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20 Day Cuba Group Tour – Indulgent Cuba


About this tour

Cuban B&B's, English-speaking local Cuban guide, the 'best of' excursions

Our 20 Day Cuba Group Tour is for those that want to explore Cuba – West to East and Top to Bottom. Experience Cuba’s rich culture, learn about its controversial history and meet the friendly locals that makes this destination unlike any other.


20 Day Cuba Group Tour Itinerary Snapshot

  • Day One: Tour arrival Day in Havana
  • Day Two: Cienfuegos via Bay of Pigs
  • Day Three: Trinidad via Santa Clara
  • Day Four and Five: Trinidad
  • Day Six and Seven: Camaguey
  • Day Eight and Nine: Santiago de Cuba
  • Day Ten, Eleven and Twelve: Baracoa
  • Day Thirteen, Fourteen and Fifteen: Havana
  • Day Sixteen and Seventeen: Vinales
  • Day Eighteen: Las Terrazas via Soroa
  • Day Nineteen: Return to Havana via Fusterlandia
  • Day Twenty: Tour ends

Want to see the very best Cuba has to offer? Engage in the lively culture, enthralling history and breath-taking beauty of this evocative and vibrant Caribbean island on our 20 Day Cuba Group Tour – Indulgent Cuba.  Current economic and political transformations in Cuba suggest that there is no better time to take one of our tours in Cuba. Saunter down Trinidad’s cobble-stoned streets, discover Havana’s secrets through the windows of degenerate colonial buildings and admire the rich red earth of the Pinar del Rio province. Pristine beaches, pirates, salsa and Che are all on the agenda on a tour that aims to constantly excite, enthuse and enlighten.

On our 20 Day Cuba Group Tour you will have a Locally Sourced Cuban guide travel with you from destination to destination and you will stay in Cuban B&B’s (Casa Particulares).

  • Experience Cuban hospitality at a Casa Particular
  • A Local English-speaking Cuban guide accompanies all of our Cuba group tours
  • Lose yourself in the winding colonial streets of Camaguey
  • Dance the night away in Santiago de Cuba
  • Get inquisitive exploring the spell-binding Havana Veija
  • Explore the underwater landscape at the Bay of Pigs
  • Enjoy a delicious cocktail over stunning views
  • Visit the final resting place of the immortalised Che Guevara
  • Take in the historic french-influenced architecture of Cienfuegos
  • Visit a Tobacco Farm in Vinales

Supporting the Cuban People

All of our group tours are dedicated to supporting the Cuban people, patronizing privately owned small businesses across Cuba.

Your itinerary is designed to introduce you to the local Cuban people and steer funds towards its citizens. On our group tours you will stay in Casa Particulares (privately run Cuban B&B’s) and eat at Paladares (privately run restaurants). You will also have the chance to interact with Cuban’s from all walks of life, listening to their stories, and sharing your own.

Included Activities

On our 20 Day Cuba Group Tour, we like to include a number of ‘must do’ activities and still leave you with some free time to choose from a range of optional activities or explore independently.

Guided Orientation Walks at all destinations visited
Evening cocktail in Cienfuegos
Che memorial & museum
Informal salsa lesson in Trinidad
Bicycle taxi tour of Camaguey
Dance school visit in Camaguey
Night out in Santiago de Cuba (entry fee and 1 x drink)
Group BBQ lunch by the river in Baracoa
Full day Havana Tour including, city tour in classic car and Old Havana Walking Tour
Cocktail making class and farewell dinner on a Old Havana roof-top
Vinales Tobacco Farm and underground caves

Meet our team of Local Cuban Tour Guides

Our Cuba Tour Guides

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

Is this Cuba tour for me?

Our group tours are perfect for those who want the freedom and flexibility to travel at their own pace, along with the security, camaraderie and cultural insight that comes from travelling with a local English-speaking guide and small group.

