Havana & The Countryside
7 Nights | 8 Days

A week in Cuba gets you into the crevices, communities and rhythms of this island. There's so much to see and experience, and we pack this week full of varying perspectives. 

We start the week just like our weekend trip with music, culture, great food and late nights in Havana. We then take off into the countryside and beaches for a totally different take on Cuba, a more simple approach and a change of pace. We come back to Havana for more nuanced gatherings and conversations with our community. You'll leave with a rich understanding of the parts at play and a love for the diversity and rhythms of this magical culture. 

Friday afternoon to the following Friday morning

Current trips

February 22 - March 1, 2019
March 15 - March 22, 2019

We will be posting additional 2019 trips as well as winter 2020 trips soon.
If you are interested in a specific date, please reach out to us.

What the week looks like ⌄


We begin each trip on the porch of our Turquoise house. We gather there to ground the group and get to know one another over rum and Cuban records. Dinner is just a couple of blocks away at a rooftop restaurant followed by the night at what many consider to be the best music/art/dance space in Latin America. Fabrica is one of the many reasons our neighborhood has become such a magnet for the arts, and we are thrilled to call it our neighbor. It is open until 3am, and you can walk home when you are tired.


Mid-morning we jump in old cars to see the city and take it all in! We lunch at an amazing design centric paladar. We walk the old city popping into artist studios and cool shops we love, and we learn about the context and culture of Havana. Guests then heads out on their own to explore the small streets and varied energy of Havana Vieja and back to their homes on their own in time for siestas and showers. We have dinner at a hidden gem that is chic and upscale and see some of Havana’s best music after in a famous venue.


A morning filled with studio visits and/ or salsa dancing depending on preferences, then off to a member beach club for lunch, relaxing and swimming. In the evening we see a theatre performance by one of Havana’s most incredible playwrights and directors, and get the chance to speak with her after. Those who do not speak Spanish need not worry, the work is always multi-sensory and we will get the chance to connect about it after. We talk theatre and culture over traditional food at a magical paladar and spend the rest of the evening sipping rum overlooking the water and digesting all that we have seen and sensed.


Early morning drive 2.5 hours to Viñales. The energy is so very different outside of Havana and it’s an important shift. The day is spent on horseback taking in the lush national park, majestic cliffs, and different way of life. We have lunch while out in the park and stop to see tobacco fields and drying huts. Dinner is at a favorite spot of ours in this lovely chilled out town. If you are not too tired, you can dance late into the night off the town square or explore the dark streets and relaxed energy.


We head out for a day at the beach, which is about an hour and a half fascinating and beautiful drive away. Once at the beach you can find secluded areas to read all day, snorkel, drink coconut water or just swim in the turquoise warm water. This is truly a day of rejuvenation and reflection. There is a lot of energy moving in Cuba, and it can be intense. We have a relaxing dinner back in Viñales and have time to wander and see the stars.


We head back to Havana early and get settled back in the casas you lived in earlier in the week. We have lunch at our home and learn about Cuban cooking. Over lunch a charismatic and lovely friend talks about life in Cuba before the Revolution. We leave the afternoon open for requests that have come up or desires to get out and explore on your own. Our music Wednesday is at a tiny spot filled with our community who will be thrilled to meet the group and dinner at a funky place nearby.


Depending on the cultural calendar we spend the late morning into afternoon at studios or exploring Vedado We lunch at an arts café and in the early evening see music in the place where underground American music was played in secret when it was banned in the 60s and 70s and end our last evening back in a magical place for dinner in Old Havana under sparking lights and likely a wander around the beautiful dark streets.


Breakfast at your host home, as always, and personal exploration before your transport back to the airport.

Pricing & Details ⌄

  • 7 nights
  • Intimate 10 person group with two guides
  • Flexible traveller attitude and insider local perspective and access
  • $2,895 / per person based on double occupancy includes all lodging, meals, activities / entrance fees and transport within Cuba
  • Depostit of $950 to secure your booking with the balance due 60 days before departure
  • Single room supplement of $240

The Fine Print ⌄


  • Lodging in Havana and Viñales in local homes (casa particulares)
  • Breakfasts on your own at the Casa where you are staying
  • Lunches & Dinners with the group at our favorite spots (ranging from the best restarants in Havana to holes in the wall that have incredible food)
  • Transportation within Cuba (exclduing late taxis home at night)
  • Airport transfers
  • Entrance to all cultural venues, concerts and activities
  • Tips for musicians, speakers and artists


  • Airfare to Havana's Jose Marti Airport & visa
  • Mandatory travel insurance
  • Alcoholic drinks
  • Transportation pertaining to personal exploration and late night returns home
  • Tips for guides


Please book flights that land no later than 5pm into Jose Marti Airport in Havana. Trips start at 6:30pm sharp on Friday evening at our turquoise house in Vedado. It is an important gathering to ground the group and get to know one another before heading out to a special evening. You are welcome to land in the morning, drop your bags at your casa and explore on your own until we meet. Some of our guests also choose to fly a day early and we can help with rooms if this is the case.


If you need to cancel your trip with us, we need your cancelation request in writing via email.

  • 61+ days prior to departure: full refund (minus the nonrefundable deposit)
  • 31 to 60 days prior to departure: 50% refund (minus the nonrefundable deposit)
  • 0 to 30 days prior to departure: no refund


- 7 nights | 8 days
- Intimate 10 person group with two hosts
- Flexible traveler attitude and insider local perspective and access
- $2,895 / per person includes all lodging, meals, activities / entrance fees and transport within Cuba

Sound good? 
We think so too! 

To make sure we are on the same page, and that this trip will meet all that you are looking for, check to see if you fit our first description and not our second! 

This trip is for you if... 

You are flexible and don't attach to certain outcomes.

You are curious about how different cultures view the world.

You love great food and nice venues, but also appreciate the more exploratory side of traveling.

You enjoy connecting with people and learning their stories.

You can stay up late a few nights in the name of great cultural experiences and good fun.

You are physically fit enough for some long walks, a horseback ride and some bumpy car rides.

Sitting by the side of the road waiting for a flat tire to be changed is an adventure rather than an inconvenience to you.

You are comfortable with contradictions.

This trip is NOT for you IF... 

You are interested in seeing rather than engaging with a culture.

You need a set schedule that is adhered to with precision.

You need an early bedtime every night.

Long walks or a horseback ride can feel burdensome.

You are interested in a trip that consists of high-end hotel stays, multiple museum visits and the highest standard of comfort.

You need concise answers when trying to understand a society.



Plans in Cuba change for a million different reasons, and this itinerary can shift with those changes. It is one of the most beautiful and frustrating things about the culture, but there is no changing it. We go to great lengths to make sure your trip is fluid, exciting and fun, with few hiccups. But to experience Cuba is to experience change (and a flat tire every once in awhile). 

This trip adheres to the U.S. Government Support of the Cuban People Licensed Trips and you will be given all documentation necessary for legal travel to Cuba.

Otros Ojos is part of TwelveTwelve Projects LLC. By coming with us on this trip, you understand that all activities are voluntary and neither Otros Ojos nor TwelveTwelve Projects is liable for your choices.