Tailor-Made Holiday

The Complete Cuba

A complete Journey from Havana to Santiago de Cuba

33 days

from £8,950pp

This Complete Cuba holiday is a fantastic private journey across the length and breadth of the island. The route links together a great selection of highlights.  From Vinales in the far west to Santiago de Cuba on the eastern tip, it is filled with colonial towns, scenic valleys, historic bays and charming beaches in between.   This month long private road trip will take you through the very best of this delightful and fragile island, that’s on the cusp of transformation.

  • Private driver/guide for the duration
  • Private gallery viewings including a meeting with Castro’s personal photographer
  • Stay in authentic Cuban Homestays
  • Spend time on Cuban’s most unspoilt beaches

Direct flights with Virgin to Havana ensures an easy and comfortable to start to this holiday to Cuba.  Spend time in the famous luxury Hotel Saratoga and explore Havana.   A guided city tour will take you through an extraordinary time warp to witness the fading grandeur of Havana Vieja’s colonial architecture and maze of narrow alleys filled with classic cars that (against all odds) continue to grumble over the cobble stones. Spend an afternoon exploring the ‘new’ town in a chauffeur driven Cadillac.

However, scratch a little deeper and there is more to Havana than rum and cigar factories.  Havana has an extraordinary cultural scene to discover.  Art holds a prominent place in Cuba, and the Roberto Salas Gallery is a tremendous afternoon tour. Meet Roberto himself, and browse through his photo collection. As Fidel’s Castro personal photographer, he will explain about their relationship as well as 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.  Steppes Travel can organise a behind the scenes tour and even a viewing of National Ballet rehearsals.

West of Havana lies the beautiful valley of Vinales.   Picturesque limestone cliffs form the unique geology of this prime tobacco growing region.  Lunch in the private home of Finca Wildfredo, an agro-ecological farm passionate about organic produce.

Continue this holiday to Cuba via the rolling hills of Las Terrazas (home to old French fincas) to Playa Giron. Giron is the location of the historical Bay of Pigs. Visit the fascinating museum and the National Park of Cienega Zapata.

The enchanting town of Trinidad was the centre of the sugar mills and sits at the foot of the Sierra Escambray mountains that overlook the south coast. Stay in a Cuban Homestay (Casa Particular) for a fully authentic experience and some of the best lodging and food in the area.

This private journey continues East to Camaguey and then on to Bayamo and the Sierra Maestra. These mountains are famous for being the hideout for Fidel and his band of revolutionary brothers, including Che Guevara.  Bayamo is a romantic and intriguing town. 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 allegedly described by Columbus as “the most beautiful place in the world”.

Finally conclude this incredible road journey through Cuba in Santiago de Cuba. Physically closer to Kingston, Jamaica than it is to Havana, Santiago de Cuba is the stronghold of Afro-Cuban culture in Cuba and is a stark contrast to Havana City. Laid back, hot and humid with music filling the night air, there is a strong cultural and political heritage in Santiago.  To make the most of this tropical, rumba loving city, visit in August for the summer long carnival.


For a more detailed itinerary with great ideas on what to do and where to stay, please get in touch with our experts.

  Click here to see what is included/excluded

what is included

  • International flights
  • Internal flights
  • All accommodation and meals as stated in the itinerary
  • All transfers

what is excluded

  • Gratuities


Itinerary at a glance

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Day 1

Fly London to Havana

Romantic, beautiful and fascinating, Havana is a must for anyone's visit to Cuba. Fortifications, colonial buildings and churches tell of a rich history, whilst a Communist regime and erosion from the sea lend a faded glory to the city. The old heart gives way to Soviet starkness, whilst the 1950s playground of Vedado, neighbours the historic mansions of Miramar. Quite simply, stunning.

You will be staying at Hotel Saratoga

Day 2

Old Havana Walking Tour
Half day walking tour of Old Havana. Walk in the footsteps of Havana´s colonial past visiting the four plazas of Old Havana, a UNESCO world heritage site. Visit Plaza de Armas, Plaza San Francisco de Asis, Plaza Vieja and Plaza de la Cathedral with your expert guide offering insightful history along the way.

