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From colonial architecture to Cuban cigars and even big gay Havana, this Support for the Cuban People tour is legal for Americans, and gets up close and personal with the Caribbean island’s distinct Latin culture. It also happens to coincide with New Year’s Eve, so pack your fun pants and prepare to celebrate. Throw in some friendly locals, a few old cars, and even a splash of salsa, and the new year is off to a stellar start!
Can’t make NYE? Also check out our Cultural Cuba tour, with multiple departures throughout the year. To our American friends, please review the Cuba Info section of our Important Information Page to learn more about legally travelling to Cuba.
Hola! Welcome to Cuba. Our adventure begins about 6PM with a group meeting. Get familiar with fellow travellers and our fabulous guide, then join us for an included Welcome Dinner, cocktails, and perhaps a visit to a gay-welcoming bar.
After breakfast, we’ll enjoy an Afro-Cuban tour of the iconic, graffiti-ridden Hamel Alley with a passionate expert on the gems therein. We’ll then uncover a queer side of Havana, beginning with a visit to a local theatre where we’ll meet the director of the theatre company and an LGBT activist. Next we’ll enjoy a guided tour of Hemingway House and learn about the novelist’s life, including his trans daughter. This evening we’ll reconvene for dinner (included), followed by free drinks at a local gay bar.
After breakfast today, a walking tour of Old Havana awaits, where many significant buildings have been restored, and are reliving their glory days. We’ll stop at an art and clothing store run by a local artist, followed by an optional lunch. We’ve left the afternoon free to either explore Havana on your own or to rest up at the homestay for New Year’s Eve, which kicks off with a festive dinner. Tonight’s countdown will be at one of the local gay bars.
After a big night out, we’ve planned a leisurely afternoon at Mi Cayito, a gay beach in the burbs. We’ll grab lunch (optional) en route, then leave you to soak up the sun and meet some locals. Tonight’s dinner is optional, and we’d recommend getting to bed early as we have an early morning tomorrow.
After breakfast, our Cuban adventure continues in the Spanish Colonial settlement of Trinidad. With a rambling drive of seven hours ahead of us, make yourself comfortable and enjoy the ride. We’ll stop in Santa Clara en route to stretch our legs, and visit the Che Guevara Mausoleum & Museum while there. Once in Trinidad, we’ll check in to our homestays, then gather for an included dinner.
Home to many churches and colonial buildings, our day in Trinidad begins with a cultural tour of the town. We’ll visit museums, including the Afro Cuban temple to Yemaya. In the afternoon we’ll visit the local headquarters of a private dance company, and learn about this prominent form of Cuban culture. A salsa class is included, revving up appetites for another included dinner!
Today we move on to Cienfuegos on the Caribbean coast. Founded by the French, then heavily developed by Americans, “the Pearl of the South” will impress you with its elegance, architecture and style. After we explore the city, we’ll visit a local art cooperative and chat with the artists before savouring sunset from the stunning Palacio del Valle. Our day wraps up with another included dinner.
This morning we hit the road for another lengthy drive to Viñales (about 8 hours). This includes a stop at Bay of Pigs, where CIA-sponsored Brigade 2506 failed to overthrow Fidel Castro’s government in 1961. The museum here offers a solidly Cuban perspective on the events that unfolded, so it’s worth checking out. Once in Viñales, we’ll learn to cook like a Cuban through a lesson with a local chef, then feast upon our creations.
This morning we’ll learn about the Cuban cigar industry from a farmer and expert cigar maker. Peek into how the communist system works, and how people make ends meet. Learn the process, from planting tobacco, to rolling each cigar. Dinner tonight is at a stunning organic farm, followed by cocktails al fresco at a nearby bar.
After checking out of our homestays, it’s back to Havana, with a stop in Jaimanitas. This town was made famous by artist Jose Fuster. His home – Fusterlandia – is definitely a highlight, a living art project entirely covered in eclectic mosaics. Back in Havana we’ll visit interesting areas outside of Old Havana in classic convertible cars, then savour our bittersweet Farewell Dinner in a renovated former factory.
There are no activities planned today, so you are free to depart at your leisure.
Amazing country with a rich history. Wonderful people. I came back a more educated and better person thanks to the experiences on this trip.
Be ready for the cultural experience of your lifetime!
Fantastic trip. Exceeded my expectations. Great tour leader and a wonderful driver. I really felt I was shown the best Cuba had to offer.
We had an amazing time—made even better by a guide who spoke the language and went above and beyond to make sure we were happy.
Amazing country and amazing guide. Willmar really puts a lot into making this a memorable experience. He’s very personable and accommodating and fun.
One of the best trips I have ever gone on. To date, I have visited 13 Countries, and this trip was amazing. Will is an exceptional guide
10 Reasons this gay traveller loved visiting Cuba with Out Adventures.Read More
Havana isn’t the only Cuban gem. Consider these three World Heritage Cities on your next Cuba Tour.Read More
While these trips typically attract gay men, all genders are welcome, and we encourage friends and family to join the fun as well.Learn More
All accommodations on Out Adventures tours include breakfast and are located in areas central to our activities. All amenities are examples only, and may differ from hotel to hotel.
Homestay: Expect a private, comfortable room, typically with a private bathroom. Although amenities range widely, none of our homestays have a pool. Customer service is usually friendly—like being with family, and makes up for the lack of other services.Learn More
2.5 – Light/Average
This trip is fully booked but cancellations occur. If you’d like to be contacted if space opens up, please click “Book Now”, select the appropriate departure and you will be prompted to provide limited information.
If you are a solo traveller willing to share a room with another solo traveller, please select Shared/Twin Room when booking this tour.
If you are a solo traveller interested in booking a private room, please select single supplement when booking this tour (based on availability). If you are willing to share a room with another solo traveller, please select Solo Shared.
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