Cuba Express: Havana, Trinidad and Santa Clara
The trip in a nutshell
This itinerary has departure dates until April 2025
If you are looking for departures starting from April 2025, you can find them all on this page!
In the heart of the Caribbean lies a land of vibrant energy and unwavering spirit: Cuba. A tapestry of colours and charm, where every street corner tells the story of a proud nation that leaves a lasting impression on every traveller fortunate enough to visit. From classic vintage cars to fragrant cigars, from the cobbled streets of Havana to the pristine beaches of Varadero, we’ll spend 9 unforgettable days surrounded by history, music, and mojitos in one of the most unique destinations in the world.
Our journey begins in Havana, where we’ll immerse ourselves in its captivating atmosphere, sharing a Cuba Libre or a cigar with the locals. From there, we’ll travel to Trinidad, a UNESCO World Heritage Site, where we’ll embrace the spirit of this perfectly preserved colonial gem. Along the way, we’ll explore lush natural landscapes and enjoy seaside escapes before arriving in Matanzas, a charming town where we’ll dive into the authentic local culture. Finally, we’ll unwind in Varadero, one of the island’s most iconic beach destinations, soaking up the sun and tropical vibes.
Cuba is more than just a destination; it’s an emotion that stirs the soul. It tells stories of triumph, freedom, and hope, inspiring us to seize the moment, chase our dreams, and dance through life together. Are you ready to feel the magic of Cuba?
Trip type
Express: jam-packed itinerary to make the most of the few days of holiday allowance you have.
Physical rating
MODERATE - this itinerary may involve hiking or other activities that require a moderate amount of physical effort. Be prepared for some potential long transfers and early wake up calls!
Entry requirements
Please visit your country's official government website to find out the necessary requirements for entering the country of destination.
Arrival and departure
This trip will begin and end in Havana. Aim to arrive on the first day by 6pm - on the last day you are free to leave whenever!
What's included
8 nights accommodation in shared rooms
All long-haul domestic transport
- All breakfasts
Walking tour of Old Havana and 2-hour vintage car tour of the city
Travel coordinator services
Cancellation up to 31 days before departure — 100% refund (deposit refunded as a gift card) or option to change trips.
Itinerary
Welcome to Cuba!
Check-in: Our adventure starts from Havana
Roundtrip flights are not included in the package, so you can decide from where and when you want to leave! This gives you complete freedom of choice to adjust your travel itinerary to your needs.
Check into your local homestay in Havana. Get ready, this is the start of our adventure in one of the most joyful and fun-filled countries on the planet!
Included: overnight stay with breakfast
Not included: airport transfers, meals and drinks
Heading to Trinidad
An enchanting paradise
Today, we leave Havana and head to the first destination of our journey: Trinidad, a place that will capture your heart in just a few hours. This enchanting paradise is a blend of vivid colours, rich culture, and time-honoured traditions, where the spirit of life is alive in every corner. The streets come alive with brightly painted buildings and the warm smiles of the locals, welcoming us into their world.
We’ll be mesmerised by the breathtaking landscapes that surround us: from lush rainforests to majestic mountains, from unspoiled beaches to charming pastel-coloured houses, this tropical gem showcases Mother Nature’s finest creations.
Tonight, we’ll embrace the magic of Trinidad and let its infectious energy inspire us to live life with joy, unity, and boundless optimism. As the sun sets behind the horizon, the music fills the air, and we’ll dive straight into the vibrant streets of Trinidad, perhaps with a Piña Colada or a Mojito in hand. Let’s celebrate life, Cuban-style!
Included: overnight stay with breakfast and transfer from Havana to Trinidad
Money pot: any entrance fees, extra activities, etc.
Not included: meals and drinks
Exploring Topes de Collantes and Caburní Falls
Forest and waterfalls
Just outside Trinidad, we’ll find Topes de Collantes, a natural park of rare beauty nestled in the heart of the Cuban jungle. The air is thick with humidity, but the experience more than makes up for it. We’ll encounter giant butterflies, colourful hummingbirds, and a variety of tropical plants, immersing ourselves in nature at its finest.
Our journey continues to Caburní, a trail renowned for its dense vegetation and stunning views. We’ll pass through coffee plantations and traditional houses before arriving at the breathtaking Salto del Caburní waterfall, surrounded by natural pools. Here, we can take a refreshing dip or simply cool off, soaking up the magic of this serene spot.
