How to Plan a Daysail

By: Cruising Tips, Learn To Sail

So you’ve just added that ASA 101 seal to your logbook, and you’re excited to get underway for your first day sail. After all of your hard work, studying, and practicing, it’s finally your time to rally some sailing friends (your crew) and reap the rewards of the sailing lifestyle. 

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, it’s time to craft a plan for the day.

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


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.


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 skills and confidence, setting the stage for the rest of your sailing career.


Use a chart to help plan your first daysail. Even though it will likely be known or local waters, you’ll want to play it by the book and chart your course. 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, whether using paper charts or a GPS chartplotter.


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

Begin planning for these elements 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.

Set a time for your crew to meet up early enough in the day so that you have plenty of time before sunset, if you’re planning to complete the sail before dark. Check the wind, perhaps using one of our member partners like PredictWind. Too much or too little wind can make for a more adventurous sail than you want, or leave you stuck out on the water longer than you hoped for. As you begin your sailing career you should avoid sailing in wind over 15 knots or when whitecaps are prevalent. You should become familiar with currents and tides if your local sailing area is prone to these factors so that you don’t end up in a precarious situation.


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, as well as provisions for any snacks or meals, and plenty of water.  

Here are a few items that you should always have when sailing:

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

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. Tell your contact where you plan to sail, who you are sailing with, and when you expect to return.


The most important part is always your why. You learned to sail because you enjoy the freedom of being on the water, feeling the wind against your skin, and the joy of friendships on the boat as you live your sailing stories together.

Now it’s time to get out there!