One rule of thumb when traveling anywhere by boat is never tell guests to meet you at a specific port on an agreed upon day. The primary reason for this (and an obvious one of course) is that you can't predict the weather. You also can't predict the next thing to break on the boat that could potentially side-line you indefinitely...
With the two of us being extremely naive and refusing to take the advice of every salty dog and retired cruiser we encountered along the way, we did the complete opposite. We had two sets of guests pre-planned and keen to join in on the adventure. The first guests were our dads. Their plan was to join us in Florida and cruise through the majority of the Bahamas with us before we made the push to the rest of the Caribbean. It made sense for them to fly to West Palm Beach in early December and we thought we could easily achieve the rendezvous there. The second visitor to book a trip down was a good friend Mike D whose flight to San Juan, Puerto Rico was booked for Dec 26th. His plan was to sail with us to the British Virgin Islands where we would ring in the New Year. We were told on a daily basis that we would have a hard time making both deadlines with the strong suggestion that it would be next to impossible.
With the cold at our backs and the first of two deadlines fast approaching it was time to continue south through Georgia and cross the state line into Florida. Due to the beating we took going around Cape Fear, we decided to continue our journey in the ICW. This would be the best bet for us and allow us time to work at fixing the breakdowns and to get our sail repaired. As we made our way down the ICW we started to experience warmer weather with daily dolphin sightings becoming the norm. We also experienced more engine issues. One day while leaving the dock at Jekyll Island the engine died out completely. We were able to make our way back to the dock by using our anchor to inch ourselves backwards and avoid being swept down stream in the current. We plugged back into shore power and after several attempts were able to re-start the engine. This time it seemed to be running without issue.
After crossing into Florida we decided that it was time to launch the dinghy which had been folded up and stored in front of the wheel. We knew we would have to anchor out some nights to avoid the pricey marina fees but still wanted to be able to make it to shore to surf and provision the boat. After a few exciting days cruising through Florida and catching waves we experienced yet another engine issue after departing Harbor Town Marina in Ft. Pierce. Unable to start the engine we had to tow the boat north back to the the marina with our trusted dinghy. This slow and lengthy process was the straw that broke the camels back and we decided it was time, once again, to have the engine looked at by a mechanic. We made multiple calls home informing our dads of the daily struggles and never ending engine issues, so they were more than aware that we might not make it to West Palm Beach for the arrival of their flight on Dec 3. It took two full days to get the engine running properly and our head sail repaired. After all of these unexpected delays, we pushed on to West Palm Beach and arrived with a day to spare. Spirits were high and we were both extremely stoked for our dads to join us on the next leg to the Bahamas.