5 Day Private Cuba Tour

5 Day/4 Night Private Cuba Tour


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

Tour Pricing

Please enquire now for information about pricing and accommodation options. We can book a range of accommodation options including authentic, upgraded or superior Casa’s/B&B’s.

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 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 itinerary will introduce you to all the charm and romance of Cuba, from Havana to Hemingway and everything in between.

*B,L,D denotes breakfasts, lunches and dinners included.
*Please note that the map is for illustration purposes only and does not indicate the path you will follow across Cuba or the type of transportation included. 
Included Activites

⭐ Guided orientation walk (dependent on arrival time). ⭐ Old Havana Walking Tour. ⭐ Classic Car Havana Tour. ⭐ 1 x drink at Hotel Nacional over-looking Malecon OR Salsa Lesson OR Mojito making lesson. ⭐ Vinales Day Tour with lunch at an organic farm. ⭐ Havana Rum Museum + Havana Cigar Factory + Floridita OR Farm to Table cooking experience. ⭐ Museum of the Revolution OR Museum of Fine Arts. ⭐ Classic Car to visit Callejon de Hammel and El Morro.

A Selection of Activities and Excursions

We have hand selected some of the best and most interesting activities for you to participate in, while in Havana. There is also the flexibility to choose from a number of options, based on your interests and expectations.

Private Air-Conditioned Transportation

Your transportation between Havana and Viñales will be in a private, comfortable air conditioned vehicle. There’ll be no waiting at bus stops for you.

Airport Transfers

Transfers between the airport and your accommodation is included for both your arrival and departure.

Meals Included

Your breakfasts and 3 lunches are already taken care of, ensuring you’ll get to sample some of the best cuisine in Cuba.

Local English-Speaking Guide

Speaking no Spanish is not a problem as you will be accompanied by a local Cuban guide who speaks fluent English.

Your Choice of Accommodation

We think you’ll love our authentic pick of casa particular bed and breakfasts, family-run establishments unique to Cuba. There is also the option to upgrade to hotels as well.

Download our 5 Day/ 4 Night Private Cuba Tour Brochure here:

About This Tour

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 – or 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 group tour.

Is this trip right for you?

As this is a private Havana tour, we can tailor the tour to suit your mobility and fitness levels. You will also have the guide 100% to yourselves, so you can focus on the activities and excursions of most interest to you. 

We love that our 5 Day Private Cuba tour is informative, exciting, and relaxing, offering you freedom and flexibility. Our local guides love their country and also love to share their wonderful home with you.

Want to experience the real Cuba? Enquire today!

Estimated travel times:

Since travel between destinations is limited to your return journey between Havana and Viñales a minimum amount of time will be spent travelling. The journey from Havana to Viñales takes approximately 3 hours.

To download our Cuba drive times map (click here).


All private transportation is included between destinations and for any activities/ excursions included in your itinerary that require transportation to and from the activity. Any extra transportation requirements can be organised through your Cuban guide and paid for locally in Cuba.  

You’ll be transported from Havana to Viñales in comfort, using air conditioned private transport, so you won’t have to rely on (or wait for) Cuba’s sweaty and ageing public transport system to get about.

Spending money on tour:

Most of your major expenses, such as accommodation and transport to Viñales, are included as part of the tour. However, you’ll want to bring between 50 and 60 CUC (Cuban convertible pesos, 1 CUC equates to 1 US$) per person per day to cover additional expenses. As well as dinners and drinks, you’ll probably want to take home some souvenirs, and may be interested in additional excursions and activities.

The CUC (Cuban Convertible Peso) is valued 1:1 with the US$ (not taking into consideration exchange fees or penalties).

Travel to Cuba from the U.S.:

For those traveling to Cuba from the U.S. (regardless of nationality), please note that the documentation we will include with your booking 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.

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 will 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.


  • Upgraded Boutique Casa’s/ B&B’s (Hotel upgrades available)


  • Airport Transfer


  • No meals included on this day

After a good night’s sleep and your first Cuban breakfast you will be ready for a lively full day of activities. You will start 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.

You will have 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 you will set off for another highlight of your tour, 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.

At the end of your Classic Car Tour we will let you choose from one of three great and quintessentially Cuban options.


