Singles Sailing Holidays – What Options Are There?

Singles sailing holidays are wonderful for everyone! It is by far the best option to meet new friends in the most natural way. Whether you are single or married, without exception, everybody can enjoy this type of trip!

What are the Sailing Options?

There are several options for singles sailing holidays. For example,

  • You can join a flotilla, meaning sailing with other boats accompanied by a skipper or crew that runs the sailing trip.
  • You have the possibility to hire a cabin on a crewed yacht charter
  • Another option is to share a skippered yacht with a few other people.
  • The sailing course is also an excellent opportunity to learn and meet new friends.
  • If you have the competencies, you can get a bareboat charter with members that you have met on the sailing course or anywhere else.
Croatia Marinas

3 Useful Tips to Have an Enjoyable Sailing Holiday?

Sailing with strangers may be extremely pleasant, while it can be disagreeable. In fact, it’s like gambling and may be very exciting. Something is for sure; it will awaken the adrenaline that was buried deep inside of you. No matter what your choice is, if you decide to share a sailing holiday with one of the options mentioned above, there are several things to take into consideration.

  1. Call your charter broker as early as possible to organize a nice trip with people of the same age.
  2. Try to be very flexible when sailing with others.  The trip will be in any way an unforgettable experience.
  3. Book a few months in advance and make sure that the period of the year allows you to share a sailing trip. There are not always boats that are available, especially in the peak season, since yacht charters are packed with families.

How to Fully Enjoy?

The most important things to keep in mind when sharing a sailing holiday are,

  • Take the trip as an adventure
  • Your goal is only to enjoy and explore beautiful spots.
  • Don’t have too many expectations. You can be disappointed as well as be very surprise
  • Take it easy, no matter what happens; adjust the right radio channel on your positive waves, and you’ll thoroughly enjoy your sailing vacation

Activities to Do on a Sailing Vacation

A sailing holiday offers the chance to enjoy while meeting new friends in the most natural way. Nothing is better than getting up in the morning with the sunrise reflecting on the clear blue water and starting the day with a delicious breakfast.
Who wouldn’t want to discover beautiful isolated islands, make wonderful excursions ashore to stroll in bohemian cities, or do scuba diving with a group to explore the spectacular aqua life?


Whether it’s to discover unknown beautiful places, learn to sail, enrich your history, or increase your sailing skill while meeting new friends, a single sailing trip will be, without any doubt, a lifetime shared memory.

Have you been sailing with other like-minded people? If so, feel free to share your experience in the comments below.

18 thoughts on “Singles Sailing Holidays – What Options Are There?”

  1. Funnily enough these just started up in my area and the guy who owns it ( I know him ) seems to be doing pretty well. We live in an area of South Wales called ferryside – it’s an estuary area!
    A lot of sailing lessons have gone on there over the years and now people are starting to ‘rent’ out vessels for a few days. I’ll have to show my mate this article – it will interest him greatly

    • Hi Chris,

      Thank you for passing by!

      It’s always nice to meet new people especially with the same passion.

      Have a nice day

  2. I never considered a sailing excursion as a single, but it sounds like it would be a lot of fun. I enjoy meeting new people and visiting small areas. I enjoyed my cruise last year as a single and it was fabulous. I am planning my next vacation now, Sailing sounds like a hoot. So, I need to look for a singles sailing or age related sails? What is the best time of year for these, or actually, can you suggest a charter for singles over 60?

    • Hi Kitty,

      As a single I would recommend an organised flotilla with age related. The best time of the year will depend on your chosen destination. I am sure you will enjoy and if you like adventure, then this the perfect holiday.

      If you have any question, please let me know and I will be more than happy to help you

      Thank you for passing by and wish you a nice day

  3. I have always thought about going on a sailing trip. I have been on many cruises and they are nice, but I have thought about the sailing trips and think they would be much more enjoyable. I have even thought about taking some lessons. Do you have any suggestions on good places to take lessons or is it really region specific?

    • Hi Marc,

      They are a big difference between a cruise and a sailing trip. I have a nice article about this subject

      I would definitely suggest you the RYA course.

      Thank you for passing by and wish you a nice day

  4. I have to say, this sounds a lot more relaxing and enjoyable than my first sailing experience. Do not misunderstand, I enjoyed my first sailing trip as well, but I was also doing a lot of work seeing as my dad volunteered my brother and I to help the captain on our short expedition.

    I understand this to be a singles only deal, however I am married and curious if this is available in that format? Also, where I am from now there are not many sail boat trips going on and was wondering where would one find this trips? In U.S. or other countries?

    Great Post!

    • Hi Chris,

      Yes, usually the captain and the teamwork harder than passengers, but it’s a great experience and I am sure you enjoyed it. I personally think that controlling a boat by your self gives a lot of confidence. But today many boats are easy to control .Sailing is for everyone, not only for singles, this is a great way to meet new people if you are a single person. You can take a look at the destinations on my website to give you an idea.

      I hope it helped and if you have any other questions, feel free to ask!

      Have a nice day:)

  5. Taking a yacht charter seems like a great vacation! My wife and I have gone on cruises before. Theses were on very large ships with hundreds of other travelers. A yacht trip sounds like a much more intimate setting. We will have to try it out someday! Thanks for the info.

  6. Hi,
    Wow what an enticing idea.
    I didn’t know there were so many different ways to have a sailing holiday and it’s definitely something that would interest me.
    Is there a particular part of the world and time of year you would recommend? I do love to travel.

    • Hi Alison,

      Great to see you again on my website. It depends on your personal choice, but I personally love the Bahamas, especially in the winter, the only inconvenient at that time of the year it’s usually crowded and it’s also more expensive. The summer is hot and humid, not crowded at all and the prices drop down.

      Thank you for the comment and wish you to sail soon

      Have a wonderful day:)

  7. I’m not sure how I feel about the idea of a sailing holiday alone although a mate of mine was considering it about a year back ( I’m not single so I don’t qualify! ). I would of thought the dangers of the sea and the isolation may put me off a bit – however it doesn’t seem to have put him off!

    • Hi Chris,

      How nice to hear from you again 🙂

      I personally think it is much more dangerous to be on the roads than to navigate on the sea .The percentage of car accidents is much higher than boat’s accidents.

      Thank you for the comment and I wish you a wonderful day!

  8. What a great article and such a great idea! Sailing is one of the most relaxing and exciting activities out there. There is nothing better than listening to the water rush up against the boat. This seems like such a great way to see a lot of great places and stop at bustling towns. Have you been on one of these sailing singles trips?

    • Hi Eric,

      Yes, I did and still do:) I love the Mediterranean sea, that’s where I spend my time sailing:)

      Thank you for the comment, I really appreciate!

      Have a wonderful day!

  9. I have to admit. There are moments in life where you just want to be single and you’re not into relationship because you’re not ready with the commitment.

    I’m one of them and personally, I am not looking for someone right now. Now on the sailing part, firsty, thanks for listing out the options.

    There’s more than just to sail in the sea. It’s about network, getting to know more people, being sociable.

    Nice of you to put such context here, which I think sailing is a super fun activity overall.

    • Hi Tar,

      I am very happy to see again on my website:)

      Yes, you’re right, you need to be ready for commitment, but you know, most of the time life can surprise us and sometimes it can be very fun, especially when we don’t expect it:)

      It’s always great to share the same passion with other passionates and sailing is a fantastic activity to practice!

      Thank you for passing by and for the comment. I really appreciate:)

      I wish you a wonderful day!


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