Cuba Tours

InsightCuba, the foremost provider of legal people-to-people travel to Cuba, has nurtured its relationships in Cuba for more than 13 years. We are considered family in each of the communities we visit; as our guests, you will be, too.

Our people-to-people tours, led by seasoned Cuban guides and accompanied by storied insightCuba tour leaders, offer insider access to people and places the average tourist rarely sees. Whether embarking on an epic, 13-day coast-to coast exploration or a long weekend in Havana, each of our 100+ tours is designed to ignite meaningful, engaging experiences with the lifelong residents that give Cuba its spark.

Get to know local artists in the enchanting 500-year-old city of Trinidad. Tap your feet to the tempo of timba at a percussion and dance workshop. Indulge in laughter and play with Cuban school children. Make new friends, and allow the gentleness of the Cuban people and their stories to intrigue you.

At insightCuba, we’re as passionate as you are about travel, and there’s nothing we enjoy more than carefully crafting your experience to fully immerse you in the sights, sounds and flavors of Cuba that we know so well. Rest assured that each one of our people-to-people departures is always custom designed; you’ll never find us offering a “cookie cutter” tour.  

Read on to learn more about the insightCuba experience, browse our Signature tours below. Feel free at anytime to contact our team of travel specialists with questions: 1-800-450-CUBA (2822).

Signature Cuba Tours

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    Undiscovered Cuba

    13 Days / 12 Nights

    For those of you with a real zest for adventure and a desire to leave no stone unturned, this is the ultimate excursion. Learn More & Book Now!

    Next Date
    November 16, 2014

    Price
    $5695

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    Classic Cuba

    9 Days / 8 Nights

    Gain amazing insight and a genuine perspective of the people and places of Havana. Then travel beyond the capital and back in time when you explore the charming colonial town of Trinidad. Learn More & Book Now!

    Next Date
    October 25, 2014

    Price
    $4495

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    Scenic Cuba

    9 Days / 8 Nights

    Experience Havana and all of its cultural glory. Then journey to one of Cuba's most scenic areas to explore the province of Pinar del Rio, where the world's finest tobacco and incredible landscapes define the region. Learn More & Book Now!

    Next Date
    November 7, 2014

    Price
    $4495

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    Vintage Cuba

    7 Days / 6 Nights

    While Cuba is changing more than ever, its one-of-a-kind yesteryear is the inspiration for insightCuba’s newest tour: Vintage Cuba. This six-day trip takes guests on an extraordinary journey through Cuba’s colorful, complex history via the places and people who bring it to life. Learn More & Book Now!

    Next Date
    December 11, 2014

    Price
    $3795

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    Jazz in Havana

    6 Days / 5 Nights

    Join insightCuba for this spectacular opportunity to get up close and personal with Havana's vibrant Jazz scene. Discover how Jazz has thrived on this Caribbean Island by meeting the people behind the music. Learn More & Book Now!

    Next Date
    November 25, 2014

    Price
    $3495

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    Weekend in Havana

    5 Days / 4 Nights

    For the traveler with little time but a lot of interest, insightCuba offers 4 Days and 3 Nights jam-packed with cultural highlights and authentic Cuban experiences in Havana. Learn More & Book Now!

    Next Date
    December 23, 2014

    Price
    $2795

Specialty Cuba Tours

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    Havana Marathon 4-Day Tour

    4 Days / 3 Nights

    Want a chance to see Cuba while it’s still legal for Americans to do so? Better run! For only the second time in 50 years, insightCuba offers U.S. runners the opportunity to legally take part in the Marabana Havana Marathon and half-marathon, under a special amateur sports license issued by the U.S. Department of the Treasury. Learn More & Book Now!

    Next Date
    November 14, 2014

    Price
    $2495

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    Havana Marathon 8-Day Warm-Up Tour

    8 Days / 7 Nights

    Are you like 99% of all Americans and never been to Cuba? Want a little extra mileage from your visit to Cuba? Then join us on the Havana Marathon 8-Day Warm-Up tour. This tour gives you a chance to learn the lay of "the land" before the big race. Learn More & Book Now!

    Next Date
    November 10, 2014

    Price
    $4395

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    Havana Marathon 8-Day Cool Down Tour

    8 Days / 7 Nights

    Want to discover more of Cuba after seeing 26.2 miles of it, or 13.1 if you prefer? Then join us on the Havana Marathon 8-Day tour Nov 14 – Nov 21, 2014. This tour gives you a chance to explore Cuba after the big race. Learn More & Book Now!

    Next Date
    November 14, 2014

    Price
    $4395

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    Cuba by Land & Sea

    12 days / 11 nights

    A land so diversely rich as Cuba’s isn’t easily defined. Whether you’re drawn by its renowned cities or by its unexplored blue waters, the island beckons to be fully explored. From its most classic sights, all the way to its most sheltered, why should you settle? Learn More & Book Now!

    Next Date
    January 6, 2015

    Price
    $4995

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    Havana Art Biennial

    7 Days / 6 Nights

    Havana, Cuba’s capital and the world’s most sought-after time capsule, is often referred to as the cradle of colonial architecture—a mirage of exuberant color, rhythm and faded glamour. It’s all of that, and so much more. Learn More & Book Now!

    Next Date
    May 22, 2015

    Price
    $4195

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    Baseball in Cuba

    7 Days / 6 Nights

    For years—five decades, actually—Cuba was off limits to its near neighbor. An island nation rich in culture, heart-warming people, explosive rhythms, and BASEBALL is waiting to be explored at last. Learn More & Book Now!

    Next Date
    December 12, 2014

    Price
    $4395