US Compliant Cuba Itinerary

Day 1 — Havana

Clients will be met off their international flight at Havana’s Jose Marti airport and transferred the short distance to their hotel in the city.

As the vast majority of flights arrive from late afternoon onwards, what remains of the day is free for clients to relax, perhaps stretch their legs and enjoy the first of many mojitos.

Day 2 — Havana

One of the world’s truly iconic cities, Havana is an absolute must-visit on any visit to Cuba.

Located on the island’s northern, Atlantic coast, the city enjoys a picturesque location with its sweeping seafront promenade known as the Malecon. Bordering the Malecon is Old Havana, the historic heart of the city with its colonial era buildings and plazas. Combine this with concrete relics of the Soviet era, vintage cars lurching around every corner, kids tossing baseballs in the plazas and music absolutely everywhere, and you get one of the most intoxicating cities in the world.

Of course, like any city with so much history, Havana has plenty of wonderful museums you can visit, including the famous Museum of the Revolution, but this is very much a city that rewards casual wandering.

Accordingly, after a tasty breakfast at your accommodation, you will be collected by your Guide for an introductory, approximate 3-hour walking tour of Old Havana.

Strolling from one plaza to the next, you will learn all about the city’s colourful history, taking in countless buildings of historic and architectural note on the way.

On completion of your walking tour of Old Havana, and a deserved break for lunch at a restaurant recommended by your guide, you will then have the opportunity to enjoy another of Havana’s truly iconic experiences, a tour of ‘New Havana’ from the comfort of one of the many, aforementioned classic cars for which, again, the city is justifiably famous.

Together with the driver and your guide, you will head out of Old Havana, drive around the concrete delights of Revolution Square, gazing up at Che Guevara as you do, and past the University of Havana. You will then stop briefly to visit the haunting Necropolis Cristobal Colon, before continuing to Miramar with its broad avenues and handsome mansions.  Finally, you will return along the Malecon to your accommodation.

The rest of the day is free for you to explore further on your own or simply relax.

Day 3 — Havana

After a leisurely breakfast, your guide will meet you once again at your accommodation in Old Havana. Together, you’ll set off by taxi, passing through the Havana Tunnel to reach La Cabaña de La Habana, a majestic 18th-century fortress overlooking the bay.

Widely regarded as one of the largest forts in the Americas, La Cabaña was commissioned by the Spanish in 1763 following their brief loss of Havana to the British. Determined never to repeat that humiliation, they completed this formidable stronghold just a decade later.

Over the centuries, La Cabaña has witnessed much of Cuba’s turbulent history — serving as a military post, a prison, and even, for a short time, Che Guevara’s headquarters during the Revolution. Today, it stands as a fascinating museum within a broader historical park that also encompasses the nearby Morro Castle, offering sweeping views of the city and sea.

From La Cabaña, a short stroll brings you to another of Havana’s iconic landmarks — the Cristo de La Habana. Designed by Cuban sculptor Jilma Madero, this elegant marble statue was inaugurated on Christmas Eve 1958, just weeks before the triumph of the Cuban Revolution and the long years when religion would all but disappear from public life. From this vantage point, you’ll enjoy some of the most spectacular panoramas of Havana.

Descending from the hill, you’ll wander into the tranquil, picture-perfect neighbourhood of Casablanca, once the departure-point for the storied Hershey Electric Train.

You’ll then board a local ferry for the short, scenic crossing back across Havana’s harbour to Old Havana, arriving in time for lunch. The remainder of the afternoon is yours to relax or explore at leisure.

Day 4 — Havana

It’s hard to visit Cuba, especially Havana, and not reference one of the most iconic writers of the 20th century, Ernest Hemingway.

Accordingly, this morning you will depart Havana for Cojimar, the nearby fishing village that served as the inspiration for ‘The Old Man & The Sea’.

On arrival, you will enjoy a Cuban Cuisine & Mixology class at the Ajiaco Restaurant, interacting with local suppliers and learning how to cook Cuban style, not to mention preparing a mojito or two.

After lunch in Cojimar, you will continue the Hemingway themed day with a visit to Finca Vigia, the author’s home on the outskirts of Havana for many years, and barely touched since he left.

