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VANISHING CUBA | HAVANA

Old Havana, Central Havana, Vedado, Regla and Vinales

VANISHING CUBA

HAVANA

EASTERN CUBA

CUBA PRIVATE

The Boxers, Ballerinas, and Barrios of Havana.

This 5-Day Havana Photo Tour and Cultural Adventure will take you on a journey through the grand boulevards and rough and ready backstreets of this spectacular Caribbean capital. A city steeped in romance and nostalgia, Havana has also managed to forge its own cutting-edge contemporary culture despite being cut off from the modern world for over sixty years. Arguably one of the most photogenic cities in the world, we will delve into the city’s hidden corners and treasured cultural institutions, experiencing the best of dance, sport, religion, and music.

The streets of Havana are a time capsule of vintage cars from the fifties that cruise past collapsing colonial architecture. Instead of the classic car ride in a squeaky clean Chevrolet enjoyed by most tourists, we will step into a workshop to observe the challenging restoration process behind the scenes that keeps these beauties up and running after decades of use.

Taking a short ferry across the bay, we will land in the Regla neighborhood, Havana’s heart of Afro-Cuban religion and culture. On Regla’s shore sits a humble church whose white and blue interiors pay homage to the Black Madonna, also known as Yemayá, the spirit of the ocean in Cuba’s Santería faith. This neighborhood, with an imposing cityscape of Old Havana in the distance, may seem rather unassuming. However, walking through its rundown streets will reveal secretive Afro-Cuban symbols at every turn: evil eyes painted on the walls and religious shrines in the doorways stemming from African folk practices.

Our Havana photo trip will also take us into a sweat-soaked boxing gym to catch young athletes honing their craft. A great chance for sport and live-action photography, our cameras will snap partners sparring, muscles tensing, and faces glistening. Havana is a city of raw grit but it is also one of grace and beauty. With an old mansion as our backdrop, we will shoot a group of Cuban ballerinas as their bodies create delicate yet powerful shapes, channeling their emotions and hopeful aspirations for the camera.

OUR RECIPE FOR SUCCESS:  It’s been said that we really know how to do Cuba right. We stay in the finest and most authentic Casa Particulars (privately owned Cuban hotels and bed & breakfasts). We travel by air-conditioned vehicles and beautifully restored vintage American automobiles. We dine in world-renowned Cuban restaurants and authentic hidden gem paladars. And lastly, we expose you to not only a truly amazing and authentic Cuba but the most photogenic Cuba. We always travel to Cuba under the General License 31 CFR § 515.574 – Support for the Cuban People.

This immersive 5-day photography tour is more than just a quest to capture exceptional images; it’s an invitation to elevate your craft and see the world through a new lens. Our expert photographer guides will not only lead you to the most photogenic locations under the best light but also help you master the art of visual storytelling. Along the way, you’ll refine your camera techniques and discover how to navigate the challenges of photographing in a foreign land. You’ll also learn to anticipate a scene before capturing the decisive moment, elevating ordinary photos into extraordinary works of art.

Join us for spirited discussions, enriching camaraderie, and moments of unforgettable inspiration. Every photographer should come to Havana to discover the artistry of boxing and ballet and the secrets behind its classic cars and Afro-Cuban religion. Your visual odyssey begins here!

The streets of Havana are a time capsule of vintage cars from the fifties that cruise past collapsing colonial architecture. Instead of the classic car ride in a squeaky clean Chevrolet enjoyed by most tourists, we will step into a workshop to observe the challenging restoration process behind the scenes that keeps these beauties up and running after decades of use.

Taking a short ferry across the bay, we will land in the Regla neighborhood, Havana’s heart of Afro-Cuban religion and culture. On Regla’s shore sits a humble church whose white and blue interiors pay homage to the Black Madonna, also known as Yemayá, the spirit of the ocean in Cuba’s Santería faith. This neighborhood, with an imposing cityscape of Old Havana in the distance, may seem rather unassuming. However, walking through its rundown streets will reveal secretive Afro-Cuban symbols at every turn: evil eyes painted on the walls and religious shrines in the doorways stemming from African folk practices.

