Cuba Travel – Art and Culture Gay Tour

Classic car on the HE Travel gay tour in Cuba

 Future  Dates to be announced

Gay Cuba Culture Tour

Physical Challenge:

All Cuba tours have been modified to comply with all current regulations.

Join us for a gay tour that blends together the sophistication, heritage and promise of Cuba’s capital with three days of exploring smaller towns that are rarely visited by foreigners. On this trip we will have a special emphasis on the arts of Cuba, and the role of the LGBT community. Click to read a Blog Post about a November 2011 trip to Havana or here to read about Cuba’s rising LGBT Culture!


For a more active experience, see our Cuba Cycling Tour.

  • Tour the studios and galleries of artists working in Havana
  • Explore the gay gathering places in Havana
  • Visit the city and country residences of Ernest Hemingway
  • Dine in critically acclaimed restaurants and paladares
  • Learn more about the roles and rights of LGBT Cubans
  • Tour fascinating historic colonial and revolutionary landmarks of this island nation
  • Travel to the less-visited colonial cities of Cienfuegos and Trinidad and small agricultural communities along the way

After five decades during which our Florida Straits have served as a wall instead of a water bridge, the recent announcements by the Presidents of Cuba and the United States herald the start of rapid changes to daily life in Cuba. At this momentous time we invite you to join us for a People-to-People exchange with leaders of social change in Cuba and some of the country’s most creative artists.



Day 1: Welcome to Havana!

Havana on the HE Travel gay tour in Cuba

Plan your flight to arrive in Havana this morning, in time for a lovely group luncheon. When dining together, we’ll discover unexpected cuisine at some of Havana’s top-rated private restaurants (paladares).

After lunch, we’ll visit the community art project of Muraleando. Artists, musicians and dancers have turned this once neglected neighborhood into one of the city’s centers of self-expression.  Hear the stories of the project from community leaders and local residents.

After settling in, you will have time to exchange currency at the hotel.  Later we’ll go as a group to a charming, privately-owned restaurant nearby.


Day 2: History and Hemingway in Old Havana

cathedral on the HE Travel gay tour in Cuba

Each morning during our time together in Cuba, we will have breakfast at the hotel before meeting in the lobby around 9 am to embark on our historical, arts and studio tours.

This morning enjoy a presentation from a representative of the City Historian’s Office of Havana.  We will learn about the city’s accomplishments and the ongoing challenges in restoring Havana. With this meaningful perspective, we will explore Old Havana, founded in 1519, on a walking tour through the city’s historic squares.  We will see examples of the city’s colonial architecture and meet with some of Havana’s cuentapropistas (independent business owners).

Our lunch today will be at a popular paladar, located near Cathedral Plaza.

After lunch, we will continue our exploration of Old Havana, stopping at a graphics workshop cooperative and an architectural restoration training facility, where workers are learning how to bring run-down buildings back to their original glory.

We will end the afternoon at Hotel Ambos Mundos, which was home to author Ernest Hemingway for seven years. For those who wish, visit room 511, which now serves as a small museum to Hemingway. A bit later, join the rest of the group at the hotel’s rooftop for a cocktail and share stories of the day.

After returning to our hotel for a chance to rest and freshen up, we’ll depart for a delicious dinner in Old Havana. For those who desire a later night out, we’ll catch some live music at Café Taberna.


Day 3: Studios and Sex (Education)

classic cars on the HE Travel gay tour in Cuba

This morning we will visit the National Center for Sex Education (CENESEX). The center’s mission is to contribute to “the development of a culture of sexuality that is full, pleasurable and responsible, as well as to promote the full exercise of sexual rights.”

A special highlight of the day (schedules permitting) will be to meet CENESEX’s Director and LGBT rights activist Mariela Castro Espin. She is the daughter of President Raul Castro, and uses her powerful name to advocate for LGBT Cubans, especially those with HIV and AIDS. In 2008, she also ensured that Cuba’s national health system will provide medical care and legal assistance for trans-gendered Cubans who wish to change gender.

We’ll have lunch together then visit the University of Havana for an enlightening discussion with students and staff. This afternoon we will also visit KCHO, a self-supported, non-profit art studio, gallery and cultural center.

