
Cuba 360°: from Havana to Trinidad
The trip in a nutshell
A trip to Cuba will stay with you forever: the largest island in the Caribbean has a thousand facets and a controversial history, being the ultimate symbol of revolution. Escape the modern era – in Cuba you can truly get away from it all, and this is where all its charm lies. Who knows how long Cuba will stay the way it is, so now's the time to plan a trip here.
Our trip starts in Havana and quickly moves towards Viñales, where we visit the local tobacco plantations and learn how the famous Cuban cigars are made. Any trip to Cuba wouldn't be complete without some beach time, so let's head to Cayo Jutías. Next stop is the town of Matanzas, where we'll experience Cuban culture at its best before spending a well-deserved day on the dreamlike white-sand beach of Varadero. After a quick stop in Santa Clara and a visit to Che Guevara's Mausoleum, we'll be mesmerised by the colours of Trinidad, where we'll try our hand at salsa and we will spend a whole day on a boat off Playa Ancón. We will then cross the jungle in the Topes de Collantes Nature Reserve Park, looking for hidden waterfalls, as well as exploring the Valle de Los Ingenios among sugar plantations. We'll get another dose of beach life in Playa Larga and Playa Girón, both of which overlook the famous Bay of Pigs – the ideal place for those who love snorkelling. Finally, we'll return to Havana to round off this incredible trip in style.
Trip type
360º - it's our great classic that allows you to discover the destination in all its aspects. We recommend packing a backpack rather than a suitcase as there will be lots of moving around.
Traveling to Cuba requires maximum flexibility due to current historical challenges, including occasional nighttime blackouts. Many accommodations have generators to ensure basic services like lighting. As travellers, we should be mindful that we are guests of a welcoming and resilient population facing difficult times.
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 by 5pm on the first day – on the last day you are free to leave whenever!
2 people interested
What's included
11 nights accommodation in shared rooms
- All breakfasts
- Welcome dinner
- All long-haul transport
Local Experience: a relaxing horse ride among the tobacco plantations in Viñales
An exciting excursion by catamaran (or boat depending on availability) to Cayo Iguana
Walking tour of Old Havana with local guide
Guided 2-hour vintage car (cabriolet) ride in Havana
- Travel Coordinator services
Free cancellation with 100% refund up to 31 days before departure
Itinerary
Welcome to Cuba!
Check-in: our adventure starts in Havana!
Roundtrip flights or transportation to reach the destination 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, breakfast
Not included: airport transfer, food and drinks
Viñales: horses and tobacco
Heaven on earth
We set off from Havana to reach Viñales, a small town cradled by a nature reserve park and home to just a few thousand inhabitants. Surrounded by breathtaking scenery, Viñales is a typical example of Caribbean life.
World-famous Cuban cigars are predominantly produced in… yep, you got it right, in Viñales! When we’re there it'll feel like the set of a film – WeRoaders on horseback, surrounded by stretches of tobacco plantations and mixing with the locals. Needless to say, not only will we see how the cigars are produced, but we’ll be able to try them (and it’s perfectly legally to bring a few back home, don’t worry!).
What a better way to start getting to know each other than with Cuban specialities at our welcome dinner? Arroz con pollo, some ajiaco... and of course plenty of cuba libres to toast to the beginning of our adventure.
Included: overnight stay, breakfast, transfer from Havana to Viñales, welcome dinner, horse ride, plantation entrance fee
Money Pot: local transport
Not included: food and drinks if not mentioned
Cayo Jutías
Beach, nature and culture
We're off to the coast today! Just an hour away from Viñales, the white beaches and crystal clear water of Cayo Jutías await us, but first there is an unmissable stop: the Mural de la Prehistoria. This painting has gone down in history for being the largest open-air mural in the world – it took 4 years to finish! It was designed by Leovigildo González Morillo and 40 people worked with him to complete it. A quick group photo and we're back the minivan on our way to our first Caribbean beach! We need to find the chiringuito (beach hut) that offerts the best piña coladas – served directly inside a coconut!
We will spend the day basking in the sun and enjoying the sea – or maybe having long walks to reach the mangrove forests that grow directly into the sea: the perfect place to take breath-taking photos which will make your colleagues back in the office so jealous! Alternatively, we can opt for a boat trip to Playa de Las Estrellas. This is an unspoiled white-sand beach with crystal clear water filled with so many wonderful starfish – but please don't touch them! In the evening we'll return to Viñales where we will have the chance to experience the famous Cuban hospitality – and who knows, perhaps we'll be taught a few steps of salsa!