  • Cuban B&B’s (Casa Particulares) are family run business which are set-up to provide B&B style accommodation to foreigners – a unique cultural experience. Casa’s are generally much nicer than normal Cuban dwellings but can be more basic than foreigners are used to. It is important to remember that each room at a Casa is unique in its size and set-up. Whether you stay in a hotel or Casa, sometimes power cuts and breaks in hot water are unavoidable in any developing country.
  • Part of the experience of traveling through Cuba is experiencing Cuban resourcefulness. Spare parts are often difficult and expensive to come by, so don’t be surprised if your notice that ‘Cuban innovation’ has been used to keep various things working.
  • Access to the internet in Cuba is getting better but can still be variable, slow and unreliable. It is also relatively expensive to get online at a hotel or one of the various Wifi zones that have been set-up across the country. Traveling through Cuba offers a great opportunity to take a break from your electronic devices and have a truly relaxing experience.
  • Cuba is a unique travel destination and that is what makes it so popular. It is part of the ‘laid back Caribbean’ and things don’t always go to plan or schedule. A great sense of humour and patience are qualities that will go along way in making your stay in Cuba an enjoyable one.

Estimated Travel Times

Below are the estimated travel times between destinations on this 20 Day Cuba Group Tour. For the longer journey’s on all of our tours in Cuba, our guides like to break-up the journey by stopping for lunch and at various points of interest along the way.

You can download our Cuba drive times map here

Havana to Cienfuegos via Bay of Pigs: 5 hours
Cienfuegos to Trinidad via Santa Clara: 3 hours
Trinidad to Camaguey: 5 hours
Camaguey to Santiago de Cuba: 6 hours
Santiago de Cuba to Baracoa: 5 hours
Havana to Vinales: 3 hours
Vinales to Las Terrazas: 2 hours

Transportation on our tours in Cuba

For the greatest efficiency and comfort, all of our Cuba group tours use air-conditioned  private transportation between destinations wherever possible.

An internal flight from Baracoa to Havana is included as part of this tour. Please note that on occasions, due to flight availability, the group might need to be transported to Santiago de Cuba or Holguin to fly from there.

Spending Money on Tour

Everyone is different in the amount of money they will spend on one of our Cuba group tours. Your main expenses on our 20 Day Cuba Group Tour will be food, drinks, airport departure transportation, souvenirs, optional activities, and tips.  For our 8 Day Cuba Group tour we estimate that you will need approximately CUC50.00 – CUC60.00 per person, per day to cover your local expenses.

Our Single Supplement Policy

We believe that you should be able to have the privacy that comes with having your own room on tour, and not have to pay anything extra for this. That’s why it is our policy is to waive the single supplement fee on all of our Cuba Group tours. Of course you can still choose to share a room with a fellow traveller, as this can often be part of the fun of traveling – it’s your choice!

Airport Transfers

Our small Cuba group tours include your arrival transfer from the airport to your joining accommodation (Havana airport only) on arrival. When you’re ready to leave, your local Cuban guide can arrange your airport transfer on departure at local prices.

Fitness Requirements

As a minimum, you will need an average level of fitness and mobility to join this tour. Partaking in small group travel can be more physically demanding than your more conventional holidays. You should be able to walk without the aid of another person, climb a couple of flights of stairs, step on and off buses and other forms of transport, and carry your own luggage.

Planning on taking one of our tours to Cuba?

Please consult our comprehensive Cuba travel guide for all of the information you will need to prepare for one of our Cuba group tours.

Tour video



Visit Hemingway's haunts on a Havana Tour

Day One: Havana

Known as the capital of fun during the 40’s and 50’s, this spellbinding city immediately captures the curiosity of her many visitors. But where do you start? We recommend those booked on our 20 Day Cuba Group Tour put on your walking shoes and take in Havana’s rich history, grand monuments, world famous cigars and scrumptious cocktails. You can easily get lost in Havana Vieja (old Havana), the old city of cobble stoned alleyways and colonial buildings, ancient squares and noted churches. The perfect day to get your bearings and meet your guide and group for an optional evening meal.

Please note that the first day of the tour is a joining day with no formal activities planned. We do organise your accommodation for this evening and a optional dinner with your guide and group.

Meet the locals on a Family Cuba tour

Day Two: Cienfuegos

Stop off at Playa Girón/ Bay of Pigs, long associated with the USA’s first military failure in Latin America. The natural beauty of this area is stunning, with cave systems, coral formations and an abundance of sea life making it a must for snorkelers, divers and ocean lovers alike.