Our Havana photo trip will also take us into a sweat-soaked boxing gym to catch young athletes honing their craft. A great chance for sport and live-action photography, our cameras will snap partners sparring, muscles tensing, and faces glistening. Havana is a city of raw grit but it is also one of grace and beauty. With an old mansion as our backdrop, we will shoot a group of Cuban ballerinas as their bodies create delicate yet powerful shapes, channeling their emotions and hopeful aspirations for the camera.

OUR RECIPE FOR SUCCESS:  It’s been said that we really know how to do Cuba right. We stay in the finest and most authentic Casa Particulars (privately owned Cuban hotels and bed & breakfasts). We travel by air-conditioned vehicles and beautifully restored vintage American automobiles. We dine in world-renowned Cuban restaurants and authentic hidden gem paladars. And lastly, we expose you to not only a truly amazing and authentic Cuba but the most photogenic Cuba. We always travel to Cuba under the General License 31 CFR § 515.574 – Support for the Cuban People.

This immersive 5-day photography tour is more than just a quest to capture exceptional images; it’s an invitation to elevate your craft and see the world through a new lens. Our expert photographer guides will not only lead you to the most photogenic locations under the best light but also help you master the art of visual storytelling. Along the way, you’ll refine your camera techniques and discover how to navigate the challenges of photographing in a foreign land. You’ll also learn to anticipate a scene before capturing the decisive moment, elevating ordinary photos into extraordinary works of art.

Join us for spirited discussions, enriching camaraderie, and moments of unforgettable inspiration. Every photographer should come to Havana to discover the artistry of boxing and ballet and the secrets behind its classic cars and Afro-Cuban religion. Your visual odyssey begins here!

100% Compliant and Legal Travel to Cuba for U.S. Citizens

Photo Workshop Adventures LLC travels to Cuba under the General License 31 CFR § 515.574 - Support for the Cuban People.

Group Size

4-8 Guests

Experience | Difficulty

  • Beginner, amateur, enthusiast, and semi-pro photographers
  • Travel by AC van, vintage American cars, taxis, and bicycle taxis
  • Minimal elevation changes and lots of walking
  • (non-photographers are also welcome)

Weather | Sun

October to November –  Temps 85/71 F  29/21 C  Approx. Sunrise 7:26 | Sunset 7:04 (19:04)
December to March –  Temps 80/63 F  26/17 C  Approx. Sunrise 7:10 | Sunset 6:17 (18:17)
April to May –  Temps 88/69 F  30/20 C  Approx. Sunrise 6:56 | Sunset 8:00 (20:00)

Includes

  • 5 Days
  • Travel, street, people, landscape, and architecture photography
  • Meet with Cuban photographers, students, musicians, artists, and entrepreneurs
  • Professional photographer | guide
  • Cuban guide and driver (English speaking)
  • Photo walks & discussions
  • Small group (4-8 guests)
  • Upscale Cuban Casas
  • All breakfasts 
  • 3 meals 
  • Local transportation in vintage American cars and air-conditioned vehicles
  • Travel under the General License 31 CFR § 515.574 – Support for the Cuban People

What To Expect

Cuba is not just unique but one of the most rewarding photographic and cultural experiences you will ever encounter. Because Cuba is so different, it requires an open-minded and rewarding sense of adventure. As is often said in Cuba, “It’s not what you want; it’s what we have.” Prepare yourself to be completely wowed.

Accommodations

The finest Cuban Bed & Breakfasts

Travel Information

Book your commercial flights to the corresponding airports noted below.
Arrival and Departure Airport: Havana José Martí International Airport (HAV) – Transfer time 45min.
Our adventure begins on the first day at 2 PM at our hotel and ends at checkout on the last day.

