FROM: $3395 USD

UPCOMING: Dec. 29, 2019

Cuba: New Year Fiesta

Pack Your Fun Pants and Celebrate NYE on this Gay Tour of Cuba!


From colonial architecture to Cuban cigars, 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 on this gay foray. 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 gay tour, with multiple departures throughout the year. To our American friends, please review the Cuba Info section of our Trip Notes to learn more about legally travelling to Cuba.


Duration: 11 Days/10 Nights
Starts In: Havana
Ends In: Havana
Group Size: Min 4, Max 16
Deposit: $750, full payment due 90 days prior
Accommodation: Local Homestays
Physical Rating: 2/5


Dec. 29, 2019 to Jan. 8, 2020 - 3395.00 USD
Dec. 29, 2020 to Jan. 8, 2021 - 3495.00 USD


• Explore the charm of Old Havana
• Ring in the New Year, Cuban style
• Enjoy a salsa lesson in the colonial settlement of Trinidad
• Lay on remote and immaculate beaches
• Dine under the stars in an open Viñales tobacco field
• Be a guest at local homestays, a distinctly Cuban experience
• Learn about Afro-Cuban Folklore in Trinidad
• Visit the Che Guevara Mausoleum and Museum
• Enjoy an expert lesson in the Cuban cigar industry



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 local gay 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. Feel free to explore on your own in the late afternoon, and 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 the city 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 to 2018 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. After lunch, we'll enjoy a guided tour of Hemingway House and learn about the novelist's life, including his trans daughter. Back in Havana, we’ll check in to our homestay, 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.

• Arrival & departure transfers to/from Out Adventures’ joining/finishing point hotel
• Group leader from beginning to end of tour 
• 10 breakfasts, 9 dinners 
• Local accommodation in Casa Particlares (10 nights)
• Che Guevara Mausoleum & Museum 
• Introductory Salsa Lesson 
• Entrance to Bay of Pigs Museum
• Visit to local art cooperative 
• Cooking class 

• Gratuities for all specialized guides and activities
• Dinner on an organic farm in Viñales 
• Entry to Palacio del Valle 
• New Year's Eve Celebration in Havana
• Walking tour (Old Havana, Trinidad & Cienfuegos)
• Hemingway House Tour 
• Gay beach visit

• International Airfare
• Meals & Activities not mentioned in itinerary
• Travel insurance is mandatory for all travellers. Visit www.outadventures.com/insurance for more details.

• Gratuities for Tour Leader ($50-$100 USD)
• Gratuities for driver (approximately $30-$50 USD)


Martin Z.

Cuba: New Year Fiesta

Amazing trip. Willmar's heartfelt priority was that everyone's needs and concerns were attended to, and he went above to ensure an incredible experience was had by all. From start to finish, the trip was well-organized and fun. The group truly bonded as well and made for additional fun free-time excursions.






Nathan L.

Cuba: New Year Fiesta

Amazing country with a rich history. Wonderful people. I came back a more educated and better person thanks to the experiences on this trip.