Cuba Sailing Adventure

Our saving
US $ 1,477
Cost/day $164
Unlock $38 in extra savings
Check availability
24/7 Customer SupportAsk a question
This tour is operated by
Cuba Sailing Adventure - Intrepid Travel
Cuba Sailing Adventure - Intrepid Travel
Nick "An incredible experience! Small groups of 8 max on a very comfortable 55ft Yacht. The local crew cooked incredible meals daily, most of which were fresh fish caught that day! We hit a beach and a reef daily while onboard the Yacht and also got to experience Havana and Cienfuegos in depth. To top it all off, Cervezas were $1 onboard! Highly recommend this trip to anyone who is looking to unwind and..."
7 reviews


Start and end in Havana! With the sailing tour Cuba Sailing Adventure, you have a 9 day tour package taking you through Havana, Cuba and 3 other destinations in Cuba. Cuba Sailing Adventure is a small group tour that includes accommodation in a hotel as well as an expert guide, meals, transport.
Age range
15 to 70 year olds
Berth / Cabin, Guesthouse
Max Group Size
Coach / Bus, Boat, Local Transport
Travel style
Sailing, In-depth Cultural

7 Reviews

Rather Poor
Write a review
  • D
    Written on April 16, 2018
    5.0 - Excellent

    A totally different side to Cuba! What's not to love about waking up on the crystal clear water of the Caribbean. Despite not being a food trip, the fresh lobster was a highlight! Make sure you book days either side of the sailing trip so you also get the local cuban experience on land for the complete Cuban holiday.
    Intrepid Travel commented on this review
    Hi Drew, thanks for taking the time to share your experience with us! Sounds like you got to see many different sides of Cuba – it really is an incredible country, isn’t it? Hope to see you on another trip with us again soon! Kind regards, Intrepid
    Show detailed ratings

  • Cuba Sailing Adventure reviewer 2
    Written on February 1, 2018
    4.5 - Excellent

    This was such a great way to relax towards the end of our time in Cuba! Sailing around the Caribbean, relaxing on beaches in the sun, Cuban cocktails on was bliss. Our skipper and chef were absolutely incredible! So friendly and professional. We had such a great time with them. There were a couple of days where the weather was not the best but they managed to keep our spirits up and kept us entertained. This is probably a more cost effective way to explore what could be perceived as the rich mans paradise. We will remember this experience fondly! Would definitely recommend!
    Intrepid Travel commented on this review
    Hi Ayesha, Thank you so much for sharing your experience with us. I’m writing to you from a very cold Toronto and now you’ve got me dreaming of beaches in the sun and Cuban cocktails! We’re delighted to hear that you had a great time, and we look forward to seeing you on another trip again soon! Kind regards, Intrepid
    Show detailed ratings

  • M
    Written on January 4, 2018
    1.0 - Bad

    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.
    Intrepid Travel commented on this review
    Hi Maryd, Thank you for taking the time to share your comments with us. We were disappointed to read that the Cuba Sailing Adventure did not meet your expectations. We would love an opportunity to more fully understand your experience as feedback from our passengers is essential towards improving all that we do. Please feel free to contact our Customer Relations team who will be happy to further address your concerns: Thanks again and we look forward to hearing from you. Kind regards, Intrepid
    Show detailed ratings

  • JS
    Written on March 30, 2017
    5.0 - Excellent

    EXCELLENT ADVENTURE Overall, the sailing trip exceeded expectations in many aspects: the care and condition of the vessel (with a few minor exceptions*) , quality of customer service on board, professional talents of the chef (A++) who produced 5 different meals and 2 appetizers featuring fresh lobster, the skillfulness of the Skipper, and the great rapport between the two. Appreciated the less-than-maximum group size. The five passengers, including a Parisienne transplant from the UK, a German, an Australian and 2 Canadians (who normally live thousands of miles apart) - 1 male/4 females - met for the first time the night before we set sail for a week of adventure. Awesome group! Amazing trip. Could do without the personal remarks and "hook-up" offers from the employees; only flaw in the otherwise great atmosphere on board. As a sailing trip, it was less hands-on than expected, by indications in pre-departure info. You won't need to purchase sailing gloves, as I did, and don't worry - there's no quiz on terminology by the Skipper. There are no "'guided activities" on land such as hiking, and "fishing" is a spectator sport only on this trip - although quite spectacular at times! TIPS: -buy a wifi card (ETECSA) in Havana - you may not have the time or opportunity to get one in Cienfuegos -stock up on cash in CUC's (min. 250 pesos) before leaving Havana. Foreign currency is useless on this trip. ATMs at one bank in Cienfuegos, but they are iffy; several of our group had credit and bank cards declined, and my Canadian VISA card - usually the preferred option, was eaten by a bank machine in the middle of a transaction, for no apparent reason. Big bloody pain. Had to borrow cash from shipmates and pay them back in Havana. Since the trip departs and returns to Cienfuegos on a Sunday - the banks are closed, so there's no one to help out if anything goes wrong, and cell phone calls to Canadian banking customer service numbers did not connect.
    Show detailed ratings

  • KB
    Written on February 14, 2017
    5.0 - Excellent

    Amazing trip, you won't regret it!!
    Show detailed ratings

  • L
    Written on April 27, 2016
    5.0 - Excellent

    I did this sailing trip in November last year. I did an overland 2 week tour of Cuba and the sailing trip after. It was a great way to finish of my trip, kicking back, relaxing while sailing through Caribbean islands. The yacht had 4 cabins all with private bathrooms, very clean with really comfortable beds. So only 8 people, which was perfect, plus the shef and skipper who were very helpful, friendly and always smiling. The food was amazing and all your meals on board included with lots of fresh fish, straight from the sea! And when your out snorkelling you can get close to the skipper and the shef and watch them spearfishing under water. The islands were spectacular, clean turquoise water and white sand. The tour i did before the sailing trip was Cuba dance and music which was also amazing!
    Show detailed ratings

