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15 May, 2025

Family Sailing Vacations: The Best Family Sailing Holidays

author
The Sunfos team
5 mins read

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Family of four enjoying a golden sunset aboard a sailing yacht during a peaceful vacation in the Aegean Sea

A family sailing vacation is more than just a trip; it is an adventure that family members are connecting, exploring and creating lasting memories together. Whether you are an experienced sailor or new to the world of yachting, setting sail with your loved ones offers a unique way to explore breathtaking destinations, embrace the beauty of the open sea and strengthen family bonds.

 

Why Choose a Family Sailing Vacation and why its the Best Family Holidays?

Quality Time Together

One of the greatest benefits of a sailing vacation is the quality time spent together. Unlike traditional vacations where distractions like screens and crowds are common, a sailing trip provides an intimate setting where families can reconnect, share experiences and enjoy each other’s company without interruptions.

Adventure and Exploration – Direct Connection with Nature

Sailing allows families to explore multiple destinations in one trip. From hidden coves and secluded beaches to charming coastal villages, every day is a new adventure. Activities like snorkeling, fishing, paddleboarding and hiking create an exciting and varied itinerary that keeps everyone engaged. The thrill of discovering a new island or anchoring in a pristine bay adds an element of excitement that both children and adults will cherish. It is a beautiful way to blend in with nature, immersing yourself in landscapes and seascapes that soothe the soul and ignite curiosity.

Two children snorkeling in clear turquoise waters near a sailing yacht during a family holiday

Educational Opportunities

Sailing provides children with hands-on learning experiences. They can discover marine life, understand navigation and wind patterns and even take part in basic sailing tasks. These experiences not only build knowledge but also responsibility, teamwork and problem-solving skills. Observing constellations at night, learning about sea currents or exploring historical sites along the way make for an enriching educational journey.

Customization and Flexibility

Unlike standard resort vacations, a sailing trip is highly customizable. Families can choose their own pace, destinations and activities, ensuring that everyone—from toddlers to grandparents—has a fantastic time. Whether it is anchoring in a quiet bay for a relaxing afternoon, snorkeling in clear blue waters or exploring a bustling island town, the itinerary is tailored to your preferences and can be adjusted depending on the day’s mood and weather conditions. Wind force and direction are always important factors to consider, ensuring a smooth and comfortable ride.

A Balance of Relaxation and Excitement

Sailing offers the perfect balance between relaxation and adventure. Parents can enjoy sunbathing on deck or indulging in fresh seafood, while kids explore nature, swim and play. The gentle rocking of the boat and the soothing sound of waves create an atmosphere of tranquility that is hard to match. Meanwhile, the thrill of sailing to a new location each day keeps the journey exciting and full of surprises.

Rediscovering Simple Joys

Perhaps one of the most beautiful gifts of sailing life is how it teaches you to appreciate the little and simple things around you. Watching the sunrise over calm waters, feeling the wind on your face, hearing the splash of waves around the boat or spotting a shooting star at night — these simple moments spark a profound sense of happiness and peace. Away from the noise and clutter of daily life, sailing enhances your connection first with yourself, allowing some time of reflection and mindfulness, and then with your family, strengthening bonds through shared wonder and calm.

 

Top Destinations for Family Sailing Holidays while in Mykonos

Mykonos

A vibrant and world-famous island, Mykonos offers more than just its cosmopolitan charm. Families can explore its picturesque old town, stroll through whitewashed alleys lined with colorful bougainvillea, visit iconic windmills and enjoy family-friendly beaches like Ornos and Agios Ioannis. The crystal-clear waters and rich history make it an excellent base for sailing excursions. Beyond its party reputation, Mykonos has plenty of quiet spots perfect for families, from organized beaches to traditional Greek tavernas serving delicious local dishes. The island also offers fun activities like horseback riding along the beach, visiting local farms to experience authentic Greek culture, sea-kayaking and catching an open-air movie under the stars.

For adventurous families, sailing around Mykonos reveals secret coves perfect for snorkeling into beautiful salty waters and picnicking on board. Do not miss a sunset sail along the island’s west coast — watching the sun dip behind Little Venice is a magical, family-friendly highlight.

