Preparation Suggestions for taking Friends on a Day Sail

Preparation Suggestions for taking Friends on a Day Sail

Are you taking some friends (especially non-sailing friends) out for a day sail on the water? What preparation suggestions do you have for them?

Here are a few suggestions:

Overall Suggestions

  • Check Weather Forecast
    Monitor weather forecasts leading up to the day of sailing to ensure safe conditions.
  • Plan the Route
    Decide on a sailing route considering factors like wind direction, currents, and points of interest.
  • Inspect the Boat
    Conduct a thorough inspection of the boat, checking for any mechanical issues, fuel levels, and safety equipment.
  • Safety Briefing
    Provide a safety briefing for all passengers, highlighting emergency procedures, location of life jackets, and how to move around the boat safely.
  • Pack Essentials
    Bring along essentials such as sunscreen, hats, sunglasses, water bottles, snacks, and any necessary medications. (additional details in next section below). Beverage containers (including for water) should tightly seal closed, to not spill while on the boat.
  • Dress Appropriately
    Advise guests to wear appropriate clothing for the weather conditions, including layers, non-slip shoes, and waterproof gear if needed.
  • (additional details in next section below)
  • Discuss Sailing Basics
    Familiarize guests with basic sailing terminology and concepts, such as points of sail, tacking, and jibing. If you are interested in participating / helping with tacking and jibing (sailing maneuvers), consider buying some sailing gloves, such as:
    Short Fingers 
    Long Fingers
    (no endorsement or verifying any product claims).
  • Assign Roles
    Assign roles to each guest based on their experience level and interest, such as helmsman, trimmer, or lookout.
  • Contribute
    At the end of the trip you’ll be asked to help clean up and put away the boat. Do your part.
  • Emergency Preparedness
    Ensure everyone knows how to use safety equipment, including life jackets, fire extinguishers, and emergency signaling devices.
  • Communicate Expectations
    Clearly communicate expectations regarding behavior on board, such as staying seated while under sail and helping with tasks when needed.
  • Respect the Environment
    Emphasize the importance of respecting marine life and the environment, including proper waste disposal and avoiding damage to coral reefs or sensitive habitats.
  • Enjoy the Experience
    Encourage guests to relax and enjoy the sailing experience, taking in the scenery and bonding with fellow crew members.

By following these preparation suggestions, you can ensure a safe, enjoyable, and memorable day sail with friends.


Additional details for “Pack Essentials” and “Dress Appropriately”:

  • Dressing in Layers
    Wear a short-sleeve shirt, it can be quite warm in the sun
    Consider bringing long pants or sweats if wearing shorts.
    Bring a jacket or hoodie to ward off chilly ocean winds, even on sunny days.
    Pack foul weather gear if there's a chance of rain or strong winds.

  • Hat and Sunglasses
    Consider a wide-brimmed hat with a strap to shield from the sun.
    In cooler weather, a beanie/ski cap will help keep you warm
    Wear sunglasses with a strap to keep them secure, especially if you wear regular eyeglasses (consider bringing cheap sunglasses). Wearing jewelry, such as rings or bracelets, is not recommended.

  • Sunscreen
    You’ll get plenty of UV rays, even on an overcast day.
    Make sure to protect any skin showing including the back of your neck, your face (including nose and ears), and the tops of your feet (if you’re wearing sandal-style boat shoes)

  • Footwear
    Opt for light-soled sneakers or non-marking boat shoes for safety and deck protection (so you don’t leave marks on the deck). Closed-toed light-soled / non-marking boat shoes are recommended.

  • Drinks and Beverages
    Bring water to stay hydrated. 
    Beverage containers (including for water) should tightly seal closed, to not spill while on the boat.
    Consider bringing ginger ale for motion sickness.
    Pack canned or plastic-bottled drinks to share; avoid red wine due to potential staining.

  • Coffee
    Yes, we had to call this one out :)
    Bring it in a travel mug/container (one that can seal closed so coffee will not spill while on the boat).
    Use promo code "sailwithfriends" for a discount.

  • Coolers
    Soft-sided coolers are preferable to avoid scratching the boat's interior trim.

  • Food and Snacks
    Choose shareable finger foods; disposable plates and utensils ease cleanup. Avoid snacks that are messy or leave a residue on your fingers. 

  • Hand Sanitizer
    Essential for hygiene, especially if using the head (toilet) onboard. Depending on the size of the sailboat, it might not have an actual head (toilet).

  • Camera and Binoculars
    Use a waterproof or pocket-sized camera; secure with a lanyard to prevent loss.
    Binoculars are optional but useful for wildlife spotting.

  • Motion Sickness Medication
    Consider taking medication in advance if prone to seasickness; ginger candies can often be effective against nausea.
    In the event that you don’t feel well, you must stay on deck. Going below, where the difference between what your eyes see and what your inner ears feel is even greater, and there may be smells, will make it worse; you and/or your kids will not get to the head (toilet) in time.
    Looking at the horizon, or closing your eyes can help. Steering the boat for a while often helps.
    Sit on the leeward (downwind) side of the boat (the side of the boat where the sails are) in case of urgent need. Hold on to the rigging or lifelines when you (or your kids) lean out over the edge of the boat.

  • Cash
    Bring cash to contribute to rental costs if applicable. Obviously the rate may vary depending on the time of year, the size of the boat, and the number of passengers, so ask ahead of time how much you need to chip in.

  • Positive Attitude
    Embrace the adventure, even in adverse (rough, cold, or rainy) weather conditions.


Going on a Day Sail? Don't make other plans for later in the day.

Embarking on a day sail is a liberating experience, as you let the wind dictate your course and direction. It's a journey filled with spontaneity and adventure, where each moment unfolds organically with the rhythm of the waves. With no set return time, you're free to immerse yourself fully in the sailing experience, savoring the beauty of the open water without the constraints of a predetermined schedule. So, leave your plans on land behind and embrace the serendipity of the sea as you set sail into the unknown. 

Think of it as an all day activity (or at least a 4+ hour activity for a half day). Even as a picnic excursion on the water. Don't make other definitive plans for later in the day. Sailboats operate at the whim of the wind, the tide, and the weather; the skipper may have to change plans depending on the conditions. We may get back to the dock later than planned. That means you get to spend even more time having fun on the boat.


What additional preparation suggestions would you include?
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