5 Day Private Cuba Tour

5 Day/4 Night Private Cuba Tour

Experience the Real Cuba with Locally Sourced Cuba Tours

5 Days/ 4 Nights Private Air-Conditioned Transportation Upgraded Casa's and/ or Hotels Local English-Speaking Guide Group Booking Discounts Available

Below is a great example of the type of itinerary you can follow if you have 5 days in Cuba. However, our specialty and strength as an organization is creating tailor-made private Cuba Tour itineraries that focus on your interests and expectations.

Start building your perfect tailor-made Cuba tour itinerary today

Tour introduction

If you have 5 Days/ 4 Nights in Cuba we think this itinerary forms the perfect base from which to tailor your private Cuba tour experience. Please note that we can be 100% flexible with the activities and accommodations included. We can tailor the itinerary to focus on your interests, expectations and budget. This Private 5 Day / 4 Night Cuba Tour is perfect for those looking for a fun, educational and cultural introduction to the birthplace of Fidel Castro. Hear the beat of the music and feel the salsa rhythms stir your soul as you watch a perfect sunset, cocktail in hand. Our fabulous example itinerary will introduce you to all the charm and romance of Cuba, from Havana to Hemingway and everything in between.

What's included

A Selection of Activities and Excursions

Based on your interests and expectations, we will hand select some of the best and most interesting activities for you to participate in, while in Cuba.

Local English-Speaking Guide

Your Private local English (and/or Spanish) speaking guide will be on hand to share their magical country with you.

Your Choice of Accommodation

We think you’ll love our choices of authentic, upgraded or superior B&B Style accommodation (Casa’s). These are family-run establishments unique to Cuba. There is also the option to upgrade to 4-5* hotels as well.

Meals Included

Where meals are included we aim to showcase the best of Cuban cuisine by frequenting the growing number of paladares (privately run restaurants). Where meals are not included, your guide and our Havana office team will be happy to make recommendations and reservations as required.

A range of transportation options

We can tailor your Cuba tour experience to include a range of accommodation options including convertible classic cars, modern air-conditioned vehicles, coco-taxis, bicitaxis and more!

Airport Transfers

Forget having to worry about how you’ll get from the airport to your accommodation and vice versa, we’ve got your airport transfers sorted on both arrival and departure.

Start building your perfect tailor-made Cuba tour itinerary today

About This Tour

Tour philosophy:

“Locally Sourced Cuba Tours is dedicated to providing you with an authentic and unforgettable Cuba tour experience. We can help you achieve in one adventure what has taken us years – to go inside the country in a deeper, more personal way. With Locally Sourced Cuba Tours you will have unrivalled access to local people from all walks of life while you experience an island that simply has so much to offer. Our tours are focused on introducing you to the Cuba that we know and love. You will spend time getting to know the locals, immersing yourself in Cuban culture, and supporting the Cuban people through your responsible tourism efforts.”

Why we love this trip:

  • Experience true Cuban hospitality at a wonderful family-run casa particular (Cuban B&B) or let us choose a historic Havana hotel for you.
  • You’ll tour some of Havana’s main sights in an enigmatic American classic car.
  • Explore the crumbling facades of Havana Vieja, the Old Town, as you walk the cobbled streets and absorb the unmistakable atmosphere of the capital.
  • Our 5 Day Private Cuba Tour will take you to the rural township of Viñales, where the island’s natural beauty is breath-taking.
  • You might choose to follow the mighty footsteps of Nobel Prize winning author Ernest Hemingway or explore Cuba’s rum and cigar industry.
  • A local Cuban English speaking guide means you don’t have to worry about the language barrier.
  • With lunches included, you will go to some of our favourite paladares (family run restaurants), the best places to experience true local food and hospitality.
  • The people of Cuba. Meeting the locals might well be your most-loved part of your 5 Day Private Cuba tour.

Is this trip right for you?

A Tailor-made 5 day private Cuba tour gives the right balance of informative cultural experiences and periods of relaxation. You can choose to have the freedom to explore on your own without missing out on vital sights of interest. Being a private tour means you’ll never feel lost in the crowd as your private local Cuban guide shows you around at a pace suitable to your fitness levels.

Start building your perfect tailor-made Cuba tour itinerary today

Travel to Cuba from the U.S.:

For those traveling to Cuba from the U.S. (regardless of nationality), please note that our intention will be to create an itinerary that ensures your compliance with current U.S. travel restrictions (515.574 Support for the Cuban People). In addition to retaining your itinerary, please keep records of your booking receipt, airline receipt, and any supplemental insurance purchased. You should retain these copies for 5 years after your travel. Some of our travelers have been asked to furnish these upon application for Global Entry, Pre-Check, and other programs with TSA oversight.

Start building your perfect tailor-made Cuba tour itinerary today

Tour Itinerary

Your 5 Day Private Cuba Tour starts with a personal meet and greet at Havana’s José Martí International Airport, followed by a private transfer to your chosen accommodation in an air-conditioned vehicle.

