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    Steppes Travel is made by the people who work here. Incredible holidays are made possible because of their vast travel experience and the great enthusiasm they bring to their work.

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Vinales Valley, Cuba

One Month in Cuba

  • TAILOR-MADE HOLIDAY IDEA

Duration

32 Days

Prices Start from

$10,528 ex. flights

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

Classic Cars, Havana, Cuba 1

Private Road Trip

Travel in the company of a private driver and guide who will unveil the secrets of the island.

Cigar Rolling, Havana, Cuba 2

Exclusive Access

Watch experts hand roll cigars and meet with Fidel Castro’s personal photographer.

Cayo Levisa, Cuba 3

Pristine Beaches

Spend time on some of Cuba’s most unspoilt and unknown white sand beaches.

Old Havana skyline, Cuba 4

Havana Hubbub

Join a walking tour of Old Havana, visit the Ballet School and drive a vintage car.

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.

Don't forget, we will customise this journey to suit you.

Explore our suggested itinerary

  • 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
Havana, Cuba
Havana, Cuba

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.

Tobacco Plantation, Vinales Valley, Cuba
Tobacco Plantation, Vinales Valley, Cuba
Vinales Valley, Cuba
Vinales Valley, Cuba

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, Pinar del Rio Province, Cuba
Las Terrazas, Pinar del Rio Province, Cuba

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.

Caribbean Beach
Caribbean Beach
Rooftops, Trinidad, Cuba
Rooftops, Trinidad, Cuba

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.

Sierra Maestra Mountain Range, Cuba
Sierra Maestra Mountain Range, Cuba

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”.

Santiago de Cuba, Cuba
Santiago de Cuba, Cuba
Castle San Pedro de la Roca del Morro, Santiago de Cuba, Cuba
Castle San Pedro de la Roca del Morro, Santiago de Cuba

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.

Accommodation

Below you can see some of the wonderful places we recommend you stay on your journey.

Gran Hotel Manzana Kempinski £££££

  • Cuba
  • City

Constructed between 1894 and 1917 as the first European style shopping arcade in the country, this handsome building is now a high-end hotel, located in the centre of Havana that faces the Capitolio building and the Gran Theatre.

View Property

Plaza Vieja 1912 £££££

  • Cuba
  • Boutique

This two-bedroom casa particular is on the top floor of an historic building that overlooks Plaza Vieja, in the heart of Old Havana. Lovely and clean and in a very atmospheric setting, it is a great base from which to wander the old town.

View Property

Villa Maguana £££££

  • Cuba
  • Beach and Island Escapes

Located next to 2kms of the white-sand beach of Maguana – possibly the most beautiful in Cuba – sit four cottages, each housing 4 rooms, perfect for boho beach living. This is a great area for nature lovers as you can explore the nearby biosphere and UNESCO World Heritage site of Cuchillas del Toa or swim in the nearby rivers.  

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Finca Kenia £££££

  • Cuba
  • B&B, Motel and Guesthouse

Built in the second half of the nineteenth century, on the edge of Santa Rosa Valley, Finca Kenia (also known as La Casona) is one of the oldest houses in Trinidad. It offers a home from home in a delightfully, rustic and unexplored area of Trinidad.  

View Property

Let’s chat

Speak to our experts

Our team is waiting to help you tailor a trip that will leave you with stories for a lifetime. Call us on

01285 601 784

Send us an enquiry

Or send us a quick email below and start your next journey.

Call us

John knew the ins and outs of Cuba and was able to answer every question (big and small) that we had. We really feel that we had an off the beaten track experience in this already mysterious country.

Destination: Cuba
Travel Expert: John

A note on price

This Itinerary
Price
From $10,528 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.

Why Choose Steppes?

Our knowledge and expertise sets us apart. So too our curiosity. A curiosity of the world and of you, and your passions. It is this that drives us to create a journey that is really bespoke to you.

Are you ready to discover extraordinary?


Why Steppes

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