Rhenia

Just a short sail from Mykonos, Rhenia is an uninhabited island known for its stunning turquoise waters, powdery beaches and tranquil coves. It is perfect for families seeking a peaceful escape with opportunities for swimming, snorkeling and beach picnics in a serene, natural setting. Its untouched beauty makes it an ideal stop for those who want to experience the raw splendor of the Aegean Sea without the crowds.

The shallow, calm waters also make it a safe and enjoyable spot for younger children to swim and play. Families can beachcomb for shells, organize sandcastle competitions or enjoy storytelling nights under the stars, sharing myths and legends of the ancient Aegean. Rhenia’s simplicity is its charm — pure nature, endless skies and sparkling waters.

Delos

A UNESCO World Heritage site, Delos is one of the most important archaeological sites in Greece. Families can step back in time while exploring ancient ruins, temples, statues and mosaics. A guided tour brings the fascinating history of Greek mythology and civilization to life, making it an educational and entertaining stop for all ages.

Once a thriving trading hub, Delos holds legendary significance as the mythical birthplace of gods, Apollo and Artemis. Kids can engage in a fun scavenger hunt among the ancient streets, looking for lions, columns and mythical symbols, making history come alive. For parents, walking amidst the ruins while surrounded by the stunning Aegean seascape is both moving and awe-inspiring.

Family walking among ancient ruins on Delos island during a guided historical sailing tour

Dragonisi

For families with older kids who love nature and adventure, Dragonisi is a must-visit. This small, uninhabited islet near Mykonos is home to impressive sea caves and a vibrant array of marine life. It is a fantastic spot for snorkeling, with its emerald waters offering excellent visibility to discover colorful fish, reefs and even the Mediterranean monk seal, rarely seen.

With its dramatic rock formations and azure coves, Dragonisi is a natural playground for children. Weather permitting, adventurous families can explore the sea caves by kayak, sup board or tender boat and older kids will love diving off the rocks into the refreshing water. Parents can relax on deck with a cool drink while the kids enjoy splashing and discovering this wild, unspoiled heaven.

Tinos

A traditional gem in the Cyclades, Tinos offers an authentic Greek island experience away from the usual tourist trails. It boasts charming villages with narrow cobblestone streets, beautiful beaches and a rich culinary scene. Families can visit the famous Church of Panagia (the Virgin Mary) Evangelistria, explore local art studios and experience traditional Greek hospitality in picturesque mountain villages.

Tinos is also known for its marble craftsmanship, with many local artisans showcasing their work in villages like Pyrgos. The island offers family-friendly hiking trails leading to scenic viewpoints and hidden beaches and families can take part in farm-to-table cooking classes, learning to prepare traditional Greek dishes together. The peaceful atmosphere makes it a perfect choice for families seeking relaxation, nature and culture in equal measures — and the best part is, it is easily accessible from Mykonos either by chartering a sailing yacht or taking the regular ferry for a day trip at sea.

 

Family-Friendly Activities to Enjoy a Sailing Yacht

Life aboard a sailing yacht offers endless activities to keep the whole family entertained. From water-based adventures to onboard games and evening rituals, there is something for everyone:

  • Snorkeling and Swimming: Explore underwater life in sparkling bays.
  • Paddleboarding and Kayaking: Safe, fun and perfect for both kids and adults.
  • Fishing: A relaxing pastime and a chance to catch your own dinner.
  • Onboard Games: Card games, board games and treasure hunts keep kids engaged.
  • Stargazing: Enjoy spectacular night skies away from city lights.
  • Storytelling Nights: Share tales of Greek mythology under the stars.
  • Sunset Picnics: Anchor in a quiet cove and savor a family meal with a view.
  • Play live music: Bring a guitar, ukulele or any small, portable instrument onboard and enjoy impromptu jam sessions on deck. No need for perfection — it is about fun, interaction and shared vibes.

