Writing & Waking up to PLace
5 Nights

This retreat is designed for travelers looking for culture and adventure while learning a new approach to writing and a mindful and aware life.

Together with writing teacher Sarah Cyr, we will move through Havana blending prompted writing sessions and meditation with the cultural immersion and insider access that Otros Ojos is known for.

Live in comfortable unique residences in our neighborhood near theaters, music venues and restaurants that we visit. Write and observe in a culture that balances space and intensity in equal measure. See concerts and art studios that will give you new perspectives outside of your writing practice. Spend a morning reflecting on writing ritual in the house where Hemingway wrote some of his most beloved books.

As we prepare to go to Cuba, we will read short books, poems and excerpts from a range of Cuban writers and those greatly influenced by this magical place.

Retreat Dates

January 22 - 27, 2020



- 5 nights
- Intimate group of mindful and curious writers
- Workshops and writing practice paired with insider local perspective and access
- $2,195 / per person inclusive of lodging, meals, transport and arts access


Because our trips cater to the cultural calendar of Havana, specifics of our Cultural activities may shift.


Day 1 / Wednesday

You arrive into Jose Marti Airport. One of our divers will be waiting for you and will take you to Vedado, the creative neighborhood of Havana where you will be living. You will say hello to one of our team members, get settled in your casa and spend some time getting to know the area on your own with a map and tips from us. In the early evening we will gather with the group for introductions, intention setting and initial writing exercises & reflections. We head to a special local paladar (privately run restaurant) for a welcome dinner and walk to a historical hotel and bar afterwards to take in history, context and amazing views.


Day 2 / THUrsday

We begin our day with a writing session to dig into where we are. We then make our way to the other side of Vedado to our favorite art gallery. This space is an incredible way to begin to grasp the depth of work and ideas present in Cuban art. It also shines a beautiful light on the intensity and power of Cuban culture. We lunch at an amazing design centric paladar afterwards do an observational walking and writing session followed by a group gallery and artist studio walk. Guests have time in the late afternoon to explore the small streets and varied energy of Havana Vieja on their own or head home for a siesta. Dinner is just a couple of blocks away from where we stay at a rooftop restaurant, followed by an evening at what many consider to be the best cultural space in Latin America full of art, music and dance.



We start the day with a long writing session before heading to a secret city beach club for lunch, on your own writing, meditation, sun and swimming. In the evening, we head to an artist’s home/studio for dinner surrounded by art and colorful conversation. If you still have energy, we have a music recommendation for you to explore on your own.



After a short morning writing session, we head out to see how Hemingway wrote in Cuba. Finca Vigía is a pilgrimage for many writers and a special time to think about our own writing practice. We’ll tour his house and get a chance for quick in place writing observations. We return to Havana for a late lunch at an arts centered café and do a writing and walking session in Vedado, our neighborhood filled with local markets, art murals and a view on daily Cuban life. In the evening we head to see experimental theatre with a director talk or go to see some of Havana’s best music in a famous venue followed by dinner at a hidden gem that is chic and upscale.



We’ll dig back in for a final intensive writing session in the morning and have lunch together at The Turquoise House with an incredible professor who has lived in Havana for over 80 years. The afternoon will give you time to explore and write on your own before meeting the group at a farewell dinner back in a magical place in Old Havana under sparking lights. Late night music recommendations are likely at a great Latin Jazz club.



Enjoy a last relaxed breakfast at your casa reflecting back on all you have seen. Depending on your flight, you will have time for personal exploration in a place that now has so much more meaning. Then farewells before jumping in cars back to the airport. A taxi will be waiting for you at your casa three hours before your flight to take you back to Jose Marti Airport.

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 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.

Details &
The Fine Print

Feel free to reach out to us with any questions. You can also find more information about travel regulations and logistics here.

Details ⌄

  • 5 nights
  • Intimate group of mindful and curious writers & travelers
  • Workshops and meditation paired with local perspective and access
  • $2,195 / per person based on single occupancy includes all lodging, meals, activities / entrance fees and transport within Cuba
  • $950 deposit to secure your booking by Nov 15 though places may go before this date
  • Balance due 60 days prior to departure

The Fine Print ⌄


  • Lodging in beautiful casa particulares (local, licensed homes)
  • Breakfasts at the Casa where you are staying
  • Lunches & Dinners with the group at our favorite spots (ranging from the best restaurants in Havana to holes in the wall that have incredible food)
  • Airport transfers
  • Transportation to all group activities and events
  • Entrance to all group cultural venues, concerts and activities
  • Writing classes and exercises
  • Recommendations for late night music each night
  • 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
  • Entrance to late night music venues on your own


Please book flights that land no later than 5pm on Wednesday into Jose Marti Airport in Havana. Retreat begins at 7pm sharp at our Turquoise House in Vedado and customs and baggage claim are time consuming. Our first gathering is an important time 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. For those flying from the west coast, we have a few tricks up our sleeves on good flights (we have done this a lot). Please feel free to reach out as initial airline searches can look daunting.


If you need to cancel or modify your trip with us, we need your 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

If there are changes in law by the US government that make a trip legally impossible for you to travel, a full refund (including deposit) will be refunded.



Plans in Cuba change for a million different reasons, and this itinerary will 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.