How to go Sailing for Free

Yesterday, we got a wild ride out on the Long Island Sound. The weather forecast had predicted some stiff winds blowing at 20 knots, but the sound was much angrier. The water seemed calm enough as we headed down wind out of the harbor then just as we went to jibe, the wind picked up. A strong gust threw the main sail across so hard it tore from the mast.


6.5 kts with one sail, yee-haw!

That was the end of our racing day, but we hoisted the genoa and continued on for a pleasure sail. Winds were blowing at 36 knots and even with only one sail, we were booking it at 6.5 knots. While the salty waves flew off our bow, some nice local craft brews were enjoyed without a worry. As much as I felt for our skipper and the damage incurred to his mainsail, this wasn’t my yacht. I was just one of the crew, sailing for free.

Owning a boat is expensive

If you are trying to become financially independent, buying a large boat is probably one of the worst ideas. They are money pits. On the other hand, there is something alluring about sailing. Nothing can compare to being on a sleek vessel that is healed over and cruising through the waves all under the raw power of a strong wind: the satisfaction that you can travel for miles without burning an ounce of fuel, the lack of motor noise allowing you to really experience the howling wind and crashing waves.

Through sailing, you can really learn to read the winds, currents, tides, and become one with the sea. While a 30 ft yacht is not in my inventory, it didn’t have to be – every skipper needs a crew.

Go sailing for free as crew

A large sailboat cannot be manned by a single person efficiently. More often than not, skippers are looking for crew. I met my skipper, Captain Arrrggghhh, through a sailing club at work before I quit my job. One venturing sailor who had sold his boat started the club to help bring together skippers with crew. He would find captains and match them up with crew of varying experience levels for trips where several boats would sail to a destination then raft up for a cookout.

Learn to sail for free

Most captains are more than happy to have newbies on board and teach them how to sail. In return, you simply become their swabbie. There is no democracy at sea, when the captain barks out an order, it’s your job to do their bidding. It’s not so bad though – usually the orders involve fetching beers or tightening sails.


Things calmed down for beer time

How to find an opportunity to go sailing for free

There are several ways to find a captain who is looking for crew. Local sailing clubhouses can be a good spot. Some have social memberships so you can enjoy the club and participate in parties and events where captains are always looking for crew. Another good place is through a sailing club at your work or school. I’ve even seen ads online in places like Craigslist or boating classifieds where captains are seeking crew.

Often times, the skippers are looking to race on a regular basis. In this case, they may be willing to bring on new crew so long as you can remain dedicated to helping them race through a season. As you gain more experience and meet more sailors, it becomes easier to find opportunities to go sailing for free.

Great sunset out on the water

Great sunset out on the water

How to be good sailing crew

If you do manage to get on a boat, here are a few guidelines you should probably follow to be a good swabbie. First, it’s not your boat, but you should still respect it like it is. Wear boat friendly shoes with white or light colored soles. You don’t want to be leaving black scuff marks from you shoes all over you skipper’s boat. Second, be reliable and punctual. Again, it’s not your boat so even if the schedule is not ideal, make it work if you want to go sailing for free. Third, the captain is in charge on the boat, especially when racing.

Have fun and get invited back for more free sailing

Things can get tense – a good sailor obeys orders and doesn’t get sore about a stiff tongue lashing when they screw up. Lastly, bring some beer or snacks to share. Many skippers (and crew) love their rum and ale.

Sailing conditions can range anywhere from a 36-knot rager, to being stuck in a squall with sideways rain and gusts up to 50 knots, to having no wind and sitting idle. Regardless of the conditions, everyone is there to have fun so don’t be a downer and you will surely be invited back for more adventures!

11 thoughts on “How to go Sailing for Free

  1. Very cool. I’ve always wanted to get into sailing but never wanted the hassle of boat ownership. Maybe I’ll try to land some swabbie gigs and learn the ropes.

    • I never invested in anything bigger than a kayak. Boats are great, but finding friends with boats is even better 😉

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  3. Great idea and sounds like a fair trade. Doing some “work” like that can be fun and challenging especially if you just do it every so often. Otherwise, I would imagine it could cost you at least a few hundred $ to take a ride on a boat like that. I’d definitely do it. Good way to have an experience without spending much money.

    • Yep, another way to get on a boat for a sail is to pay for a booze cruise, but this is much cheaper, the beer is better, you make friends, and get to learn something.

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