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5 Day Private Cuba Tour – Charming Havana

From US$695

Based on two people sharing - B&B accommodation
Hotel upgrades available

About this tour

English-speaking Local Cuban Guide, Full Day Havana Tour, Vinales Day Tour, Hemingway Tour

Indulge all your senses as you come with us on a Private Cuba Tour that highlights of Cuba’s romantic history and culture.  The perfect Cuba tour experience awaits!

Hear the beat of the music and feel the Salsa rhythm stir your soul as you watch a perfect sunset, cocktail in hand.  We have put together a fabulous itinerary to introduce you to all the charm and romance of Cuba. This tour is perfect those looking for a fun, educational and cultural introduction to Havana.


  • Experience true Cuban hospitality at a wonderful Casa Particular (Cuban B&B) or let us choose a historic Havana hotel for you
  • Walk in the footsteps of Hemingway and find out why he fell in love with Havana
  • Explore the slightly crumbling facades of Havana Vieja – the Old Town as you walk the cobbled streets and listen to the unmistakable Cuban beat
  • Take in the sights in a Vintage American Car
  • Enjoy the vibrant nightlife and learn to Salsa dance
  • Visit beautiful Vinalès for a glimpse of rural life in Cuba
  • Shop for some wonderful Cuban Exports to take home – your friends will love you!


This Private 5 Day Havana Tour is priced from USD$695 per person (2 people sharing) staying in Casa Particular (Cuban B&B) accommodation. If you wish to upgrade to hotel accommodation for your time (or part of your time) in Cuba, just contact us and our team will be more than happy to provide you with some recommended hotel accommodation options and updated pricing.

Meet our team of Local Cuba Tour Guides

Our Cuba Tour Guides

Our team of passionate Cuba tour guides are dedicated to making your Cuba tour the best it can possibly be.


Habana-192  Habana-71 
Hotels or Casa’s? It’s your choice

For the Cuba tours we run, we can book authentic Casa Particulares (Cuban B&B’s) or Hotels (3, 4 or 5*) or a mixture of both. Staying at a Casa Particular and interacting with Cuban locals provides an enriched cultural experience and is often a highlight for many of our tour participants.

You are welcome to request extra accommodation before or after your tour with us in Cuba. This can be done using our online form at the time of booking.

Spending Money on Tour

Your main expenses will be food, drinks, airport departure transportation, souvenirs, optional activitiesairport departure tax (25CUC) and tips.

Airport Transfers

We include an airport transfer on arrival and departure for this tour.

Getting Ready to Travel to Cuba

Please consult our comprehensive Cuba travel guide for all of the information you will need to plan your next Cuban adventure.

Tour video


Arrival, Meet & Greet

Your private tour starts with a personal Meet-and Greet at the airport, followed by a transfer to your chosen accommodation in a vintage American car.  You will have the opportunity to discuss some of the finer details of your tour with your guide and meet your hosts at your Casa Particular or hotel.  In the evening your guide will escort you to one of our favourite local Paladares for your first meal in Cuba.  A Paladar is a family-run restaurant where you can enjoy authentic Cuban cuisine and experience your first taste of local hospitality.  If you are not too tired from your journey, you can visit one of Havana’s famous Jazz clubs to get acquainted with Cuba’s lively music and dance, that will become a central theme during your visit.  The perfect start to your perfect Cuba Honeymoon or getaway.

Old Havana and Classic Cars

After a good night’s sleep and your first Cuban breakfast you will be ready for your lively full day tour of magical Havana.  We will start off with a walking tour through the romantic winding streets of Havana Vieja – Old Havana.  Today the slightly 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 sights and sounds of 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.

You will have lunch at one of our favourite private restaurants, with views of the famous Havana Malecon.

After lunch you will set off for another highlight of your tour, exploreing several Havana neighbourhoods in your private chauffeur-driven Classic American car.  Some of the places you will see are Havana Vedado, the Malecon, the up-market suburb of Miramar and the cemetery of Colon.  A wonderfully romantic way to end your first full day in Havana would be to enjoy a cocktail at La Torre in Havana Vedado, where you can enjoy 360 degree views of the city.

There are numerous choices for evening entertainment and dining and your guide will be happy to make recommendations and bookings for you.  If you would like to immerse yourself in Cuba’s musical scene, why not visit a dance club?  No-one does the Salsa (also known as “Casino” in Cuba) better than the Cubans, as you will see when you visit one of Cuba’s vibrant dance clubs, where everyone seems to be a brilliant dancer.   Active participation is encouraged, so get on the dance floor and show off your moves.  (Salsa lessons are widely available if you want to really learn the ropes and show off your dancing when you go home!).

