cuba

11 days/10 nights: March 5-15, 2026

Detour with dean

As soon as you think you know Cuba, it changes. This small country is in constant flux, with shifting currencies, rules, and political landscapes making it hard to grasp in a given moment. It takes slowing down to appreciate its nuanced elegance. When I first visited Cuba in 1997, I was seduced by the tough-as-nails spirit of its people. I felt the powerful salsa of energy bouncing off every street, mural, and alley. The rich scents of fresh coffee, fine rum, hand-rolled cigars, and the salty Caribbean etched their way into my memories. If you embrace uncertainty and step away from Western norms, Cuba will reward you in ways you never expected.

highlights include

  • Cruise Havana’s colorful streets in a vintage Cuban car

  • Relive Hemingway’s Havana from Cojímar to Finca Vigía

  • Pulse to Afro-Cuban rumba in Callejón de Hamel

  • Roll cigars and savor rum in Viñales’ karst country

  • Dive into Cold War history snorkeling in the Bay of Pigs

  • Explore Trinidad’s colonial charm

  • Salute Che Guevara’s legacy in revolutionary Santa Clara

itinerary

“If you tremble with indignation at every injustice, then you are a comrade of mine”
— Ernesto "Che" Guevara

Cuba is an island pulsing with contrasts. Classic Chevys rumble past horse-drawn carts under Havana's crumbling grandeur. Salsa rhythms ignite smoky clubs while guitars strum in rural villages to the setting sun. Education and healthcare shine, a testament to revolution's ideals, yet scarcity lingers, a reminder of life under an embargo's grip. Cuba, a land of contradictions, cradles both resilience and longing, its beauty etched in weathered smiles and sun-bleached flags. We’ll embrace the island’s rhythm of revolution and romance on this detour through Cuba’s contrasting communities.

day 1: ¡Bienvenidos a Cuba!

Thursday, March 5, 2026

Havana hums with history, from classic cars to the echoes of revolution. After a siesta, we’ll meet in the early evening at our hotel before setting out to explore. Our first stop is the Plaza de la Revolución, where towering murals of Che and Camilo watch over the city. Then, we’ll toast our adventure with mojitos at the iconic Hotel Nacional Gardens. As the sun sets, we’ll enjoy our first taste of Cuba together over a group dinner, enjoying the musical pulse of Havana. Welcome to Cuba!

Hotel: Azul Habana | Meals: B, D | Activity Level: Strenuous

day 2: colonial havana

Friday, March 6, 2026

This morning we enjoy new discoveries in Old Havana. on a guided tour of this UNESCO World Heritage Site. Havana houses a labyrinth of cobblestone streets lined with colorful buildings showcasing Havana’s Spanish colonial and Baroque architecture. After lunch, we’ll visit the National Museum of Fine Arts showcasing artistic movements from colonial to contemporary times. After a siesta, we’ll cruise Havana in classic vintage cars, enjoying the city's lively energy from a classic perspective. As the sun sets, we’ll enjoy a Cuban specialty dinner before heading to the at Fábrica de Arte Cubano, a dynamic cultural space where live music, art, and energy fuse.

Hotel: Azul Habana | Meals: B, L, D | Activity Level: Strenuous

DAY 3: Guevara & Hemmingway

Saturday, March 7, 2026

Apart from their first names, Ernesto “Che” Guevara and Ernest Hemmingway had two things in common: a deep affinity for Cuba, and a love of the written word. Today we’ll get to know them both on a visit to Hemmingway’s home, where he wrote some of his most famous works, including The Old Man and the Sea. We’ll grab lunch in the seaside town of Cojimar before visiting Guevara’s Morro-Cabaña Fortress, housing the Cuban revolutionary’s headquarters during the Cuban missile crisis before returning for a well-earned siesta. This evening we’ll get our groove on over dinner and dancing at the Muraleando Community Art Center.

Hotel: Azul Habana | Meals: B, D | Activity Level: Moderate

Day 4: Rumba & Afro-Cuban Roots

Sunday, March 8, 2026

Rumba, a traditional Cuban dance with deep Afro-Cuban roots, is a lively expression of Cuba’s African heritage, blending rhythmic drumming and passionate movements. After a leisurely morning, we’ll experience this cultural gem at Callejón de Hamel, where the streets pulse every Sunday with the sounds of rumba, drawing on Cuba’s rich religious and musical history. The afternoon offers free time, with an optional excursion to Las Playas del Este, a serene beach just outside Havana. Our last Havana evening is yours to soak up some jazz or a visit to the iconic Tropicana.

