Cuba Beyond the Classics
15 Days of Rhythms, Mixology & Secret Caribbean Beaches
5 Good Reasons To Do This Trip!
Lose yourself in the daffodil-coloured buildings of Havana’s old town, feed your literary soul at Hemingway’s Ranch and cut laps in a classic car – are you swept up in Havana’s spirit already?
Loads of Cuba trips totally ignore the less-visited east of the island. That won’t happen on our watch! Come, embrace the jungled canyons, river swims and… chocolate!
You might arrive in Cuba on your own but it won’t last long. Fencox trips are like friendship machines – individuals go in one end and adventure-bonded travel crews come out the other.
Can you see yourself taking a dip in the Bay of Pigs and bathing in the warmth of Trinidad’s wonderful sands? These are not Cuba’s tourist hotspots. They’re off-radar and all the better for it.
The rural side of Cuban life is right on your doorstep as you roam the island’s famous tobacco growing region with your local guide – roll your own cigars and taste the coffee bean aroma straight from the farm.
Trip Details
Trip Breakdown
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Length
15 days / 14 nights
Details
- 2-week cooling-off period applies.
- Lifetime Deposit. If you need to cancel, your deposit is transferable to other trips.
- Private Room for every guest every night.
Please refer to our payment terms in the FAQs.
Arrival
Havana, Cuba
Departure
Havana, Cuba
Group Size
12
Included
- 14 breakfasts, 4 lunches and 9 dinners
- A top rated English speaking local tour leader throughout
- 14 nights of family-run guesthouse accommodation
- Private and air-conditioned transport throughout
- Tourist E-Visa for Cuba
- Welcome cocktail
- 2 dance classes
- Motor around Havana in a classic car
- Visit Hemmingway’s home
- Guided walks in Old Havana, Vinales, Cienfuegos, Camaguey, Baacoa and Trinidad
- Specialist local guides in Vinales, Las Terrazas and Camaguey
- Farm to Fork and local Baracoa cuisine cooking demonstrations / meals
- Roll cigars at a tobacco farm
- Look for flamingos by boat on Guanaroca Lagoon
- Watch local ballet rehearsals and meet the dancers
- Explore Camaguey by Bicitaxi
- Make chocolate at a cocoa farm
- Swim time at the Bay of Pigs, Duaba River and Ancon Beach, Trinidad
- Boat ride and lunch on an island off the coast of Santiago
- Mix it up with a group cocktail class
- Enjoy a night out at a live Cuban music venue
- Visit Yudit Vidal Faife’s art gallery
- Arrival and departure transfers
Not Included
- International Flights and travel insurance (necessary)
- Additional hotel nights & late checkouts
- Drinks and other personal expenses
- Tip kitty (See FAQs for more information)
Accommodation
Your Fencox accommodation means having a private room, all to yourself – every single time.
Accommodation Preview
La Posada de Chacón, Havana, Cuba
Hostal La Moda, Trinidad, Cuba
Villa el Habano, Viñales, Cuba

Day 1: Havana
It’s time to stop dreaming of sipping Cuba Libres and sunning yourself on Caribbean beaches and start actually doing it. Today’s the day you finally jet into Havana; gritty, age-stained, jazz-jumping Havana. Feel the tropical warmth hit your face as you emerge from the airport. We’ll have someone ready and waiting for you there – you know, to stop you gawping at all the vintage Chevies from the 1950s and get you to your hotel in good time.
There should be a welcome note in your room that explains the logistics of the evening, so prep to meet your fellow Fencoxers later on. Dancing shoes might be a good pick!
Accommodation: Premium Guesthouse, Havana
Included: Dinner

Day 2: Get to know Havana
If Havana were human, she’d be a Samba-dancing dame with fruit in her hair and a cigar in her mouth. Today’s your first date with Cuba’s irresistible and irascible capital. We think you’ll get on just fine. Dive headlong into the beautifully chaotic streets of La Havana Vieja, the old town, where you’ll unravel the history by hitting the four principal plazas and spying out Baroque cathedrals. You’ll also feel the unending fizz of local life as you navigate the markets with your guide and devour home-cooked food in a proper Cuban paladar (a local tavern).
Keep room for extra culture in the afternoon. We fit in a visit to Finca Vigía, the ranch where Hemingway lived for 20 years, scribbling away at some of his most famous novels. And you’ll do a driving tour of the more modern side of the capital. No need to ask: it’s on vintage wheels, of course!
Accommodation: Premium Guesthouse, Havana
Included: Breakfast, Dinner

