ICW Week 5: Golden Islands > St. Augustine, FL
Slowing down, a BIG first and anticipating what's to come!
Wow! What a week it has been on the ICW. Over the past seven days, I feel like so many things have come together for us. We enjoyed a more relaxed pace, celebrated a big “first,” and felt the joyful anticipation of the holiday season and our upcoming crossing to the Bahamas.
This week we also began studying our Bahamas charts in earnest and started planning the next phase of our journey. I’m excited to share an early look at those plans with you, but first, here’s an overview of our route from the past week.
Route Overview
Saturday 11/29: Brunswick, GA → Jekyll Island, GA
Sunday 11/30: Jekyll Island, GA → Cumberland Island, GA
Monday 12/1: Cumberland Island, GA → Sisters Creek, FL (outside Jacksonville)
Tuesday 12/2: Zero day in Sisters Creek, FL
Wednesday 12/3: Sisters Creek, FL → St. Augustine, FL
Thursday 12/4 – Saturday 12/6: Zero days in St. Augustine, FL
A Slower Pace
If you read our last blog post, you’ll remember that we decided to slow down after Thanksgiving. Our slower pace is reflected in the route overview above, with us moving only half of the days. On most travel days, we also cruised just 2–3 hours instead of our usual 6–9. This pace allowed us to rest, explore on land, tackle a few chores, and enjoy the cruising community!
A big factor in our decision to slow down was our desire to explore Georgia’s Golden Isles. Georgia has been our favorite state on the ICW so far, and before heading into hectic Florida, we wanted to soak up the unique beauty of two of Georgia’s more than 15 barrier islands—Jekyll Island and Cumberland Island.
We hadn’t done much research about Jekyll Island beyond hearing from a few friends that it was well worth a visit. After anchoring on the southern end of the island, we took the dinghy ashore and found a walking trail that eventually led to the beach, a resort area, and a car-free village shopping center. We enjoyed our first panoramic view of the Atlantic Ocean since Beaufort, NC—even if it was a very windy one!
We almost turned around at this point, but I’m glad we didn’t! Michael pulled up a map and found a historic district on the northern end of the island. Without fully calculating the distance, we decided to start walking in that direction. We ended up walking 8 miles that day, but what we discovered was worth every step: a charming historic area—fully decked out for Christmas—with beautifully preserved Gilded Age mansions.
While exploring the historic district, we learned a lot about Jekyll Island’s past. In the late 1800s, it was purchased by a private group called The Jekyll Island Club, and by 1888, its members represented one-sixth of the world’s wealth. Jekyll Island is also where the Federal Reserve was founded, apparently under quite a bit of secrecy. I’m now interested in diving deeper into that history—so if anyone has recommended reading or viewing on the founding of the Federal Reserve, please let me know.
The next day we traveled to Cumberland Island, which holds similarities and differences to Jekyll. The Jekyll Island Club was famously exclusive—so exclusive that Lucy Carnegie (Andrew Carnegie’s sister-in-law) was denied membership. After being rejected, she built her winter house, Dungeness, on Cumberland Island. Years later, she built a second home—Plum Orchard—as a wedding gift for her son and daughter-in-law. Michael and I spent a few hours touring Plum Orchard, including its indoor pool, squash court, and extensive servants’ quarters.
Unlike Jekyll, Cumberland Island was not primarily a resort area. The Carnegies were fond of the outdoors and kept the natural habitat largely intact. Years later, the National Park Service purchased the island. Today it can be visited by anyone—but only by boat or bike. Wildlife still abounds. We saw sea birds, wild horses, and—surprisingly—armadillos! Maisie was especially entranced by those.
We were grateful for our decision to slow down. Otherwise, we might have missed these unique and beautiful islands.
Into the Ocean — A First for the Osprey Crew
If you’ve been following us for a bit, you’re familiar with our autopilot woes and how they interfered with our desire to get out of the ICW and do some proper sailing in the Atlantic Ocean. If you read our last post, you’ll recall how our friend Ryan sat beside Michael for hours the day after Thanksgiving trying to fix the autopilot.
Well, in further support of the mystery that is all things sailboats, during our trip to Jekyll Island, the autopilot suddenly began working seamlessly.
Because the fix was entirely unexplained, we didn’t immediately trust it. We monitored the autopilot during our trip to Cumberland Island, and after two days of proper functioning, our confidence grew. But to really trust it, we knew we needed to test it in tougher conditions—with a sea trial.
We also decided it was high time to test the seaworthiness of Osprey’s crew. None of us had sailed in the ocean before, and we knew that ocean sailing was in our near future for the Bahamas crossing. We didn’t want the crossing itself to be our first time offshore—and for good reason.
When we cross from Florida to the Bahamas, we’ll spend 50+ nm in the open ocean, including crossing the Gulf Stream. To ensure a safe and comfortable passage, we monitor weather forecasts closely and wait for conditions that are both safe and comfortable. A few important factors for a good crossing include:
Wind direction from the south, southwest, or southeast
Wind speed around 10–20 knots
Calm to moderate waves
We’re comfortable with wind forecasts, but waves are different. Having sailed only in the Chesapeake Bay, we aren’t familiar with how ocean waves feel.