Hotel: Azul Habana | Meals: B | Activity Level: Moderate

day 5: Havana to Viñales

Monday, March 9, 2026

We bid Havana “hasta la vista” and set out for Viñales, Cuba’s western gem. We stop first in Fusterlandia, a vibrant art community where colorful mosaics and murals transform the neighborhood into an open-air gallery. After getting inspired by the creative spaces, we’ll stop for lunch in Las Terrazas, a picturesque eco-village known for its lush landscapes. We’ll then press on to Viñales, a stunning valley famous for its dramatic karst mountains and rich tobacco farms. By late afternoon, we arrive in Viñales, check into our accommodations, and gather for a relaxing dinner together, raising a rum to the day’s adventures.

Hotel: Casa Ana Luisa y Jorge | Meals: B, L, D | Activity Level: Light

day 6: The art of Tobacco

Tuesday, March 10, 2026

Today we enjoy the breathtaking landscapes of Viñales Valley, where dramatic karst mountains rise above lush farmland. Our morning begins with a guided trek through this stunning region, offering panoramic views and a glimpse into rural Cuban life. We’ll then visit a traditional tobacco farm to learn about the art of cigar-making firsthand from local farmers. A hearty, farm-to-table lunch awaits us at Finca El Paraíso before we continue to El Despalillo, a tobacco processing farm. The afternoon is yours to relax or explore Viñales at your own pace before enjoying dinner at a locale of your choice.

Hotel: Casa Ana Luisa y Jorge | Meals: B, L | Activity Level: Moderate

day 7: Bay of Pigs

Wednesday, March 11, 2026

Leaving Viñales behind, we journey to Playa Larga, a tranquil coastal village on the Bay of Pigs. Upon arrival, we’ll head to Caleta Buena, a stunning natural pool teeming with marine life—perfect for snorkeling in crystal-clear waters. We’ll enjoy a leisurely lunch by the sea with plenty of time to take in the marine life. After checking into our accommodations, we’ll end the day with a delicious dinner at a local restaurant, savoring fresh seafood and Cuban flavors by the water’s edge.

Hotel: Horizontes Playa Larga | Meals: B, D | Activity Level: Moderate

day 8: Cienfuegos to Trinidad

Thursday, March 12, 2026

This morning, we shift from nature to history with a visit to the Girón Museum, where we’ll uncover the dramatic story of the Bay of Pigs invasion. We’ll then press on to Cienfuegos, the “Pearl of the South,” known for its elegant French-inspired architecture and seaside charm. After lunch, we continue to Trinidad, a perfectly preserved colonial town frozen in time. Cobblestone streets, pastel-hued buildings, and lively plazas welcome us. The evening is yours to soak in Trinidad’s old-world charm—perhaps with a sunset stroll or a sip of canchánchara, the town’s signature honey-lime cocktail.

Hotel: Casa Zenia | Meals: B | Activity Level: Moderate

day 9: Trinidad

Friday, March 13, 2026

Step back in time as we explore Trinidad, a perfectly preserved colonial town and UNESCO World Heritage Site. Founded in the 16th century, Trinidad flourished during the sugar trade boom, leaving behind grand mansions, cobblestone streets, and vibrant plazas. Our walking tour takes us through Plaza Mayor, flanked by pastel-hued buildings and historic churches, and into the Palacio Cantero, a mansion-turned-museum showcasing the town’s opulent past. Fill your free afternoon with a visit the Romantic Museum, browse local crafts, or sip canchánchara. In the evening, dance beneath stalactites at Cueva Ayala, a cave-turned-nightclub.

Hotel: Casa Zenia | Meals: B | Activity Level: Moderate

day 10: Santa Clara to Havana

Saturday, March 14, 2026

Our journey through Cuba’s revolutionary past culminates in Santa Clara, a city forever tied to Che Guevara’s legacy. At the Che Guevara Mausoleum and Museum, we’ll honor the iconic revolutionary, whose decisive 1958 battle here led to the fall of Batista’s regime. The museum offers a glimpse into his life, from guerrilla warfare to global activism. This afternoon we reutrn to Havana where we’ll enjoy a final mojito before our farewell dinner, reminiscing about our adventure and toasting to the spirit of Cuba’s history, music, and culture.

Hotel: Azul Habana | Meals: B, D | Activity Level: Moderate

day 11: Detour Over

Sunday, March 15, 2025

This morning, we say “hasta la vista” to Cuba, reflecting on the unforgettable experiences, rich history, and vibrant culture we've encountered. We’ll help arrange transportation to the Havana airport, carrying with us our memories of music-filled nights, colonial streets, and Cuba’s revolutionary spirit.

