April 30, 2023

Sailing holidays for singles

Are you tired of the same-old shoreside getaways? Why not set sail and experience a sailing holiday tailored to singles? You'll love exploring the open ocean while making new friends and reconnecting with yourself.

After my divorce in 2004 I felt awkward going sailing with crews that other than myself were all couples. So I stopped sailing as part of a crew for a while and went solo. Now nearly 20 years later I'm quite happy to sail solo but straight after the divorce it wasn't such a good idea to be alone at sea for long periods so I stopped sailing altogether for about 8 months.

Luckily for me a friend spotted a "sailing holiday for singles" and showed it to me. I said no at first but after a week or two of thinking about it I took the plunge. I soon realised that I missed the sailing so much that to get out there again, I'd happily endure the perceived embarrassment of going on a singles trip.

Turned out to be a brilliant holiday and I am still in touch with some of the friends I made on that trip.

So take the plunge yourself and let this article be your guide to finding the perfect sailing holiday for singles.

Table of Contents

What should you expect from the trip?

Discover the extraordinary experience of a sailing holiday for singles. Immerse yourself in the stunning beauty of nature, the freedom of the ocean and spontaneous encounters with interesting people. Expect days filled with adventure and relaxation, as well as an opportunity to increase your self-awareness and confidence among like-minded individuals.

During your time on board, expect to learn new skills like hoisting sails, navigating, or even taking the helm under guidance from professional crew members. Take advantage of swimming stops for snorkelling or diving in clear blue waters, exploring hidden coves or hiking scenic trails.

Join group dinners on deck or shore excursions to taste local specialties and socialize with other solo travellers.

You can expect a unique combination of individual freedom and group cohesion while sharing your passion for sailing - without any prior experience required.

Unforgettable memories await you whether sailing along rugged coastlines, discovering secluded beaches, or enjoying an island paradise.

If you’ve ever thought of this type of one-of-a-kind travel experiences, tailored specifically for singles, what are you waiting for? Explore the world by sea!

Single and ready to mingle, doesn’t mean all these holiday goers are looking for love on the high seas, but you never know what might happen!

What sort of people take these holidays?

Individuals seeking adventure and a chance to make new friends are drawn to sailing holidays for singles. These voyages provide unique opportunities to socialize with like-minded individuals who share similar passions for exploration.

Additionally, throughout these holidays, individuals can learn or improve their sailing skills while enjoying the beauty of the surrounding landscapes.

Sailing holidays cater to singles who value independence, freedom, and love thrilling experiences. Often comprising small groups, these trips allow for personalized attention from experienced crew members who ensure that all participants enjoy a safe and enjoyable voyage.

With diverse age ranges of 20-70 years old, sailing holiday enthusiasts include solo travellers, who are looking for a break from everyday life getting new perspectives, and travel adventurers.

If you’re an in-experienced sailor don’t let put you off, because regardless of experience levels with sailing you’ll be welcomed if you’re prepared to muck in and help.

Training is always provided before setting sail, so you’ll at least have the basics.

Therefore, prior experience is not usually required to join sailing holidays for singles.

Pro Tip: Ensure you have adequate protection against sunburn as it may ruin your trip aboard any ship. To see what you should pack read “What to take on a sailing holiday”.

You're never too old to sail the high seas...or to find love on board.

Sailing holidays for singles over 50

There has been a significant increase in the number of sailing trips for mature singles seeking adventure and companionship. So why not discover the joys of sailing with like-minded individuals over 50.

Whether you're experienced or just starting, I’m confident that joining a crew to set sail will be a unique and memorable vacation.

Sailing for singles over 50

There are many companies that offer a variety of sailing packages that cater to your preferences and budget, including luxury cruises or bareboat charters.

You can explore coastal towns, bays, and hidden beaches while enjoying good food and the company of other single travellers, in your age group.

Professional skippers ensure your safety and comfort throughout the voyage, allowing you to focus on relaxation or learning new skills. You can participate in various activities like snorkelling, hiking, kayaking, or simply sunbathing on deck.

Take advantage of special events such as sunset cocktails or beach barbecues to connect with fellow passengers and build meaningful relationships.

Don't miss this golden opportunity to create lifelong memories while exploring the world's most beautiful destinations. Experience the best sailing holiday for singles over 50!