Roberto Salas Gallery Visit
Roberto Salas was born in New York City in 1940, son of the accomplished Cuban born photographer Osvaldo Salas. Spend a few hours with Roberto browsing his numerous iconic photographs at his own private colonial home. Here he will explain his close relationship with Fidel Castro as his personal photographer, and his time behind the Vietcong lines as a war correspondent.

You will be staying at Hotel Saratoga

Day 3

Visit to the Ballet School
This morning, take a tour of the ballet school, a Havana eclectic architectural gem. Take in a ballet class. You will have the opportunity to talk with teachers and students during this tour which lasts approx.45mins.

Classic Car drive
4 hour drive in a vintage open top car. Nelson's vehicle is a genuine 1959 Buick and your tour can be tailored to take in the highlights of Havana as well as themed around Hemingway. En route you´ll be able to take;Panoramic shots from El Morro, the fortress at the mouth of Havana harbour, the Malecon, the iconic cinemas such as La Rampa & Chaplin and the impressive Bacardi building, the Revolution Square; home to a large image of Che Guevara, The woods in Kholy, Playa and the river Almendares.

Cruising with the roof down along the malecon at sunset while listening to Sinatra is a magical experience.

You will be staying at Hotel Saratoga

Day 4

Havana Art Tour
Leave your hotel with your guide for an Art Tour. You will visit 4 emerging Cuban artists in their studios. Get behind the façade and interact with this thriving community. We can adapt the visits depending on your particular interest. Photography, sculpture or painting. Specify whether you would like to see well known or up and coming artists.

You will be staying at Hotel Saratoga

Day 5

Drive from Havana to Vinales via Pinar del Rio

Pick up your rental vehicle at 10am. You will have the use of a mid-size car and guide-driver for the duration of your time outside of Havana. The drive to Vinales Valley will take around 3.5 hours and on the way you will stop in Pinar del Rio City to visit one of Cuba's finest cigar factories (Francisco Donatien), where you will be able to watch workers expertly hand roll cigars.

Explore Vinales surrounding area
Day at leisure to explore the beautiful area around Vinales, a landscape of distinctive conical limestone monoliths. Just west of the town of Vinales is the Mural de la Prehistoria, a large, generally disliked mural painted by a pupil of the celebrated Mexican painter Diego Riviera. Explore the caves in the area, most notable ogf which is Ceuva del Indio where you can take e a boat trip on the underground river.

You will be staying at Casa Doctora Maria Luisa

Day 6

Vinales Specialist Day Trip
Viñales is a small town in the Pinar del Rio province. It's the centre of the tobacco growing region of Cuba. Explore the unique geology and nature of the Viñales valley with a trip on an underground river and an exploration of caves and the famous Mogotes. Your guide, a native of the valley, will take you into the heart of the lush countryside, explaining the history of tobacco growing as you walk. You'll visit the tobacco plantations where they still plough with oxen, see the famous drying houses and have a tobacco farmer show you how to roll a cigar.
Lunch is included in a traditional house overlooking the picturesque valley, owned by a couple who work a Finca from which your food will be harvested and prepared. Ariel our local representative and former English teacher will join you for lunch and explain more about Cuba's agriculture and food production challenges. Lunch is traditional Cuban fayre with rice, beans, fresh vegetables and salad. Please let us know if you have any special dietary requirements.

Finca Wilfredo Restaurant
Lunch included at Finca Wilfredo. Overlooking the valley of Vinales, this agro - ecological farm is at the vanguard of sustainable production. The family decided to 'go organic' some years ago and opened the tiny restaurant. You'll be served fresh organic produce from their farm with wonderful Cuban flavours. Be warned the portions are massive. They are inventive with ingredients and warm and passionate about their project. Bring mosquito repellant as the verandah of the house is open.