Day Tour to Vinales

Today it is time to experience the charm of rural Cuba!  After breakfast we will set off on a day-trip to the beautiful Vinales Valley – an area of rich and fertile farmland that produces some of the world’s best tobacco.  The scenery along the way is outstanding with amazing pin-cushion shaped hills and kilometre after kilometre of lush tobacco fields.  It is tobacco from this valley that has made Cuban cigars so sought-after all over the world.  Vinales is a UNESCO World Heritage site and is remarkable for the fact that the farming in this area still follows age-old artisanal methods which you will be able to see at first hand on our tour to one of the local tobacco farms. A Cuba honeymoon highlight!

You will enjoy lunch at a local Paladar and have time to relax and enjoy the atmosphere of rural Cuba.  For something really different (and romantic!) we take a boat ride through some underground Indian caves before your return drive to Havana.

Your evening in Havana is at leisure.  A wonderfully romantic way to end your day would be to take a sunset stroll along the 8km stretch of the Malecon, Cuba’s beautifully restored sea front, and then enjoy a cocktail at the iconic Hotel Nacional.

Rum, Cigars and Hemingway

Today we have another full itinerary for you to enjoy. We will start with a morning tour to broaden your knowledge of Cuba’s two main exports, quality cigars and fabulous Rum.  Our first stop will be the Havana Rum Museum which is housed in a marvellous old Palace.  You will see the entire rum-making process from beginning to end and, of course, get to taste and buy some to take home with you.  Next it is off to the Hotel Conde de Villanueva, a beautifully restored mansion that now houses one of the city’s most popular cigar shop.  You will see how cigars are made and can then do a cigar and coffee tasting.  This is a great tour even if you do not smoke or drink as it will give you a good understanding of both these prized exports. You can also visit the Partagas Cigar Factory for a first hand look at how cigars are rolled and readied for export.

After lunch at another of our favourite restaurants you will start your fascinating Hemingway tour, visiting several of this famous author’s favourite haunts.  Walking in his footsteps through a city that has barely changed in all these years will give you a deep understanding of Hemingway’s love affair with Havana.  Visit his favourite bars, enjoy his favourite rum cocktail and then see his beautiful home, Finca Vigia, which has been preserved as a museum to his memory.

How will you spend your last precious night in Havana?  Your guide will be on hand to help you decide where you would like to go and make all the bookings.  How about a magical night at one of Havana’s most popular night-spots – drink a little rum, be dazzled by the view and fall in love all over again in magical Havana!

Leisure Time and Departure

Depending on what time you are leaving the city, your last day in Havana can be spent relaxing on a beach or perhaps taking an optional Special Interest Tour – we have several on offer including Havana Architecture and Havana Art and Culture tours for those who would like an in-depth look at the thriving Art and Culture scene in the city.  At the end of your time in Cuba we will arrange your airport transfer to depart.

Unless, of course, you simply cannot bear to leave and would like to extend your stay in Havana or explore further afield in Cuba.  We can organise anything from Scuba Diving Tours, Beach Extensions, Rustic Countryside Tours and more…

The beaches are long and white, the sea is warm and turquoise and the underwater life is simply amazing…come and explore it all before you leave this spell-binding country.

Inclusions and exclusions


5 Days, 4 Nights


Havana, Cuba


Havana, Cuba

Group size



4 x breakfasts and 3 x lunches

Single supplement



Choose from Authentic Casa's or Historic Hotels


Private car


English-speaking local Cuban guide, transportation between destinations, 4 breakfasts, 3 lunches, airport transfers


Walking tour of Old Havana

Classic Car Havana Tour

Day Tour to Vinales

Export Cuba Tour (Rum and Cigars)

Hemingway Tour

There are a range of optional activities and excursions you can also enjoy on your 5 Day Private Cuba Tour


International flights, all lunches and dinners (unless specified), travel insuranceCuba Visitor Visa & passport costs, drinks, tips & Giftsoptional activitiesairport taxes – see our Cuba Travel Library or ‘Ask Us’ for more details.

Departures calendar

Upcoming departures

    Tours depart every day on request.

  • Spaces available
  • Guaranteed departure
  • Very limited availability
  • Tour sold out

5 Day Private Cuba Tour – Charming Havana

From US$695

Based on two people sharing - B&B accommodation
Hotel upgrades available

Please review our booking conditions

About the location payment

For the tours we run in Cuba, we ask that a ‘on location payment’ is made to your tour guide at the beginning of your tour in Cuba. The 'on location' payment is not compulsory and you can pay the full amount of the tour by credit card or bank transfer if you prefer (remember 1USD = 1CUC) . These payments act as a safety blanket for our clients, help ensure our tours run to schedule and keep our prices very competitive.