After returning to the hotel, the evening will be at leisure. We will provide suggestions for nearby restaurants and activities.


Day 4: Pearl of the South

pink and blue buildings in Cienfuegos on the gay Cuba trip with HE Travel

Today we will leave Havana and journey to Cienfuegos, a city with a rich history of mixed French and Spanish Colonial influences.

Following lunch together, we’ll embark on a walking tour of Cienfuegos to learn about the French-styled architecture. We’ll have the chance to shop at some local stores and learn about Cuba’s double-currency system. Tonight we’ll enjoy dinner together and a performance of the Choir of Cienfuegos, an internationally acclaimed vocal group.


Day 5: Trinidad

bright pastels houses in Trinidad on the gay Cuba trip with HE Travel

This morning we depart for a day trip along the Caribbean coast to Trinidad, a colonial city colored in pastels! We’ll meet with a representative of the Office of the City Historian to hear about the city’s designation as a UNESCO World Heritage site and its modern challenges.

Our walking tour will take us down cobblestoned streets and past Colonial Spanish buildings to meet artisans, antique collectors, and longtime residents who have transformed their historic homes into casas particulares.

We’ll return to Cienfuegos this afternoon for an evening at leisure.


Day 6: Gardens and Arts

frangipani on the HE Travel gay tour in Cuba

Today is our last full day in Cienfuegos, and we’ll visit a former sugar mill complex that closed in 2002, impacting the town’s economy and people. We’ll meet teacher and local historian Nancy Robaina, who will inform us about the community’s transformation and how it copes in the aftermath of the mill’s closure.

We’ll stroll the grounds of the Cienfuegos Botanical Garden, once a Harvard-funded research garden for sugar cane, now an extraordinary collection of tropical specimens. A botany expert will talk about Cuba’s efforts to maintain the rich biodiversity of its extraordinary plant life.

After lunch, we’ll visit the Benny Moré Art School, where gifted students from throughout the province take classes in music, dance, and the visual arts. We’ll have time to relax a bit before dinner together tonight.


Day 7: US / Cuba Relations

bay of pigs on the HE Travel gay Cuba tour

Today we’ll journey north toward Havana, with a stop along the way to visit the historic Bay of Pigs. Trace the dramatic events of the bay’s recent past and step foot on the Playa Girón, one of the two landing sites for the 1961 U.S.-backed Bay of Pigs invasion.

Hemingway Home Finca Virgia on the HE Travel gay tour in Cuba

After lunch together, we will visit Finca Vigia, the Cuban home of Ernest Hemingway, elements of which will feel familiar to anyone who has visited The Hemingway House in Key West, Florida.

Late this afternoon we arrive back in Havana and will have the evening to explore the neighborhood around our hotel and dine independently.


Day 8: Youth, Arts, and the Future of Cuba

cuban flag in a window of a yellow building on the gay Cuba trip with HE Travel

This morning we will meet with the members of “Proyecto Palomas” a community project aimed at providing happiness for all Cubans.  We’ll listen to the stories of the LGBT youth community and the project’s goal of empowerment through art and dance.

We’ll visit the Museum of Decorative Arts, located within a beautifully restored mansion in the once-prominent neighborhood of Vedado.  The former residence of Maria Luisa Gomez Mena, the Countess of Revilla de Camargo, now houses an extensive collection of highly artistic and historic pieces from Europe and Asia.

After lunch on the famed Malecon, meet with a panel of Cuban experts from various backgrounds for a question-and-answer session to discuss such topics as economic reform and women’s and minority rights.

This evening’s cozy farewell dinner will be at a special location where we can savor our memories of our time in our neighbor to the south. Those with energy left over will be able to head out on the town for the last night in Havana.


Day 9: Homeward Bound

We will depart Havana today, and say goodbye to this charming, hospitable, and surprising country.

Head south earlier and visit the Florida Keys and Key West!

key west florida southernmost point

From the bustling gay nightlife of Miami Beach, across the gorgeous islands of the Florida Keys, our multi-sport adventure will put you on the water, on your bike, and in the sky. Enjoy excellent food & hospitality on the way to fabulous, sunny, friendly Gay Key West.