Support for the Cuban People

Throughout each day, we are committed to “Support for the Cuban People” under the General License 31 CFR § 515.574. Our goal is to promote independent activity intended to strengthen and support civil society in Cuba and constitute a full-time schedule that enhances contact with the Cuban people and results in meaningful interaction between ourselves and individuals in Cuba. We never pay for lodging at any property on the CPA List to the extent prohibited by § 515.210. In addition, we will support Cuban entrepreneurs launching their privately-owned businesses. Our only accommodations are private Cuban residences (casa particulars). We only eat at privately-owned Cuban restaurants (paladares), and we only shop at privately owned stores run by self-employed Cubans.

Visas

U.S.-based airlines will distribute Cuban Visas at the airport. A Cuban Visa costs $50 – $100 depending on the airline. International travelers who require a Cuban visa can get their visas through the Cuban Embassy or Consulate in their respective countries.

Helpful Links

> Venturing to Cuba for the First Time – by Darrell Miller
> Legal US Travel to Cuba – by Michael Chinnici
> Comparing Photo Adventures – by Michael Chinnici
> Gran Hotel Manzana Kempinski Habana – by Michael Chinnici (no longer available to U.S. Citizens)
> How to Keep Cuban Cigars Fresh – by Michael Chinnici

Vanishing Cuba 5-Day Prices & Dates

Photographer Leader

Photographer Leader

Chase Guttman

January 3-7, 2026

Photographer Leader

Photographer Leader

Michael Chinnici

March 28 – April 1, 2026

*All prices are per person and based on double occupancy. Please select single occupancy for a private room. For your convenience, we offer optional early arrival and late departure accommodations so you can extend your stay before or after the trip. We typically stay in upscale boutique hotels in the 4 and 5-star category. Not all destinations offer these types of properties. We look for unique hotels that offer cultural, historic, and/or authentic features. Depending on the size of the group, smaller boutique hotels may have limited room inventory. In some countries or in remote locations, we may be limited to lodges or branded chain hotels. In Cuba, we stay in upscale family-owned Casas (bread & breakfasts). On all of our tours, breakfast is almost always included, but not guaranteed. Meal categories listed include (B) for breakfast, (L) for lunch, and (D) for dinner.

Vanishing Cuba Book By Michael Chinnici Pwa Pages 600

ITINERARY

VANISHING CUBA | HAVANA 5 DAYS

Day 1 | Arrive in Havana

Note: Our support for the Cuban people program is woven throughout the photography opportunities listed below. Each day brings another opportunity to provide this support. 

We begin our “Vanishing Cuba Photo Adventure” with a walk through Old Havana’s historic district. We’ll have the opportunity to meet with many locals and capture some great street photography.

In the evening, we celebrate with our Welcome Dinner at the award-winning Paladar San Cristobal, located in the heart of Central Havana. A taste of colonial Cuba, San Cristobal offers wonderful entries served on 19th-century china, surrounded by stacks of books, old antiques, and nostalgic black and white photographs. You can ask owner Carlos Cristóbal Márquez Valdés all about it. A favorite among many, including the Obamas, when they visited Cuba. (D)

Day 2 | Havana – Regla – La Fabrica de Arte

After breakfast, we take an early morning ferry across Havana Bay to the community of Regla, a working-class, Afro-Cuban community with a thriving local culture. Regla is especially known for its strong ties to Santería and other Afro-Cuban religions. You will experience a more relaxed and hidden slice of Havana. Regla is a photographic masterpiece. In the afternoon, we’ll visit a fishing village known for its catches of marlin and swordfish, a favorite of Hemingway’s.

