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Day 2: Locks, Lines, and Learning Fast
We traveled from Naples to Ortona on July 7, 2025, a 76-nautical-mile day that included Sandi’s first experience at the Franklin Lock. The morning began with a windlass failure, but Dee hand-pulled the anchor so we could depart. Throughout the day Sandi learned bowlines and navigation updates while largely observing and relying on Dee and Allie’s expertise. We anchored at the Ortona Lock & Dam dolphins, where challenging conditions reinforced how much we depended on our experienced crew to complete…
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Day 1: We’re Finally Underway
On July 6, 2025, we began our journey from Marco Island to Naples, a short 16-nautical-mile first leg of our trip. After three attempts, we successfully set anchor for the night, but problems quickly emerged. The boat’s batteries failed to support onboard systems, causing voltage to drop, and while the generator was needed to resolve it, it refused to start. In the Florida heat, we faced discomfort and early mechanical challenges, marking an unexpected but real start to our voyage.
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The Chaos Begins… In the Best Way
Sandi and Joe worked together to prepare their Endeavour 44’ TrawlerCat for departure, unloading supplies, installing a freezer, and completing essential cleaning and provisioning. Joe handled mechanical upgrades while Sandi organized and stocked the boat for their new life aboard. Captain Dee’s checklist added final tasks, including anchor replacement and engine checks. Unexpected issues arose, including a generator that only started after the previous owner adjusted it and a port engine reverso problem. Despite setbacks, they steadily pushed forward toward…
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Timing Is Everything… Right?
Sandi coordinated a tightly packed schedule to prepare the boat for departure, including family obligations from Virginia to North Carolina before heading to Florida. While planning to arrive on July 1, delays at the boat yard pushed the timeline, reducing preparation time before the planned July 6 departure from Marco Island. Joe flew in to assist and see the boat for the first time, while Sandi managed mounting pressure and logistics. Despite setbacks and weather-related insurance concerns, they adjusted plans…
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What Could Go Wrong?
As we prepared to move our boat, we planned to drive a one-way rental from West Virginia to Florida loaded with essentials—but Enterprise Rent-A-Car didn’t have the reserved vehicle. Sandi pivoted, driving the Durango instead, creating a new challenge of getting it back home later. At the same time, repairs at the boat yard were moving slower than expected. Despite the setbacks and shifting plans, we kept moving forward, learning that in boating, even the best plans rarely go exactly…
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Finding the Right Captain for the Journey Home
We searched for a captain to deliver our Endeavour 44’ TrawlerCat from Marco Island to the Chesapeake Bay and train Sandi along the way. Early referrals didn’t work out, and nothing felt like the right fit. Everything changed when the previous owner introduced us to Dee and Allie Long of Solmates Journey, who own the same model boat. Their experience, teaching approach, and shared lifestyle made them the perfect choice. It turned out to be one of our best decisions…
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Getting Ready to Bring Her Home
After completing the surveys, we began preparing the Endeavour 44’ TrawlerCat for her delivery to the Chesapeake, addressing key repairs such as cutlass bearing replacement along with smaller maintenance items. From the start, we planned to hire a professional captain to make the journey, knowing it was beyond our experience. We hoped Joe could join Sandi for the trip to learn the boat firsthand, but work commitments kept him home. The delivery became an important early step in learning our…
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The Next Steps in Bringing Her Home
After deciding to purchase our Endeavour 44’ TrawlerCat, we moved into the essential next steps of the process. We secured a documentation company to properly handle the private party transfer, arranged marine and engine surveys, and began working through the complexities of obtaining insurance for a liveaboard vessel. At the same time, we searched for the right marina on the Chesapeake Bay to serve as our home port. Each step brought us closer to turning our dream into reality.
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The Search for the Perfect Boat
We spent months searching for the right liveaboard boat, focusing on practicality, comfort, and long-term livability. The Endeavour 44’ TrawlerCat quickly stood out as meeting all of our requirements. After Sandi retired in August 2024 and Joe continued working full-time, we discovered one for sale in Marco Island in April 2025. Sandi made a quick trip to see it, supported by FaceTime calls and videos for Joe, followed by a test run. It was clear—we had found our boat and…