Cuba’s rich history, vibrant art, and welcoming soul make it a bucket-list destination—and yes, traveling to Cuba is completely legal for Americans when done correctly. This tested Cuba travel guide is based on our firsthand experience navigating the island using the “Support for the Cuban People” travel license.
At Travel Deliciously, we believe in immersion. Our recent journey focused on Cuba’s prized national treasure—tobacco—while taking an in-depth look at traditional Cuban paladares and spirits. If you’re looking for an authentic Cuba travel itinerary, here is exactly how we spent five unforgettable days.
The Magic of Havana
Day 1: Classic Cars and Sunset Drives
With our travel visas secured, we arrived in Havana to begin our adventure. Our Cuba travel itinerary kicked off with a panoramic tour of the city’s emblematic landmarks: the 18th-century University, the historic Paseo del Prado, and the eye-catching Capitol.
The Highlight: A fleet of antique American cars met us at the Four Points by Sheraton. Our drivers—masters of keeping these “rolling museums” running—took us to a local paladar (privately owned restaurant) for a welcome dinner. Pro tip: Time your drive for the sunset; seeing the Havana skyline change colors from the back of a convertible is stunning.
Day 2: Old Havana and Cigar Factories
No Cuba travel guide is complete without a deep dive into the craft of cigars. We visited the Romeo y Julieta factory for a behind-the-scenes look at how these world-renowned products are hand-rolled.
Afterward, our escort Yasel led us on a walking tour of Old Havana. We recommend stopping to chat with local vendors at the San Jose Craft Market to get a feel for the heartbeat of the city.
Day 3: Hemingway and Choice Adventures
We began the day at Finca Vigía, the Ernest Hemingway House & Museum, followed by a visit to the Revolution Museum. For the afternoon, our travelers chose their own path:
The Cigar Tasting – A rum and cigar pairing at Conde de Villanueva.
The Food Walk – Sampling local chocolates, Cuban coffee, craft beer, and street foods from hidden gems in the city.
The Valleys of Viñales
Day 4: Tobacco Farms and Mogotes
We checked out of Havana and headed west toward the Viñales Valley, a UNESCO World Heritage site. This is a crucial stop for any Cuba travel itinerary.
Los Jazmines Lookout – The best spot to see the “mogotes”—unique limestone mountain formations.
Casa de Benito – We visited a local farmer’s home to learn about tobacco growing and traditional rolling techniques.
Traveler Tip – We also explored the nearby caves, which include an underground boat ride—a “must-do” that we have officially added to our future tested guides.
Day 5: Organic Farms and Farewell
Our final day in the countryside offered a choice between horseback riding through the valley or a tobacco stripping facility tour. We enjoyed a farewell lunch at Finca Paraiso, an organic farm that offers the best countryside views on the island, before heading back to Havana for our final night.
Why Follow This Cuba Travel Itinerary?
Legally Compliant – This guide is built around the “Support for the Cuban People” license, ensuring you support local entrepreneurs.
Tested & Verified – We’ve walked these streets, eaten at these paladares, and met these farmers.
Small Group Intimacy – We focus on the “Chinese Fire Drill” moments of joy that you can’t get on a big bus tour.
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