Sailing Vacations for Singles – 3 Best Options!

The thought of Travelling alone can sometimes be scary and intimidating, especially when you find yourself in a country you’ve never been to and among people you don’t know. But… When you think about it, though, it can be very exciting!

In fact, there are many advantages to traveling alone, and the option of sailing vacations for singles will not only offer you the getaway of a lifetime but will make you discover things you didn’t know about yourself!

However, there are a few ways to enjoy a sailing vacation with other like-minded people, and in this article, I have broken down all the different possibilities to have an unforgettable sailing experience.

What Are the Best Options?

There are three possibilities to sail with singles, which are:

  • Rent a cabin (by the cabin charter)
  • Flotilla
  • Sailing tour

Not everyone knows about these alternatives, so before going any further, let me explain what these options are all about and what to expect!


Option 1# – A Flotilla

A flotilla is a group of yachts that sail together on the same route and are specially arranged for singles, small groups, and couples who wish to sail with other passionate. Anyone can participate in a flotilla and choose either to charter the whole yacht or just reserve a place on the boat. Both options offer the possibility to hire a vessel with or without a skipper.

What’s great about a Flotilla is that it allows you to sail in your proper rhythm, and you can also spend the day on your own if you wish or enjoy sailing with all the participants. In any way, all the yachts will meet at a designated destination where the lead crew will welcome you and your boat.

Boats sailing in flotilla


What to Expect On a Flotilla?

Arriving at the base, you’ll get to know the crew and the schedule of your week, and you’ll have a welcome party. There you meet all the participants as well as all the skippers, engineers, and hostesses. The leader will give brief instructions about the security on board, the weather forecast, the daily itinerary, and safe anchorages.

After this pleasant meeting, the flotilla adventure will start by sailing among beautiful destinations, but sailing is certainly not the only activity you’ll be practicing.

Here is a summary of all the fun things you will enjoy doing:

  • Visit exciting sightseeing
  • Participate in wine-tasting Tours.
  • Eat together at the restaurant
  • Explore local attractions
  • Enjoy water sports
  • Dance in a fun bar atmosphere

At the end of the flotilla, if you wish, you can join a thrilling regatta to compete with other participants and show all the skills you have gained during the sailing trip. Who knows, you might be the winner!

But that’s not all! After the regatta, you’ll have a nice party with all the members to have fun, exchange some of your experiences and maybe your contacts as well.

What Type of Flotilla?

There are two types of flotillas, bareboat and skippered. Let’s see what these mean:

Skippered flotilla

A professional skipper navigates the boat and takes care of all the sailing tasks. This option is great if you don’t have any sailing experience or you choose to enjoy the trip thoroughly without worrying about navigation.

Bareboat Flotilla

Bareboat means that you are the one who takes care of the navigation. This option is great if you have a sailing certification and the skill to manage your own yacht.

Advantages and Disadvantages of a Flotilla


  • No need for any sailing skill (With a skipper)
  • Excellent for singles to meet new friends
  • Complete support of a professional crew
  • Superb organization
  • Full freedom to manage your own cadence.(If you are the captain or you have a skipper onboard)
  • Help children to meet new friends quickly
  • There are many kinds of flotillas, and not all of them will meet everyone’s needs.
  • If you prefer to enjoy your own company and don’t really like night parties, then a private yacht charter will be the best option.

 Option 2# – By the Cabin Charter

By the cabin, charter means renting a single cabin on a crewed or a skippered yacht charter without having to hire the entire boat.
This option is fantastic for people on a budget, couples, singles, and even experienced sailors that don’t want to bother with navigation.

A cabin yacht charter


What to Expect on a Cabin Charter?

First of all, you will have a cabin with a double bed and a private bathroom for yourself, and you’ll be sharing the entire boat with 6 to 8 passengers. A cabin charter is a perfect choice to sail in luxury, allowing you to enjoy all the exclusive services that a crewed yacht charter offers, and all this for the price of a cabin charter. Isn’t great! Not just you’ll be pampered the whole trip by the crew while sailing through beautiful destinations, but you will meet new friends.
Also, there are many activities you will do on a charter boat, such as:

  • Watersports
  • Onshore excursions
  • Historical tours
  • Dining at the restaurants
  • Night parties
  • Strolling and shopping in towns

Advantages and Disadvantages of a Cabin Charter


  • There is no need to charter the entire yacht to sail
  • The cost of a cabin is much cheaper than a yacht charter
  • Sailing experience is not required
  • An excellent way to meet new friends


  • It can be a bit stressful to sail with strangers
  • You’ll be dependent on the schedule of the boat
  • You don’t have control of the boat

Options #3 – Sailing Tour

A sailing tour is a group of people of all ages sharing the same boat and the same activities. It is a fantastic way for solo travelers wanting to sail on a budget, have fun, and meet new friends.

What to Expect on a Sailing Tour?

You’ll be sailing with a small group of a maximum of 8 people on a skippered yacht. Don’t expect to have a private room and a private bathroom for yourself unless you decide to add a bit of extra. You can choose the sailing tour and the destination you wish to, except the boat, as it is a tour company and not a charter company. However, you will spend more time outside your room, sailing, exploring beautiful places, and making friends. If sharing the room is a concern for you, then slipping on the deck under the stars would be a great alternative.