Later in the evening, we will visit La Fabrica de Arte Cubana for live music, art, and photography following dinner. La Fabrica de Arte Cubana was founded by Afro-Cuban rock star X Alfonso, who has turned this into a meeting place for young and eclectic Cubans and foreigners. (B) (L) (D)

Day 3 | Havana – Boxers – Ballerina’s – Vedado Mansion – Classic Cars

We begin our day at a famous Havana boxing gym and community center run by local Cubans. Here we’ll enjoy a private photo session with Cuban boxers. Our private session will allow us to capture both environmental portraits and live-action sparring bouts after we’ll drive to Vedado. After, we’ll visit a “lost in time” centuries-old Cuban Mansion for a photography session with ballerinas in this nearby suburb. Built at the turn of the century, this home is truly a masterpiece and has remained untouched since the revolution in 1959.

After lunch, we will visit an American Classic Car restoration garage that has put together a fleet of over 20 pristine “Clasicos” (as Cubans refer to them), to provide professional car service to their clientele. Learn firsthand how they restore these classic American beauties from the 1950s. This setting makes for some amazing photography. Interacting with Cuban businesses and helping them learn how to improve is always our goal under “support for the Cuban people”.

Afterward, we’ll spend the afternoon in these beautifully restored cars, driving along the Malecón (Havana’s seawall), visiting the mansions in the Miramar neighborhood, and experiencing the bustle of Neptuno and San Lazaro streets in the city center. (B) (L) (D)

Day 4 | Vinales – Havana

After breakfast, we depart Havana for a day trip to Viñales Valley, a UNESCO World Heritage Site. People don’t come to Viñales for the music or the mojitos; they come to dip indulgently into the natural world, hiking, horse-riding, or photographing some of the most beautiful landscapes in Cuba. In the valley, you’ll experience craggy limestone monoliths, and cigar-chewing guajiro’s driving their oxen and plowing through the rust-colored tobacco fields.

Despite its longstanding love affair with tourism, this slow, relaxed, wonderfully traditional settlement is a place that refuses to put on a show. What you see here is what you get – an agricultural town where front doors are left wide open, and everyone knows everyone else. We’ll be talking with local farmers and learning about their lives. We’ll enjoy lunch at an organic farm with a stunning view of the valley. We’ll visit the family farm of a private tobacco grower known for their world-famous Cohiba cigars.

In the evening, we’ll enjoy our “Farewell Dinner” in Old Havana upon our return to Havana. (B) (L) (D)

Day 5 | Old Havana – Art Deco – Malecón – La Guarida Paladar

Our final day includes a walk through Old Havana, except this time on the less iconic side of the city, home to the working class. Here we’ll find a lot of great street photography opportunities.

After checkout, we’ll arrange your transfers to the airport. (B)

Photo Workshop Adventures provides 100% legal and compliant travel for U.S. Citizens under the U.S. Treasury Department’s OFAC “Support for the Cuban People” category. 

SUPPORT FOR THE CUBAN PEOPLE

Throughout each day, we are committed to “Support for the Cuban People” under the General License 31 CFR § 515.574. Our goal is to promote independent activity intended to strengthen and support civil society in Cuba and constitute a full-time schedule that enhances contact with the Cuban people and results in meaningful interaction between ourselves and individuals in Cuba. We never pay for lodging at any property on the CPA List to the extent prohibited by § 515.210. In addition, we will support Cuban entrepreneurs launching their privately-owned businesses. Our only accommodations are private Cuban residences (casa particular). We only eat at privately-owned Cuban restaurants (paladares), and we only shop at privately owned stores run by self-employed Cubans.

(B) Breakfast, (L) Lunch, (D) Dinner, (E) Excursion

 

May all who come as guests... leave as friends®

 

Cuba Havana Photoworkshpadventures V2

OPTIONS AND BENEFITS

Pricing

All prices are per person and based on double occupancy. Please select single occupancy for a private room. For your convenience, we offer optional early arrival and late departure accommodations so you can extend your stay before or after the trip. We typically stay in boutique hotels in the 4-star category. Not all destinations offer these types of properties. We look for unique hotels which offer cultural, historic and/or authentic features. Depending on the size of the group, smaller boutique hotels may have limited room inventory. In some countries or in remote locations, we may be limited to lodges or branded chain hotels. Breakfast is included only if included in our room rates.

