Sail Away on Schooner Freedom


Since 1565, St. Augustine has been a seafaring town. The fort, the cross, the lighthouse, the Bridge of Lions and the low, beautiful skyline of the Historic District are all uniquely appreciated from the water. Since 2001, one St. Augustine water tour has sailed beyond the rest- the premier tall ship Freedom.

Sail Freedom St Augustine
The Schooner Freedom docks at the St. Augustine municipal marina in the heart of historic St. Augustine.

I’ve heard it said that a good Cap’n keeps a tight ship. By these standards, Captain Jon is a fine man. His crew is friendly and playful yet respectful. The Freedom is clean and orderly and everything is in its proper place.

Once the ship is underway, the crew calls on passengers to lend a hand. Even those inexperienced in sailing are invited to hoist and trim the sails. Don’t be nervous about messing up… with a little coaching you’ll do just fine! Wesley and I decided to watch this time but hubby joined the crew in hauling up the main sail and did a mighty fine job.

Schooner Freedom Sailboat St Augustine
Crisply coiled ropes are orderly and functional- they won’t trip up sailors or get tangled.
Schooner Freedom St Augustine
I’ve never seen this lifering wet… but it’s there if needed!
Freedom Sunset Sail
El Galeon and The Bridge of Lions from the Schooner Freedom’s sunset sail.

The Schooner Freedom’s Sunset Sail was our second date since Wesley joined the family. Although adult passengers are more common, he was well behaved (ahem, of course!) and the time on the water was soothing for all of us and for our fellow sailors. The crew offers beer, wine, soda and water for passengers to enjoy throughout the two-hour sunset sail.

We haven’t taken the whole family on the sunset sail- although our kids have grown up on boats, it’s nice to relax for a few hours and not worry about a curious preschooler leaning too far over the ropes! They do offer a family sail during the day that I’m thinking of joining- special dolphin tours partner with a Marineland educator to teach about these graceful mammals and include a ticket to Marineland afterward! This is going on my family bucket list!

Simply St Augustine Sunset Sail
Baby Wesley’s first time on the water… he loved it! It’s in his blood.

The Freedom hosts a small crowd- I believe they counted off 28 passengers when we went out. This allows for personal interaction with the crew which I love! Some couples snuggled up in quiet parts of the boat and just took in the scenery which is perfectly fine, too. But Captain Jon swapped history and lore with some Navy guys, gave restaurant advice to a couple next to us and laughed with my hubby about life here in St. Augustine. We’re so spoiled to call St. Augustine home!

Captain Jon Freedom Sailboat
Captain Jon giving baby Wesley his first lecture on sailing.

Our time on the water was pretty evenly divided between the Intracoastal South of the Bridge of Lions and the bay N of The Bridge. Your experience will be unique each time depending on the wind, the waves and the mood of your captain. I hear on super calm days they’ll head out through the inlet to the Atlantic! Personally, I prefer to stay where I can swim to shore. 😉

freedom sailboat st augustine
Head sail gaskets hang limply until needed. Once the sail is lowered, the crew furls it and uses these lines to safely store the sail on the bowsprit. {Thanks to Katherine for helping me increase my sailing terminology!}
baby captain freedom
Wesley takes the wheel. Shall I call him Dread Pirate Roberts in these moments? {Princess Bride reference. Yes, I named my kid after a movie character. Inconceivable!}

Wind fills the sails and the little ship speeds along just fast enough to provide a cooling breeze. If you’re trying to decide whether you should splurge for an evening aboard the Freedom, take Mark Twain’s advice:

“Twenty years from now, you will be more disappointed by the things you didn’t do than those you did. So throw off the bowlines. Sail away from safe harbor. Catch the wind in your sails. Explore. Dream. Discover.”

Sunset Sail St Augustine Freedom
St Augustine Sunset Sail on Schooner Freedom
Let Freedom Ring St Augustine
Captain Jon uses the hourglass to keep time. He rings the bell every hour on the hour… it’s tradition.

The Schooner Freedom does not offer a “tour” experience. The crew is happy to point out local sites but you’re as likely to hear about their childhood memories exploring local beaches as you are the history of the fort and when the lighthouse moved to its current location. Instead, set aside time for a relaxing sail on the Freedom to unplug from the bustle of busy streets. Breathe the salted air deeply and whisper a prayer of thanks!

El Galeon St Augustine from the water
El Galeon, St. Augustine’s tall ship museum. She does not sail but you can tour her.

Schooner Freedom’s Sunset Sail
Departure depends on time of sunset- call for current times.
$45 per person

Freedom offers many other sailing experiences- from family sails to moonrise sails. Be sure to check out their website to choose the perfect St Augustine Sailing experience for your family!

Hubby, Wesley and I were invited to sail aboard the Freedom in order to share our experience with you. Thanks, Captain Jon & team!


  1. says

    You managed to capture this experience and truly put it to words. The Schooner Freedom is an amazing excursion..

    • says

      Thanks Kathy! I loved reading your memory as well! Viva blogging! Viva St. Augustine! ~Allie O

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