Havana Cultural Walking Tour

Absolutely. Havana’s magic is found in its bustling plazas, charming side streets, and hidden courtyards. Walking through this historic city allows you to move at a relaxed pace, stop for encounters with locals, and soak up the atmosphere – often with live music being played on street corners – as you immerse yourself in Cuba. Unlike bus tours or large groups, you’ll be in the middle of the action with expert local guides who’ll give you insider access and ‘only with Classic Journeys’ experiences that you’ll never forget. Exploring on foot each day, our curated walks include guided strolls through Havana, visits to cultural sites, and meetings with locals during exclusive encounters.

Our Havana walking tour blends iconic sights—like exploring Old Havana, riding in classic cars, and visiting a cigar factory—with exclusive experiences you won’t find elsewhere. You’ll enjoy ‘only with Classic Journeys’ access to experiences like visiting Hemingway’s home with the curator, meeting Castro’s personal photographer and sitting down with a diplomat for in-depth discussions into geopolitics. You’ll also cook alongside a local chef, enjoy private music performances, and get a private salsa lesson, as well as engage in conversations with entrepreneurs and artists along the way. These exclusive encounters go far beyond what an independent traveler or a large tour group could arrange, giving you an inside look at life in Havana.

You can rest assured that Classic Journeys operates fully under the general license in 31 CFR § 515.574, “Support for the Cuban People,” authorized by the U.S. Department of the Treasury. This means your trip to Havana is both legal and designed to maximize authentic cultural exchanges with local entrepreneurs, artists, and communities. All compliance details are seamlessly handled on your behalf, as all Classic Journeys Cuba travel programs are operated under the authority of the U.S. Treasury Department’s Office of Foreign Assets Control (OFAC).

Our Havana trip includes most meals, expert local guides, all cultural activities listed in the itinerary, and stays in carefully selected casas particulares (privately owned and beautifully restored mansions) that reflect Cuban character and hospitality. You’ll eat like (and with) the locals as your meals feature a mix of paladares (family owned restaurants), chef-hosted experiences, and curated group dinners. This ensures both comfort and immersion in Cuba’s traditions while being in full compliance of the U.S. Treasury Department’s Office of Foreign Assets Control (OFAC), pursuant to the general license in 31 CFR § 515.574, Support for the Cuban People. What’s not included are international flights, gratuities for your tour leader, and any personal expenses. Our Travel Experience Team can provide clear guidance on arranging flights on regularly scheduled commercial flights, packing tips, and answer any questions to ensure that you’re fully prepared before departure.

Booking our Havana tour is simple and secure. You can reserve your spot online directly or by communicating with our Travel Experience Team. They can be reached by calling 800-200-3887, emailing moreinfo@classicjourneys.com, or by communicating with the online chat feature. With small group sizes, spots are limited, so we recommend reaching out and booking early to guarantee your preferred dates to experience the best of Havana. After booking, you’ll have a dedicated Guest Services Coordinator who will be your pre-trip concierge. They will be your Havana tour expert who is available to answer questions and assist you along the way, even calling you while on tour to make sure you are having the trip of a lifetime.

When you travel to Havana in our small group—usually fewer than 10 guests and never more than 18—you’ll get access, flexibility, and genuine connections on tour in Cuba. This ensures personalized attention from your expert local guides as well as camaraderie from your travel companions while exploring Havana

Yes, if you’re heading to Cuba, U.S. citizens must have a visa known as the Cuba Tourist Card or eVisa before travel. The visa process is straightforward, and your Guest Services Coordinator at Classic Journeys will handle it promptly and effortlessly on your behalf. For more information and to start your application, visit the U.S. Department of State’s Cuba travel page here: Cuba Visa Services – Apply for a Cuba Tourist Card with our Cuban Visa online application before your travel to Cuba. We’ll make sure your visa is ready so you can focus on exploring Havana.

Flying to Cuba is easier than ever—no need for charter flights. There are scheduled commercial flights from key U.S. cities such as Miami, New York, Houston, Dallas, and Atlanta served by American, Delta, United, Southwest, and JetBlue. Your Classic Journeys Guest Services Coordinator is here to help select the best flight options for your schedule, making travel to Havana simple and worry-free.