In the evening, we’ll return to joyful Trinidad, where we’ll enjoy an authentic Cuban dinner before dancing the night away at La Cueva, an incredible nightclub set inside a vast underground cave. This truly unique venue will leave us speechless and ready to make memories that last a lifetime.
Included: overnight stay with breakfast
Money pot: excursion to Topes de Collantes
Not included: meals and drinks
Ancón Beach: Let's enjoy the Caribbean Sea
Day at the beach
In the morning, we head to Playa Ancón, one of the most stunning beaches along the Cuban coast. With its white sand, turquoise waters, charming kiosks for drinks and snacks, straw umbrellas, and towering palm trees, Playa Ancón is the perfect spot for pure relaxation. If we’re in the mood for adventure, we can set sail on a catamaran to Cayo Iguana, channeling our inner pirates of the Caribbean! Once we return to shore, we’ll gather for the perfect moment: a group photo at sunset over the sea, capturing a memory that will last forever.
Included: overnight stay with breakfast
Money pot: local transport and optional catamaran excursion
Not included: meals and drinks
Exploring History: Manaca Iznaga and Che Guevara’s Legacy
Che and Cuban History
This morning, we’ll reluctantly say goodbye to Trinidad and head west. Our first stop is Manaca Iznaga, located in the heart of the Valle de los Ingenios, a UNESCO World Heritage Site. This area offers a fascinating glimpse into Cuba’s colonial past, focusing on its sugar industry and the enduring legacy of slavery.
Afterwards, we continue on to Santa Clara, home to the iconic Che Guevara Mausoleum, a sacred site dedicated to the revolutionary spirit of Che Guevara. Che, a Marxist revolutionary, doctor, author, and guerrilla leader, played a pivotal role in the Cuban Revolution alongside Fidel Castro. Today, we’ll have the opportunity to learn more about this legendary figure who became a symbol of revolutionary ideals and anti-imperialism worldwide.
Included: Overnight stay with breakfast and transfer from Trinidad to Santa Clara
Money pot: admissions and any extra tickets
Not included: meals and drinks
A relaxing day in Varadero
Varadero
Today we have a day of real relaxation on the beach in Varadero. We wake up relatively early and set off towards one of the most famous beach resorts on the island, to get there we have about 3 hours of transfer. But once we arrive the trip will be worth it, because we will have the whole day at our disposal to customize together with our coordinator based on what we want to do! This city offers a lot of options: diving and snorkeling, wandering around the postcard beaches, diving into the sea, taking a nice break for a nice fish lunch. We will be able to enjoy the sunset from the beach before setting off towards the city that will host us tonight: Matanzas.
Included: Overnight stay with breakfast, transfer from Santa Clara to Varadero and from Varadero to Matanzas
Money pot: any transport and activities
Not included: meals and drinks
Return to Havana
Return to the capital
Today we can finally wake up calmly and leave without rushing to return to Havana. Once we arrive in the capital, we will dedicate the afternoon to discovering the places and history of the Cuban city. We will start with a guided walking tour of the heart of the city and enjoy the atmosphere of Habana Vieja . The entire neighborhood is a UNESCO heritage site and at every street corner there will be something to photograph: the typical pre-revolution American cars, the hotels that during the American prohibition hosted the parties of the Thousand and One Nights, the Bacardí palace where the famous Rum was invented, the Payret cinema, the legendary Floridita restaurant. After walking through the main streets and squares, immersed in five centuries of colonial history reflected in the various architectural styles of Plaza de Armas, Plaza Vieja and Plaza de la Catedral we can relax sipping a good mojito at the Bodeguita del Medio , an iconic place of the city frequented in the past by Ernest Hemingway and Pablo Neruda.
Vintage car experience
We continue the day by moving to explore the Habana Nueva area, but not on foot this time. Vintage cars await us that will transport us back in time as we tour the streets of this area of the city for about a couple of hours. In this part of Havana, we certainly cannot miss a stop at Plaza de la Revoluciòn where the faces of two very famous revolutionaries such as Che Guevara and Camilo Cienfuegos stand out and where the majestic memorial to Jose Marti stands, another key figure in the independence of the Caribbean island. From there, we can go out of the city center a little further to reach the very particular Fusterlandia neighborhood created by the artist Josè Fuster, where we will feel like we are entering a fairy tale while we are surrounded by thousands of colorful mosaics. If we are not yet tired of exploring, it might be a good idea to reach the nearby Morro Castle , the highest point in the city, to enjoy the last sunset all together and discover the historic Cañonazo ceremony before reaching the restaurant for the last dinner all together.
