• Old-world charm, rich history, exciting nightlife – evocative Havana is like nowhere else on earth. Wander the cobbled laneways of Habana Viejo or head to Vedado for a taste of the world-famous Copellia ice cream
  • Beaches don't get much better than this. The islands of the Canarreos Archipelago offer miles of pristine white sands and sparkling turquoise reefs to explore
  • The underwater world of Cayeria Los Majaes is a snorkeller's dream, thanks to its warm, shallow pools that you could bask in for hours
  • From lobsters and loggerhead turtles to iguanas and monkeys, this trip spans the most eclectic spread of sea life and wildlife. Not to mention those odd Carribean creatures, the jutias
  • This being a true sailing trip, there's plenty of leisure time. When you're not soaking up your idyllic surrounds on deck, you can while away evenings in beachside restaurants feasting on delicious Cuban cuisine
  • 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

Spend eight unforgettable days sailing through the island paradise of Cuba. After being captivated by the time capsule that is Havana, venture offshore on a yacht for a Cuban encounter few people get to experience. Take in an array of natural wonders and get up-close to marine- and wild-life while sailing from Cienfuegos around the islands of Cayo Guano, Cayo Largo, Cayo Cantiles and many more. Uncover heavenly, untouched islands, swim in crystal-clear waters, snorkel over stunning reefs and spend days soaking up the chilled out vibe of irresistible Cuba. Find out why this vivacious country, so blessed with natural beauty and an abundance of cultural delights, is one of our favourite destinations.

Travel Theme
Cities & Attractions
Rivers & Seas
  • Caribbean Sea

Intrepid Travel Travel Reviews & Ratings
Has very high quality customer experiences and demonstrated commitment to responsible travel practices. read more
98% Recommend

4.7 out of 5
Excellent 2,324 Great 623 Average 99 Disappointing 34 Terrible 36
4.7 Guide
4.7 Activities
4.7 Lodging
4.7 Transportation
4.7 Meals
Cuba Sailing Adventure


Does Not Recommend

I would highly recommend travelling with Intrepid if you want a tour where: January 2018

  • Value 1.0
  • Guide 1.0
  • Activities 1.0
  • Lodging 1.0
  • Transportation 1.0
  • Meals 1.0
I would highly recommend travelling with Intrepid if you want a tour where:

You are not given the address of your accommodation, in a country with no Wifi, where your mobile phone won’t work and you don’t speak the language.

You will meet a local who knows nothing about your visit or your tour, or much of anything really, who has no idea that ATM machines are open 24 hours, and he will be your guide. You will call him Lizard.

The theme of the tour is your favorite activity, and that’s the reason you booked the tour, and then you don’t do that activity at all, even though you could, and no one tells you why.

You are expected to share not only a room with a same sex stranger, but also share a bed with them. And if you’re really lucky, a member of the tour crew will be sleeping in the same room too!

You’ll be asked what you’d like to eat, but none of what you asked for will be provided. And there won’t be any other source of food for miles.

And when you’re not sleeping, everyone on the tour will be crammed into a space the size of a small garden shed for cooking, eating and pooping, and no one will clean the space for more than a week, and by the end of the week the little buckets of poo paper will make the space smell like a sewer.

But there are serious risks with this tour. You may meet six other amazing people who you will laugh and drink copious amounts of rum with you, and make jokes about Lizard.
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Operator Intrepid Travel



Great leader! January 2017

  • Value 5.0
  • Guide 5.0
  • Activities 5.0
  • Lodging 5.0
  • Transportation 5.0
  • Meals 5.0
Our leader, Antonio Mass made the trip perfect for us, every day was planned, we were given lots of options for activities for the days and the night whether for dining or night life or shopping. He was so knowledgeable in every aspect of the trip from knowing where a bank was to post office to best places for shopping or location of beaches. Based on his experience as a travel guide, I will always recommend Intrepid.
I also noticed how he made us and every other couple feel special on the trip. Super great person and leader, well done!
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Operator Intrepid Travel



Incredible tour leader. January 2017

  • Value 5.0
  • Guide 5.0
  • Activities 5.0
  • Lodging 5.0
  • Transportation 5.0
  • Meals 5.0
I thoroughly enjoyed the approach of our tour leader, Ivan. He was warm, friendly, professional, knowledgeable and looked after every aspect of our trip. He is an incredible representative of the company.
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Operator Intrepid Travel



Amazing trip! January 2017

  • Value 5.0
  • Guide 5.0
  • Activities 5.0
  • Lodging 5.0
  • Transportation 5.0
  • Meals 5.0
A truly amazing trip of a fascinating island. Our tour guide Ivan organized everything extremely well, and had an excellent relationship with all of us.

