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Cultural Cuba

Our ever-popular gay Cuba tour is legal for Americans!

Our 10-day ‘Support for the Cuban People’ Cuba tour is legal for Americans and is all about spectacular scenery with lots of colourful history thrown in! Even better, the island’s friendly locals make it a fantastic place for LGBTQ+ travellers to discover. Wander through Havana’s glittering colonial architecture, breathe in the immaculate air of Viñales. Throw in a few vintage cars, some fragrant cigars, a splash of salsa, and it all adds up to a sunny escape that’s muy caliente.

If you’re looking to avoid the usual holiday hustle, consider our Cuba New Year Fiesta. And to our American friends, please read this blog post to learn more about legally travelling to Cuba.


Quick Facts


HIGHLIGHTS

  • Explore charming Old Havana
  • Enjoy Cuba’s nightlife in Havana
  • Get a sense of the struggles of LGBTQ+ people in Cuba by meeting with local activists
  • Learn to salsa in Trinidad
  • Dine under the stars in Viñales at a stunning organic farm
  • Be a guest at local homestays, a distinctly Cuban experience
  • Learn about Afro-Cuban Folklore in Trinidad
  • Visit the Che Guevara Mausoleum and Museum
  • Learn to cook up a fantastic Cuban meal
  • Bask in the eclectic mosaics of Jaimanitas, a town made famous by artist Jose Fuster
  • Tour Hemingway House and learn about the novelist’s life, including his trans daughter
  • Stroll through famous graffiti-ridden Hamel Alley

DATES AND PRICES

2024
November 15-24, 2024 (From $2,695 USD)
OPEN
  • Tour Prices - All tour prices are in USD and based on double/twin occupancy
    • Tour Price _ SALE PRICE (Regular Price $2995.00 per person) Until April 18: $2,695.00 per person
  • Single Supplement (Optional) - All single supplement prices are in USD and additional to the tour price
    • Single Supplement: $530.00 per person
  • Payment Terms: $750 Deposit - Balance Due 60 Days Before Departure
  • Guides and Hosts for this trip: Wilmar
2025
February 7-16, 2025 (From $2,995 USD)
OPEN
  • Tour Prices - All tour prices are in USD and based on double/twin occupancy
    • Tour Price: $2,995.00 per person
  • Single Supplement (Optional) - All single supplement prices are in USD and additional to the tour price
    • Single Supplement: $530.00 per person
  • Payment Terms: $750 Deposit - Balance Due 90 Days before trip
  • Guides and Hosts for this trip: Wilmar
November 14-23, 2025 (From $2,995 USD)
OPEN
  • Tour Prices - All tour prices are in USD and based on double/twin occupancy
    • Tour Price: $2,995.00 per person
  • Single Supplement (Optional) - All single supplement prices are in USD and additional to the tour price
    • Single Supplement: $530.00 per person
  • Payment Terms: $750 Deposit - Balance Due 90 Days before trip
  • Guides and Hosts for this trip: Wilmar
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Tour Map

ITINERARY

Day 1 Old Havana

Hola! Welcome to Havana. The adventure begins around 6PM with a group meeting. After getting familiar with your fellow travellers—and fabulous guide—we’ll venture out for an included Welcome Dinner with a few included welcome cocktails, followed by optional drinks at one of Havana’s gay bars.

Day 2 Trinidad

After breakfast and a trip discussion, we’ll hit the road for a rambling ride (approximately 7 hours) to the Spanish Colonial settlement of Trinidad. En route, we’ll stop in Santa Clara and visit the Che Guevara Mausoleum & Museum for an interesting perspective on his life. Once in Trinidad, we’ll check in to our homestays, then grab an included dinner.

Day 3 Trinidad

The beautiful colonial city of Trinidad is home to numerous churches and many gorgeous colonial buildings. We begin with a cultural tour of Trinidad where we will visit various museums including the Afro Cuban temple to Yemaya. In the afternoon we’ll head to a private dance company’s very “local” headquarters to learn about the cultural and social importance that dancing has to Cuba. We’ll be welcomed into the venue where they train before taking on a Cuban salsa class (no experience necessary). Another fabulous dinner is included this evening.

Day 4 Cienfuegos

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 to chat with artists before savouring the sunset from the stunning Palacio del Valle. We’ll round off our day with another local dinner.

Day 5 Viñales via Bay of Pigs

This morning we hit the road for another long drive to Viñales (approximately 8 hours). This includes a stop at the Bay of Pigs, where CIA-sponsored Brigade 2506 failed to overthrow Fidel Castro’s government in 1961. We’ll have a quick visit to the museum, which provides a uniquely-Cuban perspective on the events of 1961. Once in Viñales, we’ll learn to cook Cuban-style with a cooking lesson from a local chef. Fun to cook, but even better to eat!

Day 6 Viñales

Today we spend the morning learning the tradition of Cuban cigars from a farmer and expert cigar maker. Get an insight as to how the communist system works, how much tobacco they will keep, how much produce they give back to the government, and how they make ends meet! You will learn about the process from tobacco planting to rolling the final cigar. Then, we’ll enjoy dinner in the countryside at a stunningly beautiful organic farm, followed by drinks at a nearby outdoor bar.

Day 7 Havana

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. Tonight, we’ll have an included dinner and drinks.

Day 8 Havana

Today we’ll enjoy a walking tour of Old Havana, where you’ll learn about the most significant buildings (many of which have been restored to their original glory). We’ll stop at a new art/clothing store run by a local artist, and have an optional lunch. In the afternoon we’ll enjoy a guided tour of Hemingway House and learn about the novelist’s life, including his trans daughter. Then, you’ll have free time to explore the city before we meet for an included dinner this evening, followed by drinks at a local gay bar, with drinks included.