If Cuba had a Paris then it would probably be Cienfuegos, which stands out for its rich French-influenced architecture. A harbour city by location, the ‘Pearl of the Caribbean’ has seduced Cuban travellers for years due to its elegance and beauty. Founded in 1819 by Don Luis de Clouet, Cienfuegos luckily managed to remain free of pirate attacks, allowing this popular city to prosper. Explore the wide streets and promenades or enjoy a walk by the Malecon, the longest promenade on the island.“Cienfuegos is the city I like the best”, wrote Beni More, one of Cubas most important musicians in the first half of the 20th century. Check it out for yourself and see what you think.

Day Three, Four and Five: Trinidad

Stop at the Che Guevara mausoleum and memorial in Santa Clara, where Che’s remains are immortalized following their discovery in Bolivia in 1997. Santa Clara holds a special place in Cuban history, where in December 1958, Commander Ernesto Che Guevara led his revolutionary rebels in the derailment of the armoured train carrying the ammunition Batista had sent to defeat Fidel – the revolution was won.

Then it’s on to the favourite destination of many a traveler to Cuba. Trinidad was founded in 1514 by Diego Velázquez and is considered a jewel in Cuban colonial architecture. For some, Trinidad is a living museum, stuck in the time of Cuba’s first War of Independence when local sugar plantations were devastated by fire. The vibrant colours and soulful music littered along cobbled streets will simply take your breath away.

Take the opportunity to visit a local waterfall, historic sugar mill or one of Cuba’s best beaches – Playa Ancon. An evening at one of Trinidad’s effervescent music venues is a must!

Travel to Camaguey on our 15 Day Cuba Group tour

Day Six and Seven: Camaguey

Don’t get lost in “La Ciudad Confusa” (the maze)! The labyrinth of winding streets and alleys of Cuba’s third largest city shouldn’t be enough to put you off visiting the beguiling city of Camaguey – a city built to confuse pirates.

With its large number of squares and parks, colonial architecture and enriched spiritual persona, Camaguey is a mecca for Cuban arts and culture. Plan a visit to a famous historical landmark or  explore a myriad of art galleries and handicraft exhibits – it’s entirely up to you! There are also some of Cuba’s best beaches close by at Playa Santa Lucia.

A guided tour on the back of a bicycle taxi is our gift to you!

Day Eight and Nine: Santiago de Cuba

The second largest city in Cuba is surely its most dynamic. With a myriad of ethnicities calling Santiago home, it’s hard not to get swept away in its joyous and prepossessing surroundings. Plus its music and dance scene is quite possible the best in Cuba.

As the most Caribbean of Cuban destinations with a backdrop of mountains and rugged terrain, Santiago de Cuba has many things to show off and be proud of. It is the hub of most of the music genres in Cuba and the locals are hospitable, resourceful and virtuous.

Make sure you visit one of Santiago de Cuba’s famous tobacco factories when in town and take in a famous music venue or two in the evening on your 20 Day Cuba Group Tour.

Travel to Baracoa on our 15 Day Cuba Group tour

Day Ten, Eleven and Twelve: Baracoa

Cuba’s first colonial capital, Baracoa is set amongst a mixture of palm, chocolate and banana tress. It is a land blessed with many rivers and a healthy annual rain fall, that has worked to create some of the most lush vegetation and rainforest you will ever encounter. The town has remained relatively unchanged over the years, with several houses dating back to the 19th century and a system of colonial fortifications that includes Matachin Fort and La Punta Fort.

From Baracoa there are many outdoor excursions to go on, each making use of its beautiful surroundings. Explore the bountiful rivers in the area or go boating between the tall cliffs at the mouth of Yumuri River. You can also see over 900 species of endemic flora, including around 360 that are found only in this area.

Baracoa’s cuisine is world famous in Cuba and a BBQ group lunch is the best way to sample the delicious local produce.

visit wonderful Havana on a Cuba group tour

Day Thirteen, Fourteen and Fifteen: Havana

Back in Havana you have the opportunity to explore some more and experience Cuban nightlife . A full day tour of the city including time in a classic American car and an Old Havana Walking Tour is included as part of our 20 Day Cuba Group Tour.