Included: overnight stay, breakfast
Money Pot: transport and entrance fees if any
Not included: food and drinks
Matanzas: the Athens of Cuba
Cuban vibes
After a nice breakfast we leave Viñales for a full day of history, culture (and a bit of nature): welcome to Matanzas! Known as 'the Athens of Cuba', this is a city of bridges where the musical genres of rumba and danzon apparently originated. On our way to Matanzas, though, a quick stop on Bacunayagua Bridge is a must-see to take in the best views of the Yumuri Valley.
Once in Matanzas in the early afternoon, a new adventure awaits. We take the back seat of a moped (with driver) for an relaxing 20-minute ride to the mouth of the Canímar River. Change of transport: off the mopeds, on board 4-seater small boats – and we'll be the ones in control this time as we explore the Canímar River in small groups. This will be an opportunity to discover indigenous culture and traditions from a different point of view.
So now let's go on a walk through the city – Libertad Square, the Cathedral and Vigia are enough to feel the real Cuba. A few minutes away from the town centre we could also visit Bellamar Caves, San Severino Castle and Monserrate Church. As night falls, why not sipping a drink by the bank of the San Juan River? Salud!
Included: overnight stay, breakfast,transfer from Viñales and Matanzas
Money Pot: boat excursion with motorbike transfer, other transportation and entrance fees if applicable
Not included: food and drinks
Varadero: welcome to the Caribbeans!
Caribbean beaches to the full
Only 30 minutes away from Matanzas and here we are by the picture-perfect sand and crystal-clear water of Varadero – a 22 kilometre-long white-sand beach for a day of total relaxation. On our way to Varadero, we will also stop at Saturno’s Cave or Playa Coral (the coral beach) for some snorkelling or diving. We’ll have all day to enjoy the best of the Cuban sea, then it’s back to Matanzas for dinner! Overnight stay in Matanzas.
Included: overnight stay, breakfast
Money Pot: transport and entrance fees if any
Not included: food and drinks
Trinidad via Santa Clara
The heart of Cuba
Adiós Matanzas, next on our list is Trinidad. First though, let's stop in Santa Clara, which is famously known for the battle where the dictator Batista was defeated by Ernesto 'Che' Guevara and his revolutionary forces. We’ll also have the chance to visit Che Guevara's mausoleum, where we’ll be able to trace back all the key moments that shaped Cuba’s modern history.
Later in the day we’ll arrive in the pristine streets of Trinidad, which are peppered with colourful buildings and warm Cuban hospitality. The atmosphere of the streets is unparalleled – music fills our ears whilst our stomachs will be filled by the freshest fish and fruit. We’ll have dinner on a terrace, enjoying a mesmerising rooftop view of the city. As the night draws in, the music gets louder, all set for the steady flows of piña coladas and mojitos!
Included: overnight stay, breakfast, transfer from Matanzas to Trinidad
Money Pot: local transport and any admission fees if needed
Not included: food and drinks
Topes de Collantes Nature Reserve Park
Forests and waterfalls
Buenos días, it’s time for more adventure! Topes de Collantes is a fascinating nature reserve park situated just outside Trinidad. We’re off to the Cuban jungle today – here we’ll be hiking accompanied by giant butterflies, vibrant hummingbirds and tropical plants. Yep, it probably will be hot and humid, but the sweat is definitely worth the views! Our destination is Caburní on a trail lined with thick, lush vegetation and breathtaking panoramic views. We’ll walk through coffee plantations and traditional Cuban villages before arriving at the famous Salto del Caburní waterfall, where glinting natural pools await. Anyone up for a refreshing dip? We’ll then head back to joyful Trinidad for dinner and, if you remembered to pack your dancing shoes, it's salsa lesson time!
Included: overnight stay, breakfast
Money Pot: local transport and any admission fees if needed
Not included: food and drinks
Boat tour to Cayo Blanco
Vamos a la playa!
In the morning we’ll be driven down to Playa Ancón, one of the most beautiful beaches on the Cuban coast. White sand, turquoise waters, beach huts, straw parasols and palm trees... Playa Ancón is the perfect place to wind down.
Right before lunch we’ll get on on a catamaran to Cayo Blanco… feeling just like Pirates of the Caribbeans! It wouldn’t be a proper day by the sea without a boat trip – which will be topped with mojitos and cigars all day long. Once we’re back on dry land we’ll just have to wait for the right moment: a group picture at sunset on the Cuban seaside is a must do!