Last up today will be a visit to the Clandestina project, one of the most iconic fashion entrepreneurs in Cuba. Who knows, you might even find something nice to take back with you.

To round off your stay in Havana, after dinner you’ll be collected from your accommodation and taken to Legendarios del Guajirito — an intimate, vibrant venue where the rhythms of Cuban son and salsa fill the air. Sit back and soak up a memorable night of live music, dance, and authentic Havana energy.

Day 5 — Havana to Vinales via Soroa

After a leisurely breakfast and check-out from your accommodation, your private Driver / Guide will collect you for your journey west from Havana.

Leaving the bustle of the capital behind, you’ll travel for around 90 minutes through the lush Cuban countryside to reach your first stop of the day — the Soroa Botanical Gardens.

Tucked away in the verdant Sierra del Rosario Mountains, these peaceful gardens were originally established in 1943 by Don Tomás Felipe Camacho, a wealthy lawyer who created them in memory of his beloved daughter.

Today, the gardens are celebrated for their remarkable diversity of flora and tranquil natural beauty. While a picturesque waterfall adds to the serenity of the setting, Soroa is best known for its extraordinary collection of orchids — thousands of species, including more than a hundred found only in Cuba.

From Soroa, your journey continues for another 90 minutes or so to your home for the next four nights — the breathtakingly scenic Viñales Valley. After checking in to your accommodation, the remainder of the day is yours to relax and unwind amid the region’s serene landscapes.

Day 6 — Vinales

After breakfast at your accommodation, your Driver / Guide will collect you for a full-day exploration of the enchanting Viñales Valley.

Your journey begins at the area’s most famous viewpoint, where you’ll take in breathtaking vistas of the valley below — a landscape of dramatic karst limestone formations, traditional tobacco-drying houses, and rustic family-run farms scattered among the greenery.

Descending into the valley, you’ll follow the scenic Dos Hermanos route, flanked by the region’s distinctive limestone mogotes, before pausing at the striking — and somewhat eccentric — Mural of Prehistory. Commissioned by Fidel Castro in 1961, this vast, 120-metre mural depicts the evolution of life in prehistoric Viñales and stands today as one of the largest outdoor artworks in the world.

Continuing your exploration on foot, you’ll enjoy a gentle walk across the fertile valley floor, visiting one of Viñales’ world-renowned tobacco plantations. Here, your guide will explain the intricate process of cultivating, drying, and hand-rolling the leaves that become Cuba’s legendary cigars.

You’ll also stop at a small, family-run tobacco farm, where you’ll meet the farmer and visit a traditional selection house, learning how the leaves are graded for use in different cigar brands.

Your next stop is El Palenque de los Cimarrones, a cave hidden within the cliffs that recreates the secret shelters established by runaway slaves in the 19th century.

A short drive away lies Cueva del Indio, discovered in 1920 and believed to have served as both a refuge and burial site for the indigenous Guanahatabey people. After walking through the illuminated caverns, you’ll board a small boat for a 400-metre underground ride, emerging dramatically into the sunlight at the end of the cave network.

Lunch is recommended at Finca Paraíso, a charming organic farm and restaurant offering delicious homegrown produce and sweeping views over the serene Silencio Valley.

At the conclusion of your tour, your driver will return you to your casa accommodation, with the rest of the day at leisure to relax or explore independently.

Day 7 — Vinales

Today, embark on a full-day hike through the Three Valleys of Viñales, a journey that immerses you in the region’s breathtaking landscapes and rural charm.

As the name suggests, the tour explores three distinct valleys, two of which remain largely untouched by tourism. Along the way, you’ll pause to meet local farmers tending to a variety of crops — from mangoes and sugar cane to the world-famous tobacco leaves that define the valley.

The aptly named Valley of Silence offers a glimpse into a way of life preserved by just a handful of families, while a stop at Paradise Farm provides a truly authentic experience: a farm-to-table lunch prepared from produce grown right on the property.

After your hike, you’ll return to your accommodation in the afternoon, with the remainder of the day at leisure to relax or soak in the serene surroundings.