Included: Overnight stay with breakfast, transfer from Matanzas to Havana, Walking tour and 2-hour ride in a vintage car
Money pot: any entries
Not included: meals and drinks
The tobacco plantations of Viñales
A free day to enjoy
Today we have the day at our complete disposal: we can decide to relax in Havana, enjoying the unique atmosphere of this city, or to dedicate ourselves to an excursion out of town, discovering rural Viñales: a village of a few thousand inhabitants surrounded by the majesty of the green nature where the famous Cuban cigars are produced. We can go on a discovery of the tobacco plantations on horseback , accompanied by the local growers... obviously the time will also come to buy and taste them!
What is certain is that in the evening we will all meet again for the last group Mojito: let's toast to us and to this fantastic adventure.
Included: overnight stay with breakfast
Money pot: horseback excursion to Viñales, any entrance fees and local transport
Not included: meals and drinks
Goodbye Cuba!
Check-out and goodbye
Check-out and goodbye – until your next WeRoad adventure!
Not included: airport transfers, meals and drinks
End of services. The itinerary may undergo some variations that differ from what is stated above. These variations may not be predictable nor depend on WeRoad’s will, i.e. climate conditions, national holidays, strikes, etc.

The travel coordinators
Our travel coordinators are chosen because they are people like you. Not only are they the best travel buddy you could hope for, but they're trained professionals guaranteed to show you a travel experience like never before
Info to know
Please note
In Cuba, currently some areas of the island are experiencing disruptions in the energy sector. We are working to reduce the impact of this on our travels.
Available dates
FAQs – Frequently Asked Questions
About Cuba
Cuba is GMT-4 in summer and -5 in winter, so double-check the time before your flight.
Cuba uses the Cuban Peso (CUP). Euros and pounds may be accepted in some tourist spots, but the exchange rate can vary. It’s better to use local currency.
Cash is king in Cuba, especially outside tourist hubs. UK-issued Visa cards sometimes work in hotels or ATMs, but Mastercard can be trickier. Bring GBP in cash and exchange it in local banks or Cadeca offices—rates are often better in town than at the airport.
Yes, tipping is common in Cuba. A 10–15% tip is standard in restaurants unless already included. For guides or taxis, a few CUP equivalent to one or two pounds is appreciated.
Internet access is limited and slow in Cuba. Buy a local SIM from ETECSA or consider an eSIM if supported. Public hotspots exist, mainly in tourist areas, but don’t count on fast speeds.
In Cuba, they speak Spanish. In touristy spots, some people also speak English, but learning a few words in Spanish goes a long way to really connect with the locals. Here’s a quick Spanish vocab list to help you not look like a total basic tourist – travelling is also about embracing new languages, so let’s make a tiny effort:
- hi: hola
- thanks: gracias
- yes: sí
- no: no
- please: por favor
Cuba uses type A and B plugs at 110V. UK devices will need an adapter and possibly a voltage converter.
Cuba is mostly Catholic, but Afro-Cuban religions like Santería also play a strong cultural role. Religious coexistence is generally harmonious.
The perfect backpack doesn’t exist – and no, this list doesn’t cover everything (yes, we’re trusting you to remember your underwear). Always check the weather and the forecast before packing like a pro. That said, here are a few must-haves for Cuba:
- mosquito repellent (they don’t mess around here!)
- sunscreen (SPF 50+, the Cuban sun is no joke!)
- power adapter
- comfy shoes
- swimsuit (or two... or three!)
- power bank
- hat or bandana
The weather in Cuba is tropical and humid. Dry season: November–April. Rainy season: May–October, but showers are usually short, even in rainy season.
About WeRoad
Round-trip flights are not included in any of our trips because we like to give you autonomy and flexibility: you can choose the airline you want to fly with, the departure airport that suits you best, and how many and which stops you want to make.
Since flights are not included, you also have more flexibility with your travel dates: if possible, you can arrive at your destination a few days earlier or return home a bit later – or even continue independently to a nearby destination!