Operator Intrepid Travel



Great tour leader! January 2017

  • Value 5.0
  • Guide 5.0
  • Activities 5.0
  • Lodging 5.0
  • Transportation 5.0
  • Meals 5.0
The tour leader - Tony Mas was excellent. Tony's product knowledge, his patience and organization skills are impeccable. His command of English language made it easy for the group to relax and enjoy the trip. Tony showed and promoted a sense of teamwork among the group and showed total care for each and every person in the group. His time management abilities ensured we did all activities successfully and on time.
Read more

Operator Intrepid Travel


Day 1 Havana

Bienvenido! Welcome to Cuba. Your trip begins with a welcome meeting at 6 pm. A local representative will brief you on what to expect over the course of the trip and after the briefing there is the option to join the group for dinner and an orientation walk. For the first night of your sailing adventure you will be staying at a local family-run guesthouse. Depending on numbers, the group may be split across two guesthouses which are located close to each other. The main guesthouse will be the central meeting point. If you arrive early and have free time, be sure to check out Habana Viejo (Old Havana) and its wonderful architecture. There are plenty of good museums to check out too, like the Museo de la Revolucion and the Museo Nacional de Bellas Artes. Sports fans can go to a baseball game between October and May for a taste of Cuba's number-one ball game. Lining up for a famous Copellia ice cream is also well worth it. As you'll depart from Havana to Cienfuegos early tomorrow morning and only have a short amount of time in Cienfuegos before setting sail, we recommend that you bring all the toiletries and sunscreen that you'll need for the trip from home. Please refer to the packing section for a comprehensive packing list. There may be an opportunity to access the internet on Cayo Largo. You will need to have an an ETESCA card to access the internet and on this trip the only time you will have to purchase one of these cards will be in Havana. For more information on the purchase of ETESCA cards please see money matters.

Day 2 Cienfuegos

Rise early and head off to Cienfuegos to begin your sailing adventure. After breakfast with your guest house family, your local representative will meet you and transfer you to the main bus station for the 8.20 am bus to Cienfuegos. They will accompany you on the bus to Cienfuegos. The bus journey will take approximately 5 hours and will include a short stop for refreshments and a restroom break. The bus will drop you off close to the yacht club where you will drop your bags and quickly meet your skipper. The skipper will collect your passports to complete the sailing permit process while you head off to a typical Cuban casa for a home cooked lunch with a local family. After lunch you will head back to the yacht club for a trip and safety briefing before setting sail at 3pm for for the Canarreos Archipelago. 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 are flexible on the day's itinerary. The itinerary is subject to change and may vary depending on weather and berth availability. Your skipper will make the final call to ensure your safety at all times.

Day 3-7 Canarreos Archipelago

Spend the next five days sailing the idyllic islands of Cuba, which are set among the beauty of the Caribbean Sea. Discover hidden beaches with untouched sands, clear blue waters and, if you're lucky, a turtle or two. By day, relax and chill out on the deck of the yacht, taking in the glorious Carribean surrounds; by night, enjoy island-style barbeques and unwind with new friends beneath the stars. Some of the spots you might visit over the coming days are: Cayo Largo del Sur The second-largest of the islands in the Canarreos Archipelago, home to some of the best beaches in the region. One stretch of beach is 13 km of the cleanest, whitest sand. The island is also home to nesting sites of loggerhead and green turtles. For those that way inclined, nudism is tolerated on certain beaches. Cayeria los Majaes A small group of beautiful islands with surrounding sand banks and shallow pools, excellent for snorkelling. The pools are less than half a metre deep, and with a sea temperature of around 30°C they are perfect for lazing around in. Look out for a large colony of iguanas on the eastern shore of the western pool. Cayo Alcatraz Pristine beaches of white sand where you can spot stingrays and manta rays. If you are not fond of snorkelling in deeper waters, you will find these more shallow waters a dream. Cayo Rico Arguably the perfect beach, with brilliant waters, soft white sand and a bar that serves up a range of cocktails. There are many umbrellas under which to enjoy a drink. There are also friendly resident iguanas here. Cayo Estopa An uninhabited island with a deep water channel. This is the perfect place to throw out a line and catch the night's dinner. Cayo Rossario Also uninhabited by people, this island teems with sea life – moray eels, groupers, barracudas, lobsters and the odd reef shark to name a few. The nearby reef is great for snorkelling. Cayo Cantiles Known as 'Monkey Island', Cayo Cantiles is uninhabited, with the exception of a small number of workers who tend to a monkey sanctuary. This island too is home to iguanas, and a funny rodent-like animal called a jutia.

Day 8 Canarreos Archipelago - Cienfuegos

Your sailing adventure is coming to an end as we sail back towards Cienfuegos. Tonight there's the option of having dinner on board and then heading to a bar to have one last drink with your fellow travellers. You might also like to check out the live music scene later, or take to a dance floor for some salsa. Whatever the choice nothing will take away from the most remarkable week of sailing around the islands of the Canarreos Archipelago!