Day 3: Viñales
Bid farewell to the pink Cadillacs and palm-lined plazas of Havana. Don’t worry, you’ll be back! Today, your road leads west to the UNESCO-listed Viñales Valley. Watch as the landscapes become green and rugged, as high bluffs begin to shoulder above the farms and palms. It’s here that you’ll get acquainted with two of Cuba’s greatest exports: Coffee and tobacco. With a local guide by your side, you’ll explore Viñales town, learn how to roll up those iconic Cubano cigars, sip fresh-ground cuppas and feel the rhythms of rural Cuban life.
The day ends with a farm-to-fork meal. Put your feet up – you’ve earned the rest!
Accommodation: Premium Guesthouse, Viñales
Included: Breakfast, Dinner

Day 4: Bay of Pigs
Here’s the deal: Today will be a long drive. Like, five hours long. But how about we throw in window viewing that includes orange orchards and mangrove-laced swamps to make it more bearable? Even better, how about we promise cloud-white beaches when you arrive? If we’re lucky, there might even be time to jump straight from the car into glass-clear waters to snorkel in the company of triggerfish and seahorses! The end goal is the utterly idyllic Bay of Pigs.
The region might be beautiful, but you’ll also learn about a troubled past – this was the site of a failed US-backed takeover of Cuba back in 1961. Later, discuss snorkelling spots and counter-revolutionary coups over fresh-caught seafood in nearby Playa Larga, where you’ll stay for the night.
Accommodation: Standard Guesthouse, Bay of Pigs
Included: Breakfast

Day 5: Cienfuegos
Today, you’ll find out why they call the city of Cienfuegos the ‘Pearl of the South’. Wander the wide boulevards, catching wafts of coffee and plantains frying as you dodge the sun in the collonaded walkways. There might be moments when you have to pinch yourself here. This is not Paris, we promise! The French capital is almost 4,800 miles away, but Cienfuegos does a good impression with its neoclassical facades and cup-clinking cafés. Your local guide will explain why there’s such a whiff of France about it all – and there’s a good reason – during your city walking tour!
Accommodation: Premium Guesthouse, Cienfuegos
Included: Breakfast, Dinner

Day 6: Flamingo spotting and Camaguey
You’ll be bouncing out of bed early today to give yourself the best chance of spotting the local residents of the Guanaroca Lagoon. Flamingos! Pink and proud, they stalk the waters alongside pelicans and other amazing birds just outside of Cienfuegos.
From there, it’s a long-ish drive to Cuba’s third-largest city, Camaguey. After arriving, you’ll embark on an orientation walk, which is very much needed since this town was designed to be a labyrinth of alleys and lanes and plazas to discombobulate pirates back in the 1600s. If you manage not to get too lost, you’ll discover why it’s now Cuba’s cultural capital by visiting the Camaguey Ballet Company.
Accommodation: Premium Guesthouse, Camaguey
Included: Breakfast

Day 7: Baracoa
You’re almost midway through your Cuban trip, so let’s slow the pace a little, rest up and take stock of the flamingo-filled, cigar-smoke-plumed adventure you’ve been on so far. There’s nowhere better to do that than Baracoa, a place that inspired Christopher Columbus to declare Cuba “the most beautiful land that human eyes have ever seen.” Big words. We’ll let you see why it had him waxing so lyrical, first on a walking tour of the wonderfully ramshackle old town – the oldest in Cuba, no less – and then with some free time. Spend it on people watching, sipping rum cocktails or gazing out to sea, imagining the ships of European explorers appearing on the horizon back in 1492.
Accommodation: Comfort Guesthouse, Baracoa
Included: Breakfast, Lunch