You will be staying at Casa Doctora Maria Luisa

Day 7

Day at Leisure
Free day

You will be staying at Casa Doctora Maria Luisa

Day 8

Travel from Vinales to Las Terrazas

Leave Vinales with your guide to drive back towards Havana, to Las Terrazas. The quickest route will be to retrace your steps through Pinar del Rio City and along the autopista however, you may wish to complete a circuit that will take you north out of the valley complex and then east through La Palma and La Guira National Park to the Moka Ecolodge.

You will be staying at La Moka Hotel

Day 9

Coffee Plantation visit
Visit the ruins of an ancient coffee plantation established by French immigrants in the early 19th century. They add an historical interest to the beauty of the Rosario Range. After several centuries, remains of the coffee plantations are still well preserved and along with vestiges of the original structure of the fields, they stand as mute witnesses to different agro-industrial techniques.
Original elements of houses, plantations, trails, coffee pulping machines and dryers can be found here. The outstanding ruins of the Buena Vista plantation are located high in the Rosario Hills (with road access) and offers one of the best panoramic viewpoints over western Cuban.

You will be staying at La Moka Hotel

Day 10

Day at leisure
Free day.

You will be staying at La Moka Hotel

Day 11

Las Terrazas to Playa Giron

This will be a three hour journey that skirts south around the edge of Havana before continuing along the eastern Autopista. Turn south at Central Australia towards the Bay of Pigs. En-route, you may choose to visit the crocodile breeding centre.

You will be staying at Casa Ronel

You will be staying at La Moka Hotel

Day 12

Visit to the Bay of Pigs Museum
Bay of Pigs Museum visit. There is little to see at the Bay of Pigs relating to the sea and air attack. However, this small museum provides 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, that was used by the Cuban military, is proudly displayed in front of the museum along with a rather Soviet looking monument but you must ensure that your guide also takes you behind the museum to see the debris of US aircraft, tanks, trucks and landing craft.

Enigma de la Roca Tour
Take a ride on a horse and cart into the protected woodland area of the Cienega Zapata. Then continue on foot (about 3km total) with your guide as he explains the unique geology and ecology of this vast national park. You'll get a chance to do some bird watching (some of the most important national species live in this area) and there is also a vist to a special reserve which protects turtles. You might even get to see the famous Cuban species known as Jutia (Tree Rat).

You will be staying at Casa Ronel

Day 13

Playa Giron to Trinidad via Bay Cienfuegos

It's a 3 hour drive on to Trinidad and we suggest that you break your journey with a stop in Cienfuegos along the way. Cienfuegos is a working Cuban port town with French colonial architecture, an interesting mudejar style palace and the Tomas Terry Theatre where Caruso and Sara Bernhardt once performed. Continue to the Cienfuegos Botanical Gardens. 94 hectacres of garden offer a soothing setting of palms, orchids, bamboos and myriad other tropical plants. This is Cuba's largest botanical garden and houses 2,000 species of plants including 280 types of palms (purportedly the greatest variety found in one place anywhere in the world). We suggest taking lunch in Cienfuegos at Villa Lagarto (spectacular views of Cienfuegos harbour while dining on tasty fresh criolla cuisine - to be paid for locally).

Trinidad is arguably the most beautiful town in Cuba. Said to be dozing in an 18th century time warp and where the pace of life remains as slow, it is a perfect relic of Spanish colonialism with plazas, churches, palaces and cobbled streets. Trinidad is also gateway to several Caribbean beaches, as well as and the trekking trails and sugar mills of the Escambray Mountains.

You will be staying at Finca Kenia

Day 14

Walking tour of Trinidad
Meet your guide for a three hour walking tour of Trinidad’s historic city centre. Your guide will talk you through the history of Trinidad by visiting its architectural high points before finishing at Bar Canchancharra for a local mojito of wild mint, honey and rum and, of course, some Cuban music.

You will be staying at Finca Kenia

Day 15

Sugarmill Valley tour
This afternoon explore the area outside Trinidad, in particular the Sugarmill Valley in the Sierra Escambray, one of the most beautiful landscapes in Cuba. Learn about the sugarcane industry and climb up the famous Iznaga slave tower, which was built to control the slave workforce. The tour focuses on slave history, the working plantation homes of the sugar barons and looks at the enormous impact sugar production had on this area.

