Frequently Asked Questions

What Should I Wear?

Always dress for the season. When you are on the water it is typically cooler than being on shore so consider layering and if rain is possible, bring a light rain jacket or poncho. Soft-soled, non-marking shoes are a great way to protect the boat and yourself!

Can I Bring Food And/or Drinks?

You are welcome to bring already prepared snacks and drinks of your choice. Messy or sticky food items that are likely to spill and items that need preparation, heating or cutlery, should be left at home, as well as hard alcohol (whiskey, rum, tequila, etc.) and glass containers (wine bottles are fine, but will need to stay in the cockpit and poured into plastic containers). The amount of food you bring should also be appropriate for the number of guests and the length of your charter. The snacks that work the best in our experience includes light sandwiches, dried or fresh fruits, raw cut veggies, nuts, pre-cut cheese blocks, and cold meats like salami and pepperoni. Always consume alcoholic beverages responsibly while out on the water. 

What Is Your Policy on Drugs and Smoking/Vaping?

Our vessels are completely drug free and we ask that you don’t smoke or vape for safety and welfare of all onboard.

What Else Should I Bring?

Sun Protection – All our boats have biminis for shade, but you should consider bringing sun protection that suits you best, including sun glasses, a hat or cap, sunscreen and UV protective clothing.   

Motion Sickness Remedies – Depending on the length of your charter, we will probably spend a lot of time on inter coastal waters with little or no swell. If we head out into the Atlantic that could change, and if you suffer from motion sickness, you should consider appropriate medications, pressure point wrist bands, patches behind the ear, and other remedies typically available from pharmacies. 

Camera Equipment – You may see a range of wildlife on your trip, including dolphins, sea turtles, manatees, the wild horses of Cumberland Island, and a variety of aquatic birdlife. You will see Fort Clinch from a different perspective and if you timed it right, some of the most amazing sunsets in the country. Take a deep breath and soak it all in, but you may want to capture the moment for your social media page or favorite trip-album, so make sure you have a camera or phone ready!

What Do We Do if There Is Poor Weather?

Sailing is inherently depended on the weather but the range of possible sailing conditions is larger than many people think. While safety is our top priority, we try and make the best of what mother nature provides us and tailor our sailing area accordingly. We will let you know if we think the conditions will not allow for a safe experience and reschedule to a time that suits you.

Should I Tip the Captain?

Tipping your captain is optional, and much appreciated. They work hard to make sure you have a safe and fun time out on the water. Feel free to tip your captain directly or add it into your credit card payment.

Where Is the Marina?

The boats are located at 3 S Front St, Fernandina Beach 32034, the dock next to Brett’s Waterway Cafe in the Historic Downtown of Fernandina. Walk down the dock on the left side of Brett’s Waterway Cafe and take the second ramp to the left (dock “E”). Follow down the ramp and you’ll see the boats with Windward decals. Your captain will be waiting to welcome you onboard! There is plenty of free parking, but try to arrive 15 minutes early as you may have to walk a block or so. 

Do You Provide Personal Flotation Devices (PFD’s)?

Each boat is equipped with sufficient adult and children PFD’s. While on a captained charter, adults are not required to where a PFD, although they will be easily accessible. Depending on the age of the child or infant, the captain may require the use of a child or infant PFD.

Can I Bring a Pet?

Your safety is our top concern, and pets could create unnecessary distractions and obstacles while we navigate, manage sails and keep a proper lookout for dangers. Thanks for leaving your animal companions at home for this one!

Is the Boat Handicap or Wheelchair Accessible?

Our aim is to get as many people out on the water as possible, but the reality of a sailboat requires some physical dexterity. Call us to discuss any challenges that might make your sailing experience a little harder and we will see if we can accommodate your needs. However, the sailboats are not wheelchair accessible and you will need to be able to climb steps, be able to step over from the dock to the boat and then step down into the cockpit.


What if I Need to Cancel My Reservation?

We get it, life happens! We will try and accommodate any reasonable cancellation and refund requests made more than 48 hours prior to the charter sailing date (30 days for ASA courses). Our favorite option is to reschedule to a future date so that you can continue to experience the magic of sailing in our beautiful location. 

Do You Offer Gift Certificates?

What a wonderful gift idea for a loved one! Gift Certificates are available to purchase online or call us for more unique or specific requests.  

Do You Cater For Special Occasions?

At Windward Sailing we have been fortunate to be part of many special moments, from romantic wedding proposals, anniversary celebrations, couple photoshoots and Valentine surprises, to girls weekend getaways, and scattering the ashes of a departed loved ones. Contact us to let us know what you have planned and we’ll go above and beyond to make it extra special for you! 

Where Do We Sail?

It all depends on the length of your charter but we typically start from the protected waters off the Fernandina Historic Downtown area and head for the north-west corner of Amelia Island, leaving Fort Clinch to starboard and heading across to Cumberland Island to spot some of its famous wild horses, and with our onboard binoculars, the Dungeness Ruins (the remains of a 59-room Queen Anne style mansion built by the Carnegie family in the 1880’s).  If you spend enough time with us and the weather allows, we can sail east into the Atlantic Ocean to see the wildlife and beautiful beaches of Fort Clinch State Park and the south end of Cumberland Island. Be prepared to spot dolphin, sea turtle, manatees and many bird species, including white and brown pelican, herons, egrets, ibis, spoonbills and wood storks!

Is the Catamaran or Keelboat a Better Option?

It all depends on your level of comfort and expectations. Sailors typically opt for one of our keelboats that tend to provide a little more exhilaration. While within the protected waters of the Amelia Sound and Cumberland River, you’ll typically experience little or no swells, but the wind and right sail trim provide enough excitement and sense of harnessing mother nature’s power in a clean and sustainable way.  If you don’t like the boat heeling (not falling over!) and prefer a more laid back and even keeled trip while still being under sail, the catamaran is for you!