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Sailing Holidays for Singles Over 50

By Sandra Roussy January 19, 2024 Travel

Are you over 50 and looking for an exhilarating new adventure? Do you enjoy the wind in your hair, the gentle sway of the waves, and the camaraderie of like-minded individuals? A sailing holiday may be in your future!

  1. St Lucia & Martinique: 5-day explorer – Adventure sailing holiday in the southern Caribbean –Sail with Rubicon 3 Adventure to explore St Lucia’s beauty, venture to Martinique, and immerse yourself in Caribbean culture. This 6-day journey is perfect for beginners and solo sailors, offering a curated experience with a crew size capped at 9.
  2. Greece & Turkey Sailing Adventure – Discover a Mediterranean sailing adventure with Best Single Travel, exploring the waters of Greece and Turkey. This carefully planned journey ensures a mix of cultural exploration, relaxation, and the thrill of sailing, accommodating a maximum of 22 participants. 
  3. Caribbean Sailing Holidays for Singles & Solo Travellers – Explore solo sailing with Yacht Ibis. You can be an experienced sailor or a beginner, these trips offer comfort and a specially prepared yacht for a delightful sailing experience, from coastal exploration to relaxing sunsets on the deck.
  4. Single Traveler Sailing Holidays – Kefalonia, Greece – Discover this tailor-made solo sailing adventure with Beyond Beach to explore the beauty of Kefalonia, Greece. Created exclusively for solo adventurers, the yacht ensures comfort with a thoughtful itinerary blending relaxation and excitement, and a friendly crew ready to make your journey memorable.
  5. New Year’s Eve in Ibiza sailing from Denia – Join Sailwiz for a thrilling New Year’s Eve celebration in Ibiza, Spain. Sail from Denia to the vibrant island, experiencing a unique holiday adventure with a blend of sailing and festive celebrations.

Sailing holidays for those over 50 are not just vacations; they are opportunities to explore the world, discover hidden gems, and create unforgettable memories. So raise your anchor, hoist your sails, and get ready to sail away! 

Types of Sailing Holidays

Sailing holidays come in a variety of types to cater to different preferences and levels of experience. Whether you’re a seasoned sailor or a complete novice, there’s a sailing trip suited for you.

Bareboat Charters

For those with sailing experience, bareboat charters provide the freedom to captain your own vessel. You can choose your destination, set your itinerary, and sail at your own pace. It’s an ideal option for more independent and adventurous sailors.

Adventure Sailing

Adventure sailing holidays are designed for thrill-seekers and explorers. These trips often include activities such as snorkeling, scuba diving, and hiking in addition to sailing. They provide a more immersive experience in exotic and off-the-beaten-path locations.

Learn-to-Sail Vacations

If you’re new to sailing or want to improve your skills, learn-to-sail holidays offer instruction by certified instructors. These trips are perfect for beginners and provide a combination of education and leisure.

Local or Day Sails

If you’re looking for a shorter, more casual experience, consider local or day sails. These provide a few hours of sailing within a specific region, making them perfect for those who want a taste of sailing without committing to an extended voyage.

What to Look for in a Sailing Trip

When considering a sailing vacation, several key factors must be considered to ensure a memorable and enjoyable experience. 


Decide where you want to sail. Research the region, climate, culture, and attractions to make sure they align with your interests and preferences.

Type of Sailing

Choose the type of sailing experience that suits you, whether it’s a relaxed cruise, bareboat charter, flotilla sailing, adventure sailing, or another option. Your level of experience and desire for independence will influence this choice.


Determine the length of your sailing vacation. It can be a short day sail, a week-long trip, or an extended voyage. Ensure it aligns with your available time and budget.

Boat Type

Consider the size and type of boat – monohull or catamaran. A monohull sailboat has a single hull, offering efficiency in upwind sailing but may heel (lean) when sailing. A catamaran has two hulls, providing greater stability, spacious living areas, and a shallow draft. 

Catamarans typically offer a smoother ride and reduced heeling compared to monohulls, making them popular for those prone to seasickness or seeking a more comfortable sailing experience. 

Smaller boats are more intimate, while larger vessels offer more space and amenities. Ensure the boat suits your comfort and space requirements. 


