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Get ready to step back in time and party like it’s 1953. Hang in Havana, get serenaded in Santiago, play in pretty Camaguey, haggle your heart out and sprawl on the beach in Trinidad, learn a bit more about old Che in Santa Clara and hike, drink and enjoy village life in Vinales… Then one last salsa and cigar in Havana and your Cuba’d.

In the words of Whitney Houston, “Havana Dance with Somebody”. Ok, she never said that. But find yourself a partner, grab a mojito and let Havana work its magic. You’ll be coming up with clever Cuban puns in no time.

Havana, Cuba
Havana, Cuba
Physical rating
Min 15 , Max 0
Group size
Min 1, Max 8


Bienvenido! Welcome to Cuba.
You can arrive at any time on day 1 as there are no activities planned until the important welcome meeting tonight at 6pm. For the first night of your sailing adventure you will be staying with a local family in a homestay. At the centralised meeting point (the main homestay location) you will be met by our local representative who will confirm which family you will be staying with. Depending on the size of the group you could all be staying together or split between two or three families. All the homestays are within a couple of blocks of each other so after meeting your family and dropping off your bags you will meet back at the main homestay. Here our local representative will give you an important briefing on what to expect for the next 8 days.
After the briefing there is an option of joining the group for dinner and orientation walk.
Havana grew from an obscure port to a bustling hub when gold and silver was being pillaged by the Spanish from New World and taken to Spain. While the ships gathered in growing numbers, the pirates were not far behind and the treasures resting in Cuba's ports were attacked again and again by Dutch, English and French pirates. The Spanish built fort after fort for protection but the English eventually captured the territory. An economic boom followed due to the English lifting the Spanish trade restrictions. Spain eventually exchanged the Florida territory for the island, but these years left an indelible mark on the city and the country, and Havana is slowly restoring its beautiful colonial buildings.
If you have booked additional nights’ accommodation you might want to check out Havana's Old City, designated a World Heritage Site in 1982. The streets are lined with colonial architecture, 16th century fortresses and countless churches. Make sure you visit La Catedral San Cristobal de la Habana, described by the novelist Alejo Carpentier as 'music set in stone'. Also worth seeing is the Palacio de los Marqueses de Aguas Claras (now a restaurant) and the Plaza de Armas, complete with a statue of Manuel de Cespedes, one of the leaders of the independence movement. There are plenty of good museums to check out including Museo de la Revolucion and the Museo Nacional de Bellas Artes.
While in Havana you must try a Coppelia icecream. You can join the hundreds of locals who line up to eat the delicious ice-cream that is heavily subsidised by the government to keep the populace happy. There is a Coppelia in every major town in Cuba and the one just up the road from our Hotel in Havana is the biggest on the island. Sometimes there is just one flavour available, a whole bowl of which could set you back about 10 cents. You can however pay up to $3 if you want to skip the queue and go the section where the prices are in Convertible Dollars (CUC) rather than the local pesos (CUP).
Ice cream in hand, why not head to a local baseball game. This is a great experience as the local atmosphere is very colourful and unique and can get quite rowdy at times. Baseball is by far the number 1 sport in Cuba so the locals can get very passionate about it. It is also interesting to note that the only advertising is government community announcements such as: sport is good for your health! The season runs from October to May.
With extra time in Havana pre or post tour you may want to book some of the optional extras.
Meals Included
There are no meals included on this day.
Today we have an early start as we head off to Cienfuegos to start our sailing adventure. After breakfast with your homestay family our local representative will meet with you and transfer you to the main bus station for an 8.20am bus journey. The bus will take approximately 5 hours and includes a 30 minute stop at ‘Finca Fiesta Campesina’ (Fiesta Country Farm) at Jaguey Grande for refreshments and some great photo opportunities.
You will be unaccompanied for the bus journey but will be met at the bus station in Cienfuegos by your Skipper. You’ll know how to find him as he will be the one holding the Intrepid sign!
Cienfeugos will be your last chance to stock up on a few things like white rum, sugar, yerba buena, limes & club soda (or better known as the ingredients for a Mojito) before setting sail for the Canarreos Archipelago.
Located on the Bahia de Cienfuegos (Bay of Cienfuegos), Cienfuegos is the embarkation point of our Cuba Sailing Adventure. A delightful city referred to as 'La Perla del Sur' (Pearl of the South], Cienfuegos is the only Cuban city that was founded by the French, resulting in beautifully designed and distinctly different Cuban city – that still oozes a Caribbean vibe.
Cienfuegos' appeal lies partly in the European flavour of its colonial centre, with a wide Parisian-style boulevard and elegant colonnades. There is ambience enough here to have inspired Cuba's most celebrated 'son' singer Benny Moré to write the words 'La ciudad que más me gusta a mí' (the city I like the best). He was born nearby, which may have helped.

