Private Road Trip
Travel in the company of a private driver and guide who will unveil the secrets of the island.
Our years of experience travelling in Cuba have taught us one thing – scratch a little deeper, and there is more to the nation than rum and cigar factories.
An all-encompassing journey from Havana to Santiago de Cuba, this show-stopping private journey across the length and breadth of the island links together a hand-picked selection of colonial towns, scenic valleys, historic bays and charming beaches. A month-long exclusive road trip, this fully guided itinerary brings to the surface the very best of this delightful and fragile island that is on the cusp of transformation.
Key Highlights of this Itinerary
Exclusive Access
Watch experts hand roll cigars and meet with Fidel Castro’s personal photographer.
Pristine Beaches
Spend time on some of Cuba’s most unspoilt and unknown white sand beaches.
Havana Hubbub
Join a walking tour of Old Havana, visit the Ballet School and drive a vintage car.
Why Steppes?
Rated Excellent
on Trustpilot
One of the World's Top 5
Travel Specialists
Transparent and
Accountable
Why we like it
Imagine yourself cruising in an open-top vintage car along the Malecon at sunset while listening to the croons of Frank Sinatra, or trying your hand at rolling an artisan cigar in a factory in the Vinales Valley. Perhaps you can see yourself lunching with locals on an organic farm, hiking in the mountains where Fidel Castro and Che Guevara took refuge, or sipping a mojito on a white sand beach. These truly memorable moments are part and parcel of this month-long Cuban adventure that operates on a tailor made basis in the company of an expert local guide, ensuring interactions with the Cuban people and access to little-known hot spots. Sprinkled with opportunities to experience Afro-Cuban culture, attend behind-the-scenes ballet rehearsals and have private meetings with Castro’s personal photographer, this trip encapsulates an eclectic mix of Cuba’s most coveted experiences that makes it ideally suited to culture-loving wayfarers.
-
Days 1-4
Havana
-
Day 5
Havana - Vinales
-
Days 6-7
Vinales
-
Day 8
Vinales - Las Terrazas
-
Days 9-10
Las Terrazas
-
Day 11
Las Terrazas - Playa Giron
-
Day 12
Playa Giron
-
Day 13
Playa Giron - Bay Cienfuegos - Trinidad
-
Days 14-16
Trinidad
-
Day 17
Trinidad - Camaguey
-
Day 18
Camaguey
-
Day 19
Camaguey - Bayamo
-
Day 20
Bayamo
-
Day 21
Bayamo - Playa Maguana
-
Days 22-25
Playa Maguana
-
Day 26
Playa Maguana - Santiago de Cuba
-
Days 27-29
Santiago de Cuba
-
Day 30
Santiago de Cuba - Havana
-
Days 31-32
Havana
Days 1-4
Havana
Join a walking tour of Old Havana, visit the Ballet School and drive a vintage car.
Day 5
Havana - Vinales
Days 6-7
Vinales
Try your hand at rolling an artisan cigar in a factory in the Vinales Valley.
Day 8
Vinales - Las Terrazas
Days 9-10
Las Terrazas
Drive through the rolling hills of Las Terrazas.
Day 11
Las Terrazas - Playa Giron
Day 12
Playa Giron
Day 13
Playa Giron - Bay Cienfuegos - Trinidad
Days 14-16
Trinidad
Stay in a Cuban home stay for an authentic experience and home-cooked meals.
Day 17
Trinidad - Camaguey
Day 18
Camaguey
Day 19
Camaguey - Bayamo
Day 20
Bayamo
See the place where Fidel and his band of brothers hid to plot the 1959 Revolution.
Day 21
Bayamo - Playa Maguana
Days 22-25
Playa Maguana
Day 26
Playa Maguana - Santiago de Cuba
Days 27-29
Santiago de Cuba
Visit the main historical and cultural points of interest of the city including Revolution Square.
Day 30
Santiago de Cuba - Havana
Days 31-32
Havana
More Details
Behind the Scenes Havana
Join a guided chauffeur-driven Cadillac tour that expertly weaves through the extraordinary time warp that is Havana, witnessing the fading grandeur of its colonial architecture and the maze of narrow alleys filled with classic cars that grumble over cobblestones. Discover its extraordinary cultural scene, learning about its esteemed art collections and the prominent artists that hold a place in Cuban history. Tour the Roberto Salas Gallery and meeting Roberto himself – as Fidel’s Castro personal photographer, he will touch on their relationship and his time behind Vietcong lines as a photographic war correspondent. Some of the world’s best ballet dancers come from the Cuban National Ballet School, the largest in the world, and we can arrange a behind-the-scenes tour and an exclusive viewing of rehearsals.
Local Lunch in Vinales
Travel west of Havana to the beautiful valley of Vinales, where picturesque limestone cliffs form the unique geology of this prime tobacco-growing region. Stop in Pinar del Rio City to visit one of Cuba’s finest cigar factories and watch as artisans hand roll the national treasures. Against a landscape of distinctive conical limestone monoliths, have lunch in Finca Wildfredo, an agro-ecological farm. The private home of a Cuban family, expect to be served organic produce with wonderfully inventive Cuban flavours (and massive portions) on an open veranda. Explore the unique geology and nature of the valley with a trip on an underground river in the company of a native of the valley who will take you into the heart of the lush countryside, explaining the history of tobacco-growing as you walk.
