Morning

• Arrive at Havana’s José Martí International Airport (HAV) in Cuba by 11 a.m., ready to begin your adventure.
• Your Trip Leader will pick you up from the airport, and we’ll head to the historic center of Havana! (~30-minute drive)
• Get settled into your locally owned accommodations and prepare for five exciting days ahead.

Afternoon

• Explore Old Havana, a UNESCO World Heritage Site, by walking its historic cobblestone streets to admire its colonial architecture. Iconic spots include Plaza de la Catedral, Plaza Vieja, Plaza de Armas, and the famous Bodeguita del Medio.
• A visit to a stained glass workshop, showcasing the work of young local entrepreneurs, offering you a chance to take home a unique souvenir from Cuba.
• To wrap up our experience, we'll enjoy a panoramic ride in classic American cars, owned by a local small business, cruising along the Malecón, through the modern Vedado district, and stopping at Revolution Square.

Evening

• Your first dinner and drinks in Cuba at a family owned restaurant, where you can enjoy traditional Cuban flavors, live music, and a mojito.
• Time to relax in your "casa particular" after your long travel day.

Morning

• After a delightful breakfast, we’ll head to Cienfuegos, the “Pearl of the South,” known for its elegant French architecture and stunning waterfront. 
• We’ll stop at the historic Bay of Pigs, about a two-hour drive from Havana. This iconic site, famous for the 1961 invasion, offers you a chance to swim and snorkel in the crystal-clear waters of Punta Perdiz or Caleta Buena, where you can explore vibrant coral reefs and tropical fish. This is a key opportunity to learn about the history of Cuba and it's natural ecosystem.

Afternoon

• The journey continues to Cienfuegos (~1.5-hour drive). Upon your arrival, you can admire the splendor of the neoclassical buildings that line the streets, each revealing its unique story. The gentle sea breeze and the soothing sound of waves lapping against the shore make the city's historic charm feel welcoming.
• Quick stop in Cienfuegos for a snack before continuing to Trinidad  (~1 hour drive).
• Trinidad, one of the best-preserved colonial gems in Latin America, will make you feel you’ve traveled back in time. As you wander through cobblestone streets adorned with pastel-colored houses, you’ll hear the rhythmic sounds of traditional Cuban music fill the air, transporting you to a bygone era.

Evening 

• Your accommodation for the next two nights will be in charming colonial-style casas particulares, so you can enjoy a cozy and authentic stay in the heart of the historic center. 
• Casas particulares are private Cuban homes licensed to host guests. They offer a more personal and authentic experience than hotels, featuring local hospitality, home-cooked meals, and a glimpse into everyday Cuban life.
• A delicious dinner at a local restaurant called a "paladar" will let you taste some of the exquisite Cuban specialties. Don’t miss ropa vieja, lechón asado, picadillo, and tostones!

Morning

• After breakfast prepared by your Cuban host in the casa particular, we’ll head to Marina Ancón to board our catamaran for a scenic journey across the crystal-clear Caribbean waters. Depending on the weather, the catamaran will set sail toward Cayo Iguana or Cayo Blanco, both known for their stunning beauty, soft white sands and vibrant turquoise seas.

Afternoon

• During the boat trip, you can relax on deck, swim, or snorkel among pristine coral reefs rich with marine life. Once on the island, enjoy a freshly prepared seafood lunch with refreshing drinks.

Evening

• After returning to Trinidad around 4:00 p.m., you'll have the rest of the afternoon free to explore at your own pace.
• This afternoon you'll have the opportunity to engage in another cultural exchange, this time with a local pottery artist who hones is craft in his family home.
• You can stroll through the charming streets, soak in the town's bohemian atmosphere, and, if you like, enjoy live Cuban music at the famous Casa de la Música or one of the local bars.
• Spend another night in the cozy casa in Trinidad.

Morning

• The group will have one final Cuban breakfast together, reflecting on the connections and memories made.
• Depart for Havana’s José Martí International Airport (HAV) on included transportation (~30-minute drive).
• Arrival at the airport at 11:30 a.m. Say hasta luego (never goodbye!) to your new friends, as you make plans to keep in touch with our travel community.
• Many of our groups plan reunions in cities in the United States, book new trips together, or even become such close friends they attend each other’s weddings!
• Carry home more than souvenirs — take with you a deeper understanding of Cuba, its people, and the impact of your visit.
• Leave inspired to continue supporting communities and seeking meaningful travel experiences wherever you go.