Cuba Street Culture and Old American Car Photography Tour
Overview
A ten-day Cuba photography tour shaped around street scenes, portraiture, architecture, and the country's old American cars. The route moves through Havana, Viñales, Cienfuegos, and Trinidad, with planned sessions at golden and blue hour, private car shoots, a tobacco farm visit, and time to photograph musicians, dancers, and local residents. Travel is grounded in the Support for Cuban People category: guest houses, private transportation, and small local restaurants are part of the experience. The physical level is Easy, and the schedule includes free time for independent street photography. Guests are encouraged to bring gifts for Cuban people as a gesture of goodwill.
Why I created this expedition
The photographic narrative begins in Havana, where the old city is not treated as a backdrop but as a working streetscape. Mornings move through Havana Vieja with portrait and street photography, followed by a planned visit to document a boxing training session. Later, Paseo del Prado, the Chinese quarter, Havana Centro, and the Capitolio area offer changing light and a steady rhythm of street portraits and impromptu models.
From the city, the tour shifts west to Viñales. The pace slows around tobacco fields, a working farm, and elevated viewpoints for sunrise and sunset. This is the section where landscape and labor come into frame, with the day built around early light and the soft color of the valley at dusk.
The final arc runs through Cienfuegos and Trinidad. Cienfuegos adds a short stop at its main square and boulevard. Trinidad is the deeper study: early morning streets before breakfast, palace interiors, a session with a musician, horse carriage photos, panoramic views from Manaca Iznaga, and street portraits into blue hour. On the hike into El Cubano Park, the itinerary includes the chance to photograph Cuba's national bird, the Tocororo, and the Javira Waterfall.
Photographic opportunities
Planned opportunities include street and portrait work in Havana Vieja, a boxing training session, and a dedicated shoot with old American cars. Golden and blue hour are repeated across Havana, Viñales, and Trinidad. In Viñales, the itinerary includes a tobacco farm visit, ecological walk, and sunrise and sunset from elevated viewpoints. Trinidad adds colonial facades and squares, a musician portrait session, a horse carriage shoot, and panoramic views from Manaca Iznaga. Cienfuegos offers a shorter architectural stop at its main square and boulevard. The El Cubano Park hike includes Javira Waterfall and the chance to photograph the Tocororo, Cuba's national bird. Afro-Cuban music and street dance are noted as cultural highlights.
Who this journey is for
The tour is designed for photography enthusiasts and amateurs alike, with a physical level rated Easy. It will appeal to photographers who want to work close to the street: portraits, impromptu models, old American cars, and colonial architecture, rather than a wildlife-focused itinerary. Days include free time for independent exploration at your own pace. Travel uses guest houses, private transportation, and local restaurants, and the itinerary is grounded in the Support for Cuban People category. Anyone who enjoys slower observational photography, cultural contact, and flexible street wandering will find the format well matched.
Highlights
- The Amazingly Kind & Welcoming People of Cuba!
- Private shooting with old American Cars in Havana
- Live Street Photography Workshop
- Afro-Cuban Music & Street Dance
- The Beautiful Rural Tobacco Region of Viñales
- Magnificent Spanish & French Colonial Architecture
The journey at a glance
Following the route
The journey moves gradually through 5 distinct overnight bases.
Route shown schematically for orientation.
Itinerary
Day 1
Bienvenidos a Cuba!
Arrival day Meeting with Tristan at the airport and transfert to your Guest House Meeting and tour presentation First relax photo walk to get acquainted with the city Meeting Dinner in the center
Day 2
Havana Old Town
Stroll and street and portrait photography in Havana Vieja Privilege to document a boxing training, national sport in Cuba Lunch in a charming restaurant Discover of the iconic sites and squares Street photography and meeting with impromptu models Golden and Blue Hour
Day 3
Havana Centro & Surroundings
8am Morning walk in Paseo Del Prado 9am Chinese quarter 10am Havana Centro for a street photo session 11am Capitolio Area 1:30pm Free Time 3:30pm Riding in an American car & discovery of the surroundings of Havana 6pm Blue hour in the center
Day 4
Havana to Viñales
8:30am Departure to Viñales 12:30pm Lunch in a charming restaurant 2pm Check-in at the Guest House and rest 3:30pm Viñales Discovery tour 5pm Sunset from Hotel Jasmin 6:30pm Dinner
Day 5
Viñales
6am Sunrise from a nice viewpoint 7:00am Walk ecological herbolistic walk Viñales’s field 9am Visit of a Tobacco farm 10:30am Break (or optional walk to los Acuaticos hills for a lunch – 2hours) 12:30pm Head to a charming restaurant in the valley 2pm Head to Cayo Jutias Beach or Horse Ride in Valle Palmaritos 5:30pm Sunset from Hotel Jasmin 7pm Dinner
Day 6
Viñales – Cienfuegos – Trinidad
8am departure from Viñales Classified as a Unesco World Heritage Site Lunch on the road 13:30pm Stop in Cienfuegos for a walk in its main square and boulevard. 3:30pm Check-in 4:30pm first walk in Trinidad to discover the city 6:00pm Golden and blue hour photos 7:00pm Dinner
Day 7
Trinidad
7am Morning walk before breakfast to see the city waking up. 8am Breakfast 9am Visit of the palaces of the city 10am Photo shooting with a musicien and Street Photography 12:30pm Lunch 13:30pm Break 3pm Car ride to Manaca Iznaga for some nice panoramic pictures 4:30pm Back in the center for more street photography with impromptu models 6pm Golden & Blue Hour shots and dinner
Day 8
Trinidad
8:30am Departure to El Cubano Park for a morning hike and photography “ 10am Arrival Javira Waterfall. Possibility to swim 11am Return by the same way and photograph the Tocororo, national bird of Cuba 12am Lunch followed by a Break 2pm Free time for indepandant Street photography 3:30pm Photoshoot with a Horse Carriage 4:30pm Shooting from a tour of the city 5:30pm Street photos with impromptu models until sunset and blue hour 6:45pm Dinner
Day 9
Trinidad - Havana
9am Return to Havana. 11am Lunch on the road 2pm Check-in 3pm Break Photo walk in Havana Centro & Malecon or free time for solo street photography 6pm Cocktail on a Rooftop with one of the best view of the city 7pm Farewell dinner at one of our favorite restaurant.
