Cultural Cuba

An All-Gay ‘Support for the Cuban People’ Tour of Havana and the Island.


This 10-day Gay Cuban adventure 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 LGBT travellers to discover. Wander through Havana's glittering colonial architecture, breathe in the immaculate air of Vinales. 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. To our American friends, please review the Cuba Info section of our Trip Notes on your right to learn more about legal travel to Cuba.


Duration: 10 Days/9 Nights
Starts In: Havana
Ends In: Havana
Group Size: Min 4, Max 16
Deposit: $750 USD
Accommodation: Local Homestays
Physical Rating: 2/5
Itinerary Disclaimer: Please see trip notes for Alternate December Itinerary
Prices: Based on double occupancy


Nov. 22, 2019 to Dec. 1, 2019 - 2995.00 USD
Feb. 14, 2020 to Feb. 23, 2020 - 2995.00 USD
Nov. 20, 2020 to Nov. 29, 2020 - 2995.00 USD


• Explore the charm of Old Havana
• Go back in time on a walking tour in Havana
• Enjoy the vibrant gay nightlife in Havana
• Get a sense of the struggles of LGBT people in Cuba by meeting with local activists
• Learn to salsa in Trinidad
• Dine under the stars in an 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 meal

Hola! Welcome to Cuba. Our 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.

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.

The beautiful colonial city of Trinidad is home to numerous churches and many beautiful 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.

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 sunset from the stunning Palacio del Valle. We'll round off our day with another local dinner.

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!

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.

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 optional dinner and drinks.

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.

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 activists who fight for LGBT rights and equality in Cuba. For our final evening, we'll enjoy an included feast at one of the best restaurants in town, and head out for optional drinks.

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
• 9 breakfasts, 8 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

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

• Gratuities for Tour Leader ($50-$100 USD/CUC)
• Departure tax (25 CUC) if applicable

OUT Adventures is all about good times with likeminded guys. Whatever's on the itinerary - from fireside camping to five-star decadence - our goal is to make the experience magical. We're also committed to supporting the communities we visit by hiring local guides, staying at locally-owned accommodations when possible, and celebrating local cuisine. It all adds up to a great way to immerse yourself in the culture.

CULTURE SHOCK: On this trip, we'll share with you the Cuba we love, but also want to manage your expectations. The level of service may not be what you're used to, choice of food may be limited, the roads aren't great, and poverty is wide-spread. Keep an open mind, and realize things may go wrong. That said, what makes Cuba amazing is this rapidly-changing island has been cut off from Western civilization for decades and is just coming into its own.

LOCAL LGBT SCENE: LGBT Cubans were not able to choose where they lived until recently, so there was never a gay ghetto. Now that people are permitted to live where they wish, the gay scene in larger cities is blossoming. Not surprisingly, the most vibrant gay nightlife is in Havana.

WEATHER: December through March are the coolest months of the year in Cuba. The average daily maximum temperature is 25C/77F, dropping to about 18C/65F at night. During these months, occasional cold fronts may come through from North America, which can mean a few cool nights (around 5C/40F), and possibly rain.

REQUIRED VACCINATIONS: Based on the entry requirements for Cuba, there are no vaccinations needed for entry. To determine if you should take preventative measures to reduce the risk of illness, you should consult your doctor or a travel medical clinic, as OUT Adventures cannot provide vaccination recommendations.

ELECTRICITY: You will need an international travel plug/adapter for type A/B/C/L sockets. Visit for more information.

CONNECTIVITY: It can be tough to stay connected with the outside world, as Wi-Fi is rarely available. When it is, you may not be able to access email or social media. Rather than fighting it or getting frustrated, why not disconnect your electronics and connect with this amazing culture and place? You can always post your photos later.

AMERICAN TRAVEL TO CUBA: This tour meets the legal requirements of "Support for the Cuban People" category and incorporates a full-time itinerary featuring exchanges and cultural activities that better the Cuban people. OUT Adventures works and plans the logistics of this tour through a US-based agency that is subject to the jurisdiction of the United States. For more information, please click the "Have a Question" button on your right, and ask away!

For everybody's peace of mind, medical travel insurance is required on all Out Adventures tours. At a minimum, your travel insurance must provide cover against personal accident, death, medical expenses, emergency repatriation and personal liability, with a minimum medical coverage of US $50,000.

For more details, visit

All OUT Adventures are led by a gay (or gay-welcoming) guide. Whenever possible, we hire destination locals. And we can also connect you with the right people if you'd like to delve deeper into the local culture. If you're pleased with your guide, we recommend a tip of US $5-10 per person, per day...they'll certainly appreciate it!

OUT Adventures are a great way to meet people from around the world and all walks of life. Bear in mind that everybody's there for a good time, so mutual respect will go a long way. Please be on time for any meet ups, empathetic to the needs of others, and ready to roll with whatever the adventure brings.

Although we can't tell you who your fellow travellers will be for privacy reasons, we can tell you many great friendships began with an OUT Adventure. And just because we're a gay tour operator doesn't mean we're exclusive: friends and family are always welcome to join the fun.

If you've never travelled on your own, it's an amazing way to get to know yourself while making new friends along the way. We can arrange for you to share a room with people in your age range at no charge, or you can pay a supplement for your own room. And if there's an odd number of solos, we'll rotate a single room on a random basis.