$5,895 per person double occupancy

+$1,000 per person single supplement

$10% deposit

Save $300 with EARLYPAY coupon until July 5

FAQs

  • Can Americans legally visit Cuba?

    Yes, but not for tourism. U.S. citizens can visit under 12 authorized categories, including educational and people-to-people exchanges—which is exactly what we do. These requirements simply formalize what our trip is all about: immersing ourselves in Cuba’s history, culture, and daily life.

    Do I need a visa?

    Yes, you’ll need an e-visa to travel to Cuba. Don’t worry, we’ll help you with the simple process when the time comes.

    How do I get there?

    Currently, there are direct flights to Cuba from Houston, Tampa, and Miami. If that changes, we'll keep you updated and make any necessary adjustments.

    Can I use ATMs in Cuba?

    ATMs in Cuba don’t accept U.S. cards, so bring cash. We’ll help you plan a budget and exchange your money at the best rate.

    Is there WiFi?

    Yes, but it’s slow. Hotels have WiFi, and your phone should work, but think if it as an excuse to unplug.

    Will U.S. policy changes affect this trip?

    While we can’t predict the future, historically, changes in U.S. policy haven’t impacted already-booked trips. That’s why we’ve locked in hotels for 2026. While the future is uncertain, we’re making sure everything is in place so we don’t miss out.

    Is travel insurance hard to get?

    No. We recommend World Nomads for trip cancellations and medical emergencies. Plus, Cuban health insurance is included with flights from the U.S. and Europe.

    Is Cuba safe?

    Yes, Cuba is generally considered a safe destination for travelers, especially in tourist areas. The country has a low violent crime rate, and the local authorities take safety seriously.

  • Each detour includes the price of all admissions to sights seen as a group; tours by local guides, meals as listed in the trip itinerary; accommodations each night of the detour including breakfasts; all domestic flights; all transportation required for group activities from the first hotel to the last hotel of the detour including in er-country flights (transportation for optional group activities and independent travel during the detour is not included), travel consultations and advice from our staff, guides, and vendors including suggestions, tips, and directions, and all trip leader, local guide, driver, and hotel tips. Prices do not include airfare to and from the detour, nor ground transportation to/from airports.

  • Detour prices do not include international airfare or ground transportation to/from the airport.

  • Each detour includes all breakfasts and about half of your lunches and dinners as indicated in the meal guide included in each itinerary: B=breakfast, L=lunch, D=dinner.

  • Yes! Our detours are the perfect way for children (and adults) to learn in action. We welcome and celebrate multi-generational travel. History class was never so fun!

  • Our detour begins and ends in Havana. Please book your airfare into and out of José Martí international Airport (HAV).

  • While this varies by detour, we generally plan to meet between 5-6 pm at our hotel on Day 1. If you plan to arrive a day early and want to stay in our trip hotel, please make arrangements with the hotel directly, indicating that you are part of our group.

  • Please plan to fly in and out of José Martí international Airport (HAV).

  • Each trip page has a “book now” button that links to our online registration and payment system. There you can pay the 10% per person deposit and choose to pay in installments or to pay the full amount.

  • Deposits are refundable for 30 days from receipt. After 30 days they are nonrefundable.

  • Final payment is due 90 days prior to detour commencement but you may pau in full any time prior to this.

  • Cancellations are allowed without penalty (excepting deposit) until the final payment deadline. After the final payment deadline 100% of funds paid are nonrefundable.

  • Each trip page has a “book now” button that links to our online registration and payment system. There you can pay the 10% per person deposit and choose to pay in installments or to pay the full amount.

  • Yes, all published prices are per person, based on double occupancy, or when available, single occupancy. Please contact us for triple occupancy pricing.

  • During the registration process you will have the opportunity to request single occupancy, if it is offered. Due to the boutique nature of our hotels, we are not always able to offer single accommodations, but are happy to pair you with another single traveler.

  • Yes. You must be able to carry your own luggage up at least three flights of stairs and on uneven ground for up to a quarter mile.

  • Dressler Detours are physically demanding. To enjoy the experience, you must be in good walking shape. The most active days may average 5 miles of walking (often over uneven surfaces and including lots of climbing/steps), lots of standing while listening to your guide during group sightseeing, and possibly stair-climbing while carrying your own bag up to your hotel room. This detour includes boat travel as well. We’ve included an activity guide for each day of our itinerary: light=mostly sedentary, moderate=walking 1-3 miles on mostly even ground, strenuous=walking 3+ miles on hills/uneven ground.