on the island, resulting in lifelong memories for our guests. With five Small Group Cuba tours, and a select group of Specialty Cuba tours, and numerous Private Departure and Custom-Made tours offered across hundreds of departure dates, insightCuba offers the broadest selection of trips available.

LEGAL TRAVEL TO CUBA

InsightCuba is authorized by the U.S. Department of the Treasury's, Office of Foreign Asset Control (OFAC), under a general license allowing any American who books a Cuba tour with insightCuba to travel to Cuba legally. As a registered guest on one of our tours, you are permitted to travel to Cuba and re-enter the U.S. legally. InsightCuba handles all the paperwork and requirements for your trip. Simply register for one of our Cuba tours and leave the rest to us.

05/06/2024

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15/05/2024

09/04/2024

03/04/2024

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04/02/2024

02/02/2024

31/01/2024

17/01/2024

13/01/2024

Address

Opening Hours

Website

Alerts

Contact The Business

Videos

Classic Cuba

insightCuba's Classic Cuba Tour

'Making it in Cuba' Documentary

insightCuba's 2019 Havana Marathon Package

insightCuba Havana Marathon Package

insightCuba Tours

insightCuba's Undiscovered Cuba Tour

insightCuba Classic Cuba Tour

insightCuba_Weekend in Havana Tour

2019 Havana Marathon

insightCuba_Weekend in Havana Signature Tour

insightCuba Jazz in Havana Tour

insightCuba Undiscovered Cuba Tour

insightCuba Classic Cuba Tour

Set Sail with insightCuba!

Marabana Havana Marathon

Classic Cuba Tour

Legendary Cuba Tour_insightCuba

insightCuba: Undiscovered Cuba Tour

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