Due to ongoing changes in Cuba Travel restrictions, reservations must be made by phone (305-294-8174).

This tour is subject to strict cancellation policies that may differ from our other group tours. A portion of your deposit ($250) is non-refundable and non-transferable. You will receive this policy in writing prior to your commitment. For this tour, we strongly recommend purchasing Trip Cancellation and Interruption Insurance to protect your investment in the event of an unforeseen cancellation.

Price includes: Airport/hotel transfers within Cuba; all breakfasts and lunches plus 5 dinners, with alcoholic beverages at the welcome and farewell dinners; Accommodations: 8 nights of comfortable lodging including 5 nights in Havana and 3 nights in Cienfuegos; All activities, entrance fees, and transportation as described. This tour will include complimentary Cuban Medical Insurance.

Not included: Airfare to and from Havana; Personal items including: alcoholic beverages, snacks, laundry, telephone calls; and Gratuities for guide(s) and HE Travel host.


Optional Tour Choices:

$1400 Single Supplement (for solo travelers who wish to enjoy a private bedroom and bathroom)

“In April 2015 I made my third visit to Cuba over a 15-year period. During each day we met creative – and sometimes provocative – artists and had discussions about Cuba’s place in the world. At night we dined in privately owned paladars then returned to our deluxe hotel in one of the most historic buildings in Havana. The common theme of each of my visits is the impressive resilience and good humor of the Cuban people despite the economic challenges of the past five decades.” – Philip Sheldon, President, HE Travel

US relations with Cuba are a hot topic in the media, and clients ask us daily whether American citizens still need to follow special rules in order to go to Cuba.


While there are many business and political changes announced in the news each day, we still advise American citizens to use care and caution when booking travel to Cuba. It is best for visitors to Cuba to be part of a legal and licensed educational and cultural experience. Our tour will follow the strictest set of rules, which simplifies entry into Havana and ensures a smooth experience with Immigration and Customs upon return to the USA. This trip is permitted by a special People-to-People license from the Department of the Treasury’s Office of Foreign Assets Control. The itinerary was designed to provide an in-depth cultural experience with numerous opportunities for meaningful interaction with Cubans.


As travel restrictions to Cuba change, our itinerary may change in order to enrich our group experience. This is an exciting time to visit this island nation on the verge of many historic changes.

You will need a Visa to visit Cuba, and we will provide detailed instructions as the tour approaches.

Most of our trips draw more single travelers than couples. When couples do join us, it’s usually because they’re looking forward to interacting with a gay group; if they wanted a holiday by themselves, they wouldn’t have signed up to travel with us. Furthermore, the activities included with our trips serve as natural ice-breakers. Within a day, you’ll be traveling with friends. You don’t need to pay the single supplement if you’re traveling alone. We’ll be happy to match you with a roommate. Pay the single supplement only if you want a bedroom to yourself.

For selected trips, including cruises, we will charge half the single supplement if you request a roommate but we can’t match you with someone.

This tour starts and ends in Havana, Cuba. Limited commercial flights are now available between select US cities and Havana.

Physical Challenge Level 1

Cuba travel requires a great deal of patience due to unpredictable changes to the planned itinerary. Cuba is not a destination for people with a severe health condition or mobility issues. Although the country has many doctors, there is a shortage of medical supplies. Anyone with a serious medical problem, whose medical situation might be adversely affected by strenuous travel or who might have difficulty walking, should not join this expedition. There will be several walking tours over uneven surfaces and cobblestone streets, and at times, ascending or descending stairs without the use of a handrail. All travelers should be able to walk 2 – 3 miles per day, unassisted, over potentially uneven terrain.


Travel to Cuba by American citizens is heavily regulated by the U.S. Government’s Department of the Treasury. You are permitted to travel to Cuba under the People-to-People License issued by the Department of the Treasury. In order to comply with the requirements of this license, we must ask that you participate actively in all activities planned (unless you become ill) and do not deviate from the itinerary.

For answers to your additional questions, please email or call 305-294-8174

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