  • Upgraded Boutique Casa’s/ B&B’s (Hotel upgrades available)


  • Old Havana Walking Tour
  • Classic Car Convertible Tour

Choose from one of three options:

  • Visit the iconic Hotel Nacional to enjoy a cocktail while overlooking the 8 km seawall esplanade known as the Malecón
  • Experience salsa dancing with an informal salsa lesson
  • Take part in a mojito-making class on a roof-top in Old Havana


  • Breakfast
  • Lunch at Cuban Paladar

Today your Private 5 Day Cuba Tour will help you experience the charm of rural Cuba! After breakfast you will 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 will 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 will 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 is 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 any bookings for you, or to host you if required.


  • Upgraded Boutique Casa’s/ B&B’s (Hotel upgrades available)


  • Los Jasmines look-out point
  • Farmland walk/ cylcle
  • Tobacco Farm
  • Mural Prehistoria


  • Breakfast
  • Lunch at an Organic Farm

Today your 5 Day Private Cuba Tour has another full itinerary for you to make the most of your time in Cuba. Not only that, but you also have a choice of activities both morning and afternoon to best suit your interests.

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 will 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.

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.

In the afternoon you have the choice of visiting the Museum of the Revolution or the Museum of Fine Arts, two of the best museums in the entire country. Needless to say 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.

Whatever option you choose for the afternoon, you’ll then board one of Havana’s classic American cars 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.

* Please note that activities scheduled for Day Two and Day Four of this tour might be switched around to accommodate availability.


  • Upgraded Boutique Casa’s/ B&B’s (Hotel upgrades available)


  • Classic Car to Callejón de Hamel and El Morro

Choose One Experience from:

  • Cigar and Rum Experience
  • Farm to Table Cooking Experience

Choose One Museum from:

  • Museum of the Revolution
  • Museum of Fine Arts


  • Breakfast
  • Lunch

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.

* Please note that some activities are not available on certain days of the week or times of the year. Where this occurs, your guide will offer a selection of alternatives for your consideration.


  • Upgraded Boutique Casa’s/ B&B’s (Hotel upgrades available)


  • Airport Transfer on Departure


  • Breakfast

Tour Pricing

Please enquire now for information about pricing and accommodation options. We can book a range of accommodation options including authentic, upgraded or superior Casa’s/B&B’s.

Meet our locally sourced team

Your Evenings in Havana:

For your evenings, we leave the itinerary flexible. You guide will be able to organise you transfers and tickets to the best of Havana’s nightlife including the Tropicana Cabaret, world-famous Buena Vista Social Club at La Taberna, Parisien Cabaret at Hotel Nacional, Cannon Shooting Ceremony, Gran Teatro Habana, and Vixen and Crow Jazz Café to name just a few.

You can learn more about the evening options available to you by downloading our ‘Things To Do in Havana Brochure here.

Not quite what you are looking for?

It is possible to modify the activities and excursions included as part of this tour, so for more ideas about what you might like to do in Havana during the day or in your evenings, please download our ‘Things To do in Havana’ brochure here.

A note about our restaurant choices for your tour in Havana:

We include a range of different locally-run restaurants (paladares) to showcase the best of Havana’s burgeoning private restaurant scene. Your guide will also help you select the best restaurants for the tour based on your individual tastes and dietary requirements. As a guide, these are some of our favourite restaurants: Mercaderes, Café Laurent, O’Reilly 304, Alta Habana, Vista Mar, El Cocinero and El Atelier

Airport transfers:

Transfers between the airport and your accommodation is included for both your arrival at, and departure from Havana’s José Martí International airport to and from your Havana accommodation

Accommodation on tour:

Choose from historic hotels, beautiful resorts and authentic Casa Particulares .

The upgraded Casa’s we have hand selected are more expensive than the standard Casa’s you will find in Cuba. They are run more like your traditional B&B’s but still 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.

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

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

– Casa Alta Habana
– Hostal San Juan
– Casa Maletas
– My Proud Havana
– Havana Dreams

Not sold on staying at a Casa?

That’s OK, we can certainly look to upgrade your accommodation to a 4* or 5* property, 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. 

Interested in booking a Cuba Tour with Locally Sourced Cuba Tours?

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.