Cuban Culture & Exploration
7 Nights

A week in Cuba gets you into the nuances 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 and great food in Havana. We then take off into the countryside 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. 

Upcoming trips

November 15 - 22, 2019 — SOLD OUT

December 27, 2019 - January 3, 2020

February 14 - 21, 2020

April 3 - April 10, 2020



- 7 Nights
- Intimate group of curious and cultural travelers with two hosts
- $2,895 / per person, inclusive of lodging, meals, transport and arts access


Because our trips cater to the cultural calendar of Havana, specifics of our itineraries shift from trip to trip. 


Day 1 / FRIDAY

You arrive into José Martí Airport. One of our drivers 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 that will be your home for a week and spend some time getting to know the area on your own with a map and tips from us. In the evening we gather for the first time as a group. We begin each trip on the porch of our Turquoise House to get to know one another over rum and Cuban records. Dinner is just a couple of blocks away at a rooftop restaurant. After dinner we let you loose into an incredible art space next door filled with music, art and dance.



We make our way in the morning 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 then make our way towards Havana Vieja and get dropped at a fabulous salsa school so that we can begin to get the unique Cuban rhythm into your system. With a full morning behind us, we lunch on the rooftop of an amazing design-centric paladar. We then head out on foot to see a bit of Old Havana and to visit the studio of one of our artist friends. You have the rest of the afternoon to wander with one of our custom maps or take a siesta back at your casa. In the evening we head out to see big band salsa (and practice your dance moves!) before having dinner at one of Havana’s more exquisite restaurants run by a Spanish chef. As always, we will have details on where to see the best late night music, if you are keen to explore more.



We spend the morning having two studio visits with emerging artists before heading to a relaxing waterside beach club. There is no sand, but the water is perfect and protected from the waves, so always swimmable. We enjoy a relaxed tapas lunch and spend the afternoon taking in some sun, swimming and taking it easy. We either see an early theatre performance or stop into the Hotel National for a drink overlooking the ocean and a talk about the historical significance of this impressive hotel. We then walk to dinner at an exquisite paladar run by friends of ours who feel more like family. Late night music recommendations are not far away at a great Latin Jazz club.



In the morning we take a two and a half hour drive to Viñales. Viñales is a beautiful town deep in the mountains of tobacco country. The energy is so very different outside of Havana, and it’s an important shift to understanding Cuba. We have a long lunch overlooking the valley at a local farm that grows all of its own food. You get some time to settle into your Viñales home before we head out into the majestic national park on horseback to see a different way of life and learn about tobacco farming and cigars. We head back at sunset and have dinner at a relaxed tapas bar.



This is the day when exploration really kicks in. We head out for a day at the beach, which is about an hour and a half fascinating, beautiful and bumpy drive away. Some of our travelers choose to stay in Viñales to relax a bit more and hike in the beautiful scenery, which is another great option. If you have come to the beach, you can find secluded areas to read all day, snorkel, drink coconut water or just swim in the warm turquoise water. A good beach that is not attached to an all inclusive hotel is hard to find in Cuba. This is one of them. At the end of the day we all gather back together in Viñales for a relaxing traditional dinner at an outdoor family restaurant and have time to wander and see the stars.


DAY 6 / Wednesday

We say goodbye to Viñales in the morning and head back to your home in Havana. We have a relaxed lunch near your casa trading stories and perspectives on the last few days. The early afternoon you spend exploring on your own with our custom maps, and we all meet back together in the late afternoon at the Turquoise House for a private concert by the band of our co-founder Norberto. It is a great time to get to know musicians who are working in Cuba and get an intimate look into the workings of the creative practice in Cuba. We then head to an artist’s home/studio for dinner surrounded by art and colorful conversation. The night’s music recommendations will take your into the heart of local Latin Jazz, a very Cuban place that has incredible people watching!



We start the day jumping into restored 50’s convertibles to see more of the city you are getting to know so well. We visit an art collector or an exhibition at one of the galleries we know and love before having a light lunch at a famous paladar. After lunch we head to a large art and printing collective filled with friends of ours. Spend the rest of the afternoon with our map full of recommendations or go stock up on rum and cigars. Many of our travelers just like to wander the streets of Havana Vieja with an ice cream cone and a camera. We have cocktails with a professor who grew up in Havana in the 40s and who is full of stories and perspective. We then head for a final dinner together at one of Havana’s oldest and best restaurants. We swap stories and lessons and thoughts about the trip. If you want more music on your last night in Havana, the arts club you visited on your first night is open again . It is so big and full of energy that many like to return. It’s only a two or three block walk home.



Enjoy a last relaxed breakfast at your casa reflecting back on all you have seen. If you have a later flight, plan to explore areas we did not see or go back to places you loved. 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.

A taxi breaking down 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 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 ⌄

  • 7 nights
  • $2,895 / per person based on double occupancy includes all lodging, meals, activities / entrance fees and all group transport
  • Deposit of $950 to secure your booking
  • Balance due 60 days before departure
  • Single room supplement of $240

The Fine Print ⌄


  • 5 nights lodging in beautiful casa particulares (local, licensed homes) in Havana
  • 2 nights lodging in more simple countryside casa particulars in Viñales
  • 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
  • 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 to arrive no later than 5pm into Jose Marti Airport in Havana. Our trips start at 7pm sharp on Day 1 at our Turquoise House in Vedado. This is an important gathering to coordinate logistics. You are welcome to land in the morning, drop your bags at your casa and explore on your own until 7pm. Some of our guests also choose to fly a day early and we can help with extra accommodations.


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.