CUBA
Cuba is dim corners, peeling paint, a saxophone player working a side street in Centro Habana at 11pm, salsa pouring from a second-floor window onto a street where five generations of one family are sitting on the curb together because that's where the breeze is. After visiting Cuba, people feel like they've been on a far-off adventure, even though they were just off the coast of Florida. Cuba attracts people for all of the famous things they are known for—classic cars, rum, cigars, dance, music—but the experience stays with them because of the people they meet and the amazing stories they share about resilience, creativity, and strength against the odds.
A Taste of What's Possible
Visit the home of a Cuban Chef and learn about the challenges of preparing gourmet food in Cuba with limited resources.
Spend the day in a hidden nook of Viñales at the home of a local Cuban farmer, learning the family's story and exploring the tobacco farm via ox cart.
Explore a contemporary art gallery with a young Cuban curator and visit with two local artists in their home studios over coffee.
Where You'll Stay
We spend a lot of time obsessing over the perfect accommodations. Our favorites tend to be smaller, boutique properties with a unique sense of style and fantastic service.
Here are just a few of our favorites...
Three of Our Favorite Spots
ViñALES
01
The mogotes — those improbable limestone towers — rise straight out of tobacco fields that have been worked the same way for centuries. Mount a horse or bicycle, find a valley road, and let the afternoon disappear. This is quintessential Cuban rural life.
CIENFUEGOS
02
A port city of neoclassical elegance, wide boulevards, and a sense of order that feels nothing like the rest of Cuba. Spend a slow afternoon at the Malecón watching the bay turn copper at sunset, and you'll understand why Benny Moré sang about this place his whole career.
TRINIDAD
03
A perfectly preserved colonial sugar town where the cobblestones have been worn smooth by 500 years of feet and the music starts in the Plaza Mayor around eight and doesn't stop until sunrise. Stay long enough to hear the difference between son and bolero, and to delight in getting to say 'canchanchara' to the bartender one more time.
“At a quick glance, Cuba appears in a surreal state, paused in time with classic cars, historical, neoclassical architecture, antiques, and other ubiquitous homages to the past. However, if one looks deeper, into the soul of Cuba today, one finds a rapidly changing and developing culture of entrepreneurship bubbling with hope, excitement, and opportunity.”
– Cynthia Carris Alonso // Cuban author
Sample Itinerary
Vintage Cars, Tobacco Farms, and Cobblestones: Cuba in Seven Days
Day 1: Welcome to Cuba! On arrival in Havana, you will be met in the arrivals hall and escorted to your private vehicle for the comfortable transfer to your luxurious accommodations. Enjoy an authentic Cuban dinner to kick off your adventure
Day 2: Step back in time and explore the colonial history of Habana Vieja (Old Havana) before hopping into a vintage convertible for a cruise of the city’s highlights. Finish the day with an invigorating salsa lesson and dine under the stars at a local favorite rooftop.
Day 3: Venture to the countryside of Viñales, home to breathtaking limestone cliffs and tobacco farms. Learn the secrets to rolling the perfect cigar at a multi-generational family farm, then take in the views of the colorful cliffs before returning to city life.
Day 4: Dive into Cuban culture today, hands-on. Start by preparing a classic Cuban meal before meeting with local artists during a private studio tour. Collect local finds at the artisan craft market, and enjoy a rum tasting while learning the history of the island’s iconic spirit.
Day 5: Travel by private vehicle from Havana to Trinidad, with a stop en route to visit the historic French town of Cienfuegos for lunch. Settle into your lovely accommodations in one of Cuba’s oldest cities, and enjoy a delicious dinner along the Plaza Mayor.
Day 6: Start the morning with a local cup of coffee as you visit the home of a local coffee farmer. Feeling energized, take a dip in the waterfalls of Topes de Collantes and hike the lush surroundings. Spend the afternoon relaxing on the beach, taking in the turquoise waters (and perhaps a mojito!).
Day 7: In good time for your flight today, you'll journey back to Havana Airport for departure.