Day 8: Canyons, Chocolates and Cocktails
Chocolate, cocktails, canyons crammed with jungles – the things you’ll experience today showcase the highlights of Cuba’s incredible Oriente province. We start, of course, with chocolate. Finger-lick your way through a local cacao farm, seeing how everyone’s favourite treat goes from bean to bar, even making your own chocolate and then, no doubt, eating it promptly. Next, it’s the turn of the Yumuri River canyon, where you can burn off those calories gained by exploring the riverways and forests and searching for strange Venus fly-catchers. Don’t forget your swimming stuff!
Let a blissful day come to a perfect end when you join your Fencox crew in a cheeky rum or three in a cocktail-making session!
Accommodation: Comfort Guesthouse, Baracoa
Included: Breakfast, Dinner

Day 9: Cook, Eat and Swim
No trip to the Baracoa region of Cuba could possibly be complete without a foray into the famous cuisine. The food here is largely unique because it was heavily influenced by the Spanish, and the town was only reachable by boat until 1960! You’ll learn how local ingredients have been put to use to create some enticing dishes, cooking up a smorgasbord under the guiding hand of a local chef. Without giving too many culinary spoilers, dinner might just include stewed calalu greens, lobsters in coconut milk and honey-doused desserts shaped like a cone. Mouth a-watering yet?
Accommodation: Comfort Guesthouse, Baracoa
Included: Breakfast, Lunch and Dinner

Day 10: Santiago and Salsa
Have a strong coffee before setting off on this morning’s drive – you’ll want to be wide awake the whole way! This is a spectacular one; a montage of grass-green sierras and then sparkling coastline. You’ll hairpin up mountain bends in the road, drop down to see remote beaches and even pass through the notorious Guantanamo Bay area, where the infamous US military prison makes its home.
We won’t dwell long there because Santiago, the second-largest city on the island, is calling. It’s a chance to experience a whole other side of Cuba, setting foot in a city that’s now legendary as the birthplace of the revolution, and deeply influenced by the peoples of Haiti and Jamaica. Mainly, though, we come for the music! Be ready to twirl and twist and dance the night away with your fellow Fencoxers as you join in with a traditional Noche Santiaguera, a whole night of local samba and jazz. Don’t worry, you’ll handle tonight like a pro – after all, you’ve got three dance classes under your belt by now!
Accommodation: Premium Guesthouse, Santiago
Included: Breakfast, Lunch

Day 11: Exploring Santiago
Remember when we said that Santiago was the birthplace of the Cuban Revolution? Well… its history goes way further back than the 1950s. You’ll trace it to the 17th century this morning when you head across to the imposing San Pedro de la Roca Castle. It’s a UNESCO-tagged fort that clings like a limpet to the shores south of Santiago. Stand on the outer wall and imagine yourself firing cannons out at marauding pirate ships. When your career as a buccaneer is over, you’ll sail across to an island in the middle of Santiago Bay, where Cuban seafood taverns promise a memorable lunch set to the sound of sloshing Caribbean waves.
Accommodation: Premium Guesthouse, Santiago
Included: Breakfast, Lunch

Day 12: Trinidad
Bid adios to Santiago and ola to Trinidad. The drive takes a while, but it will be worth it! Not only are you heading to one of the handsome-est towns on the island, but it’s arguably the best place to sample the legendary Cuban nightlife. But before you dust down your samba outfits, let’s at least try to fit in some culture. Head out on a walking tour of the city, treading the dusty streets to find elegant buildings that look like something plucked from Spain. You’ll find out why UNESCO describes Trinidad as a “bridgehead for the conquest of the American continent” and learn all about the boom and bust of the region’s sugar industry. Then, as you brim with thoughts of 18th-century neoclassical architecture, it’s time to get funky in the local jazz joints!
Accommodation: Premium Guesthouse, Trinidad
Included: Breakfast, Dinner