We set sail in the evening, after dinner, so that we can wake up in the morning in the islands surrounded by turquiose waters ready to go for a morning snorkel.
Meals Included
  • Breakfast
  • Dinner
Spend the next five days sailing the idyllic islands of Cuba, which are set among the world-renowned beauty of the Caribbean Sea. Discover hidden beaches, untouched sands and pristine blue waters. Grab snorkelling gear to witness some of Cuba’s magnificent underwater scenery and, if lucky, you may even spot a turtle or two. Relax and chill out on the deck of the yacht, bask in the glorious sunshine and soak up the laidback vibe of the Caribbean. Discover Cayo Largo, an island that boasts some of Cuba’s most beautiful coral reefs and where sugar-white sands dissolve into turquoise waters. Unveil the hidden gems of Cayo Los Majaes, Cayo Rico, Cayo Estopa and Cayo Cantiles, all of which stand out for their natural beauty. During the day, hit the water for a spot of swimming, snorkel with curious marine life, laze on white-sand beaches, relax on the boat and taste the flavours of Cuba. In the evenings, enjoy island style barbeques and unwind with new friends beneath shimmering stars.
Here are some of the sights you may enjoy over the next 5 days.
Cayo Largo del Sur
The second largest of the islands in the Canarreos Archipelago and home to some of the best beaches in the region. One stretch of beach is 13km of the cleanest and whitest sand you will ever see. The island is also home to nesting sites of loggerhead and green turtles. And, if you are that way inclined, nudism is tolerated on certain beaches.
Cayeria los Majaes
A small group of beautiful islands surrounded by sand banks, making it a great destination for snorkelling, and a number of shallow pools. The pools are less than 1/2 a metre deep and with a sea temperature of around 30C they are the perfect place for basking. For wildlife watchers there is also a large colony of iguanas on the eastern shore of the western pool.
Cayo Alcatraz
Pristine white sandy beaches where you can spot sting rays and manta rays. If you are not fond of snorkelling in deeper waters then you will find this, shallow water option, a dream!
Cayo Rico
If you could design your perfect beach it would be Cayo Rico. Turquoise water, soft white sand and a bar that serves you a choice of cocktails while sitting under palm fronged umbrellas. Oh, we forgot to mention the friendly resident iguanas.
Cayo Estopa
An unhabited island with a deep water channel this is the perfect place to throw out a line and catch the night's dinner
Cayo Rossario
Although the island may be uninhabited (if you don't count the iguanas and hermit crabs) the same cannot be said for the seas surrounding the island. There's an abundance of sea life including moray eels, groupers, barracudas, the odd reef shark and lobsters. It's also a great place for snorkelling as you have a nearby reef.
Cayo Cantiles
Known as 'Monkey Island' Cayo Cantiles is an uninhabited island with the exception of a small number of workers who tend to a monkey sanctuary. The island is also home to iguanas and a rodent like animal called a jutias.
***PLEASE NOTE: The beauty of sailing is that each day is unique and, while we have a destination to reach, if the weather changes or something takes the group’s fancy, we can be flexible on the day's itinerary.***
Meals Included
  • Breakfast (5)
  • Lunch (5)
  • Dinner (5)
Our sailing adventure is coming to an end as we sail back towards Cienfuegos. Tonight we have the option to head out to dinner in a nearby local restaurant reminiscing over the last week of exploration, or to check out the live music scene and get our salsa on. Whatever the choice nothing will take away from the most remarkable week of sailing around the islands of the Canarreos Archipelago!
Meals Included
  • Breakfast
  • Lunch
  • Dinner
It's with heavy hearts we enjoy one final breakfast together on board the yacht before it's time to say goodbye to life at sea and head back to Havana. The Skipper will organise transfers back to the bus station where you will board your bus (unaccompanied) back to Havana. The bus departs at 10.30 and you should be back in Havana at approx 3.30pm. The trip finishes on arrival in central Cuba at the NH Parque Hotel.  Post tour accommodation can be booked at the homestay which is about a 4 minute walk from the drop off point.
If you have planning on flying out on the last day please do not book a flight out before 8pm to take into account any delays that may occur.
If you wish to book additional nights in Havana pre or post tour, or stay on in Cienfuegos please let us know at the time of booking so we can make the appropriate arrangements.

Adiós y esperamos verte de nuevo.
Meals Included
  • Breakfast


8 breakfasts, 6 lunches, 7 dinners


Catamaran, Public bus


Homestay, Catamaran

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Important notes

Like all sailing trips, at the end of the day ours are ultimately at the mercy of the elements. So while the above itinerary is a pretty good indication of what you'll get to see on this trip, the course isn't set in stone. After all, who really wants to spend a full day battling headwinds if there's another option for smoother sailing? Likewise, your skipper may suggest a secret spot to drop by. And if everyone's on board with the idea... well, why not?

Essential Trip Information

Want an in-depth insight into this trip? Essential Trip Information provides a detailed itinerary, visa info, how to get to your hotel, what's included - pretty much everything you need to know about this adventure and more.