Review what’s included in the package, such as meals, excursions, equipment (snorkeling gear, fishing gear, etc.), and any additional services. This can significantly impact your overall cost.


Check the proposed itinerary to see if it covers the places you want to visit and the activities you want to engage in. Make sure it allows for flexibility and exploration if you desire.

Experience Level

Some sailing vacations cater to experienced sailors, while others are designed for beginners. Choose a trip that matches your experience and skill level.


Ensure the charter company or tour operator maintains high safety standards, including proper equipment, safety briefings, and experienced crew or instructors if needed.

Reviews and Recommendations

Read reviews from previous travelers and seek recommendations from friends or online forums. This can provide valuable insights into the quality of the sailing vacation.

Environmental Practices

Consider the environmental practices of the sailing operator. Responsible and sustainable sailing vacations help protect the marine ecosystem.

By considering these factors and doing thorough research, you can select a sailing vacation that aligns with your expectations and ensures an enjoyable experience on the water.

How to Get Ready for a Sailing Voyage

Getting ready for a sailing voyage involves careful planning and preparation to ensure a safe and fun experience on the water. 

Check Passport and Visa Requirements

If you’re sailing to international waters, ensure your passport is up to date and that you have the necessary visas and travel documents.

Pack Essentials

Pack appropriate clothing, including lightweight, breathable, and quick-drying items. Don’t forget essentials like swimsuits, sunscreen, sunglasses, and a hat.

Women's HH Tech T-Shirt

Women’s HH Tech T-Shirt

Women's Quick-Dry Pants

Women’s Quick-Dry Pants

Safety Gear

Familiarize yourself with the safety equipment on board, including life jackets, first-aid kits, and emergency procedures.

Sailing Gear

If you have your own sailing gear, make sure it’s in good condition. If not, inquire with the charter company about what’s provided and what you need to bring.

Helly Hansen Newport Inshore Sailing Jacket

Helly Hansen Newport Inshore Sailing Jacket

Learn Basic Sailing Terminology

Familiarize yourself with basic sailing terms, such as port, starboard, bow, and stern, to communicate effectively on board.

Sailing Essentials by Steve Sleight on Amazon

Sailing Essentials by Steve Sleight on Amazon

Sailing Training (If Needed)

If you’re new to sailing, consider taking a basic sailing course to understand the fundamentals and gain confidence on the water. You can get certified with an ASA /American Sailing Association) accredited school.

Weather Forecast

Stay updated on the weather forecast for your destination and planned voyage. Be prepared for changing weather conditions. Websites like Windy and PredictWind offer realtime weather forecasts including wind and waves. 

Waterproof Bag

Keep a copy of your travel documents, including passports, visas, and trip reservations, in a waterproof bag. 

Waterproof Dry Bag on Amazon

Waterproof Dry Bag on Amazon

Local Regulations

Familiarize yourself with the local laws and regulations of the destination you’ll be sailing to, including customs and immigration requirements.


If you’re on a bareboat charter, plan and purchase provisions for your voyage, including food and beverages. Some charters may offer provisioning services.


Make sure you ask the sailing trip provider what type of communication or internet service they have on the boat. Starlink is now available for boats. 

Boat Briefing

Pay close attention during the boat briefing provided. Understand how to operate essential systems and equipment on the vessel and don’t hesitate to ask questions. 

Crew Roles

If you’re sailing with a group, make sure you understand roles and responsibilities to ensure smooth teamwork on board. 

Enjoy and Stay Safe

Most importantly, relax and enjoy the journey. Always prioritize safety and follow the instructions of the skipper or crew, and be respectful of the environment.

Sailing Adventures for Single Women Over 50

St Lucia & Martinique: 5-day Explorer – Adventure Sailing Holiday in the Southern Caribbean

Set sail on an amazing adventure in St Lucia with Rubicon 3 Adventure. Explore the island’s beauty, from the famous Pitons to lush rainforests and Marigot Bay. Cruise through the surrounding seas to discover a UNESCO World Heritage Site, a volcano, and soothing hot springs. Take a short trip north to Martinique, a French Caribbean paradise with mountains, beautiful beaches, and vibrant culture. 