This is the question of all questions, and here’s the answer, broken down into points!
The Money Pot is a common fund collected in local currency from all tour participants and managed by your Travel Coordinator.
It is used to streamline paymentsfor extra activities, goods and services that the whole group decides to do and to guarantee flexibility in choosing activities and excursions at the destination in line with the mood of the group.
It is typically collected on the first day of the trip in local currency, although at times, the Travel Coordinator may ask for it to be paid before departure.
You’ll find the amount of the money pot on the website under the section ‘What’s included in the money pot’ – how do you get there? Look for ‘What’s included’, scroll down to ‘Money pot? Click here’, and you’ll find the details.
The amount varies depending on the destination chosen.
It is used exclusively for group expenses that ALL participants decide to take part in.
It is estimated based on the experiences of other groups but can vary depending on the needs of the group itself. As such, the Travel Coordinator may need to increase the amount during the trip.
If not all of the money pot is used, the difference will be returned to all participants at the end of the trip in equal amounts.
The Money Pot also covers the Travel Coordinator’s share of the activities included in the money pot, except for those activities that are free for the Travel Coordinator.
If you pay in advance part of the money pot before the trip for certain non-refundable optional activities, unfortunately, the amount cannot be refunded in case of trip cancellation.
We offer several payment methods to fit every need:
1. Credit or prepaid card (Visa, Mastercard, American Express);
2. Instalment payment with Scalapay up to €4,999 (only available with the “Full trip payment” option – not available with the “Deposit and balance” option; pay in 3 instalments up to €1,200 or in 4 instalments over €1,200);
3. PayPal (for selected destinations);
4. Revolut Pay to pay even faster straight from your Revolut account;
5. Welfare credit – BEFORE BOOKING, reach out to us at [email protected].
If you choose the deposit and balance option, you’ll also be able to pay the balance via bank transfer from your Personal Area.
Anyone who books a WeRoad trip has the option to cancel or modify the trip – including both the dates and the destination – free of charge up to 31 days before departure. In case of cancellation, you will receive a 100% refund of the WeRoad trip price. (Deposits will be refunded in the form of a gift card valid for 365 days from issue date.) If you make a change, a price adjustment will be applied to the new trip chosen – meaning, if the new trip is cheaper, we will refund the difference; if it’s more expensive, you will need to pay the difference.
If you’ve purchased the Flexible Cancellation Option (which you can add in the first step of the booking process), you can request a cancellation or trip change until 8 days before departure. In case of cancellation, you’ll receive a 100% refund of the WeRoad trip price, minus the cost of the Flexible Cancellation option. Deposits will be refunded in the form of a gift card valid for 365 days from issue date.
How to request a cancellation or change to your trip? Send us an email at [email protected] or a WhatsApp on +447716573700. Please share the booking reference for the trip you want to cancel or change, and, in case of a change, the new trip you would like to join.
In general, we always choose local accommodations, avoiding large hotel chains, because we love to experience the culture of the place and, whenever possible, contribute to the local economy. Typically, our accommodations are hotels, apartments, guesthouses, and hostels run by local entrepreneurs, with the same standard maintained across all trips in the same destination.
For our Collection trips, which are our premium category, the accommodations are always 4 or 5-star or carefully selected boutique hotels.
The list of accommodations for your trip will be shared with you by your Travel Coordinator between 5 and 3 days before departure, along with other useful details for your adventure!
If you're wondering why WeRoad trips have a money pot, we’re assuming you already know what it is. If not, or if you have any doubts, we invite you to read all the information here!
Let’s quickly recap: The Money Pot is a common fund collected in local currency from all tour participants and managed by your Travel Coordinator. It’s used to speed up payments for extra activities, goods and services that the whole group decides to do and to guarantee flexibility in choosing activities and excursions at the destination in line with the mood of the group.
But let’s get to the point: why the money pot? First of all: it gives us a lot of flexibility. In all WeRoad trips you will have a bunch of Must See/Must Do activities already included - these are experiences, places or activities that simply cannot be missed! Any extra activities is decided by the group, why? Because each group is unique and may have particular wants or desires and the Money Pot allows each group to customise their trip to make it perfect for their requirements!
It also helps us speed up payments – imagine being in the subway in New York City, one by one purchasing the ticket...a nightmare right? Thanks to the Money Pot, the Travel Coordinator can simply purchase the tickets for everyone making the entire processes smoother! Any leftover money will be returned at the end of the trip and split equally amongst all participants.
