How To Not Look Like A Rookie On Your First Day Sailing

A ship at harbor is safe but that's not what ships are for. 

If you live close to any substantial body of water, chances are you’ll one day get that invite from a friend, colleague, or cousin to enjoy an afternoon out on the water via their sail boat. For seasoned watermen a day with several fathoms beneath the keel is time well spent, but to someone who doesn’t know what a fathom or a keel is, the idea of leaving the dock can be a bit intimidating. There is no need to fret! Like other many passion pursuits in life, sailing for the first time is an experience you will likely never forget.

My husband and I have taken many virgin sailors on their first voyage on “SS Big Enough.” Most of our sailing trips are relaxing but nothing can turn a relaxing day into a nightmare quicker than someone getting hurt or gear breaking due to a lack of basic knowledge.

Before I get started, I must admit my credentials as a sailor are limited. I’m no expert by any stretch of the imagination, but having lived aboard our boat for 1.5 years, I think I can offer simple practices to help you look like you’re an experienced sailor. Just a few bits of simple knowledge can mean the difference between your ego sinking or swimming. These are my top five things to know to not look like a rookie on your first day of sailing. 

Beginner Sailing Terms Everyone Should Know

These handy terms can provide a helpful overview of sailing basics you may want to become familiar with.

Stern - aka the back of the boat. The stern is also known as the aft.  

Bow - The front end of any boat is called the bow. For those slow learners, it’s the pointy end.

Port - Because “right” and “left” can become confusing sailing terms when used out in the open waters, port is used to define the left-hand side of the boat as it relates to the bow, or front. If you face the bow, everything on the left half of the boat is on the port side.

Starboard - And as you might have guessed, “Starboard” is everything to the right side when you are facing the bow.

Boom - The boom is the horizontal pole that extends from the bottom of the mast. If you’re not paying attention, the boom might make that exact sound as it hits your head, “Boom!” 

Tacking – This sailing maneuver refers to turning the bow of the boat through the wind so that the wind changes from one side of the boat to the other side. The boom of a boat will always shift from one side to the other when performing a tack or a jibe. 

Jibing - Jibing is similar to tacking because it is also turning the boat, but a jib is turning when the wind is coming from behind (or the stearn!)

Dress the part

Attire of a sailor is closer to beachwear than dinner at the country club. Shorts, t-shirts, bikinis and board shorts are always appropriate. A pair of boat shoes (like speary topsiders) is ideal footwear. Flip flops or tennis shoes are usually frowned upon, but it’s not a major faux pas. Non-marking shoes will keep the captain happy as they won’t scratch or mark up the decks.

For those with long hair, a bandana or head wrap is always useful. If you have wild hair like I do, the wind will always seem to find the right direction to whip your hair straight into your eyes. A head wrap will make for an easy transition from water to shore.

Don’t show up empty handed

When we take a group out sailing, we are always looking for a good time. Bring some snacks and drinks for everyone to share. 

Recognize the hazards

When I was younger, my Dad would take me out sailing on our tiny lazer called “Patto.” We would fly across the ocean and bounce through the waves. When he would quickly tack into the wind, there were many occasions where I wasn’t paying attention and fell right into the drink. To avoid falling into the water, it’s important to be aware of where the boat is headed and when the boom will swing. Sailors have long used the adage, “one hand for yourself and one for the ship.” 

Be a good first mate

It takes at least two people to sail SS Big Enough. However, the more help we can get from others the better it is for everyone, including for the captain. Even if you don’t know what you have to do, pay attention and ask how you can help. You might get the chance to steer the boat, or even learn how to read the wind and put up the sails.

Most of all, relax and enjoy the day! Crack a cold drink and take in the beauty of it all!

With love + blessings,