The sailing journey is carefully planned to showcase the best of both St Lucia and Martinique, offering not just scenic views but also a taste of Caribbean culture. Get ready for a sea adventure filled with breathtaking landscapes and the charm of the Caribbean.

This sailing excursion is perfect for newcomers without any prior sailing experience, offering an introductory level of adventure. Solo sailors are welcome, and the crew size is capped at a maximum of 9 individuals. The journey lasts 6 days, beginning at a rate of £899. If you’re new to sailing and going solo, this trip provides an accessible and exciting opportunity to set sail and immerse yourself in the world of seafaring adventure.

Greece & Turkey Sailing Adventure

Explore an incredible Mediterranean sailing adventure with Best Single Travel. You’ll get to sail through the beautiful waters of Greece and Turkey, discovering ancient ruins and charming coastal villages. This carefully planned journey ensures a rich experience, with opportunities for solo travelers to connect and share their adventures. 

Learn about the history, from the famous landmarks of Athens to the scenic Turkish coastline. The itinerary promises a perfect mix of cultural exploration, relaxation, and the thrill of sailing. The trip has a maximum of 22 participants.

Caribbean Sailing Holidays for Singles & Solo Travellers

Discover solo sailing with Yacht Ibis. These sailing adventures are designed just for solo travelers, offering a unique experience with a dedicated crew. Imagine navigating through stunning waters, making new friends, and exploring beautiful destinations. 

The trips are carefully planned for your comfort and enjoyment, whether you’re an experienced sailor or a beginner. The yachts are specially prepared for solo adventurers, ensuring a comfortable sailing experience. 

From coastal exploration to relaxing on the deck as the sun sets, every moment is designed for your pleasure. Get ready to set sail, make memories, and enjoy the freedom of the open sea with Yacht Ibis.

Single Traveler Sailing Holidays – Kefalonia, Greece

Experience a solo sailing adventure with Beyond Beach. This tailor-made experience is designed just for solo travelers, offering you the chance to explore the beauty of Kefalonia, Greece. Imagine sailing through crystal-clear waters, visiting charming ports, and basking in the warmth of the Mediterranean sun. The itinerary is thoughtfully planned to provide a perfect blend of relaxation and excitement. 

The yacht is designed for solo adventurers, ensuring comfort and an enjoyable sailing experience. Whether you’re a seasoned sailor or a beginner, the crew is there to assist and make your journey memorable. From the freedom of the open sea to the camaraderie with fellow solo travelers, every aspect is geared toward creating unforgettable moments. 

New Year’s Eve in Ibiza sailing from Denia

Experience a thrilling New Year’s Eve celebration in Ibiza with Sailwiz. Picture yourself sailing from Denia to the vibrant island of Ibiza, surrounded by the beauty of the Mediterranean Sea. This unique holiday adventure offers a perfect blend of sailing excitement and festive celebrations. 

The itinerary is planned to ensure a memorable New Year’s Eve, with the chance to explore the charms of Ibiza’s lively atmosphere. The yacht, equipped for comfort and fun, becomes your home on the water for 4 days, providing a unique vantage point for the island’s festivities. 

Whether you’re an experienced sailor or a beginner, the crew is there to assist and create a relaxed atmosphere. From sailing under the winter sun to counting down to the new year in Ibiza, every moment promises a mix of adventure and celebration. 

Set sail with the confidence of experience and the joy of exploration. The beauty of these journeys lies not just in the places you visit but in the empowering spirit of the sea and the incredible people who navigate it. May every wave take you to new horizons, and every sunset mark the triumph of a solo adventure well embraced. 



Let’s Have a Conversation:

Have you ever been on a sailing trip? Are you interested in going on a sailing adventure in the near future? Tell us about it in the comments below. 

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The Author

Sandra is the middle-aged woman you hear about who sheds everything she owns and sets out into the world to rediscover and redefine herself. After more than twenty years spent in the fashion industry designing collections for brands such as La Senza, Victoria’s Secret, and JACOB Lingerie, she shifted her path and pursued her longtime passion for writing, traveling, and photography. Sandra was published in the NY Times best selling book Eat Pray Love Made Me Do It. A deeply personal essay hand-picked by Elizabeth Gilbert about loss, facing fears, and going after dreams. Visit her website:

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