Day 13: Hit the Beach
If you glugged a few too many rum punches last night, no worries – you’ve got the morning off! Relax at the hotel, sip a coffee on one of the town’s plazas, or cram in a bit more culture – it’s up to you.
Later, you’ll all meet up for a trip to Ancon Beach. It’s the sort of place that those travel brochure clichés were made for. We’re talking white sand, stooping palms, turquoise waters. The real deal. Your afternoon is going to be as chilled as a Cuba Libre: snorkel, sip cocktails in the beach cabanas and work on the tan.
Accommodation: Premium Guesthouse, Trinidad
Included: Breakfast, Dinner

Day 14: Santa Clara and Havana
It’s your last full day in Cuba and your route leads back to the enthralling capital of Havana – you knew you’d return! It’s quite a long drive to get there, so you’ll make a stop at Santa Clara on the way. That’s not simply to break up the journey though. Here, you’ll get a chance to learn all about a certain Ernesto Ché Guevara. Heard of him? There’s a museum to the revolutionary and a monument to the guerrillas who fought with him. Once you reach Havana, there should be time for a final wander around the colourful streets before your farewell dinner; a last hurrah to celebrate your once-in-a-lifetime Cuban adventure with your new Fencox compadres.
Accommodation: Premium Guesthouse, Havana
Included: Breakfast, Dinner

