Cuba Private Travel invites you to an extraordinary exploration deep into the heart of Cuba’s vibrant LGBTQ+ culture. “Over the Cuban Rainbow” is an intimate, 11-day bespoke journey crafted to coincide with the island’s Annual Anti-Homophobia and Anti-Transphobia Celebration. This isn’t a typical trip; it’s a profound connection with the artists, activists, and changemakers shaping Cuba’s evolving queer landscape.
From the legendary drag shows of Havana to the revolutionary spirit of Santa Clara and the Afro-Caribbean soul of Santiago , you’ll be welcomed into private homes, underground parties, and intimate conversations. This is a bespoke journey designed to celebrate resilience, identity, and pride, weaving you into the very fabric of Cuba’s most vibrant communities.
Thursday May 14, Day 1: Havana — Welcome to the Celebration
Your journey begins as you’re met at Havana’s José Martí Airport and escorted to your charming accommodations at Hostal Boutique 25 y G, a beautiful colonial-style house in Vedado. The adventure kicks off with celebratory Welcome Cocktails, followed by an included dinner at the renowned La Bodega de la Reserva. The night truly comes alive as you’re welcomed into a private home for an authentic house party with local artists and members of the LGBTQ+ community. Your evening culminates with a dazzling drag show at the legendary Las Vegas Club, Havana’s most iconic LGBTQ+ venue.
Friday May 15, Day 2: Havana — Drag, Sun, and Skyline Parties
Embrace the spirit of the celebration with a fabulous Sunday Drag Brunch at Bahía’s Restaurant. Afterward, soak up the Caribbean sun at Mi Cayito, Havana’s famously welcoming unofficial gay beach. The evening culminates with an unforgettable party hosted by Proyecto El Divino, a dynamic LGBTQ+ entertainment company, at the iconic Habana Libre’s Salón Turquino, where you’ll dance against the stunning backdrop of the Havana skyline.
Saturday May 16, Day 3: Havana — Hemingway, History, and Hidden Haunts
Delve into Cuba’s literary history with an open-top vintage car ride to Finca Vigia, the former estate of Ernest Hemingway. Following a walking tour of Old Havana, a UNESCO World Heritage site, savor a daiquiri at Hemingway’s other favorite haunt, El Floridita, the world-famous birthplace of the daiquiri. As evening falls, unwind with cocktails on the stunning terrace of Bleco Havana, overlooking the Malecón , before diving into the vibrant energy of the XY Club, one of the city’s premier LGBTQ+ venues.
Sunday May 17, Day 4: Havana — Art, Activism, and Electric Nights
Today is dedicated to the intersection of art and activism. Begin with a Curated Art Tour celebrating the powerful work of Cuba’s LGBTQ+ artists. In the afternoon, engage in a deeply insightful meet-up with local Cuban LGBTQ+ activists. This is followed by a powerful screening of the documentary “¡Quba!” by Kim Anno at Theater 23 y 12, complete with a Q&A session. The night is a spectacular celebration, attending another Proyecto El Divino event, this time at the glamorous and historic Capri’s Salón Rojo.
Monday May 18, Day 5: Las Terrazas — A Natural Escape
Journey outside the city to the pioneering ecovillage of Las Terrazas, a UNESCO Biosphere Reserve dating back to a 1968 reforestation project. After exploring this vibrant art community, enjoy an authentic, included farm-to-table lunch at Casa del Campesino Restaurant. Spend the afternoon cooling off with a refreshing swim in the crystal-clear natural pools of the Rio San Juan before returning to Havana.
Tuesday May 19, Day 6: Santa Clara — Revolutionary Heart & Queer Legend
Travel to Santa Clara, a city of revolutionary history and a legendary queer culture. After visiting the iconic Che Guevara Memorial and Plaza, settle into the colonial charm of Suite Florencia, a private boutique property. The night is reserved for El Mejunje, the celebrated and symbolic LGBTQ+ cultural center housed in the ruins of an old hotel, known for its drag shows and artistic freedom.
Wednesday May 20, Day 7: Holguín — Farm-to-Table & Community Connection
Your journey continues east, stopping in Camagüey for an unforgettable included lunch at Finca Agroecológica El Justo, a family-run sustainable farm. Arriving in Holguín, check into the charming Villa Cristal Holguin. The evening offers a truly special experience: a private dinner and house party (INCLUDED) hosted by members of Holguín’s vibrant queer community, offering a unique window into LGBTQ+ life beyond the capital.
Thursday May 21, Day 8: Holguín — Pride & Performance
Explore Holguín, the provincial city serving as the host for this year’s “Cuban Gay Pride” Festivities. After a city tour, the afternoon is yours to explore. As night falls, join the vibrant celebration as the city comes alive with a spectacular drag show and live performances, a powerful and dazzling statement of visibility, pride, and solidarity.
Friday May 22, Day 9: Santiago de Cuba — Afro-Caribbean Rhythms
Journey to Santiago de Cuba, the island’s cultural and musical heart and its first capital. After a private tour and checking into the elegant, Art Deco-infused Hostal Heredia , you’ll connect with local changemakers over cocktails during a meet-up with members of the Santiago’s queer community. The evening is another intimate affair: a private, included Dinner & House Party, immersing you in traditional Santiaguero dishes and authentic culture.
Saturday May 23, Day 10: Santiago — Peaks, Plantations, and Farewell
Discover the spiritual side of Cuba with a visit to El Cobre Village and the Basilica of the Virgen of El Cobre, Cuba’s revered Patron Saint. Then, ascend into the mountains for an excursion to La Gran Piedra (a 63,000-ton boulder) and the 18th-century UNESCO World Heritage coffee plantation, Cafetal la Isabelica. Unwind on the secluded, turquoise shores of Playa Chiviricobefore your final celebration: an elegant, included Farewell Dinner and Private Party.
Sunday May 24, Day 11: Santiago de Cuba — Departure
After a final breakfast, your private driver will escort you to the Santiago de Cuba International Airport (SCU) for your departure, your heart full of the vibrant spirit of Cuba.
Why Choose This Journey?
This is more than a trip; it is a rare invitation to witness and participate in a pivotal cultural moment. This journey offers unparalleled, intimate access to the leaders, artists, and spaces at the forefront of the island’s LGBTQ+ movement. You won’t just see Cuba—you’ll connect with its people , celebrate its resilience, and gain a profound understanding of a community shaping its own future with activism, art, and undeniable pride.
Your Cuba Awaits
This itinerary is a starting point, not a final script. At Cuba Private Travel, no two holidays will ever be the same. We invite you to speak with our in-country experts, who are ready to get to know you and curate a journey that is perfectly, personally relevant to you.
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