The itinerary is correct at time of publishing. If anything, it will only get better based on feedback from prior travellers and our own research. It's best to reference your final trip documents rather than our website in case there have been any changes that affect your departure.

Every OUT Adventure offers optional excursions that are not included in price of this trip. Please see your daily itinerary in your final pre-trip packet to see what's available.

Your central Homestay/B&B info will be provided in your pre-trip documents approximately 21 days prior to departure.

If you are checking in to a hotel or our homestay under your OUT Adventures reservation, a complimentary arrival transfer will be included.


If you are happy with services throughout your trip, a tip is recommended. Tipping details will be provided in your final trip documentation, however we recommend budgeting approximately $150 USD.

The local currency is the Cuban Convertible Peso. We usually recommend carrying local currency for small purchases, however credit cards are accepted at most upscale restaurants, and at hotels. We also recommend carrying approximately $400 CAD to be used only in the case of an emergency, or if your credit/ATM cards are placed on hold (please note: American credit/ATM cards will not work in Cuba).

Most Out Adventures entail carrying your own luggage on occasion. And while you'll never schlep far, things can quickly get costlier than a celebrity breakup if you don't keep your baggage under 20kg/44lb thanks to costly surcharges on domestic flights. You should also bring something smaller for day trips to carry water, your camera, and any souvenirs you find along the way.

The following packing list is a guideline, not gospel. Our Out Adventure Specialists are happy to answer any specific questions about how much or little to bring.

Travel Documents:

  • Passport/Visas/Flight Itineraries/Travel Insurance
  • Pre-trip packet
  • Credit/ATM card

General Personal Items:

  • Eye mask/ear plugs
  • Smartphone/camera/tablet/charging cords/International travel plug.
  • Daypack
  • Luggage lock
  • Personal Wipes
  • Guidebook/Phrase book/Reading material
  • Protection for your devices from water
  • Travel-size towel


  • Socks
  • Walking shoes
  • Sandals
  • 'Nice' shoes for dinners


  • Underwear
  • Pants/Jeans
  • Shorts
  • Swimwear
  • 'Nice' pants for dinners


  • Short-sleeved shirts
  • Long-sleeved shirts
  • Sweaters
  • 'Nice' shirts for dinners


  • Fleece sweater/jacket
  • Waterproof jacket/poncho


  • Warm hat and gloves
  • Sunglasses/Hat
  • Small Umbrella
  • Refillable water bottle(s)

Health-related Items:

  • Small First aid kit including ibuprofen, acetaminophen, zinc oxide tape and small scissors, blister pads, diarrhea tablets, dioralyte rehydration packs
  • Personal Medication
  • High protection sunscreen/lip balm + sun barrier cream for nose/ears
  • Insect repellent/bite cream/antihistamine
  • Antibacterial gel/wipes
  • Toiletries including toothbrush, toothpaste & deodorant

We love when groups of friends join us on an OUT Adventure, whether you're celebrating a major milestone, or you just love to travel together. However, since we have travellers that will be flying solo, or as a couple, we would love your help ensuring everybody feels welcome and has an epic time. Here are some ways you can give us a hand, while also getting to know and befriending your fellow travellers:

  • Sit with (and get to know) different people at different meals
  • Mix up walking partners on excursions
  • Invite solo travellers to join you for an optional excursion or meal
  • Enjoy inside jokes in privacy, or let the group in on the secret ;)

If you'd rather relish an exclusive escape with just your own party, we also offer private departures. This is a great way to create and manage your own holiday guest list, while possibly saving money as well. Please contact one of our Adventure Specialists if you're interested in a customized quote.

All Out Adventures guests must have a good level of health. All tours, regardless of activity level, involve uneven steps, stairs, walking tours, and you will be required to carry your own luggage from time to time. Unfortunately, we are not able to accommodate individuals with limited mobility unless they are willing to absorb the cost of a private guide/assistant which varies by country and is only possible on a case by case basis. It is also your responsibility to advise Out Adventures of any pre-existing medical conditions that may increase the risk of you requiring medical attention, or that may affect the normal conduct of the tour and the enjoyment of the tour by other participants.

Below is a breakdown of our Physical Rating guide.

1 - Relaxing

  • Very little or no hiking
  • Light activities such as walking, bike tours, paddling or swimming are completely optional
  • Low altitude
  • Suitable for all fitness levels

2 - Light

  • Light walking and hiking (2 hours or less per day and at low altitude)
  • Light activities such as bike tours, paddling or swimming are completely optional
  • Suitable for most fitness levels

3 - Average

  • Light walking and hiking (3 hours or less per day, rarely at high altitude)
  • Some activities such as biking, paddling or swimming. Active days are mixed with relaxed days
  • Suitable for an average fitness level

4 - Demanding

  • Walking, hiking is a component of the tour (can range from 2 hours to 6 hours per day, at various altitudes)
  • Activities such as biking, paddling or swimming may be mixed in
  • Suitable for a good fitness level

5 - Challenging

  • Walking, hiking, biking, paddling or kayaking are the vast majority of the trip (can range from 2 hours to 8 hours per day, generally at high altitude)
  • Activities will likely happen day after day with limited rest days
  • Suitable for above average fitness level