In some destinations, buying goods or services on site is more economical as you are able to negotiate the price - places like Morocco, or South East Asia, bargaining is part of the culture. As such, our Travel Coordinators will be able to secure the best deal for all participants.
The amount of the money pot is specified in each trip – look for this button
which will take you to a detailed breakdown for each trip, like this:
Even if we don't know the flights of all WeRoaders, there are several ways to find out which flights your travel companions have purchased.
1. Each WeRoader has the ability to communicate their flight details after booking within their personal area so that other travel companions can see the details anonymously. Enter your booking and you will find this section:
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2. If you want to find out before booking, instead, you can contact us and we will support you in your search or you can ask your travel companions for direct information by joining our Facebook group 'WeRoad... let's get to know each other before leaving! (official)' – (here is the extended link: https://www.facebook.com/groups/weroadit) look for a post associated with your trip, or ask the group administrators for help in getting in touch with your future adventure companions!
If the coordinator has already been assigned to the trip you are interested in, you can easily find his/her presentation post in the group through the site: in the shift list click on 'Ask the coordinator', or in the trip tab, in the coordinator section, click on 'Ask [coordinator name] about this shift in our Facebook group'. For both cases, see the screenshots below!
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In all our groups, the Travel Coordinator and participants speak English – knowing how to speak and understand English is therefore a fundamental requirement to participate in our trips.
On average the groups are made up of 6-15 people, with a minimum of 3/4 participants and a maximum of 15.
All our travellers are in theirs 20s, 30s and 40s. If you're very curious to know the age range of the group for a tour you're interested in, you can see this by finding the trip on our website, and clicking the down arrow to see the ages & genders of participants. You'll need to have created a WeRoad account with us to do this.
Any issues finding this info just give our team in the office a call, we're always happy to help!
Regarding the male-female ratio, this is not guaranteed and varies trip by trip.
Yes! If you're curious, you can take a sneak peek at the group before booking – although, in our opinion, that kind of spoils the surprise! You’ll find the info in the ‘Group’ section for each trip on the departures page, showing how many WeRoaders have already booked. Click the little arrow and you’ll even see their gender and ages – but hey, that’s exclusive info, so we’ll ask you to log in or sign up to see that!
Yes, in all our trips you will share a room with other same-sex travellers, and the bathroom will either be private or shared only with fellow participants of the trip. The rooms we select can be doubles, triples, quadruples, or multi-bed (up to 8 people in exceptional cases), depending on the destination and availability.
There are never dorms with people outside the WeRoad group, except in certain cases for local experiences, which are specifically mentioned in the itinerary or communicated before booking. These typically involve specific nights in unique accommodations like tents, homestays, or camping, offering a more adventurous travel experience in exchange for some comfort.
During the booking process, you can also choose to opt for a mixed room: in this case, if needed, only those who have agreed to this option may share a room with travellers of a different sex. If you are booking for multiple people together and select this option, the room will not be exclusive to your group but may be shared with other travellers in the group.
The WeRoad Travel Coordinator is an experienced and skilled traveller and will be the perfect companion for your trip. They will be available for any eventuality and will manage all the logistical aspects of the itinerary (transports, timings, accommodations, meeting points, etc.), so you can enjoy the trip without any worries!
You will have the chance to get to know them when the WhatsApp group is created approximately 2 weeks before departure - this will be the moment to ask any pre-departure questions and get to know the rest of the group! If the trip you are interested in already has a Travel Coordinator assigned, you can contact them before booking – their details will be specified in the schedule or on the trip page, or you can search for their name here. After booking, you will find their contact details in your Personal Area, under ‘Bookings and Trips’ > ‘Your Upcoming Trips’ > ‘Trip Details’.
When you set off on a WeRoad trip, you’re officially a WeRoader – and as we often say, 'Once a WeRoader, always a WeRoader'. This means that once you’re part of the community, a little piece of WeRoad will always stay with you, even if you no longer travel with us.
But you’re not just a WeRoader during your trips, far from it! The community is alive and active all year round: you can stay in touch by following and interacting on our social media channels, like the Facebook group or the Instagram profile. We can also meet up for a dinner or a trek together at one of the events organised by our coordinators around the world!