Las Terrazas & Bay of Pigs
Over the course of a few days, drive through the rolling hills of Las Terrazas, home to old French fincas and remains of coffee plantations, to Playa Giron. Visit the historical Bay of Pigs Museum for a fascinating Cuban perspective on the events leading up to the invasion and a clear account of the attack and its aftermath. A British-built Sea Fury aircraft used by the Cuban military is proudly displayed in front of the museum, and the debris of US aircraft, tanks, trucks and landing craft lie behind the building. Take a ride on a horse and cart into the protected woodland area of the Cienega Zapata before continuing on foot to discover the unique geological and ecological features of this vast National Park. There will be opportunities for bird-watching as some of the most important national species live in this area, and you might even get to see the famous Cuban species Jutia.
Sparkling Beaches & Colonial Towns of Trinidad
Drive through Cienfuegos, a working Cuban port town with French colonial architecture, an interesting Mudejar-style palace and the Tomas Terry Theatre where Italian operatic ternor Enrico Caruso once performed. Continue to the enchanting town of Trinidad, the centre of the sugar mills that sits at the foot of the Sierra Escambray Mountains, staying in a Cuban home for an authentic experience and some of the best food in the area. Said to be dozing in an 18th century time warp, Trinidad is a slow-paced town and a perfect relic of Spanish colonialism with plazas, churches, palaces and cobbled streets. The gateway to a number of sparkling Caribbean beaches and the stunning Sugarmill Valley, Trinidad is the place to lounge on the white sand, hike trails and sip local wild mint and honey mojitos.
Mountains of Fidel & Che Guevara
Journey east to Camaguey and then on to Bayamo and the Sierra Maestra, the tallest mountain range in Cuba and the place where Fidel and his band of brothers, including Che Guevara, hid after they sneaked back from Mexico to plot the 1959 Revolution. Until recently, these mountains have been the reserve of lone climbers, history aficionados and adventurers, but our tailor made options allow for a private journey of discovery. From Bayamo, continue to the north coast and Playa Maguana where undeveloped palm-fringed sandy beaches await. From here, it is possible to visit Baracoa, the oldest town in Cuba and the place described by Columbus as “the most beautiful place in the world”.
Afro-Cuban Culture in Santiago
Conclude this incredible month-long road journey through Cuba in Santiago de Cuba. Physically closer to Kingston, Jamaica than it is to Havana, Santiago de Cuba is the island’s stronghold of Afro-Cuban culture and is makes a stark contrast to the capital city. Laid back, hot and humid with music filling the night air, there is a strong cultural and political heritage in Santiago de Cuba. Visit the main historical and cultural points of interest of the city including Revolution Square, the Moncada Barracks and Casa Diego Velazquez, said to be Cuba’s oldest house. A hot spot for music, you must experience some live traditional music at Santiago’s Casa de la Trova, probably one of the best music houses in Cuba.
Start planning your trip
Send us an enquiry
Complete our enquiry form and start your next journey.
Review Contact Form
A note on price
This Itinerary
Price
From $12,300 Per person
When to travel
Cuba in January
The dry season in Cuba runs from November to April. This also means that it is peak season, especially over the holiday periods. Accommodation needs to be booked well in advance, as the country’s popularity increases.
Cuba in February
The dry season in Cuba runs from November to April. This also means that it is peak season, especially over the holiday periods. Accommodation needs to be booked well in advance, as the country’s popularity increases.
Cuba in March
The dry season in Cuba runs from November to April. This also means that it is peak season, especially over the holiday periods. Accommodation needs to be booked well in advance, as the country’s popularity increases.
Cuba in April
The dry season in Cuba runs from November to April. This also means that it is peak season, especially over the holiday periods. Accommodation needs to be booked well in advance, as the country’s popularity increases.
Cuba in May
From May to July temperatures rise rapidly, and the chance of showers increase. It is the start of the rainy season, but most of the rain generally does not occur until the end of July or August.
Cuba in June
From May to July temperatures rise rapidly, and the chance of showers increase. It is the start of the rainy season, but most of the rain generally does not occur until the end of July or August.
Cuba in July
From May to July temperatures rise rapidly, and the chance of showers increase. It is the start of the rainy season, but most of the rain generally does not occur until the end of July or August.
Cuba in August
Hurricane season runs from August to October. However, there are still periods of sunshine in between, and you will find that accommodation is easier to come by with the lower visitor numbers.
Cuba in September
Hurricane season runs from August to October. However, there are still periods of sunshine in between, and you will find that accommodation is easier to come by with the lower visitor numbers.
Cuba in October
Hurricane season runs from August to October. However, there are still periods of sunshine in between, and you will find that accommodation is easier to come by with the lower visitor numbers.
Cuba in November
The dry season in Cuba runs from November to April. This also means that it is peak season, especially over the holiday periods. Accommodation needs to be booked well in advance, as the country’s popularity increases.
Cuba in December
The dry season in Cuba runs from November to April. This also means that it is peak season, especially over the holiday periods. Accommodation needs to be booked well in advance, as the country’s popularity increases.
Holiday Inspiration
Our experts have created and curated these tailor-made holiday ideas to get you started. Take the time to search through them and find something that is the spark for your unique adventure.
Why Choose Steppes?
Our knowledge and expertise set us apart. So too our curiosity. It is this that drives us to create a journey that is really bespoke to you, all the while ensuring we travel and operate sustainably.
Are you ready to discover extraordinary once again?
Featured in the press
