Sailing to Florida St Augustine

When leaving Amelia Island it was slightly above freezing!

The trip to St Augustine took 12 hours. We left our mooring in the darkness at 6 am and arrived in St Augustine Municipal Marina mooring field around 2 pm. Our aim was to leave early so to ensure a daylight arrival at our destination. Getting back into the Atlantic Ocean was uneventful. Simon motored us out with the backdrop of the industry behind us.

Once we were in the Ocean we put our headsail out leaving our main down. The wind was from behind and it was easy to simply unfurl the jib. Similar to the previous voyage, my daughter, Sienna, and I laid in bed under the covers watching movies on my laptop. It was so wonderful to relax and let my husband, Simon, and Andrew, our volunteer crew member, get us to our next stop.

Usually, Simon, Sienna, and I are all in the cockpit but with the cold temperatures, it wasn’t exactly enjoyable!

It wasn’t long before Simon came down and let us know that we were entering St Augustine. We were all excited to see America’s oldest city. Additionally, we arrived just in time to see the Nights of Lights Christmas lights and the annual Christmas Boat Parade.

After sorting ourselves out we dropped the dinghy, collected Michael on Entitled (a solo sailor joining us for the journey to Fort Lauderdale), and went into the marina dinghy dock. After paying our fees of $25/night staying for two nights, we parked Doris the Dinghy. We immediately went to the highly recommended restaurant, Harry’s, and booked a table being told that the wait was around an hour at least. In actuality, I think we waited around two hours but it was worth it.

If you go to St Augustine’s, make sure you eat at Harry’s – from what I’ve experienced and heard from others, it truly is the best value for money spent.

At Harry’s, we were hoping to get a table overlooking the harbor to enjoy the parade from inside to escape the cold weather. While waiting for our table, we took a stroll around the town. We were all so impressed with the rows and rows of cute streets, eclectic shops and old-style buildings. My husband announced, ’this is one of the most un-American cities I think I’ve ever been in…’ In other words, it had quite a bit of character…it was devoid of the standard American franchises, new builds, and high rise hotels.




We were fortunate to get a fantastic table at Harry’s. We enjoyed the parade from inside and gobble down some great food. It was the perfect night. After the meal, parade, and enjoyment of the festive lights, we took the dinghy back to the boat and all passed out.

The next day we went to St Augustine to explore the town, Castillo de San Marcos (Castle built by the Spanish), and Flagler College (all in the video). Considering I’ve covered our exploits in the video I’ll allow you to simply watch the video below to get a taste for St Augustine.

Out of all the east coast, American cities to visit, sailing to Florida St Augustine should be on every sailors ‘must-see’ list.

It’s beautiful, usually warm/hot, has something for everyone and is down-right cute. History buffs will enjoy the past. Shoppers will love the boutiques. Foodies will be filled with amazing options. And sailors will be very pleasantly pleased with the St Augustine Municipal Marina moorings, slips, and facilities.

Sailing to Florida St Augustine Video

If you enjoyed this article and video, make sure to watch the next in the series where we visit Cape Canaveral. You’ll join us for a sail/motor, a tour of the Cape Marina in Port Canaveral, and a visit to the Kennedy Space Center. Check out Sailing Florida – Cape Canaveral.

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All Our Florida Related Articles/Videos

To get an overview of our time spent in Florida, check out Sailing Around Florida.

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During Merrill's Sailing Lifestyle Experience he learned how to book out and into a different country, what it's like to fly a mainsail, genoa, and staysail, how to anchor, tie onto a mooring ball and dock up at a marina. And unfortunately/fortunately Merrill managed to experience what it was like to ride out a surprise tropical storm. If you'd like to experience what it's truly like to live and cruise on a bluewater sailboat, come join me for a week. Check out our availability here: Click here for more information.

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