Nineteen Ways to Go Sailing if You Don’t Own a Sailboat

Often we have people call and say they can’t charter a yacht because they have no experience … and how can they get experience if they can not charter a boat?

So here is a bunch of ways to get lots of sailing experience if you don’t own a boat. At NauticEd we are very practical experience-centric. We believe that competence can only be gained through both knowledge and practiced skills. Thus we have a free sailor’s electronic logbook and we encourage everyone to have at least 50 days of sailing experience in their logbook before they go charter a yacht on a sailing vacation.

Sign up here for a free sailor’s logbook and get two free sailing courses while you are at it.

nineteen ways to go sailing

The point is – in order to be a competent skipper, you must have experience as well as master of the vessel experience. To do this start easy and work higher. Jumping into an offshore cruise as master or chartering a boat for a week to cruise and navigate around a large set of islands IS NOT a prudent idea, but taking out a boat on a nice day with an easy breeze in an easy local waterway IS prudent. Then work your way up from there. Here are the ways to do that.

Call a friend with a boat

This is the top of the list because unbeknownst to all … people with boats cannot find people to go sailing with. You’d think they’d be the most popular people on the planet. But in reality, because EVERYONE is busy these days trying to get two people together who have time is difficult. Thus boats just sit in Marinas and don’t get used and the owner starts to think about selling it because he does not use it. Then along comes a shink knight in armor friend and says “I’m going sailing today on your boat, would you like to come?” Haa haa – a friend actually did that to me once. Guess what – we went sailing that day. So, while you might think it is rude to just invite yourself, it is actually fully welcomed.

Join your local yacht club.

Despite their stuffy reputation, yacht clubs are desperate for members and are quite welcoming. Club members are just like everyone else – they can’t find people to go sailing with.

Post a post-it note on the Local Yacht Club notice board that you are willing to be crew for the regatta

Yacht club members who race are desperate to find a reliable crew to show up every week to be onboard.

Join a professionally shared boat program

I invented SailTime in 2001. I did it because I wanted a really nice boat and was not willing to pay $150k for one. Thus I saw a market need. I sold it in 2007 after seeing a bigger market need to revamp sailing education – thus NauticEd.

Create your own private share boat

Outside the rule of this blog but not really. Buy a boat and put an ad on craigslist or trademe or whatever that you are looking for monthly membership partners. In Austin here my friend shares out a really nice Beneteau 373. Another friend shares a Jeanneau 410.  The boat costs them nothing as long as he keeps about 5 people in the share program. Those guys only pay about $500 per month for a ridiculously nice boat. They all use the NauticEd boat sharing software.

Join a private share group

Look on craigslist or trademe or where ever and join an existing group.

Hang out on the docks

One day I was going out sailing with my partner and we saw a couple walking the docks obviously dreaming. We invited them along.

Charter a Boat for a day

Grab some friends to reduce the cost way down and get out on the water for a day.

Join a Sailing Club

These are programs where an organization has a bunch of yachts and for a small monthly membership fee ($50-$100) you can use their boats. You pay a vastly reduced price each time you use one of their boats. You meet tons of people.

Call a friend and share his boat

Chances are every one of your friends or acquaintances are getting pressured to sell the boat because they don’t use it enough. If you offer to pay the slip fee or something each month (and are competent) chances are your friend will jump at the opportunity.

Post on facebook sailing travel groups that you’re looking to join a group who are going to the Caribbean

Usually, a group that is getting together, always want an extra person or two to help defray the costs of the yacht charter.

Post on facebook that you’re putting a group together to charter in the Caribbean

Be a bit more proactive. You’d be surprised. You’ll get people to instantly jump at the opportunity. One of our friends who was not qualified to captain gave a spare cabin to another of our friends to be the captain. Then he filled the rest of the boat and he does not have to pay for the captain – smart!

Join Local Sailing MeetUp groups

Go to

Go to a crew wanted website

  • Become a Coboaters member ( Traditional crew finder websites focus more on offshore and long-distance sailing passages, while Coboaters allows you to meet boat owners and crew for local sailing days, regattas, coastal cruises, and deliveries in North America including the great lakes and the Caribbean.

There are others

Go on a sailing training vacation

We have dozens of schools all over the world whereby you can rent a cabin on a sailing training vacation. See our sailing schools in Antigua, Italy, BVI, Croatia, or who train people to cross oceans.

Go on a Sailing Vacation

Grab a group of friends who want to take the best vacation of their lives. Then consult with NauticEd on the best place that matches your and your friend’s desires – we will hire the Captain for you. We’ve been just about everywhere so our advice is sound. We’ll organize the entire sailing vacation for you. The cost can be quite inexpensive when you divide the costs up per person. Go to Sailing Vacations to make an initial request.

Join a NauticEd Flotilla

NauticEd hosts several flotillas each year to the Mediterranean and the Caribbean. Often there is a boat where you can join “by the cabin”. Typically there are 4-5 cabins. You’re buying 1 cabin for the week.  See the sailing flotilla list here

Be crew on a yacht delivery

Yachts are constantly being moved long distances. The captains can’t do it alone, they must have adequate crew onboard.

Do a Caribbean regatta

There are 5-6 famous and fun weeklong regattas in the Caribbean each year. You can get on a boat sometimes for free or sometimes for a small fee.

Call a NauticEd School

Get some excellent training from a professional. Actually not an expensive idea. A client just called and said they wanted to charter in the Mediterranean but he was nervous because of the Mediterranean mooring technique. My response was simply, if you are nervous you should not be: just get some professional training, and then you won’t bang up the boat. NauticEd’s motto is “The More You Learn, The Greater Is Life’s Adventure”.

Bonus #20 – Virtual Reality

With NauticEd’s 3D virtual reality sailing program, you really feel like you are sailing a boat. Really! You can learn to sail and race against the AI or against friends. Try it out. All you need is a Meta Quest device. Here are the instructions to get started.

Buy a Boat

Alright, and finally if you must – buy a boat. You can get a relatively inexpensive starter boat and you can even share with a friend to upgrade the quality and share the slip.  Here is a good article written by our friends at on choosing the best beginner sailboats. At RightBoat, you can buy a sailboat or list your boat for sale.

Try Virtual Reality Sailing on the Oculus and Meta Quest
My vision for NauticEd is to provide the highest quality sailing and boating education available - and deliver competence wherever sailors live and go.
Grant Headifen
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Last updated on June 4th, 2023