Day 10
Havana
8:30am Free Morning Optional photo review or editing session with Tristan Transfer to the airport
Accommodation
Where you’ll stay
Price details
Price per person
- 2 people
- 4,595 EUR
- 3 to 4 people
- 3,895 EUR
- 5 to 6 people
- 3,295 EUR
- 7 to 8 people
- 3,095 EUR
- 9 to 10 people
- 2,995 EUR
- 11+ people
- 2,895 EUR
Prices are per person and based on twin share, unless stated otherwise.
Additional costs
- Deposit
- 30% deposit (989 EUR approx.)
What is included
Included
- Accommodation throughout the journey
- Meals indicated in the programme
- Transportation during the itinerary
- Pre-trip planning assistance
Not included
- Lunch on arrival day and departure day
- Tips
- International flights
- Travel, Medical & Cancellation insurance
- Additional drinks and meals
- Expenses not specified in the programme
- Camera equipment
From past travellers
A few kind words
You are in good hands with Tristan!
Tristan does an amazing job at putting together a culturally rich experience. He also does a great job at adapting to his clients needs and interests. He responds well to feedback. He is both professional and personable. I feel as though I had the opportunity not only to photograph many different elements of Colombia, but that I truly experienced the country and its culture. Our adventure took us from birding in the mountains outside of Cali, to visiting remote indigenous tribes, to visiting active fishing villages, to learning about local and historical musicians and customs, to beautiful settings in the mountains and along the seashore.
I give Tristan the highest recommendation as a guide for Colombia.
Colombia Birding Tour
I visited Colombia with Tristan of Remote Expeditions and would highly recommend him. He put together a wonderful itinerary with great knowledge of the areas and attention to details to give us a wonderful sampling of the country. He is personally very gentle and fun by nature and you will return home feeling very happy and satisfied. Whatever your special interest is, I’m sure he can make an itinerary to exceed your goals.
The Magical Mystery Tour!
In March 2026, I ventured out of my comfort zone and booked an 11 day photography tour with Tristan, through Remote Expeditions.
It was amazing. Truly remote, we visited several indigenous communities in the Sierra Nevada, first to meet them and find out a little about their way of life and second lay to photograph them. Additionally there were several opportunities for photographing birds, landscape and City Scenes in Cartagena.
We were fortunate enough to to be a small group, of two , which I was more that happy to pay a premium for. This gave us an intimate experience with the people we met along the way, additionally the 1:1 attention to our personal interests in photography was incredible.
Tristan was a real treat! He has spent the last 10 years living in and exploring this region of Colombia. He has cultivated relationships with the indigenous peoples of the area, and loves to share his understanding of their culture with you.
He structured the tour perfectly. He was organized, knowledgeable (about the land, its people and photography), compassionate, passionate and eager to share his vast internal encyclopedic information with you. When he didn’t know, he would quickly get you the information.
The remote places you get to, by 4x4, hiking and boating are exceptional. You could never find these places on your own.
Knowing little about Colombia, I was initially a little hesitant to take this tour. Having just returned, I wouldn’t hesitate for a nanosecond.
What ever type of tour you take with Tristan, you won’t be disappointed. He delivered everything he he promised, and a few amazing surprises more.
Why travel with us?
Expert, trusted guides
We work with carefully selected local guides chosen for their experience, knowledge of wildlife, and ability to find unique encounters ethically and safely.
Carefully selected accommodations
We choose each accommodation to find the perfect balance between comfort, location, and access to wildlife, so you can make the most of every moment of your journey.
Schedules designed for the best light
We organize activities and outings at key times of day to take advantage of the best light conditions and increase opportunities for wildlife viewing and photography.
You’ll come home with incredible photographs
We design each expedition to maximize opportunities for observation and help you enjoy unique encounters and capture the best photographs possible in the wild.
About your guide
Frequently Asked Questions
To confirm your spot we request a first payment of 50% of the total trip price. The remaining 50% can be paid up to 3 months before the departure date.
We accept payments in euros and US dollars via bank transfer. Once your booking is made, we will send you all the information and details needed to make the payment.
No, anyone who loves nature is welcome. We always recommend bringing binoculars to enjoy a closer view, and if you have a camera you'll surely capture excellent images too.
You can find all the details about cancellations, refunds and booking conditions on our page: Terms and Conditions.
No. Our trips are designed both for people with experience in photography and wildlife watching and for travelers who simply enjoy nature and want to live a different experience.
The most important thing is to have interest, curiosity and a desire to enjoy the environment and the animals.
Yes. If you wish to arrive earlier or extend your stay, we can arrange additional nights of accommodation, activities and transfers. Just let us know your plans and we'll adjust the itinerary to your preferences.
Yes, of course. Many of our travelers join the expeditions on their own. Our groups usually bring together people with similar interests in wildlife, photography and nature, so the atmosphere tends to be very friendly and it's easy to connect with other travelers.
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