Classic Cuba Tour Itinerary

Cuba is one of the most enchanting and captivating countries in the world, a pulsating and multifaceted blend of history, music, dance, gracious people and vibrant island culture. Join photographer Daryl Hawk on this unique opportunity to engage with the Cuban people and to discover the allure that is Cuba.

The people of Cuba are the country’s treasure and its most dynamic force. They are extremely friendly and generous of spirit, resourceful, resilient, and incredibly open to sharing their personal lives and their country with visitors. With our eyes and hearts open, we travel off the beaten tourist trail to better understand this intriguing country through direct exchanges with the Cuban people. Our upscale privately run hotels and casa de particulars are owned by individuals who have a flair for creating delicious breakfasts, amazing service and unique charm.

“Daryl Hawk’s ability and enthusiasm to introduce his travelers to stimulating places in Cuba made the experience so meaningful.”

David, May 2024

Customized itineraries to match your specific interests available – discount available for private groups. Some fun activities like salsa lessons, cooking classes or meeting with a renowned historian can all be added to your tour.

Day 1 – Havana

Check-in at one of our privately owned boutique hotels, La Posada de Chacon or Fresko Habana. Originally deemed “casas particulares”, the idea by the Cuban government was to allow small steps in the private sector. Over the past decade, there has been an influx of privately run hotels/bed and breakfasts that not only helped solve the demand issue for tourism, yet offered charming experiences and equal to better caliber lodging options than traditional hotels on the island.

Orientation with a local guide. Discuss the week ahead as well logistical issues such as changing money and other cultural norms.

Walk from the hotel to the Revolutionary Museum and then onward to the Malecon and watch the waves crash on the seawall. Continue to the rooftop of the Hotel Prado for a view of all of Havana. Dinner at a restaraunt near your hotel.

Day 2 – Havana – Four Historic Plazas Walking Tour, Buena Vista Social Club

Breakfast at home
9:00am: Walking tour of the Old City. Wander through the Plaza de Armas, a scenic tree-lined plaza formerly at the center of influence in Cuba. It is surrounded by many of the most historic structures in Havana as well as important monuments. See the Plaza de San Francisco, a cobbled plaza surrounded by buildings dating from the 18th century, dominated by the baroque Iglesia and Convento de San Francisco dating from 1719. Visit the Plaza Vieja, surrounded by sumptuous houses of the Havana aristocracy from the 18th and 19th centuries. Visit Plaza de la Catedral and the Catedral de San Cristóbal de La Habana.
1:00pm: Lunch at La Vitrola restaurant.
2:00pm: After lunch we then go to the Havana Club Rum Factory for a tour as well as trying samples of the finest rum.
8pm dinner at the legendary Buena Vista Social Club and enjoy a 3 course dinner and live performances of salsa, rumba, bolero, guaguanco and much more!

Day 3 – Day Trip to Soroa and Vinales

Breakfast at home. Day trip in a beautiful 1950’s Chevrolet to Soroa, “the rainbow of Cuba”, a gorgeous mountain community. Arrive in Soroa at 9:30 and experience the magnificent hillside gardens at Orquuideario Soroa, which has the largest collection of orchids in Cuba – over 700 species.

Our journey continues to Vinales, considered by many to be the most beautiful place in Cuba. The Viñales Valley is a National Monument and a UNESCO World Heritage Site. It is encircled by mountains and its landscape is interspersed with spectacular dome-shaped limestone outcrops (mogotes). Traditional techniques are still in use for agricultural production, particularly tobacco, which makes Viñales famous for being the premier tobacco growing area in the world. Our excursion will include a visit to the tobacco farm, La Guarita, to learn about the cultivation and production process. You will then get to try some of the finest cigars in the world including the Montecristo Illustre. We will then have an amazing farm to table lunch at Finca Ecological Paraiso with magnificent views of the mogotes and the Vinales Valley. We will also visit an Indian cave where you will both walk and take a boat and admire spectacular cave paintings and also archaeological remains from pre-Columbian Cuban civilizations.

Return to Havana and dinner at Cha Cha Cha, one of Havana’s most eclectic restaurants.

Day 4 – Ernest Hemingway’s House, National Ballet, Classic Car Ride

Breakfast at home
The day begins at 10am with a visit to Finca Vigia, the home of Ernest Hemingway, which was kept exactly the same as when he lived there. See his famous fishing boat, Pilar!
Lunch at La Francesa listening to live Cuban music.
Tour the world famous National Ballet Theatre.
Ride in a 1950s classic car and drive down the Malecon, the forest and then onto the National Hotel.
5pm happy hour at Ernest Hemingway’s favorite bar, La Floridita for daiquiries and live Cuba music. Dinner at Cha Cha Cha.

