Welcome to Our Cuba Fundraising Adventure!

November 7-16, 2025

We are so excited that you're considering joining us on an unforgettable journey to Cuba—an island filled with vibrant culture, powerful history, soulful music, and resilient communities. This is more than just a trip; it's a chance to experience Cuba beyond the guidebooks and to make a lasting impact through community-based travel.

At Crooked Trails, we design immersive experiences that provide travelers with a deeper understanding of the places they visit, while also supporting local communities. On this trip to Cuba, you’ll not only explore the rhythms, flavors, and landscapes of the island, you’ll also contribute to grassroots initiatives that empower Cuban families and artists, support sustainable tourism, and uplift cultural preservation efforts.

This journey supports Crooked Trails’ mission of using travel as a force for good. A portion of your trip fee will be directly invested into local partnerships that sustain education, arts, and livelihood projects in the communities you'll visit. Whether you’re dancing in Old Havana, hiking in Viñales, or dining with locals, you’ll be part of a story of solidarity, resilience, and shared humanity.

Please read on for the full itinerary, dates, and details!

November 7-16, 2025

TRIP COST: $2995 pp

(Single supplement: $450)

Does not include international flights, visa, travel insurance, alcohol, tips, or personal items.

ACTIVITY LEVEL: Moderate

(Walking tours, light hiking, warm weather, cultural immersion)

CUBA FUNDRAISING ADVENTURE ITINERARY

(Itinerary subject to change as logistics are confirmed)

DAY 1 / Havana Arrival and Welcome

• Arrive at José Martí International Airport in Havana

• Transfer to a casa particular (guesthouse) in Havana

• Sunset walking tour of the historic district and drinks on the patio of the historic Hotel Nacional.

• Welcome dinner at a Neighborhood Paladar (family restaurant).

DAY 2 / Havana - History, Art, and Culture

• Guided tour of Havana’s historical sites with local historians in Old Classic American Cars.

• Visit community-run art project like Callejon de Hamel, Fusterlandia and Muraleando.

• Special afternoon with famous artists and musicians in local home.

DAY 3 / Havana to Viñales – Tobacco, Valleys, and Rural Life

• Scenic drive to the Viñales Valley, a UNESCO World Heritage Site

• Stop at local artists home for lunch and farm visit

• Arrive in Viñales and settle into a rural guesthouse

• Sunset walk and mojito-making lesson with local hosts.

DAY 4 / Viñales – Horseback Ride and Homestay

• Guided ride through tobacco farms and mountains.

• Visit with campesino farmers to learn about traditional tobacco farming.

• Lunch at a local farm

• Evening cultural exchange with music and dinner at a homestay

DAY 5 / Viñales to Havana – Music and Community Connection

• Morning return to Havana

• Stop at a sustainable artisan project led by youth in eco-village

• Optional afternoon salsa dancing workshop in Centro Habana

• Dinner at a famous paladar.

DAY 6 / A Day with Hemingway – Literature, Legacy, and Leisure

• Morning visit to Finca Vigía, Hemingway’s Cuban home in San Francisco de Paula

• Stroll the preserved estate and read excerpts of The Old Man and the Sea

• Enjoy a countryside picnic lunch inspired by Hemingway’s favorites

• Afternoon visit to Cojímar, the fishing village that inspired his writing. Try the Hemmingway margarita.

• Chocolate, coffee, and cigar pairing experience with a local expert

• Afternoon seaside walk and reflections on Hemingway’s legacy

• Overnight in Cojimar by the sea.

DAY 8 / Matanzas – Music and Master Artists by the Sea

• Day trip to Matanzas, birthplace of rumba and Afro-Cuban culture

• Visit to the renowned Taller de Lolo (or similar artist’s workshop)

• Lunch at a seaside paladar overlooking the Bay of Matanzas

• Cultural Exchange with local Santeria Babalawo (Father of Secrets)

• Private concert by local musicians on the shore at sunset

• Return to Havana for overnight lodging.

DAY 9 / Havana – Local Lives and Farewell Celebration

• Spend the day connecting with a local NGO or social project

• Optional: Museo Nacional de Bellas Artes (National Museum of Fine Arts) or Museo de

la Revolución (Museum of the Revolution)

• Free afternoon for shopping or relaxing

• Farewell Celebration at Fabrica de Arte.-a cutting-edge, multi-disciplinary cultural

center housed in a converted 1950s olive oil factory It fuses contemporary art, live

music, performance, fashion, film, photography, and design under one industrial roof.

DAY 10 / Departure

• Breakfast and reflection circle

• Transfer to José Martí International Airport for departure

Your participation in this trip not only enriches your life through unforgettable experiences but also uplifts Cuban communities through real support and friendships.

We can’t wait to explore Cuba with you!

If you have any questions or would like to learn more about the projects we support,

please don’t hesitate to reach out. www.crookedtrails/contact-us

Gracias y nos vemos pronto,

The Crooked Trails Team