Sailing tours are well organized, and apart from taking the helm, you’ll do plenty of fun activities such as:

  • Explore ancient ruins and sightseeing
  • Discover secluded beaches
  • Kayaking through beautiful inlets
  • Visit fantastic architectures
  • Enjoy free time to stroll around lovely marinas and old towns
  • Experience vibrant nightlife
  • Hike on national parks

Advantages and Disadvantages of Sailing Tours


  • Fantastic opportunity to make new friends
  • No need to have sailing experience
  • Excellent for people wishing to sail on a budget
  • Best for solo travelers


  • You will be sharing the same room, but it could be fun if you get along with your roommate.
  • Meals are not included in the price, but it gives you the flexibility to decide where and with whom to eat.

So…What is the Best Option?

In my opinion, this will depend on the purpose of your trip.
For example, If you seek a relaxing and delightful sailing excursion, then without any hesitation, a cabin charter will be a perfect choice.
If you wish to have an exciting sailing regatta, then you should choose Flotilla!
But, if a sailing adventure is what you want, then you should definitely opt for a sailing tour.


How to Make Friends?

Maybe you’ll find this funny, but solo travelers tend to be much more approachable than groups. So this could be one of the reasons you wouldn’t hesitate to go on a single sailing voyage. Some people will find it very easy to make friends, while others will find it much more challenging. And if it’s the case for you, then these tips might help you break the ice.

  • Experience an organized trip with people you’ve never met, just for a few days or the weekend, and see how easy it is to make friends.
  • Please, turn off your phone. People will be uncomfortable approaching you if they see you talking on the phone.
  • Food has something magical; it brings people together and makes them more sociable. So don’t hesitate to have dinner with strangers; you may find things in common.

 Friends on a banana boat


What You’ll Learn About Yourself?

A few years ago, I took my courage in both hands and went on a sailing tour with Viator, more precisely in Phuket, on a catamaran. By the way, I had an amazing experience!
Did I learn new things about myself? Yes…Of course! There are several things I have discovered during my sailing trip. And some of the examples below will surely be familiar to you as well.

  • I’ve become more independent than I was once
  • My self-confidence has grown
  • I made friends easily
  • I learned to be alone
  • I got over my fears


  1. You will experience a much more intimate and friendly trip on a small boat than on a big vessel.
  2. A catamaran will offer you more privacy, comfort, and space than any other boat. So if you can, choose a catamaran for your sailing trip!
  3. Try to connect with other people who will be in the same boat on social media or forums before your departure. It can help decrease the stress.
  4. It is not rare to see people suffering from seasickness while sailing. Bring some patches and use one of the few hours before the embarkation. It will definitely help!
  5. Check what to pack for a sailing holiday. Very important!
  6. Speak with your charter or tour company and make sure that they match you well with other like-minded people sharing the same affinities.

My Conclusion

Many people are very anxious the first day when they come on board, but after spending some time together the first night, the stress begins to disappear. Most of the guests met each other during the trip and the year after came back with the same group. This means they had a magnificent time. Wouldn’t you like to enjoy it as well? If so, then what are you waiting for, pack your bag and book your trip now! You’ll be happy you did!


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Have you been on a sailing trip for singles? If so, feel free to share your experience in the comment below!

6 thoughts on “Sailing Vacations for Singles – 3 Best Options!”

  1. These are great tips for going on sailing vacations. I think I’m more of a solo traveller and would definitely love to have the whole boat to myself, with just a professional skipper to handle the navigation.

    I wonder how much can I expect to pay, if I were to opt for this type of sailing. Travelling with people might be fun, but I think 6 to 8 people in a boat is a little too much for me.

    Great article!

    • Hi Farhan,

      If you wish to sail without the company of other like-minded people, then you’ll need to rent the whole boat for yourself. It is a great option, but it will be much more expensive than a shared vessel.

      Not everyone is able to share the boat with strangers:)

      However, as I have mentioned it in the precedent comment, it is hard to evaluate the exact price as it will depend on the type of boat, the destination, the duration of the trip and many other details.

      If you want to know the accurate price, you can send an inquiry form through my website and one of my partners will get back to you with a free charter quote.

      Please don’t hesitate to contact me with any question, I’ll be glad to help:)

      Thank you for the comment and wish you a lovely day!

  2. I like the site and I love the way it’s laid out, it’s so beautiful to look at. The only thing is it doesn’t include the prices other than that the site looks really good. I’m already planning future trips with my wife and kids. We took a trip to myrtle beach earlier in the year but we love to go outside of the country.

    • Hi Randy,

      I am glad you like my website, thank you for the compliment!

      It is hard to evaluate an exact price because the rates depend on the kind of trip, the type of boat and many other important details.

      If you want further information about prices, then I would suggest you ask the company you choose to sail with.

      Also, you can send an inquiry on the website and one my partners will get back to you as soon as possible with the accurate price. I work only with reputable and reliable companies. So, you don’t have to worry about this:)

      I hope it helped and if you need to know more details, please don’t hesitate to contact me, I’ll be more than happy to assist!

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

  3. It’s on my post-divorce bucket list to a Sailing Tour with a small group (in the next couple of years, as a single). Are there any companies that do this within the US waters over a long weekend? I would like to either explore north east or west waters (Washington State/Canada, Nova Scotia/Maine/Canada). My ideal would be to fly into a major city such as Seattle, explore the city for a day then hop on the boat for a couple of days.) Not sure if these types of trips are an option. It’s not the easiest to research so I found your website very informative.

    • Hi Katie,

      I don’t know if charter companies do these routes; this is something I will have to check.
      As you plan this trip in a few years, you surely have the time to plan your trip:)
      I’ll get back to you as soon as I have an answer.
      Thank you for the comment, and I wish you a lovely day!


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