You will be staying at Finca Kenia

Day 16

Choice of activities and excursions
Time to yourself to explore the sights and sounds of Trinidad or to deposit yourself outside a street-front cafe and watch the world go by. The Museo Romantico and the Museo Municipal de Historia are both worth a visit, so too are the beautiful churches of Santisima Trinidad and San Francisco de Paula. Market stalls appear during the day and the bars and music come alive after sunset.
You may wish to visit the beautiful beaches of the Ancon peninsula, 10km south of the city or head up into the Escambray Mountains for a slice of rural Cuba.

You will be staying at Finca Kenia

Day 17

Drive from Trinidad to Camaguey (Road Journey)

Head east out of Trinidad through the spectacular Valle de los Ingenios. Continue through Sancti Spiritus, Ciego de Avila and Florida on to Camaguey. The drive from Trinidad to Camaguey will take around 5 hours.

You will be staying at Gran Hotel

Day 18

City tour of colonial Camaguey
A walking tour of the beautiful colonial city with an local guide.

You will be staying at Gran Hotel

Day 19

Drive from Camaguey to Bayamo (Road Journey)

Your driver will collect you from the hotel for the transfer to Bayamo which will take approx 3 hours 30 mins


The Sierra Maestra is the tallest mountain range in Cuba and has a rich revolutionary past: this is where Fidel and his band of brothers, including Che Guevara, hid after they sneaked back from Mexico to plot the 1959 Revolution. Here they hid in virgin jungle, guarded by Socialist-leaning villagers (for the cinematic version, rent Stephen Soderburgh's Che Part I). Until now, the Sierra Maestra has been the reserve of lone climbers, history aficionados and adventure hiking groups, but our tailormade options allow for a private journey of discovery. At the foot of the Sierra Maestra, unspoiled Bayamo, the 'capital' city - for what it's worth - of Granma Province, is an intriguing, rather romantic town, one of those places you can truly imbibe the 'yesteryear' quality of Cuba's provincial lifestyle, particularly in the cut-off East. A trek into the mountains, Castro HQ is a collection of thatched shacks, including a medical centre, an assembly room, the radio room and Fidel's austere home-from-home. The little museum is well worth a browse: you will probably have the whole thing to yourself.

You will be staying at Royalton Hotel

Day 20

Bayamo City tour
Tour of Bayamo. This was the second of the seven cities founded by Diego Velazquez de Cuellar and was established on November 5, 1513 predating both Havana and Santiago. During much of the 16th century it was one of the most important agricultural and commercial settlements of the island. Its inland location gave it relative security against the pirates who then infested West Indian seas, and the misfortunes of Santiago were the fortunes of Bayamo. Down the Cauto River, then open to the sea for vessels of 200 tons, and through Manzanillo, Bayamo drove a thriving contraband trade that made it at the opening of the 17th century the most prosperous town in Cuba.

You will be staying at Royalton Hotel

Day 21

Drive from Bayamo to Playa Maguana (Road Journey)

Your driver will collect you for the transfer to Villa Maguana via Mayari & Moa which will take approx. 6 hours.

You will be staying at Villa Maguana

Day 22

Day at leisure
Days at leisure to relax on this very undeveloped stretch of sandy, palm-fringed coast. You may wish to take a day trip into Baracoa, the oldest city in Cuba.

You will be staying at Villa Maguana

Day 23

Day at leisure
Days at leisure to relax on this very undeveloped stretch of sandy, palm-fringed coast. You may wish to take a day trip into Baracoa, the oldest city in Cuba.

You will be staying at Villa Maguana

Day 24

Day at leisure
Days at leisure to relax on this very undeveloped stretch of sandy, palm-fringed coast. You may wish to take a day trip into Baracoa, the oldest city in Cuba.

You will be staying at Villa Maguana

Day 25

Day at leisure
Days at leisure to relax on this very undeveloped stretch of sandy, palm-fringed coast. You may wish to take a day trip into Baracoa, the oldest city in Cuba.