Day 9 Havana

This morning we’ll enjoy an Afro Cuban tour in the city, followed by a walk through the famous graffiti-ridden Hamel Alley with a specialist that will explain the art. We’ll then head to a local gay-run community theatre where we’ll chat with the Director, along with local LGBTQ+ activists about Cuba from their perspective. For our final evening, we’ll enjoy an included feast at one of the best restaurants in town, and head out for optional drinks.

Day 10 Havana/Departure

There are no activities planned today, so you are free to depart at your leisure.


GUIDES AND HOSTS

CUBA GROUP LEADER

WHAT’S INCLUDED?

  • Arrival & departure transfers to/from Out Adventures’ joining/finishing point hotel
  • Group leader from beginning to end of tour
  • 9 breakfasts, 9 dinners
  • Local accommodation in Casa Particlares (9 nights)
  • Gratuities for all specialized guides and activities
  • Walking tours (Havana, Trinidad, Cienfuegos)
  • Che Guevara Mausoleum & Museum
  • Introductory Salsa Lesson
  • Entrance to Bay of Pigs Museum
  • Entry to Palacio del Valle
  • Visit to local art cooperative
  • Tobacco Farm visit
  • Dinner on a local organic farm in Viñales
  • Cooking class
  • Hemingway house visit with private guide
  • A $50 USD Rainbow Railroad donation to help resettle LGBTQ+ refugees. Read more here.

WHAT ISN’T INCLUDED?

  • International Airfare
  • Meals & Activities not mentioned in the itinerary
  • Travel insurance is mandatory for all travellers. Visit the Travel Insurance section of the Important Information Page for more details.
  • Gratuities for Group Leader ($50-$100 USD/CUC)
  • COVID-19 rapid tests, or any expenses related to a guest contracting COVID-19. Click here for more details.

LGBT INFO FOR Cuba

IMPORTANT INFORMATION

What to bring, visa information, required
vaccinations, travel insurance and more.
TELL ME EVERYTHING!

EXAMPLES OF ACCOMMODATIONS

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Courtyard
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Single Room
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Reviews

Some from our travellers

Jason G

The tour covered many things we would never have seen on our own.
Cultural Cuba
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The tour covered many things we would never have seen on our own. It was very easy. Wilmar was great.

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Jeff P

The people are kind, welcoming, and genuinely love Americans. Go! Now!
Cultural Cuba
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Go! Now! We felt so much safer in Cuba than we ever imagined. For some reason, many people are concerned with travel to Cuba. False fears! The people are kind, welcoming, and genuinely love Americans. Although it is a poor country, they have so much to offer in terms of cultural, historical, and natural beauty. The country is so much bigger than we ever imagined. It doesn’t feel like an island – it feels more like a large Spanish Colonial country in South America.

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Tony D

Cuba trip was a good mix of staying busy and seeing/doing a lot, but not overwhelming.
Cultural Cuba
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Well organized; excellent tour guide; Cuba trip was a good mix of staying busy and seeing/doing a lot, but not overwhelming; great group of people and many were repeat Out Adventures clients, so hopefully other trips would be good groups as well.

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Steven D

The longer I stayed in Cuba, the more I liked it.
Cultural Cuba
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The longer I stayed in Cuba, the more I liked it. Well organized tour, comfortable, great guide.

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Jack W & Rick K

Cuba is much more than packaged resorts
Cultural Cuba
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Cuba is much more than packaged resorts. It has rich cultural and historical traditions. The people are welcoming and much more tolerant than we are led to believe. be prepared for a very pleasant surprise

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Ken C

An amazing trip in an amazing country
Cultural Cuba
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An amazing trip in an amazing country. Our host was superb, took care of all of our logistic needs, and was as knowledgeable and upbeat as you could ever want. Our people-to-people exchanges were wonderful and made our visit very personal and more meaningful

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Greg M

Incredible trip to another world
Cultural Cuba
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Incredible trip to another world. Fantastic scenery, warm & friendly people and lots of history to learn about.

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David R & Mark A

I highly recommend it - you won't be disappointed!
Cultural Cuba
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Cuba has been on our travel list for a while. Out Adventures and Will, our group leader, had a very organized itinerary that led us to see a lot of Cuba. Will, born and raised in Cuba, gave us fantastic insight into his country. I highly recommend it – you won’t be disappointed!

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Frank M & Brian B

We would repeat this tour in a heartbeat!
Cultural Cuba
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A fabulous ten days were spent immersed in the culture of Cuba together with our wonderful guide, Willmar, and our calm driver, George. Despite the many struggles and challenges faced by them, the charm, warmth and acceptance of the Cuban people enveloped us throughout our tour. We were most impressed by Willmar’s ability to adapt to last-minute changes that inevitably arose and his calm demeanour as he successfully manoeuvred us and our seven terrific fellow travellers throughout the tour. Much to our very pleasant surprise, all of our meals were substantial, interesting and tasty. We would repeat this tour in a heartbeat!

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See All Reviews


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We can’t wait to help you plan an awesome adventure, but due to a high level of fake inquiries we now record your IP address when you submit an inquiry. This helps local authorities identify and prevent harassment against Out Adventures, or any intended recipients.

Who's it for?

While these trips typically attract gay men, all genders are welcome, and we encourage friends and family to join the fun as well.

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Accommodations

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.

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Physical Rating: 2 - LIGHT

2.5 – Light/Average

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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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This trip is available but we are close to departure and will need to confirm services such as hotels and activities before confirming you on the trip. The process can take up to 5 business days. If you are seriously interested in this trip, please complete the On Request Booking form and one of our team members will get back to you with next steps.

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