Two important measurements for understanding waves are:
Wave height
Wave period (the “tempo” of the waves)
The combination greatly affects comfort. Short waves with a long period are ideal. Tall waves with a short period are not. There’s also a wide middle ground that might be tolerable for some sailors and miserable for others. Not wanting to discover our tolerance for the first time during the crossing, we decided to do a short ocean trial in “mid-range” conditions.
The forecast on Monday 12/1 called for 15–20 knots of wind from the N–NE and 3–5 ft waves at 5 seconds. These were right on the edge of comfort for us—not dangerous, but not pleasant either. It was the perfect test for both the autopilot and the crew.
What we learned was perfectly summed up by the captain upon reaching safe harbor:
“Well, I certainly wouldn’t want to do that in any worse conditions!”
Other takeaways from our first ocean sail:
Dramamine will be helpful for First Mate Jen
Deckhand Maisie is cool as a cucumber
The autopilot still works (we have no idea how or why, and we’re not asking too many questions)
For our Bahamas crossing, we’d prefer shorter waves and/or longer periods
All in all, a successful test—and we are immensely proud to say we’ve sailed in the ocean!
Holiday Anticipation with Cruiser Friends
After our ocean trial, we spent a day waiting out weather in Sisters Creek, outside Jacksonville. From there, we pointed our bow to St. Augustine, where we planned to enjoy some holiday festivities.
We visited St. Augustine specifically for its famous Christmas celebrations. What we didn’t plan for—but loved even more—was connecting with cruiser friends who happened to be there at the same time!
Over the past weeks, we’ve connected with several cruising couples, either at the Annapolis Boat Show or through cruiser-specific social networks. Many we hadn’t yet met in person. We were delighted to learn that several would be in St. Augustine while we were there. Some highlights:
Running errands with S/V Eleanor — boys to West Marine and the hardware store, girls to Target (I was very excited about girl time at Target!)
Enjoying dinner at the Drunken Horse with S/V Sea Pearl
Watching the St. Augustine Christmas Parade with S/V Eleanor, S/V Luminary, and S/V Nara
Visiting a brewery/taco joint with several other boat families, including a family from Germany and friends we met in Brunswick over Thanksgiving
If you’re wondering what Maisie thought about St. Augustine, here are her highlights:
Reuniting with her boyfriend Rumor, a handsome English Lab we met in Oriental, NC
Meeting lots of boat kids (her favorite kind of human)
Visiting a dog-friendly museum park and attending a planetarium show (she did not enjoy the cannon demonstration)
Founded in 1856 by the Spanish, St. Augustine is the oldest continuously inhabited city in the United States and features Spanish Architecture and the original fort.
St. Augustine is known for its Christmas celebrations. Since we won’t be going home for Christmas this year, we wanted to soak in some holiday cheer and build our Christmas anticipation. The downtown light display is breathtaking. We enjoyed it both on foot and from the water in our dinghy. The Christmas Parade—touted as the largest in Florida—included floats that blew bubble snow. The verdict is still out on whether we prefer bubble snow or real snow.
We even brought a little Christmas spirit aboard Osprey by hanging stockings on the bulkhead and garland from the handrails. I’d say St. Augustine successfully got us into the holiday spirit!
The anticipation the Christmas season brings never ceases to amaze me. The slow build brings almost as much joy as the holiday itself. There’s something special about waiting that heightens the joy of the big moment. And as our anticipation for Christmas builds, so does our anticipation for our upcoming Bahamas crossing!
Anticipation and Planning
As we’ve progressed southward down the ICW, Michael and I have taken our planning in small sections. Living and traveling on a boat doesn’t lend itself to long-term planning—flexibility and adaptability are key. Still, some semblance of a plan is needed to guide shorter-term decisions. Now that we’ve reached our fifth and final ICW state, the time is right to begin planning the next phase: crossing to the Bahamas!
This past week, we reviewed our Waterway Guide for the Bahamas, discussed which islands we’re most excited about (there are more than 700!), and considered which port of call we’ll use to check in.
Our departure point from Florida will tie into that choice. We may sail all the way south to Miami, or, if a favorable weather window appears earlier, we may depart from West Palm Beach.
Before crossing, we have several items to complete:
Finish installing our watermaker, which will allow us to make fresh drinking water from sea water
Stock the boat with most of the food we’ll need for 3–4 months (Bahamas groceries are pricey!)
Complete pre-work for customs and immigration
Get a health certificate for Maisie
Purchase a few pieces of gear—like snorkel and spearfishing equipment—to help us enjoy the reefs and water
We’ll likely stop in Fort Pierce, FL for about a week to complete these items. If all goes well, we anticipate being ready to cross around Christmas. But most importantly, we will wait for the right wind and wave conditions for a safe and comfortable crossing.
Looking Ahead
The next week will likely bring more boat work than sightseeing. However, before we hunker down to complete our projects and provisioning, we have one epic tourist item on our list: watching a rocket launch from Cape Canaveral!
We’re also considering doing our first overnight sail—something we’re anticipating with a mix of excitement and nerves. But just like our first ocean sail, we trust that completing our first overnight will teach us important lessons and give us a deep sense of accomplishment.
Stay tuned for more, and cheers!
– Jen, Michael, and Maisie
Jen and Michael., I find myself being excited and nervous for you. I love that you are doing safety trials! You are two smart cookies and my admiration continues to grow. Maisie is so adorable-poor thing had to suffer through cannon fire!! We love you and are going to miss you in Williamsburg.
What a great post - thank you! We love hearing about your adventures 🙂