  • N
    Written on April 21, 2016
    5.0 - Excellent

    An incredible experience! Small groups of 8 max on a very comfortable 55ft Yacht. The local crew cooked incredible meals daily, most of which were fresh fish caught that day! We hit a beach and a reef daily while onboard the Yacht and also got to experience Havana and Cienfuegos in depth. To top it all off, Cervezas were $1 onboard! Highly recommend this trip to anyone who is looking to unwind and have a truly local experience.
    Show detailed ratings

    Cuba Sailing Adventure customer review photo 1Cuba Sailing Adventure customer review photo 2Cuba Sailing Adventure customer review photo 3


Download PDF Brochure
Expand all
  1. Introduction
  1. Day 1: Havana
  2. Day 2: Cienfuegos
  3. Day 3-7: Canarreos Archipelago
  4. Day 8: Canarreos Archipelago - Cienfuegos
  5. Day 9: Cienfuegos - Havana

Travel guide

Prepare for an adventure in this stunning destination with our travel guide.

What's included

Expand all
Download PDF Brochure
  • Accommodation

    Rated Excellent by past passengers
  • Guide

    Rated Good by past passengers
  • Meals

    Rated Excellent by past passengers
  • Transport

    Rated Excellent by past passengers

Not included

  • Flights

  • Insurance


  • Cuba
  • Main Page Video

Questions & Answers

Here we have collected and answered the most frequently asked questions about this tour.

  • As a USA citizen can I travel to Cuba legally now?

    US citizens can travel legally for one of 12 reasons or on a people to people designated tour. However this is the responsibility of the passenger to make the appropriate claim for a general license. TourRadar cannot confirm or deny entry to Cuba for US citizens including visa issuance/restrictions or airfare to Cuba.

    As per the USA treasury website, US citizens can travel legally for one of 12 reasons (see below).
    Family visits
    Official business of the U.S. government, foreign governments, and certain intergovernmental organizations
    Journalistic activity
    Professional research and professional meetings
    Educational activities
    Religious activities
    Public performances, clinics, workshops, athletic and other competitions, and exhibitions
    Support for the Cuban people
    Humanitarian projects
    Activities of private foundations or research or educational institutes
    Exportation, importation, or transmission of information or information materials
    Certain authorized export transactions

    ***If pax does not fall under one of the 12 regulations, The following tours are listed as people to people tours, eligible for American travelers:

    Please be advised travelling to Cuba and booking a tour is at your own risk and responsibility. Please refer to the US Treasury website for the most up-to-date information regarding travel sanctions in Cuba:

Ask a question logo What are people saying about TourRadar?

  • Edith, 72 years old29th September 2018
    Communication has been excellent. All queries have been answered promptly. Further information about the proposed tour has been readily available. I feel confident booking through TourRadar.



Cuba Sailing Adventure

Select Departure Month
  • Upcoming departures
  • November 2018
  • December 2018
  • January 2019
  • February 2019
  • March 2019
  • April 2019
Show more departures

Monthly price comparison

About the countries

Useful things to know before you go



Plugs & Adapters



Here is an indication for which countries you might need a visa. Please contact the local embassy for help applying for visas to these places.


These are only indications, so please visit your doctor before you travel to be 100% sure.
Recommended for Cuba. Ideally 2 weeks before travel.
Hepatitis A
Recommended for Cuba. Ideally 2 weeks before travel.
Recommended for Cuba. Ideally 2 weeks before travel.
Hepatitis B
Recommended for Cuba. Ideally 2 months before travel.


Start and end in Havana.
Hold my space
TourRadar can request Intrepid Travel to hold spaces for you for up to 48 hours without any credit card details.
TourRadar only requires a deposit of $400 to confirm this Intrepid Travel booking. The remaining balance is then payable 60 days prior to the departure date. For any tour departing before 14 December 2018 the full payment of $1,477 is necessary.
Cancellation policy
No additional cancellation fees! You can cancel the tour up to 60 days prior to the departure date and you will not need to pay the full amount of $1477 for Cuba Sailing Adventure, but the deposit of $400 is non-refundable.
Credit Cards
The following cards are accepted for Intrepid Travel tours: Visa - Master Card - American Express


Covering a total distance of approx 705 km.
  • Havana (Cuba)
  • 226 km
  • Cienfuegos (Cuba)
  • 90 km
  • Cayos de Dios (Cuba)
  • 38 km
  • Cayo Largo (Cuba)
  • 124 km
  • Cienfuegos (Cuba)
  • 226 km
  • Havana (Cuba)

Why book with TourRadar

Best Price Guarantee
If you book with TourRadar and within 24 hours you find a better price than $1,477 for the same tour, TourRadar will pay you the difference
Safely book online
All your details are safely protected by a secure connection
3,757 tours in Latin America
covered by 151 different operators in Latin America
No Cancellation Fee
TourRadar does not charge any additional cancellation fees. You can cancel the tour up to 60 days prior to the departure date.
7 Genuine Reviews
All reviews are verified from travellers who went on Cuba Sailing Adventure

Trip Details

  • Last modified (date)

  • Validity

  • Introduction

  • Style

  • Themes

  • Physical Rating

  • Physical preparation

  • Joining point

  • Joining point instructions

  • Finish point

  • Finish point instructions

  • Safety

  • Visas

  • Why we love it

  • Is this trip right for you

  • Health

  • Food and dietary requirements

  • Money matters

  • What to take

  • Climate and seasonal

  • A couple of rules

  • Emergency contact

  • Responsible travel

  • Travel insurance

  • Your fellow travellers

  • Itinerary disclaimer