 

Choosing the Right Yacht Charter Type for Your Family

Selecting the appropriate yacht and charter type is crucial for a comfortable and enjoyable family sailing vacation. Consider the following factors to ensure the best experience for all family members:

Yacht Types

  • Sailing Monohulls: A classic choice for those seeking traditional sailing experience. With a single hull, these yachts are highly agile, offering an authentic feel of the wind and sea. They are considered the safest option in varying weather conditions. Their design provides a gentle ride, even in rough seas, with no bumping or discomfort. Raising the sails also allows a smooth, eco-friendly ride with lower fuel consumption for the sailing monohulls. This not only creates a sustainable experience but also gives plenty of time to enjoy the scenery. Whether the journey is calm or a bit more energetic, monohulls offer a balance of adventure and comfort.
  • Motor Yachts: Provide speed, allowing families to cover more destinations in a short time and equipped with many amenities and facilities. They are powered by engines only, which means that in some weather conditions, the ride may not be so smooth. Additionally, motor yachts are not permitted to sail in all weather conditions due to safety concerns, as they rely solely on engine power.
  • Sailing Catamarans: Catamarans offer space and are more like a floating house rather than a real boat. While they still have sails, catamarans are often motorized but not fast and their sailing performance is not ideal under certain weather conditions.

Charter Types

  • Skippered Charter: Includes a professional skipper who handles the sailing part, allowing families to relax and enjoy the journey. This is ideal for those without sailing experience or who prefer a guided experience.
  • Crewed Charter: Comes with a full crew, including a skipper, a crew member and possibly an additional staff or chef. This option provides a high level of service and is perfect for families seeking a luxurious and stress-free vacation.
  • Bareboat Charter: Suitable for experienced sailors who wish to captain the yacht themselves. This option offers maximum privacy and flexibility but requires at least one crew member to have adequate sailing qualifications with relative sailing license and knowledge of the sailing area.

Key Considerations

  • Safety Features: Ensure the yacht is equipped with child-friendly safety features such as safety nets, life jackets in appropriate sizes and secure railings.
  • Cabin Configuration: Look for yachts with suitable sleeping arrangements for your family size.
  • Onboard Amenities: Consider yachts that offer amenities like air conditioning, entertainment systems and snorkeling equipment (e.g., mask, fin) to keep the whole family engaged.
  • Crew Experience with Children: If opting for a crewed charter, inquire about the crew's experience with children to ensure a family-friendly atmosphere onboard.

 

Safety Tips for Sailing with Kids

Ensuring the safety of your little sailors is paramount for a stress-free family sailing vacation. Here are key safety tips to keep everyone safe while having fun at sea:

  • Life Jackets: Always have properly fitted life jackets for each child and make sure they wear them during navigation.
  • Briefing on Rules: Set clear, age-appropriate safety rules and review them before setting sail.
  • First Aid Kit: Keep a well-stocked, marine-approved first aid kit onboard.
  • Sun Protection: Ensure kids wear hats, sunglasses and high-SPF sunscreen.
  • Hydration and Snacks: Have plenty of water and healthy snacks available to prevent dehydration but keep it light.
  • Supervised Water Activities: Always accompany children during swimming, snorkeling, and other water-based fun.
  • Emergency Procedures: Teach older kids basic emergency procedures like how to call for help or recognize distress signals. The crew and/or the land-based team before departure will assist you with that.

 

Book Your Adventure with Sunfos Alessia Yachting

A family sailing vacation is an extraordinary way to explore the world together, offering a mix of adventure, relaxation, and bonding. Whether you choose Mykonos, Delos & Rhenia, Dragonisi, or Tinos, the memories created on a sailing journey will last a lifetime. The beauty of the Aegean Sea, the thrill of sailing and the joy of discovering new places with loved ones make for an experience that is truly priceless. So, hoist the sails, embrace the sea breeze and embark on an unforgettable family adventure!

Ready to set sail on your dream family vacation? Sunfos Alessia Yachting specializes in unforgettable sailing experiences in Mykonos and the surrounding islands. Whether you are looking for a private family cruise or a group sailing adventure, our expert team ensures a safe, comfortable and fun-filled journey. Contact us today to start planning your perfect family sailing vacation!