Day 15: Farewell Friends!
It’s that bittersweet moment, Fencox family — your journey through the awesome land of Cuba has reached its final chapter. Over one last breakfast, be sure to swap numbers with each other and promise to keep in touch. A member of our team will drop you off at the airport with plenty of time before your flight, and then, it’s time to head home! One thing’s for sure, though – we can’t wait to welcome you back with open arms on another unforgettable adventure. So, where to next?
Included: Breakfast
Trip Map
Frequently Asked Questions
Prior to the payment of your full balance, the final price may change if there is a significant variation in the AUD:USD exchange rate. Our trip pricing is determined by what the exchange rates are at the time of publishing the trip.
The pricing on this trip is based on an exchange rate of 1 AUD: 0.65 USD.
A deposit of 25% of the total trip price is required to secure your spot. Payment can be made by credit card (fees apply) or bank deposit.
There is a cooling-off period of 2 weeks. (Applicable to all bookings made at least 120 days before trip departure.)
We have implemented a ‘lifetime deposit’ guarantee. Deposits are not refundable, but they are transferable at any time, right up until the first day of the trip.
The final balance of the trip is required 120 days in advance of the departure date. Our suppliers require upfront payment well in advance to guarantee availability.
Please refer to the full terms and conditions for further information.
Aussies and Kiwis need a visa to enter Cuba. In 2025, as a tourist you no longer need a paper ‘tourist card’, just an eVisa. The eVisa is valid for 90 days and we’ll be arranging it on your behalf – nothing more for you to pay!
Level 2
To enjoy the trip comfortably, you’ll need to be able to spend time on your feet and walk for stretches of 3-4 hours at a time (particularly for activities on Days 3 and 9). Daily activities may include:
- Walking on uneven, hilly, or cobbled terrain.
- Getting on and off various forms of transport, including boats, sometimes without formal steps.
- Climbing 3 to 4 flights of stairs, including in accommodations without lifts.
- Using over-the-bath showers.
You must be able to manage your own luggage for short periods of time – that includes on and off the bus, along cobble-stoned streets and up stairs at your overnight stays.
All activities are optional—if you need a break, you’re welcome to sit one out. That said, if a full afternoon walking tour sounds too challenging, this may not be the right trip. Unfortunately, this tour is not suitable for travellers who require walking aids.
Most of our trips have a tip kitty because many cultures have diverse rules when it comes to tips. We’ve found it to be the easiest way to combat over-tipping, under-tipping or having the tip fall into the wrong hands. Our goal is for guests to relax and know that the complexities of tipping are taken care of, on their behalf.
We’ll be updating this section with the tipping amount and how it’s distributed soon.
TBA
The dry season runs from November to April. During this time, even if you do encounter some rain, downpours are usually short and heavy, and unlikely to hinder the day’s adventures. Expect April to be warm and sunny, with a dialled-down version of the usual tropical-climate humidity. November’s temps are still warm, but the sun isn’t as fierce, which tends to balance out the slightly higher humidity.
Your accommodation will be in privately owned guesthouses, locally called “casas”. These are a lovely, authentic way to experience Cuban life, and each one varies; some resemble mini-hotels and others are more like family stays. Outside of the larger cities, you can expect that the group will stay between several nearby casas, usually with a few Fencoxers in each house.
Staying in casas is one of the most rewarding parts of travelling in Cuba. It’s a chance to connect with everyday Cubans and experience the country through their warmth and hospitality. Some casa hosts speak great English, while others communicate with a joyful mix of gestures, smiles, and laughter. It’s all part of the cultural exchange.
Guest rooms must meet certain standards of comfort for the casa to obtain a license. Each guestroom will have air-conditioning and a private bathroom with a shower. However, Cuban energy infrastructure can be unreliable (see – Will there be Power Outages, for more information), so be prepared there may be times the air-con doesn’t work through the day. Casa’s do have generators, but fuel is rationed, so owners are more likely to wait until the evening to turn on the generator, so you can have a comfortable sleep.
Your accommodation will be private; in other words, no room-sharing with anyone, throughout the entire trip.
Most Fencox travellers tend to be in their mid-50s to mid-70s.
Generally, we have no upper age limit for our trips. But, it’s important for you to know that our trips can be physically demanding and we will chat to you about your suitability. We’ll provide you with details of the health and fitness must-haves for our trips; however, we clearly are not medical experts. We will need you to obtain proper and detailed medical advice at least two months before you travel for the latest health requirements, vaccination advice and recommendations for your destination.
Age 75+
Guests over 75 years old at the time of travel, or those with pre-existing health conditions may need to have medical clearance to ensure safe travel, and must have a doctor complete a ‘Certificate of Medical Fitness to Travel’ within 30 days of booking confirmation.
Minimum age
While it doesn’t happen often, we do get younger guests joining our trips! As a general rule, the minimum age is 15 at the time of travel. All travellers under the age of 18 must be accompanied by a legal guardian, or be accompanied by someone over the age of 18 appointed by their legal guardian.
International airfares are not included.
Being tour operators (not travel agents), we are not licensed to sell flights. We recommend contacting your trusted local travel agent to book flights if you’re in need of assistance.
There are a variety of route options from Australia and New Zealand to Cuba, which do require a change. These include travelling via Chile, Doha and Madrid, or Canada.
Australia → Santiago de Chile → Peru → Havana
Australia → Doha → Madrid → Havana
Australia → Canada (Toronto/Montreal) → Havana
We do not recommend that you travel via the USA, as there are additional restrictions and documentation requirements for travel from the USA to Cuba, even for short stopovers on a longer international journey.
Both transfers from the airport to your accommodation – on arrival and on departure – are included in your price.