Day 5 – Havana – Fusterlandia, Car Museum and Fort Ceremony

Breakfast at home
9:00am: Visit Fusterlandia – a neighborhood that has been turned into a masterpiece of intricate tile work and kaleidoscopic colors by famous artist Jose Fuster.
We then continue to the Hemingway Marina.
We return to Old Havana for a stroll around Plaza Vieaja before 1pm lunch at Daryl’s favorite Palador.
We continue our stroll through Plaza Vieja to see a car museum and then walk up Obisbo street, the liveliest street in Havana!
6:00pm: Dinner at restaurant near the hotel.
8:00pm: We go to the cannon blasting ceremony at the famous Castillo Del Morro which is a tradition that dates back to the colonial era.

Day 6 – Departure

Say Farewell (for now). Depart for Jose Marti International. Recommended that you arrive at the airport at least 2.5 hours prior to flight departure.

Details

What’s Included

Private hotel as mentioned in the itinerary
Meals as per itinerary
All ground transportation in Cuba to organized activities
Admission to all scheduled educational and special activities
English-speaking local guides
24 hour english speaking concierges service at hotel
Daryl will be taking photos of all the participants throughout the trip and recieve them when you get home

Not Included

Round-trip airfare
Tips
Individual house or hotel expenses (mini bar, room service, laundry fees, etc.)
Alcoholic beverages

Pricing

Single: $3,400
Double $3,000 each

A big part of the reason that I go to Cuba is for humanitarian reasons. Due to the poor economy the Cuban people are struggling and are in desperate need of basic goods. If you wish, you can bring toothbrushes, asprin, vitamins, pens, soap, etc. which will be greatly appreciated.

TRIP DETAILS

Cuba Music Tour

NEW: Cuba Music Tour

Join us on our Cuba tours and immerse yourself in Cuba’s authentic music performances and cultural delights. Our tours offer a unique opportunity to connect with the Cuban people and their rich musical heritage. Whether you’re a musician or simply someone who loves music, our tours have something for everyone.

We provide a life-changing experience that includes Cuban dancing, top-rated restaurants, Cuban farming, mindfulness, art, education, museums, architecture, shopping, and meaningful interactions with the Cuban people. Our tours are carefully planned to take you on a journey through the history of Cuban music, where you’ll meet some of the best musicians around Cuba.

Each night, you’ll visit a different music club, theater, or event, where you can listen to different music styles, such as Son, Rumba, Latin Jazz, Boleros, Afro Beats, and maybe even some Cuban Reggaeton. We offer tours with different themes and durations designed to accommodate your interests and travel time.

NEW: Cuba Photography Tour

This trip is authorized by the US Government under the category of Support for the Cuban People.

Our Cuba Photo Tours emphasis (indeed all of our tours) is on small, group tours – usually 10 participants or less. And, wherever we travel, we focus on the best available – with local flavor of course – accommodations. Our tours are conducted with the flexibility to “stop along the road,” either for a special photo or simply to enjoy a view or activity. We also like to build in diverse cultural experiences, achieved by working closely with local guides – guides we know and trust. At The Unconventional Travelers, we seek to strike a great balance in our tours, so you get the most out of the trip from a photography standpoint, and simply as a great tour – all led by a passionate teacher of the art of photography!

Join Daryl Hawk on this memorable photo tour to the most photogenic destinations in Cuba. He has traveled to Cuba since 2016, leading photo groups there since 2020, and has established long-time relationships with many people there. We’ll get to see many of the finest iconic sights that Cuba has to offer, but we will dig much deeper into the lives of the amazing Cuban people. We will interact with Cubans from all walks of life while taking advantage of the best light, and with a flexibility that allows us to make the most of opportunities as they arise.

We will start in Havana, with its world-class street shooting and so much more. We will organize photo shoots, such as the most important boxing gym in Cuba, Afro-Cubano dancers, and ballet dancers from the Cuban National Ballet posing in an old mansion. Everywhere we go we will meet and photograph the friendly people of Havana.

Next, we will explore the tobacco-growing region of Vinales – with its stunning limestone cliffs, or Mogotes. Vinales would be an important photo destination just for the scenery alone, but it is the traditional farmers that make it so great. We are friends with many of the farmers in the area, and they will invite us into their homes, affording photo opportunities that the typical group will never have.

Finally, we will journey to the colonial city of Trinidad. Many consider this Unesco World Heritage site the most beautiful city in Cuba. With the backdrop of the perfectly preserved colonial buildings, we’ll photograph cowboys riding horses and pulling horse-carts through the cobblestone streets, along with the classic American cars. We’ll meet a local photographer there and visit a cowboy ranch outside of town, where we’ll be served an authentic country-style lunch. Trinidad also hosts a thriving local live music scene, and we will have the opportunity to photograph local musicians there.

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