If you are staying in casa particular accommodation you will meet your hosts, while if you have opted to upgrade to one of Havana’s historic hotels instead you will have time to settle in and relax there as well. There will also be an opportunity to discuss some of the finer details of your tour with your local Cuban tour guide, who will be happy to answer any questions or queries you may have.

Depending, on your arrival time, your guide can take you on a guided orientation walk around the local area, showing you important landmarks and points of interest.

As evening comes around you have the added option of having your guide escort you to one of our favourite local paladar family-run restaurant for your first meal in Cuba. Here you can enjoy authentic Cuban cuisine and experience your first taste of local hospitality in an informal atmosphere. If you are not too tired from your journey, you might be interested in visiting one of Havana’s famous jazz clubs, to get acquainted with the country’s lively music and dance scene, something that is sure to become a central theme during your visit. We aim today to be the perfect start to your 5 day Cuba tour whether this is your first time in Havana or if you’ve visited many times before.

After a good night’s sleep and your first Cuban breakfast you will be ready for a lively full day of activities. A great way to star the day is with a walking tour through the romantic winding streets of Havana Vieja – Old Havana. Today the gently crumbling and faded facades of the buildings are a reminder of the earlier grandeur of the baroque and neoclassic architecture of the Old Town, which has been designated as a UNESCO World Heritage Site. All around you will be the sights and sounds of everyday Cuba, setting the stage for your exploration. Wear some comfortable shoes, remember your camera and let yourself be carried away by the energetic atmosphere of this unique capital city. The focal point of the Old Havana Walking Tour will be exploring Old Havana’s most beautiful squares – the Plaza San Francisco de Asis, Plaza de la Catedral, Plaza de Armas, before finishing at Plaza Vieja.

Enjoy lunch at one of our favourite private restaurants. It makes for a popular spot for locals to see and been seen, as well as to absorb Cuba’s unique ambience.

After lunch we recommend exploring several Havana neighbourhoods in your private chauffeur-driven classic American car. You will be driven along the Malecón towards Vedado, the up-market suburb of Miramar and pass by the cemetery of Colon and the Revoution Square.

You might like to end the day with a Mojito Making Lesson, or visit the iconic Hotel Nacional for a drink overlooking the Malecon. Another option is to enjoy livel local music at one of Hemingway’s haunts – Floridita.

Today, on your Private 5 Day Cuba Tour we recommend experiencing the charm of rural Cuba! After breakfast you can set off on a day-trip to the beautiful Viñales Valley, an area of rich and fertile farmland that produces some of the world’s best tobacco. The scenery you will witness along the way from your air conditioned transport is outstanding, with amazing pin-cushion shaped hills and kilometre after kilometre of lush green tobacco fields, which you’ll be able to admire fully from the Los Jasmines look-out point. It is tobacco from this valley that has made Cuban cigars so sought-after all over the world. Like Old Havana, Viñales is a UNESCO World Heritage site, and is remarkable for the fact that the farming in this area still follows age-old artisanal methods. You will be able to see this at first hand on your 5 day Cuba tour as you visit one of these local tobacco farms.

You can enjoy lunch at the local Finca Agroecologica El Paraiso organic farm and have some time to relax and enjoy the atmosphere of rural Cuba before talking a walking or cycling tour around the Viñales farmland. Finally, your guide can lead you to the brightly- coloured Mural de la Prehistoria, a 120m long painting by artist Leovigildo Gonzalez Morillo on the side of one of the sheer rock faces in Valle de Viñales National Park.

The evening can be left deliberately free of planned activities so that you have time to discover your own personal Havana. Do as much or as little as you like! You might like to join the locals as they take their sunset stroll along the Malecón, or seek out some of the pro-revolutionary street graffiti celebrating the actions of Castro and Che Guevara. Alternatively, you might simply enjoy returning to the Hotel Nacional for a cocktail. Whatever you choose it will be a great end to your day on your Private 5 Day Private Cuba Tour. Your guide will be available to make recommendations and bookings, and host you if required.

Today your 5 Day Private Cuba Tour can have another full itinerary for you to make the most of your time in Cuba. We can develop an itinerary that focuses on your interests and expectations.

One option is to spend the morning broadening your knowledge of Cuba’s two main exports, rum and cigars. While tourism is vital for the Cuban economy, the country also has profited from its two most famous exports – rum and cigars. On day four of your 5 Day Private Cuba Tour you can get up close and personal with these well-known indulgences.

Your guide can pick you up from your accommodation and take you to the Partagas Cigar Factory to learn more about the cultural significance of Cuba’s cigars. You’ll then visit the Havana Rum Museum, housed in a grand former palace. There are plenty of tastings for the curious, and you can even buy some to take away with you. But if you don’t fancy drinking, you’ll still get a lot out of this visit.

There is also the option of a Rum, Coffee and Cigar tasting experience if you are interested.