Will we be picked up at the airport?
Yes! One of our friendly team will be waiting for you in the public arrivals area of the airport. You’ll transfer directly to the hotel. The transfer is free and in a private and air-conditioned vehicle, which you will only share if there is anyone else on your flight joining the tour.
When should we arrive?
Try to arrive before midday on the start day, although earlier would be recommendable. If possible, come one day early to settle in. We can organise additional hotel nights for you at cost.
Yes! Despite what you may have heard, Cuba is a very safe country, with a robust police presence and a low crime rate. Of course, you need to take the usual big-city precautions against pick-pocketing in Havana and Santiago de Cuba, and we recommend using a padlock on the zipper of your main bag because safes are not a given in typical Cuban in-room accommodation.
The Cuban Peso (CUP) is a closed currency with no value outside of Cuba, so you won’t be able to exchange money in advance. Most travellers find that it is better to pay in EUR/USD than to exchange for CUP at the official rate when they arrive.
Credit cards are not widely accepted, debit cards may not work, and ATMs are scarce, so we recommend bringing enough cash for your entire trip. Euros and US Dollars are the best currencies to take, in small denominations (1, 5,10, 20), good condition (unmarked and unfolded) , which you can use to pay at restaurants, and entertainment venues. Coins are not accepted.
Tap water in Cuba is not considered safe to drink. Most Cuban households will boil water before drinking, and travellers should follow this procedure. However, most travellers do not have any problems brushing their teeth with tap water.
Bottled water will be provided on the bus, but for times when you aren’t with the group, we encourage water purification to treat tap water rather than buying bottled water.
The Internet is becoming increasingly available in Cuba, and costs are much lower than they used to be. However, it is still more difficult to access the internet in Cuba than in most other countries, and the vast majority of guesthouses do not have the facilities to offer WiFi.
There are WiFi points, however, at different places in all the cities, such as plazas, public areas, and in most hotels. WiFi cards that give you 1 hour access to the internet can be purchased in the hotels and at the offices of the communication company ETECSA. We suggest you buy several of these in Havana at the start of your trip, as you can use them across the island. Your tour leader can assist.
Australian Telcos do not currently offer global roaming on your phone in Cuba.
Power outages, or “apagones”, are common in Cuba due to ageing infrastructure, but locals have been navigating them successfully for years.
To manage the island’s electricity deficit, there are “planned” shutdowns, which help keep things running smoothly. When they do occur, though, many hotels, private accommodations, and restaurants are well-prepared with backup generators, ensuring the guest experience remains uninterrupted.
As much as possible, your tour leader will notify the group of scheduled power outages. We recommend you bring a power bank to keep your phone and other essential devices charged.
Due to the US trade embargo on Cuba, some things we consider everyday essentials are much more difficult to get in Cuba. We recommend that you carry a small First Aid kit containing basic painkillers, bandages, hand sanitiser, anti-diarrheal medication, and tissues, as well as any personal medicine requirements.
Snacks such as muesli bars, dried fruits and nuts are often either not available in Cuba or are very expensive, so it can be a good idea to bring some with you for longer drives.
For foreign citizens visiting the US after going to Cuba, whether it is for business, tourism, or transit, you will need to have a B1 or B2 visa. The ESTA visa waiver will not apply after you’ve been to Cuba. A B1 or B2 visa requires months of planning and includes an in-person appointment at the American Embassy.
If you’re planning to visit the US directly after your Cuban adventure, please note that it is not permitted to bring Cuban rum or cigars into the USA.
Travelling for tourism reasons directly from the USA to Cuba isn’t allowed under US law. The law applies to US nationals and all foreign nationals who are either resident in the USA or travelling through the USA en route to Cuba.
While distances between destinations may look short on the map, road conditions can be rough in places, with potholes, and the occasional ox cart sharing the road. Travel is safe but often slower than expected, especially on winding mountain routes or through rural areas. Days 7 and 12 are particularly challenging, with a drive time of 8 hours or longer. We use private vehicles with air conditioning, and include plenty of rest stops and scenic breaks to keep things comfortable. It’s best to bring a little patience and enjoy the slower pace – after all, the journey is a big part of the adventure.
Cuba is a complicated and developing country, and if you go there looking for problems or expecting perfection, you’re likely to have a frustrating time. On the other hand, if you visit with an open mind, a willingness to go with the flow, and a desire to learn about the realities of the Cuban experience, your trip will be one to remember for a lifetime. In other words, Cuba is a perfect destination for our Fencoxers!
In the unlikely event of a health or security-related incident during a trip, we’ve engaged a local partner to assist. From our experience, there is not one framework that fits all, and every incident is unique and requires a different approach. With all trips, your guides are your day-to-day support. While behind the scenes, there is an active line of communication between your guide, the on-ground support team, and Australian Ops.
Fencox was created because we had so many enquiries from men and women who had heard about our amazing Patch Adventures trips for women-only and wanted the opportunity to travel solo in the same way, only in a mixed group.
Fencox caters to both men and women who are solo travellers, have a genuine sense of adventure, are aged 55+, and are physically active and young at heart. Your fellow travel mates on a Fencox trip are inquisitive about the world and love exploring new travel destinations. Fencox travel mates love meeting new people, enjoy a good chat, and are happy to share a table with fellow travel mates for dinner.
If you’re travelling solo but don’t want to feel alone, this is your opportunity to share your travel experiences with other like-minded people. And best of all …. you’ll never pay a single supplement because everyone is guaranteed their own room!