Day 9 Cienfuegos - Havana

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 bus pick up point is a hotel a short walk [550 metres] from the yacht club. You will need to make sure you are there no later than 10.15am for a 10.30am departure. There will be a representative from the bus company waiting in the foyer of the hotel who will check you off the passenger manifest before you board. The return bus journey will be unaccompanied and should have you back in Havana at 3.30pm. The trip finishes on arrival in central Cuba at the NH Parque Hotel. If you are 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.

Dates & Pricing
Checking price

Price From

$ 1,299

Price Per Day:

$ 144 per day
Checking price
Start DateFinish DateBase PriceDeparture GuaranteedAvailability 
Feb-23-2019Mar-03-2019$ 1,416Yes6 spots left Reserve
Mar-02-2019Mar-10-2019$ 1,416Yes7 spots left Reserve
Mar-09-2019Mar-17-2019$ 1,416Yes4 spots left Reserve
Mar-16-2019Mar-24-2019$ 1,299Yes4 spots left Reserve
Mar-23-2019Mar-31-2019$ 1,299Yes2 spots left Reserve
Mar-30-2019Apr-07-2019$ 1,299Yes8 spots left Reserve
Apr-06-2019Apr-14-2019$ 2,165Yes7 spots left Reserve
Apr-13-2019Apr-21-2019$ 2,295YesSold Out Reserve
Apr-20-2019Apr-28-2019$ 2,165Yes6 spots left Reserve
Apr-27-2019May-05-2019$ 2,295Yes1 spots left Reserve
Nov-09-2019Nov-17-2019$ 2,165Yes8 spots left Reserve
Nov-16-2019Nov-24-2019$ 2,165Yes7 spots left Reserve
Nov-23-2019Dec-01-2019$ 2,165Yes8 spots left Reserve
Nov-30-2019Dec-08-2019$ 2,165Yes7 spots left Reserve
Dec-07-2019Dec-15-2019$ 2,250Yes8 spots left Reserve
Dec-14-2019Dec-22-2019$ 2,250Yes8 spots left Reserve
Dec-21-2019Dec-29-2019$ 2,340Yes8 spots left Reserve
Dec-28-2019Jan-05-2020$ 2,385Yes8 spots left Reserve
Jan-04-2020Jan-12-2020$ 2,340Yes8 spots left Reserve
Jan-11-2020Jan-19-2020$ 2,340Yes8 spots left Reserve
Jan-18-2020Jan-26-2020$ 2,340Yes8 spots left Reserve
Jan-25-2020Feb-02-2020$ 2,340Yes8 spots left Reserve
Feb-01-2020Feb-09-2020$ 2,340Yes8 spots left Reserve
Feb-08-2020Feb-16-2020$ 2,340Yes8 spots left Reserve
Feb-15-2020Feb-23-2020$ 2,250Yes8 spots left Reserve
Feb-22-2020Mar-01-2020$ 2,250Yes8 spots left Reserve
Feb-29-2020Mar-08-2020$ 2,250Yes8 spots left Reserve
Mar-07-2020Mar-15-2020$ 2,250Yes8 spots left Reserve
Mar-14-2020Mar-22-2020$ 2,250Yes8 spots left Reserve
Mar-21-2020Mar-29-2020$ 2,250Yes8 spots left Reserve
Mar-28-2020Apr-05-2020$ 2,165Yes8 spots left Reserve
Apr-04-2020Apr-12-2020$ 2,165Yes8 spots left Reserve
Apr-11-2020Apr-19-2020$ 2,165Yes8 spots left Reserve
Apr-18-2020Apr-26-2020$ 2,165Yes8 spots left Reserve
Apr-25-2020May-03-2020$ 2,165Yes8 spots left Reserve
Check Current Availability, prices, specials with Intrepid Travel
Group Size:
Small Group - 24 max
Maximum Number of People in Group: 8
Guesthouse (1 nt),Overnight boat (7 nts)
Start City
End City
Guides On your Cuba sailing trip you will be accompanied by one of our skippers and a cook. Your skipper's role involves taking charge of the sailing, organising the overall operation and smooth-running of the trip, managing trip logistics, safety of the vessel and safety for all passengers on board. All skippers have extensive sailing miles experience and hold a 'yacht master offshore license' or higher. They have been carefully selected and undergone Intrepid Leader training as well as having extensive knowledge on the routes they sail. While not being leaders in the traditional sense you can expect your skipper to have a broad general knowledge of the places visited on the trip, including historical, cultural, religious and social aspects. The cook will prepare tasty local cuisine meals using the best of the local fresh produce available. The day to day itinerary indicates that some parts of this trip will be unaccompanied and some parts will be with a local guide or local transfer guide only.
Additional Information:

Finish point

  • NH Parque Central
  • La Habana Vieja,
  • Havana
  • Havana
  • CUBA
  • Phone: 53 7 860 6627

Trip ID#: intrepid-QSSC

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