You can get involved in the sailing as much or as little as you want and get guidance and tuition from experienced skippers and instructors.

Exploring beautiful destinations that are best seen from the water. You can discover stunning islands, bays, beaches and tavernas in places all around the world.

Enjoying a relaxing and flexible holiday that suits your budget and preferences. You can choose from different types of yachts, durations, and itineraries.

You can also extend your holiday with a stay at a beach club or hotel if you wish2.

Having fun and adventure on and off the water. You can swim, snorkel, dive, kayak, or paddleboard in the clear blue sea, or explore the local culture, cuisine, and nightlife on land.

If you are interested in booking a sailing holiday for singles over 50, you can check out some of the options available from specialist websites.

Sailing holidays for young adults

If you are younger and you’d like something a little livelier, then young adults can find adventure, with a sailing holiday. Here are some pointers to consider:

  • Young adults can opt for a solo sailing holiday that offers privacy and peacefulness.
  • Group sailing holidays are great ways to meet new people of similar interests.
  • Sailing lessons can be invaluable, especially for the first-time sailors.
  • Different destinations offer unique experiences, so choose your trip wisely.

It's worth noting that for those interested in a group holiday, companies typically organize themed sailing trips like partying and beach relaxation.

Pro Tip: Researching early booking discounts, group deals or packages is key when planning your sailing holiday.

How to survive sailing as a single

With the sailing aspect you’ll find yourself in good hands with a professional crew but taking a vacation as a single person does have some things you should consider.

Travelling alone isn’t for everyone, you need to have a little confidence and just be a bit better prepared that if you were going with people, you already know.

I’m sure you’ll quickly make friends onboard, so when you go ashore, you’ll be able to explore with others.

If you choose to go it alone just make sure you have your phone working in whatever country you’re in. Google maps may be very helpful if you’re in some town or city you’ve never been to before.

If you are going somewhere that you don’t speak the language, it would be wise to have a few important phrases prepared.

Frequently Asked Questions

What are sailing holidays for singles?

Sailing holidays for singles is a type of vacation where individuals can take a trip alone and mingle with other like-minded people. These vacations are designed for those who want to experience sailing, get away from everyday life, and make new friends in the process.

Is there an age limit for solo travellers?

No. There is no age limit for solo travellers who want to go on a sailing holiday. Everyone is welcome, and you will find that there are people from all walks of life on the trip with you.

What is a flotilla?

A flotilla is a group of sailors who travel together in a line of boats. This type of sailing is popular among those who want to experience a sense of community and safety while on the water.

Do I need prior sailing experience for a sailing holiday?

No, you do not need prior sailing experience for a sailing vacation. Most companies offer sailing courses and adventures that cater to beginners and experts alike.

Where do sailing holidays typically take place?

There are various destinations for sailing holidays, but some of the most popular ones include the Greek Islands, Croatia, and the Ionian. These areas offer stunning beaches, coves, bays, and turquoise waters that are perfect for sailing.

What is a cabin charter?

A cabin charter is a type of trip where you book a cabin on a shared yacht. This means you have a private room but share the yacht with other travellers.

What are some activities on a sailing holiday?

On a sailing holiday, you can participate in activities such as sailing trips, walks on the beach, dinghy rides, swimming, and enjoying a glass of wine ashore. There are also opportunities to improve your sailing skills and take part in boat trips and day tours.

Can I book a private yacht for a solo trip?

Yes. Many companies offer sailing yacht rental options, where you can rent an entire yacht for yourself or a small group. This is an excellent option for those who want more privacy or have a specific itinerary in mind.

Summary of Sailing Holidays for Singles

Sailing holidays for singles are a terrific way to meet new people and have a great holiday full of exploration and adventure. What are you waiting for?


  • John Sixthsmith

    I'm a freelance writer and avid sailor who loves to share my passion for the sea with others. I've written articles for various sailing magazines and websites, covering topics such as sailing destinations, boat maintenance, navigational tips, and marine wildlife. I went on a short sailing trip whilst on holiday as a child and was instantly hooked. I've been sailing ever since. Although I've done a fair amount of lake sailing in my time, my real passion is the ocean. I hope you enjoy reading this blog about sailing as much as I've enjoyed writing about it.