Your Next Family Sailing Holiday 

10.01.2021 Fiona Mokry

Planning a vacation that everyone in the family is onboard with definitely has its challenges. If you’re looking for a family vacation that involves everyone, a sailing holiday might be the answer.

Island hopping, swimming, snorkeling, sailing lessons, and sampling the local cuisine are all bonding experiences offered during a family sailing vacation. And, you’ll all come away with a new skill that you can continue to practice together once you’re back home.

In addition to holiday fun and relaxation, Boataffair offers a number of luxury yacht holidays with “learn to sail” experiences in a variety of locations. From Spain to the Bahamas, from Greece to the Caribbean, make your next trip a family sailing holiday and enjoy learning new skills and discovering new places together. 

Family Sailing Holidays for Beginners

Possessing little to no sailing experience shouldn’t deter you from setting sail with your family. In fact, accomplishing a new skill that involves everyone can be a great bonding experience. Boataffair offers Family learn to sail holidays that include the experience of sailing lessons, allowing families to spend as much or as little time as they want developing this skill.

When it comes to sailing, there is so much to learn. Often we find that a person's first sailing hoiday is all about fun and relaxation. However, after spending some time aboard a sailing yacht you will almost certainly become curious about what is going on around you. This is why we love to offer all levels of sailing courses to expand your understanding and passion for sailing.

Starting with basic sailing terminology, and parts and functions of the yacht, you can move on to learning helm commands, basic sail trim, points of the sails and buoyage. Seamanship and safety are important to learn and our captains are always happy to explain why they do things a certain way, including basic navigation and rules of the sea which have to be followed to avoid collisions and hazards.

For those interested in dipping their toes but leaving the rest of the trip to a licensed skipper, one or two-day sailing experiences are offered aboard luxury catamarans in stunning locations around the world. If your crew wants to take it a bit further, hourly or multi-day lessons are also available.. 

Craving a bit more independence, but unsure about going it alone? Another option is to venture off on your own with light guidance provided via twice daily radio check-ins. Whatever your skill and comfort level, Boataffair curates each experience to every guest’s needs and wants. 

If the purpose of your holiday is to come away with a good grasp on sailing (or even licensure), Boataffair caters to families seeking to learn to sail together.

Family Yacht Charter in the Caribbean

With its hundreds of islands and a tropical climate, the Caribbean provides an ideal environment for a family yacht charter. With options to island hop, partake in water sports, and call into port to taste the local cuisine, it’s easy to keep the whole family satisfied. The yacht charters in Saint Vincent and the Grenadines provide a balanced blend of training with an expert skipper while also allowing time to soak up the beautiful surroundings. After your time behind the wheel, relinquish control and enjoy a crewed charter where all you have to worry about is kicking back with your family. 

Those families who want to dedicate a significant chunk of time to sailing lessons might be interested in this ASA learn to sail package in Puerto Rico. If you’ve got the time, you can work your way through multiple ASA courses and earn your bareboat certification, enabling you to charter a boat or catamaran up to 50 feet. 

Family Sailing Holidays in the Greek Islands

The Greek islands are a dream to explore from the water. The stunning coastal scenery, temperate climate, and rich Mediterranean culture combine to create one of the most sought-after holiday destinations in the world. Greece offers a welcoming environment for amateur sailors to learn the basic skills needed to command a yacht. An expert skipper provides complimentary instruction throughout this 7-day trip on techniques like steering, berthing, anchoring, knot tying, hoisting, furling and trimming the sails, and much more. This experience strikes a happy medium between leisure time and skipper-in-training sessions. 

Kick it up a notch with Boataffair’s Greek Island Sailing Experience, which allows you to combine your family yacht charter with a learn-to-sail experience resulting in the Offshore Sailing License. Choose from a variety of luxury yachts upon which to spend seven days soaking up the Greek sun. Your skipper doubles as your instructor, preparing you to pass your licensure exam on the last day of the trip. 

Finally, for avid sailors looking to increase their knowledge and skills in the world of advanced sailing, Performance Sailing in Greece is the perfect fit. Climb aboard Nexus, a 40-foot sailing yacht claiming an impressive number of regattas and trophies. With options to learn the ropes of offshore sailing, engage in pre-race basics, and even participate in a race or regatta, this experience is best suited for families who have a strong interest in advancing their skills.


Bonding as a family over a love sailing is a holiday memory worth making. Check out Boataffair’s options for a family sailing holiday and get away this winter!

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