Sail Cuba

Sail Cuba

December 1 – 9, 2017

This Adventure was amazing!
Experience our western cayos Voyage – click for images
Our exploratory cruise through eastern cayos was surreal – click for images

Sail Cuba is four boat full!

If you have booked with us your travel is protected, grandfathered in.
If you have not, the new US restrictions on our right to travel apply to you.

All Sail Cuba pages, click here

It’s on. Cuba is a unique sailing destination that most Americans have been locked out of for decades. We have navigated the complex process and are working with our Cuba licensed affiliate to legally explore Havana and the beautiful Islas de Cienfuegos by sail.  The Cuban people are warm and welcoming, the destination is isolated and unique, the reefs and cayos are idyllic, the sailing is Caribbean trades wonderful.

We are visiting the best parts of Cuba in their best sailing season on the countries newest yachts.  Arrive into Havana and experience this legendary city before it is forever changed.  Included in your sailing vacation package is our organized transfer/tour/meals/room from Havana on down to Cienfuegos.  Our sailing itinerary includes Playa Sirena, Cayo Largo, Ballanetos, Quinto Canal, Cayo Rosario, Cayo Estopa, Cayo Sal.

The Yachts –  beautiful new sailing catamarans, first come, first served …

  • 2017 Lagoon 45 – Full
  • 2017 Bali 45 – Full
  • 2016 Lagoon 39 – Full
  • 2012 Orana 44 – Full
  • Email to get on standby list


  • State Department required paperwork for our Cuba Adventure
  • Havana to Cienfuegos Tour/Transfer with botanical gardens, meals and room
  • Seven days exploring islands of Cienfuegos on beautiful cats
  • Cool captains to guide your Adventure and share their skills
  • Yachts are provisioned with locally available foods for most meals

Price & Booking 

  • $5800 for a Couple, own cabin, own head
  • $3100 for a single, shared cabin with head
  • Deposit is $1500 for couples, $1000 for singles
  • Click to see Terms & Waiver then …
  • To confirm your spot, pay your deposit through our Cuba licensing agent.  Email CaptainWoody@AdventureVoyaging for invite and instructions

More info below images …

2017 Bali 45

Bali 45 Layout

2017 Lagoon 450

Lagoon 450 Layout

2016 Lagoon 39

2016 Lagoon 39

Lagoon 39 Layout

Orana 44

Orana 44

Orana 44 Layout

Basics …
Our Cuba tour/transfer picks up in Havana at 0830, December 1, 2017.  With cultural and food stops, we are delivered to to our hotel in Cienfuegos.  The next day we explore Cienfuegos then board the boats at 1730.  After a week of wonderful island exploration we leave the yachts back in Cienfuegos, 1100, December 9.

The Yachts …
The charter fleet in Cuba is still limited but we have secured the base’s best catamarans for this Adventure.  As so much of our time will be spent above decks, the extra deck space of a cat is great for sailing, swimming, snorkeling, dining and chilaxin’.  Our yachts will be sailing together as a flotilla.

What is included …
All of your Cuba legal licensing paperwork.  Your shuttle with the group from Havana to Cienfuegos.  Lunch at a waterfront spot.  A guided walking tour of Cuba’s famous Botanical Gardens.  Hotel room that night.  Dinner in town, Cienfuegos.  Seven days exploring islands by sailing cat, food onboard, fuel, fees etc.  You will have an easygoing captain aboard tasked with guiding your Adventure and teaching anything cruising you might want to learn.  We provision the boats with locally available food.  And there will be plenty of opportunity to absorb the local culture by dining ashore.

What isn’t included …
Flights, most shore dining and entertainment, Havana hotel if arriving early.  Last I checked flights Miami (MIA) to Havana (HAV)  and Cienfuegos (CFG) back to Miami were $277.  To check flights from your airport try

How to book …
Email Captain Woody for your personal invite with instructions on how to pay your deposit to our Cuba licensed travel agency.  They can also book additional tours and accommodations if you like.  Please wait to book your travel until we have confirmed your spot.

Usually you would find a deposit pay button here but Cuba is a special place, not yet available for the average tourist to up and fly in.  And that’s why we are going now!

Highlights …

  • Be among the first to experience Cuba, pre-US tourism
  • Tour from Havana to Cienfuegos
  • Sail roomy catamarans with fun people
  • Cuba’s primo cruising grounds …
  • Playa Sirena, Cayo Largo, Ballanetos, Quinto Canal, Cayo Rosario, Cayo Estopa, Cayo Sal
  • Sincere people, beautiful islands, Cuban cuisine; we can’t wait!

Captain Woody:
Watch for posts and live updates at:
All Sail Cuba pages … Click Here
Join our email list for (rare) updates: Click Here