Private Guided Adventures

We offer amazing private guided photo adventures, cultural tours and vacations for individuals, couples, families and groups. We can customize any of our published adventures, as well as others, to meet your individual needs, schedule, budget and interests. This may include the finest 5-star accommodations, business-class travel, and private guides and fixers who are able to make the impossible possible. If you are not interested in a photo-centric vacation, but you love our approach to private travel, we will be happy to design and deliver an amazing adventure focused on travel, culture and cuisine. Click here to request a quote. Feel free to call us at 1-888-834-0288 or contact us for more information.

Travel Insurance

We offer travel insurance through the internationally recognized Travelex Travel Insurance Company, as well as evacuation and medical transportation insurance through MedJet, one of the best in the industry.

The cost for travel insurance can be as low as 4% of the total trip cost, depending upon age and other factors. Knowing you have trip cancellation coverage can make a big difference should you have to cancel for some unforeseen reason. Travelex Insurance Services is a BBB Accredited business with an A+ rating. Click here to learn more about why you should consider travel insurance.

Rewards Program

Start earning points today and SAVE up to $750 off a future trip!

Register for one of our photo adventures and begin earning points today!

How the program works

For every photo tour reservation you make with Photo Workshop Adventures, you earn valuable points, which you can redeem on your next trip. This is a great way to save on future trips. Points may be applied towards balance payments on your next trip, or you may choose to accumulate points for a free trip in the future.

ORANGE REWARDS

On most Photo Tours and Adventures, you earn 4 points for every dollar you spend. You begin earning points immediately with your first trip. A $11,995 spend earns 47,980 points with a value of $480 USD.

VIP GUESTS

VIP Guests (guests who have registered for eight or more trips) begin earning double points, or eight points, for every dollar spent. A $11,995 spend earns 95,960 points with a value of $960 USD.

Additional VIP Benefits:

  • Advance notification of upcoming adventures and special offers
  • Receive complimentary airport transfers at certain destinations

Redeeming your points

Redeeming your points couldn't be easier. You can always log in to your account to check your points balance. When you are ready to book your next trip (scheduled to depart before your points expire), register and pay your deposit. When you pay your balance, you'll be given the option to apply your points and receive a discount.

*Points may be applied towards balance payments on your next trip, or you may choose to accumulate points for a free trip in the future. Points are awarded only after a trip is completed. Points expire after two years if no new trip is booked and paid for in your account. Points cannot be exchanged for cash and have no cash value. Points cannot be transferred or gifted. Points cannot be applied to any discounted photo adventures, and discounted photo adventures cannot earn points. Points and redeeming points are only available for 5-day or longer photo tours. Points and points redemption are unavailable on private photo tours, photo day tours, low-cost 4-day or less photo tours, online lectures, tutorials, PWA products, and NYC photo tours. 

THINK ORANGE Magazine

Subscribe to our Think Orange Magazine and eNews. THINK ORANGE is a wonderful mix of stories and tips related to travel, photography, adventure, culture, art, technology, cuisine, lifestyle, people and more. Our objective is to immerse you in a world you may only fantasize about. Raise your awareness and inspire your creativity. Perhaps even help make you a better photographer. We deliver similar experiential experiences that our guests enjoy on our photo adventures. Like all of our adventures, our blog is “photo-centric”, while also allowing you to experience all the nuances and cultural aspects of travel and adventure. Welcome to our world. We hope you enjoy. Our eNews is a great way to receive information about upcoming photo adventures, exciting new destinations, photography tips, special offers and more. Subscribe today!

Gift Cards

Give someone you know a Gift Card, good toward any of our Photo  Adventures, Photo Tours, Private Guided Tours, Online Courses, Prints or Merchandize. Our beautifully personalized eGift Cards and Certificates are delivered to you electronically. They are fully transferable and have a 2 year expiration date. They are available in any amount from $100 to $5000. It makes a great gift for anyone who loves photography, travel or adventure. Order now, or email for more information.