Travel to Cuba from the United States is near to impossible — or is it? While travel to Cuba has been mired for decades in the shifting sands of red tape, bureaucracy, and a complex network of outdated laws, it’s much easier to travel from the United States to Cuba than most people think.
In fact, now might be one of the best times to visit Cuba in recent years, especially when locals and experienced travel guides take care of all the details. A brand-new, tailormade travel experience in Cuba offered by Geographic Expeditions (GeoEx) does that, tapping local guides to help travelers experience this bucket list destination easily — and legally — while the experts sort out the details.
US Travel to Cuba
Historically, Cuba has felt much further from the contiguous U.S. than the 90-mile stretch of sea separating the two. However, travel between both countries has become easier over the last decade.
President Barack Obama’s 2014 Cuban thaw made it possible for many Americans to travel to Cuba without prior authorization from the United States government. His visit following these changes made him the first president to visit Cuba since Coolidge’s trip in the 1920s.
Though the Trump administration rolled back select Obama-era changes facilitating Cuban travel — including U.S. passport holders’ ability to visit the country for tourism purposes — the island remains more accessible than most Americans realize.
While American travelers should exercise caution — and even avoid specific Havana hotels off-limits to travelers with a U.S. passport — visitors can come to the island in “support of the Cuban people.” This designation means patronizing small, locally-owned businesses rather than government-run companies, hotels, or tour groups.
Local Experts, Hassle-Free Trip
The Biden administration has since modified some Trump-era restrictions, but for American travelers, help from niche travel companies like GeoEx simplifies Cuban excursions.
In January 2025, the specialty travel company, whose 40 years of experience connects adventurers to hard-to-access destinations, will add Cuba to its itinerary for the first time.
“We are thrilled to unveil this new trip to captivating Cuba,” says Brady Binstadt, CEO of Geographic Expeditions. “GeoEx has been navigating the country’s landscape for over 25 years, and our deep in-country expertise and longtime local guides ensure an extraordinarily immersive and impactful experience.”
Now available for booking with departure dates starting in the new year, GeoEx’s bespoke “The Soul of Cuba” excursions connect small groups — capped at one dozen guests per expedition — to some of the island’s leading cultural, historical, and culinary offerings.
The Soul of Cuba
The eight-day itinerary begins in the bustling, complex Cuban capital city of Havana. Travelers will enjoy meticulously planned, behind-the-scenes cultural encounters like a private dominoes club visit, a food market shopping tour led by the manager of a locally owned restaurant, and a hiking excursion outside of Havana culminating in a farm-to-table lunch.
The GeoEx itinerary leads guests to the historic, charming cities in the island’s center. Among them is Cienfuegos, with its surprising French influence and dramatic architecture, and the UNESCO-protected coastal town of Trinidad, considered one of the most well-preserved Spanish colonial cities in the Caribbean.
Car enthusiasts can visit a car restoration workshop for an opportunity to drive the island’s emblematic almendrones, or vintage American cars. Additionally, tourists can indulge in expert rum and cigar pairing experiences or connect with former diplomats to discuss U.S.-Cuba relations.
GeoEx Firsts
While the Cuban excursion marks the first time the brand transports travelers, its long-standing local connections promise the same reliability and enrichment as all other GeoEx trips.
Long specialized in off-the-beaten-path destinations, the company’s itineraries range from untouched destinations like Mozambique’s African Parks to countries like Saudi Arabia, Laos, Bhutan, and Madagascar. They encompass trips to 70 countries across all seven continents. These experiences are only made possible with the help of local guides with deep connections to their communities.
Additional upcoming new experiences for the company include a novel luxury exploration through East Indonesia, year-round expeditions to Istanbul & the Aegean Coast that combine cultural touring with luxurious days sailing the Aegean by private , and Cambodia: The Road Less Traveled, an intimate look into Cambodia’s little-visited southern landscapes.
Cuba Like a Local
For travelers looking to cross Cuba off their bucket list, GeoEx’s new Cuba experiences are fantastic news. In a destination like this one, where it can be extremely challenging to get off the beaten path, almost by design, local guides with first-hand expertise can make all the difference.