Alternatively, you may opt instead to take our fantastic Farm to Table cooking class and cocktail-making lesson. Allotments and small family farms have been an important lifeline to Cubans since the US trade embargo began in the early 1960s. You’ll be staggered by the amount of different produce just a small plot can produce. Lear how to cook authentic Cuban food produced by knowledgeable and exuberant staff who will teach you all they can.

There are some fantastic museums in Havana, including the Museum of the Revolution or the Museum of Fine Arts. The Museum of the Revolution is devoted to the country’s history following Castro’s 1959 revolution, but also includes exhibits relating to the War of Independence against Apain. Housed in the old Presidential Palace, its grounds also contain the yacht which brought Castro and Che Guevara to Cuba from Mexico to start the revolt, and the engine of the American U2 spyplane shot down during the Cuban Missile Crisis.

The two-building Museum of Fine Arts by contrast displays the country’s art collection from colonial times right up to the modern day, including early landscapes and the Hyperrealism movement of the 1970s. The most notable works are perhaps those of René Portocarrero and Wilfredo Lam.

Not interested in museums? We have got you covered. How about a trip to Havana’s local beach (Playas del Este) or Hemingway’s former residence – La Finca Vigia?

You might like to hop into a classic car again for a visit to Callejon de Hammel and El Morro. The Callejon is a brightly coloured narrow two-block alleyway of murals and sculptures in central Havana that has become the centre of the city for many of Havana’s artists, both established and emerging. It’s where they have their studios, and where they try and sell their finished works. More historically minded, El Morro is the grand castle constructed in 1589 that stands guard over the entrance to Havana Bay.

But how will you spend your last precious night in Havana? Your guide will be on hand, as ever, to help you decide where you would like to go and make all the bookings you require. How about a magical night at one of Havana’s most popular night-spots – drink a little rum, be dazzled by the view and continue your love affair with this magical city.

Depending on what time you are leaving the city centre for Havana’s airport, after your hearty last Cuban breakfast you might like to spend a few hours relaxing on one of Havana’s nearby beaches. They are long, with white sand and warm turquoise waters. If you snorkel, you’ll see that the underwater life is simply amazing too.. Take a look at our ‘To do in Havana’ Brochure for more ideas. Whatever your desired departure time, we will of course have arranged your airport transfer for you so that your Private 5 day Cuba tour comes to a perfect, if sad, end.


This is just one example of the type of itinerary we can run if you have 5 Days in Cuba. Our speciality is creating tailor-made Cuba tour itineraries that focus on your interests and expectations. Please take the time to fill out our tailor-made Cuba tour enquiry form so we can capture important information about your accommodation expectations, interests and sleeping arrangements.

Start building your perfect tailor-made Cuba tour itinerary today

Meet our locally sourced team

Accommodation on tour:

The B&B Style accommodation (Casa’s) we recommend for your time in Cuba offer a unique cultural experience. While they shouldn’t be compared to modern Western hotels, the rooms will have air-conditioning, private en suite facilities, hot and cold water and have generally been recently renovated to a beautiful standard.

Cuba’s accommodation is very special. Until recent regulatory changes, it wasn’t possible to stay anywhere but a government owned and run hotel. But all that has now changed and a growing number of casas particulares, bed and breakfasts owned and run by ordinary families rather than the government, are opening up.

This change allows visitors to stay in a more welcoming environment than most hotels are able to offer. You’ll have privacy while still being able to interact with the locals as much as you want. You will truly be made to feel welcome, and might just forget that you’re a paying guest and not a long lost member of the family.

These types of properties range in quality and we classify them into three groups:

  • Authentic
  • Upgraded
  • Superior

You can learn more about staying in boutique Casa’s/ B&B’s/ Guesthouses here.

Some of our preferred Boutique Casa’s/B&B’s in Havana include:




Not sold on staying at a Casa?

That’s OK, we can certainly look to upgrade your accommodation to 4* or 5* properties, depending on your budget. It is worth noting some accommodation providers are to be found in older buildings without elevators. If you believe that your physical capabilities will make it difficult to climb stairs, simply let us know. We will be able to find you a suitable alternative.

Start building your perfect tailor-made Cuba tour itinerary today

Related Tours


Local, Personal and Authentic


Our tour will take you on a fascinating and fun-filled journey of discovery into the History, Culture, Architecture and Rhythms of marvellous Havana.


Local, Personal and Authentic


Visit the Che Guevara memorial, meeting the enthusiastic locals in Santa Clara and immerse yourself in Cuban music and dance in the beautiful Trinidad.


Local, Personal and Authentic


It’s amazing to travel to a new destination and feel like you belong there, but this is exactly what will happen when you come to captivating Cuba on our 8 Day Private Cuba Tour.

Straight from our Instagram feed

Take a look at our Instagram page where we feature the best travel pictures
and behind the scenes photos taken by the Locally Sourced Team.

Comments are closed.