Included: overnight stay, breakfast, catamaran boat tour
Money Pot: local transport and any admission fees if needed
Not included: food and drinks
Snorkelling, diving and delicious lobster in Playa Girón
Playa Larga or Playa Girón?
We’ll leave Trinidad after breakfast and in less than 3 hours we will be in Playa Girón. Playa Larga and Playa Girón are two beaches overlooking the Bay of Pigs, which is particularly sought out by diving enthusiasts! We’ll be in the perfect place to practise our snorkelling skills, the sea is warm and crystal clear making the rainbow-coloured fish and corals a lot easier to see! We’ll seek out a traditional restaurant for lunch, which provides the perfect opportunity to try the local seafood. Lobster anyone?
Included: overnight stay, breakfast, transport from Trinidad to Playa Giron
Money Pot: local transport and any admission fees if needed
Not included: food and drinks
Back to Havana
Back to the capital
Once we get to Havana, we’ll have a refreshing drink by El Malecón – the famous promenade is the perfect place to admire pre-revolution architecture, grab a bite from one of the many restaurants and even hail a Cuban bike taxi – just make sure you do some haggling!
Did you know that Cuba’s most popular drink isn’t actually rum-based cocktails, but beer? Fuerte Bucanero or a Cristal, the choice of cerveza is yours!
Included: overnight stay, breakfast, transfer from Playa Girón to Havana
Money Pot: local transport and entrance fees if needed
Not included: food and drinks
Walking the streets of Old Havana
The magic of Old Havana
Our day begins with a guided tour of Old Havana, a UNESCO world heritage site. We'll try to capture the essence of this historic neighbourhood through its vintage American cars, the former party venues from the prohibition era and the Bacardí Palace where the renowned rum used to be produced. We'll explore iconic landmarks like the Payret cinema, the legendary Floridita bar, as well as and the captivating Plaza de Armas, Plaza Vieja and Plaza de la Catedral. Finally, we can relax sipping a mojito at Bodeguita del Medio, a cherished spot frequented by literary icons Hemingway and Neruda.
Vintage car tour
Our exploration continues as vintage cars drive us through the captivating streets of Havana for the next two hours. We'll visit the iconic Plaza de la Revolución, featuring the faces of Che Guevara and Camilo Cienfuegos, as well as the majestic memorial to Jose Martí. We will then move west towards the enchanting Fusterlandia district, adorned with colourful mosaics by artist José Fuster, which will transport us into a whimsical world. For a memorable finale, we'll go up to Morro Castle to watch a mesmerising sunset and perhaps witness the historic cañonazo ceremony.
Now let's find a nice local restaurant for our last dinner together in Cuba!
Included: overnight stay, breakfast, guided walking tour and vintage car tour of Havana
Money Pot: local transport and entrance fees if needed
Not included: food and drinks
Goodbye Cuba
Check-out and goodbyes
Check-out and goodbye – until your next WeRoad adventure!
Not included: airport transfer, food 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
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.
Info to know
Staff
Our trips are led by a Travel Coordinator who has been specifically trained by us to lead group travels to ensure you have the best time. A WhatsApp group with all travel participants will be created two weeks prior to departure by your Travel Coordinator.
Luggage
Backpacks are mandatory to allow easy transfers - we recommend a 45L backpack for our trips.
FAQs – Frequently Asked Questions
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 meet all needs:
1. Credit or debit card from Visa, Mastercard, or American Express.
2. Installment payments for certain countries only
If you choose the deposit and balance option, you can pay the balance from your MyWeRoad Personal Area via bank transfer.
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. 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.
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:
WeRoad is not authorised to provide this information due to privacy reasons.
However, there is a solution - you can connect with your travel buddies by joining our Facebook group. Look for a post related to your trip, or ask the group admins for help in connecting with your future travel companions!
If a Travel Coordinator has already been assigned to the trip you're interested in, you can easily find their introduction post in the group via the website: in the tour list, click on 'Ask the coordinator', or in the trip details page, in the coordinator section, click on 'Ask [coordinator's name] for information on this trip in our Facebook group'. For both cases, see the screenshots below!
Tour List
Trip details page
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 curios to know the age range of the group for a tour you're interested in, you can contact us by WhatsApp at +447716573700
Regarding the male-female ratio, this is not guaranteed and varies trip by trip.
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’.
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.
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!