Things to Do When Sailing St. Augustine Florida

Looking for things to do while Sailing in St. Augustine, Florida? Watch our video and see what we loved best, and get a view of what the inlet is really like with an outgoing tide against the wind.

St. Augustine & St. Simons Island  |  Sailing & Sightseeing

Easter Weekend 2021 we sailed from St. Simons Island, GA to St. Augustine, FL. We averaged 7 knots SOG for 12 hour sail on 15 knot winds with fairly close 6 ft waves. Although we thought it would be parasailor weather, it turned out the Genoa and the Main sailed well for the majority of the day.

Arriving at the St. Augustine inlet, we were warned of the narrow channel and numerous shoals. Our 5 AM departure got us a 5 PM arrival with plenty of light to navigate the channel. Following the markers, it was an easy entry even in the frothy seas. We headed for the Bridge of Lions to wait for the bridge opening (every 1/2 hour on request).

We had planned on anchoring just past the city marina mooring field, however were hailed on our approach that they had a mooring ball for us – thanks to being on the wait list. We settled in on mooring ball #5. A note on anchoring for masts over 65 ft – the area before the bridge can be quite rocky so try to avoid it. Salt Run (which we did later) is a good option depending on your draft and is much quieter as it is a good distance from the city.

Easter Sunday – we attended 7 AM Mass at the Cathedral Basilica of St. Augustine. They is where the first mass was held after Don Pedro Menendez celebrated the feast of the nativity on Sept 8, 1565. The site originally housed a mission. In 1793, the cornerstone of the current building was laid.

Later that day, we walked around town and soaked up the sights and sounds of St. Augustine. Three pirate ship tours, trolley rides, all types of “vehicle” rental options, distillery, winery, museums and all kind of tourist attractions abound – not really our thing.

What caught our attention was an unexpected stop on the pedestrian alley – the St. Photios Greek Orthodox National Shrine. This shrine features exhibits depicting the life of early Greeks in America with Byzantine style frescos, historical artifacts, photos and documents – definitely worth a stop.

Flagler College was also a must see. Originally opened as Ponce de Leon Hotel in 1888, by Henry Flagler, it was the first “worthy” accommodation of that time in the area. That night, we enjoyed dinner on board while we watched the sunset.

Day 2
To truly see the entire area, we rented a car and set off to see if we could find the recent pirate shipwreck that was recently uncovered as a sand dune eroded away. Just North of the Matanzas inlet boat ramp on Crescent Beach, the remains have since been removed by Flagler College. Local historians date the remains back to the early pirate days. Crescent Beach was a worthwhile stop, as well as the drive and a lunch stop at the Back 40 A1A restaurant – surprisingly good!

We then headed back north and toured the St. Augustine Lighthouse and museum, one of the few remaining Fresnel lens that is still working, casting its light 23 miles out to sea. Original keepers carried 20 pound whale oil containers up 219 stairs to keep the light shining at 165 ft.

Anastasia State Park was our next stop. They offer bike rentals, water sports rentals, hiking trails, and the St. Augustine Beach. Recently renourished, the beach was full of broken shells making the walk a bit rough on the feet. They also recreated sand dunes to help prevent further erosion.

One last adventure drive down Vilano Beach revealed an interesting find. The Castle OTTTIS, (not a mis-spelling) built in the 1980s, was created as a landscape architecture sculpture in remembrance of Jesus Christ. It resembles the Irish castles and Abbeys of 1000 years ago, but is totally open to the weather. The Castle is made available by appointment to schools, churches, colleges, universities, institutions and community groups for academic and spiritual environments and has provided a unique setting for small, intimate wedding ceremonies.

Dinner at Harry’s Seafood was the perfect ending to our day of exploration. Don’t miss this cajun, creole and southern mashup served in a historic building on the waterfront, supposedly haunted with the souls of past fire victims.

Day 3
We moved PILAR over to Salt Run today for our last night. Another mooring ball made this easy. Much quieter with access to tidal flats, the beaches of Anastasia and the Conch Bar & Marina.

Return Sail to St. Simon’s Island, Georgia

7 AM departure for our sail back to SSI brought no wind and no waves. So, we motored up to St. Mary’s Inlet where we anchored for the night.

9 AM departure the next day for SSI got us back to dock by 2. An afternoon of boat cleanup followed by dinner at Tramici on SSI, another must!

Our last day we spent bike riding around the island, with new electric bikes from Pedego. We can still ride a normal bike, but the electric option came in super handy as St. Simons Island bike trails encompass over 20 miles!

Download their trail map here.

SSI Morningstar Marina is excellent, but there really aren’t many other areas for sailboats over 65’ to actually sail, besides the open ocean. You can’t really anchor and have access to SSI, as much of it is private, as is Sea Island and Little St. Simons.

You can head down to St. Andrews Sound, and explore Cumberland Island and head down to Amelia Island quite easily. You can head north to Sapelo Sound, and anchor on the Hampton River, but considering the shoaling and water depth at the entrance, we skipped that trip. You can also reach St. Augustine in a full day of sailing.

Need more information. Reach out to us and we’ll see if we can help.