Day 8 — Vinales

After breakfast, you will depart Vinales for the day, heading north along picturesque, winding roads as you pass through Cuajani to the town of Pons. Enroute, your guide can explain about the history of the region as well as introducing you to ‘La Peña’, a site surrounded by legends and stories of Palenqueria and Afro-Cuban culture.

After approximately 90 minutes you will arrive in the town of Minas de Matahambre, where you visit the ‘Monument To The Miner’, a tribute to the thousands of people who worked in this region, considered one of the deepest mines in the Americas.

You will then take to the water to visit two idyllic, largely untouched islands, Cayo Megano & Cayo Jutias.

A light lunch will be served at Cayo Megano and there will be time to relax and enjoy the sandy beaches and warm waters that surround both islands.

Cayo Jutias is famous for the starfish that inhabits its waters so, with luck, you may spot some on your visit.

You will then return to Vinales, getting back in the late afternoon.

Day 9 — Vinales to Cienfuegos

Today begins with an early start, departing Viñales at approximately 07:00 for the scenic drive south to Cienfuegos on Cuba’s Caribbean coast — a journey of around six hours.

Aside from a brief stop for the loo, there are few sights along the route unless you choose to make a detour to the Zapata Peninsula or Bay of Pigs for an overnight visit.

Upon arrival in Cienfuegos and check-in at your accommodation, your guide will be happy to recommend a local restaurant for lunch.

In the afternoon, you will embark on a guided tour of this elegant maritime city, designated a UNESCO World Heritage site. Originally settled by the indigenous Taíno, Cienfuegos is unique in Cuba for its French colonial influence, evident in its architecture and the Francophile names of many streets.

At the heart of the city lies the tranquil Plaza José Martí, a serene square surrounded by stately colonial-era buildings. The highlight is the Teatro Tomás Terry, a stunning theatre that stands as a testament to the city’s rich cultural heritage.

Day 10 — Cienfuegos to Trinidad via Guanaroca & El Nicho

Today begins with a relatively early start, departing at approximately 08:00 for the short drive to the Guanaroca Lagoon.

Declared a national park in 1994, Guanaroca Lagoon spans 3,000 hectares and is a birdwatcher’s paradise. The lagoon is renowned for its large populations of flamingos, pelicans, and trogons, alongside a variety of other native birdlife. You will explore the area on a leisurely boat trip, taking in the lush surroundings and the vibrant birdlife in their natural habitat.

From Guanaroca, you will journey inland into the foothills of the Escambray Mountains to reach El Nicho. The waterfalls here are fed by the Río El Nicho and Río El Mamey, and are accessed via a gentle, scenic walking trail.

At the base of the falls, a natural pool offers the perfect opportunity for a refreshing swim — so be sure to bring your swimming costume. A simple nearby restaurant also provides traditional Cuban dishes and cold refreshments, perfect for a mid-morning pause.

Afterwards, you’ll return to the car and continue down to the coast to Trinidad, one of Cuba’s most charming towns. Upon arrival and check-in at your accommodation, the remainder of the day is at leisure to relax or explore this historic town at your own pace.

Day 11 — Trinidad

Founded in 1514, Trinidad is one of Cuba’s oldest settlements, rising to prominence on the wealth of the sugar trade. Today, its historic heart, a UNESCO World Heritage site, feels almost frozen in time, offering a rare glimpse of colonial life preserved across the centuries.

The town’s charm is immediately apparent in its traffic-free cobbled streets, pastel-coloured façades, and elegant plazas. The central square, framed by striking colonial buildings, is the perfect place to pause and soak in the atmosphere, watching the rhythm of daily life unfold around you.

After a leisurely breakfast, your guide will collect you for a walking tour of Trinidad, meandering along narrow lanes and exploring the architectural gems and hidden corners that make this town so captivating.

The afternoon is then yours to explore at leisure. You may choose to step back in time at the Romantic Museum, or delve into Cuba’s revolutionary past at the intriguingly named Museo Nacional de la Lucha Contra Bandidos.

For a bit of local flavour (quite literally) visit La Canchánchara, where the honey-and-rum cocktail, Trinidad’s signature firewater, offers a sweet, warming indulgence.

