Editor's Note: A few months ago, Mike Pitchford wrote about how his planned trip south on the ICW was almost delayed, but quick-haul repairs saved the day. With his trip back on schedule, we asked him to share more about his trip south.

The author's boat in Hampton and loaded for the Florida ICW trip.

As you read this near the winter solstice, shivering, it may be hard to remember back a couple of months. But, back in early and mid-October, the Chesapeake region was blessed with unseasonably balmy weather. However, knowing that winter was approaching, scores of fellow Bay cruisers began taking their boats south. Eventual destinations ranged from Hilton Head to south Florida and the Bahamas, and any place where overwintering does not include pink and purple antifreeze.

For those cruising the ICW, trip times vary. The window between the Annapolis Boat Shows and Thanksgiving is peak ICW travel season. Some snowbird cruisers leave early and are already ensconced in a winter-season location before October ends. Some make the trip a bit later, even in December. All of them enjoy a warm respite when the coldest days reach Annapolis.

We were going south, too, but our boat needed some unexpected last-minute repairs. For a few days, our long planned ICW trip to Stuart, FL, for the winter was in question. Fortunately, the local boat yards came through and we only lost a few days (read the full story at proptalk.com/quick-haul-boat-repairs).

Having lost some time, we scheduled a long day, our first day out, to catch up with our previously planned itinerary. We departed Annapolis on October 15, after breakfast at Chick and Ruth’s, and arrived in Hampton, VA, that evening. The Bay was cooperating!

Fast and then slow

The itinerary for this trip was fast and then slow. The fastest part would be a four-day push to Myrtle Beach, SC, about 500 miles from Annapolis. The boat would rest up there while we boarded a flight home for a few days. For this “delivery” push, my crew was my ever loyal and boat ready college roommates/fraternity brothers (read more about some of our past adventures at proptalk.com/lifelong-friendships-built-around-boating). You’ve got to love these guys. They are always eager for a boat trip, have boat handling skills, and will sleep almost anywhere (however, the adult beverage cost is substantial). 

The second leg was from Myrtle Beach to Stuart, FL. For this leg my crew (well actually the boss) would be my wife, Sue. For this stretch of the ICW, about 650 miles, we would slow down and smell the roses. 

The delivery leg with the “boys” was hectic but great fun. We stopped in downtown Hampton, VA, Belhaven and Wrightsville Beach, NC, and were in Myrtle Beach by noon the fourth day. Our typical day began early, after breakfast on the boat, and ended with a late afternoon marina arrival and dinner ashore. It all went like clockwork.

Charleston restaurant visit with ICW cruisers (L-R Tom Muha, Ron Ricketts, Mike Pitchford).

The “smell the roses” second leg was equally fun and very different. Sue and I flew down to Myrtle Beach and rented a car. We provisioned for a two-week trip and made the boat ready.

Our first stop was Georgetown, SC, about 50 miles from Myrtle Beach. Georgetown is a quaint little town with a now faded commercial port history. We spent an extra day there and explored the town and its restaurants (and ice cream shops).  

Cruising the ICW at a slower pace is often very social. In Georgetown we met up with fellow Annapolis cruiser Tom Muha. Tom was headed to Charleston for a few weeks and eventually to Stuart, FL, as well. We also met two other snowbird couples and enjoyed meals or cocktails with all. Ah, the pleasures of slowing down!

The next stop was Charleston, about 70 miles from Georgetown. Because of a couple of shallow spots in the ICW and the timing of low tides, we made the run to Charleston offshore. Offshore runs depend on your speed and good weather; both were in our favor for this leg.

Sunset along the ICW in Beaufort, SC.

Charleston likely needs no introduction to our readers. It is a magical town with some of the best restaurants on the southeast coast. As would become a pattern, we sampled those restaurants with our fellow snowbird cruisers. Relationships were being built!

In South Carolina and Georgia, tides can run eight feet. Significant currents can accompany a changing tide, and shallow spots along the ICW are to be avoided at low tide. Fortunately for us, high tide was generally mid-day along this stretch. This happy coincidence allowed us to cruise generally from 10 a.m. to 3 p.m. and made for easy passages.

Beaufort, SC, was our next layover destination. We have a lifelong friend there and looked forward to catching up with her. Beaufort is a larger version of Georgetown with historic buildings and some very good restaurants. We enjoyed both the town and visiting with our old friend for a couple of days.

Our next stop was the Savannah Yacht Club (SYC), about 50 miles from Beaufort. The former assistant general manager of the Annapolis Yacht Club, Leo Luistro, is the general manager. We happened upon SYC during their fall member BBQ cookoff. The parking lot was full of smoking cookers and that most excellent BBQ smell was in the air for almost our entire visit. On our lay day, the BBQ, in seven categories, was judged and the leftovers served to the assembled club members and visitors like us. It was a culinary opportunity, to say the least.    

Savanah Yacht Club stop (L-R Mike Pitchford, Club GM and former Annapolitian Leo Luistro, Sue Pitchford)

After Savannah, the Georgia stretch of the ICW is a serpentine path with good anchorages but a long stretch between good marinas. We executed a longer day, 100 miles, to get to Brunswick, GA, for the night. Like Georgetown and Beaufort, the marina slips in Brunswick afford cruisers a short walk to the downtown area. Though a little earlier in redevelopment, the downtown area offers restaurants and historical interest.  

The experience is priceless

From Brunswick our short hop destination was the first stop in Florida: Fernandina Beach. It is about 30 miles from Brunswick. Along the way you will pass the Kings Bay nuclear submarine base. It is perhaps the fourth or fifth substantial US military facility along the southern ICW with more to come.

We arrived in Fernandina Beach on Halloween. It was a Monday and things were a little quieter than the weekend, no doubt. Still, we saw a fair selection of ghosts and goblins on our walk through the nearby downtown area. 

At this point the snowbird weather is worth a mention. When we left the Bay in mid-October, we were wearing jeans and long sleeve shirts with fleeces and jackets in the evening. By the time we left Brunswick and crossed into Florida, shorts and T-shirts were the uniform of the day. 

Sunrise over the downtown marina in St. Augustine.

Florida is a long state. From Fernandina Beach, the ICW continues to Key West and covers almost 500 miles. Just when you thought you had arrived, you discover you have mile after pleasurable mile yet to discover. 

It was time for us to speed up a bit so we could get back to Annapolis. We made 100-mile-days with stops in St. Augustine and Cocoa Beach before arriving at our winter home port of Stuart. 

What about you? Ever thought about heading south instead of winterizing? Okay, yes it may cost a bit more than winterizing, shrink wrapping, etc. However, it is both a journey and a destination. The experience and the memories will be priceless.  

So, this cold winter, you should warm yourself by planning to bring your boat south next winter. The boat doesn’t matter so much. What you have probably works, from a small Downeast boat to a walkaround cuddy outboard. I have known folks who have done it on an open Boston Whaler (B&B to B&B). Whatever planning you do, start with a winter home in mind and do your homework on a seasonal marina slip (the pandemic and hurricanes have put a bit of a premium on slips in snowbird favored destinations). You won’t regret it. 

By Mike Pitchford