Planning a Day Sail

By: Cruising Tips, Learn To Sail

You finish up your ASA 101 Basic Keelboat courses and you are confident to go out sailing on your own. After all of your hard work, studying, and practicing, your next step is your first daysail.

This is a big moment in a sailor’s journey as you begin the process of performing all of the duties and responsibilities on a boat as the skipper.  Now, you must plan that first daysail.

With proper planning, your first sail will be enjoyable and safe. 

Let’s plan your first daysail.


Your first daysail should start small. This is your shake-out sail where you confirm that you have mastered your newly acquired skills. Stay close to home and ease into this first journey. Choose a nearby point to head to or a lunch spot that is an easy sail away.  Choose protected waters or a quick loop around an island. You’ll feel a sense of accomplishment and you’ll reinforce your skillset.


Use a chart to help plan your first daysail.  Utilize your aids to navigation and identify any areas that must be avoided due to depth or obstacle concerns.  On the chart identify your departure point and your destination.  Make a clear plan for your route.


Weather, tides, and currents are extremely important factors that go into planning your daysail. 

Too much or too little wind can hamper your sail and not having a good grasp on the currents or tides could put you in a precarious situation.  You should become familiar with currents and tides if your local sailing area is prone to these factors. As you begin your sailing career you should avoid sailing in wind over 15 knots or when whitecaps are prevalent. 

If you are planning a sail, begin well ahead of time. Check the extended weather forecast and study the tide tables to pick a good sailing date. Continue to check the weather every day, to see if it’s changing, especially on the night before and the morning of your planned sail. It is always important to remember that the weather on shore is not always what you will experience on the water.


For your first daysail it is a good idea to have others who have some sailing knowledge along for the trip.  You will eventually take friends and family out for a daysail but as you get started think about inviting someone with sailing experience or perhaps someone you took ASA 101 with. Having an experienced crew on your sail will give you peace of mind. 


If you are renting a boat, it should have the required safety equipment aboard, but confirm that ahead of time. Expect it to have only the bare-essential gear for sailing and plan on bringing whatever else you need, including the charts you used for planning and some basic supplies for the crew.  

Some things that you should always have when sailing:

  • An extra jacket
  • Sunscreen
  • Binoculars
  • VHF Radio
  • Water
  • First Aid Kit
  • Comfortable sailing shoes with non-slip soles
  • An extra set of dry clothes. Just in case.
  • Cell phone
  • Sailing gloves
  • Hat and sunglasses

Important Things to Remember

File a float plan!

If you’ve told someone ashore your destination and when you expect to return, you’ve filed a float plan. The purpose of a float plan is to provide information that will be helpful to authorities and others in the event you get into difficulties. The more detailed and specific the information it contains, the more useful it will be.