As dusk descends, return to your accommodation to refresh, then venture out into Trinidad’s lively evening scene. From intimate bars and authentic restaurants to venues brimming with live music and dance, the town offers a feast for the senses that lingers long after the night ends.

Day 12 — Trinidad - Valley of the Sugar Mills & Sancti Spiritus

Just a short drive east of Trinidad lies the Valley of the Sugar Mills, a UNESCO World Heritage site where history and landscape converge in a striking tableau.

Once the beating heart of Cuba’s sugar industry, the valley was home to over 50 estates, their wealth built on the labour of a vast workforce. Over time, as sugar prices fell and production moved north, these grand plantations were abandoned, leaving only ruins that now rise like silent sentinels across the rolling hills.

Among these remnants, Manaca Iznaga stands as a poignant reminder of the valley’s past. Dominating the estate is its tower, once a lookout over the fields and the enslaved labourers who toiled below. Today, climbing to the top rewards you with sweeping panoramas of the lush valley, dotted with mogotes, verdant fields, and the echoes of history whispered on the wind.

From here, the journey continues eastward, less than an hour from Trinidad, to the colonial town of Sancti Spiritus, founded in 1514. Though often overshadowed by its more famous neighbour, Sancti Spiritus charms with its tranquil streets, elegant plazas, and centuries-old architecture.

At the heart of the town, Parque Serafín Sánchez invites a leisurely stroll, while cobbled lanes reveal hidden corners and colourful facades, each building a witness to centuries of history. Following one such lane to the Yayabo River, you encounter the town’s most iconic landmark: the Puente Yayabo, a beautifully preserved brick bridge and one of Cuba’s oldest, spanning the waters with timeless elegance.

After exploring the town and enjoying a relaxed lunch, you will return to Trinidad in the afternoon. The rest of the day is at leisure.

Day 13 — Trinidad

After breakfast you will depart for the ceramic studio of Chichi Santander, where you will be taught about the art of pottery-making and the traditional methods used to create their ceramic pieces of art.

After a quick break for a light lunch in town, you will head to a privately owned dance school. Here, you will learn about the link between Afro-Cuban religion and Rumba, one of the ancestors of Salsa.

That is followed by a brief introduction to 4 basic Cuban percussion instruments and identification of the basic rhythm by playing these instruments.

Together with a local dance instructor, and a Cuban dance partner for each participant, you will learn how to dance like a Cuban or, at the very least, master some of the basic moves.

Having returned to your accommodation to freshen up, this evening you will visit the Casa de la Musica in town to either practise your newly acquired skills with an innocent bystander or perhaps just watch and enjoy the experts at play.

Day 14 — Trinidad to Havana via Santa Clara

After breakfast, and having checked out of your accommodation, you will set off from Trinidad for the two-hour journey to Santa Clara, winding through the lush Cuban countryside and small rural towns along the way.

Founded in the late 17th century, Santa Clara may lack the immediate charm of Trinidad or Cienfuegos, but it exudes a quiet, authentic character. Far less visited by tourists, the city offers a chance to experience a more genuine slice of Cuban life.

Today, Santa Clara’s appeal lies not in colonial architecture, but in its pivotal role in modern Cuban history. The city was the site of the revolution’s decisive victory, making the Tren Blindado (Armoured Train) a must-see. Standing beside the rusted train cars, you can almost feel the tension of that historic moment as your guide recounts the events that changed Cuba forever.

A short drive to the outskirts of town brings you to the Che Guevara Mausoleum, where a striking statue and intimate museum commemorate the revolutionary leader’s life and legacy. The site is both solemn and inspiring, offering a profound insight into one of Cuba’s most iconic figures.

After exploring Santa Clara’s revolutionary landmarks, you will board your vehicle for the scenic three-hour drive back to Havana. Along the nearly empty highway, the countryside stretches endlessly, giving you time to reflect on the day’s history-rich experiences before returning to the capital.

Day 15 — Havana & Home

Depending on flight times, you will be collected from your hotel for the approximate 30-minute drive back to Havana airport in good time for your return flight home.