On Day Fourteen as a special treat we’ll take you to a special rooftop in Havana’s Old Town that makes a sublime mojito (or a non-alcoholic alternative). You’ll be taught how to make a classic Cuban cocktail before enjoying a farewell dinner with your group and guide, with an unbeatable view over the rooftops of the city.

Visit Vinales on a tailor-made Cuba tour

Day Sixteen and Seventeen: Vinales

Viñales is reasonably close to Havana, and has been popular with visitors for generations. In the heart of the Pinar del Rio valley, most of Cuba’s tobacco production takes place in and around Viñales. This is the place to see where those world famous cigars come from, and to get some for yourself.

The geography in the area is stunning, and the town is ringed by stark mogotes – small hills with sheer rock faces. All of our Cuba group tours offer you the chance to take salsa lessons, and Viñales is the best place to do this.

The nightlife is lively, but not as crowded as larger cities – just in case you don’t want to have an audience!


Visit Vinales our our 8 Day Cuba Group Tour

Day Eighteen: Las Terrazas via Soroa

Today you will travel to Las Terrazas via the small village of Soroa. Referred to as The Gate to The Garden of Eden, this stunning village is the starting point for many hikes to the soaring Sierra del Rosario. After exploring the village you will visit the famous Orchid Gardens of Soroa and the nearby waterfall.


The next stop is the mountain community of Las Terrazas. Las Terrazas was constructed as a reforestation project in the 1960’s and has since been named a Unesco Biosphere Reserve. We have time in the afternoon for a walk around the town to meet the friendly locals and for a swim in the gorgeous San Juan mountain stream. In Las Terrazas there are also art, woodwork and pottery studios that are open to the public.

Day Nineteen and Twenty: Havana

Back in Havana you can tick off any last minute activities or excursions you would like to do before our guide and team bid you a fond farewell.

Please note that Day Twenty is the tour departure day, meaning you are free to depart at any time.

Viva Cuba!

Inclusions and exclusions


20 days, 19 nights


Havana, Cuba


Havana, Cuba

Group size



19 breakfasts, 1 lunch, 1 dinner included

Single supplement



Cuban B&B's/ Casa Particular's - 19 nights


Private air-conditioned transportation wherever possible


English-speaking local Cuban guides accompany all of our tours in Cuba, transportation between destinations, 19 breakfasts, airport transfer on arrival, Internal Flight


Guided Orientation Walks at all destinations visited
Evening cocktail in Cienfuegos
Che memorial & museum
Informal salsa lesson in Trinidad
Bicycle taxi tour of Camaguey
Dance school visit in Camaguey
Night out in Santiago de Cuba (entry fee and 1 x drink)
Group BBQ lunch by the river in Baracoa
Full day Havana Tour including, city tour in classic car and Old Havana Walking Tour
Cocktail making class and farewell dinner on a Old Havana roof-top
Vinales Tobacco Farm and underground caves

There are a range of optional activities and excursions you can enjoy on your 20 Day Cuba Group Tour and any other tours in Cuba we run


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

Accommodation on Tour

Our Cuba group tours use only the best Casa Particulares – Cuban B&B’s. These Cuban Bed and Breakfast establishments offer a taste of authentic life on the island. You will be staying as a guest of a family in private accommodation. You’ll have privacy while still being able to interact with the locals as much as you want. It’s a stark difference to most types of accommodation, and you will truly be made to feel welcome – you might forget that you’re a paying guest and not a long lost family friend!

A number of accommodation options are in older buildings without an elevator. If you have issues with mobility and will be unable to comfortably climb several flights of stairs, please let us know. We can happily find you a wonderful alternative to suit your needs. We’ve got you covered if you want to spend a few extra days in Havana before or after your Cuba group tour. Just use our easy online form when you make your booking.

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One of our favourite Casa’s in Havana, Casa Alta-Habana is located right in the heart of Havana Vieja just next to the beautiful Plaza Vieja.

Departures calendar

Upcoming departures

  • 26th February, 2018
  • 5th March, 2018
  • 12th March, 2018
  • Spaces available
  • Guaranteed departure
  • Very limited availability
  • Tour sold out

20 Day Cuba Group Tour – Indulgent Cuba


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.