You will be staying at Villa Maguana

Day 26

Drive from Playa Maguana to Santiago de Cuba (Road Journey)

Following breakfast this morning, your driver will collect you for the drive to Santiago De Cuba which will take you via Baracoa and Guantanamo. The journey will take approx. 6 hours.

Physically closer to Kingston, Jamaica than to Havana, Santiago de Cuba is the stronghold of Afro-Cuban culture in Cuba and has a fearsome musical, cultural and political heritage. Overpoweringly hot and humid, Santiago swings to its own laidback vibe. Though it's Cuba's second city, it feels compact, with a handful of key monuments and nightspots. Don't miss the Casa de la Trova, where the city's legendary rumba can be heard. Socialist to the core, Santiago was a key stronghold during the nascent stages of the Revolution. The Moncada Barracks, where Fidel led a failed coup in 1953, are worth a visit, as is the Castillo del Morro, the old fortress, a romantic place to watch the sunset with panoramic views. On the cultural side, don't miss Santiago's wealth of smaller museums, such as Museo Emilio Bacardi Moreau, the home of the cultural treasures of the Floridian émigré and rum king (he collected everything from Egytian mummies to creepy artifacts of slavery). The best time to visit Santiago is in sticky August, when the city explodes in a long, colourful, summer carnival.

You will be staying at Casa Granda

Day 27

City tour
Santiago de Cuba was declared a National Monument on October 10, 1978. Spend the day visiting the main historical and cultural points of interest of the city including Revolution Square and the Moncada Barracks and its museum of July 26, the Revolution Square and other historical, religious and cultural sites.

You will be staying at Casa Granda

Day 28

Choice of activities and excursions
Time to yourself to explore Santiago, capital of the “Orient” and the most Caribbean of all Cuba’s cities. The most important sights include Parque Cespedes, Calle Heredia and Plaza Dolores, Revolutionary Square and the Moncada barracks, attacked by Fidel in 1953. Casa Diego Velazquez, said to be Cuba’s oldest house, is home to the museum Ambiente Cubano with furniture from different centuries. San Pedro del Morro is the fortress, built in 1633, that towers over Santiago Bay. Santa Ifigenia cemetery is a metropolis of elaborate funereal sculpture and contains the grave of the national hero José Martí.
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.

You will be staying at Casa Granda

Day 29

Day at Leisure

You will be staying at Casa Granda

Day 30

Fly Santiago de Cuba to Havana

You will be staying at Casa Ydalgo

Day 31

Day at leisure
Full day at leisure.

You will be staying at Casa Ydalgo

Day 32

Fly Havana to London overnight


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

Hotel Saratoga

Hotel Saratoga

Hotel Saratoga is an elegant, neoclassical-style building with a legendary status for fine cuisine, eye-catching decoration and good service....

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Finca Kenia

Finca Kenia

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....

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Casa Ydalgo

Casa Ydalgo

Casa Ydalgo represents a new wave of casa particulares (private houses)....

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Villa Maguana

Villa Maguana

Located next to 2kms of white-sand beach of Maguana - possibly the most beautiful in Cuba - sit four cottages, each housing 4 rooms, perfect for boho beach living....

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For a more detailed itinerary with great ideas on what to do and where to stay, please get in touch with our experts.

Destination Experts

Our experts have unrivalled firsthand knowledge of Cuba

John Faithfull, Travel Expert

"Personalised service. Seemed to really want to get it right for us. Very impressed when I first called and John spent 40 minutes finding out what we wanted to do and tailoring it for us."

"The expertise that John has really gave us faith in where we were going, the regions, the hotels, the trips. John knew about it all, he described them in detail, and when we asked for different regions he was straight in there with suggestions and ideas. The way the whole trip was planned and presented to us, never any pressure to book or any problem to change plans /ideas."

"John Faithful was wonderfully helpful and conscientious in arranging the itinerary and was always ready to suggest alternatives or rearrange matters without any hesitation; this and his detailed knowledge gave one great confidence."

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For a more detailed itinerary with great ideas on what to do and where to stay, please get in touch with our experts.

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