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Cuba Walking Tour

Cuba is one of the most fascinating islands in the world and offers unique natural and cultural experiences for those seeking an active cultural tour. This easy walking tour takes you through verdant jungles and past fields of tobacco while also experiencing the vibrant musical and cultural traditions of Cuba. Americans are allowed to travel legally in Cuba and we’ll help guide you through the process. Join us in 2025 for what we hope will be the first of many walking trips to this amazing island!

Duration: 9 nights / 10 days
Dates: 2025: Feb 16 - 25
Trip starts/ends: Mid-day Day 1, Havana; afternoon Day 10, Havana
Activity level: 2 -- GENTLE: easy walks on rolling terrain plus lots of city walking [more info]
Group size: min 8 - max 14


* explore Old Havana with a local guide
* visit the colorful city of Viñales
* walk among surreal limestone peaks called mogotes 
* tour Ernest Hemingway’s former estate
* visit a farm-to-table restaurant to make local dishes and the perfect Mojito
* visit a lush orchid garden
* learn about traditional cigar culture, including the growing, drying, and rolling of tobacco
* explore the cobblestone streets of historical Trinidad
* walk to two waterfalls in tropical jungle settings
* enjoy private concerts with local musicians
* try and cigar & rum pairing
* try your hand at Afro-Cuban percussion
* ride in Havana’s famous Classic Cars
* take a salsa lesson
* relax on a beautiful beach (Feb/March is perfect for swimming!)
* eat at the best private restaurants, known as paladares

Trip price includes

9 nights in a mix of comfortable B&Bs; 9 breakfasts, 4 dinners and 9 lunches; all visits and transfers as per itinerary; at least 1 bilingual guide to accompany you throughout the week

Not included

5 dinners; drinks other than water at meals; Cuban visa (or “tourist card”); and anything not listed in the inclusions


Days 1 – 2: Welcome to Havana!
Start your adventure in vibrant Old Havana, whose colonial buildings and sunny squares welcome you with bright colors and music spilling out of every doorway. We’ll learn about the region’s fascinating history with a licensed city guide, visit the iconic Hotel Nacional, ride in a Classic Car down the Malecon waterfront, visit Ernest Hemingway’s former estate, and take in some fabulous music and dance performances. Our hotel in Havana is a lovely upscale B&B built into one of the city’s historic old buildings. Watch the sunset from the hotel rooftop and enjoy delicious dinners in town. 2 Nights Old Havana.

Days 3 – 4: Viñales and the Mogotes of Pinar del Rio
Explore the countryside west of Havana for two days in the Viñales Valley, famous for its rounded limestone peaks called mogotes as well as vast fields of tobacco. We’ll walk through a fragrant orchid garden and past a rushing waterfall where you can take a dip to cool off. We also have two lovely walks through the verdant countryside, into suggestive caves, past traditional homes and farms, and into the rolling hills (walks are max 6 km/4 mi but there is more walking in the towns we visit). 2 Nights Viñales at a comfortable private B&B.

Day 5: Return to Havana
Return to Havana for a day to rest up, see some more sights, or hit the beach! Overnight Old Havana. 

Days 6 – 8: The Colonial City, Beaches and Waterfalls of Trinidad
Head south for three days in one of the most beautiful towns on the island, Trinidad, a UNESCO World Heritage protected site for its unique architecture and historical importance in the Caribbean. We stay in a restored private home with colorful floor tiles and Old World charm. Dine at some of the best paladares in the region and enjoy live music and salsa dancing once the sun goes down. We have two walks to wonderful waterfalls in the lush hills nearby (max 6 km/4 mi. each plus lots of walking in town) and then time to relax on a gorgeous sandy beach. 3 Nights in Trinidad in a renovated colonial-style B&B. 

Days 9 & 10: Final day in Havana and Departures
Drive back to Havana and enjoy a magical afternoon with a famous local dance troupe, who will show you how the island’s Afro-Caribbean rhythms captivated and inspired musicians and dancers around the world. We have one final dinner together before saying a fond “Adios” to Cuba on Day 10. We’ll provide you with suggestions on flights, travel insurance, and getting your visa so don’t hesitate to ask if you have questions! Overnight Old Havana. 

Both Manu and Claire are planning on coming on this inaugural tour, so we hope to see you there!