2006 Island Pilot 395 Cruiser for sale in Englewood, Florida

This 2006 Island Pilot 395 is not your average cruiser. She is a true one-owner boat with a unique story and thoughtful upgrades that set her apart from every other 395 on the water.

Hull #3, she was originally purchased by a technician who worked for the company that brought these boats into the U.S. Because of his role and experience, he was able to work directly with Island Pilot during the build process and had this boat constructed to a higher standard than the rest. While the typical Island Pilot 395 displaces around 30,000 lbs, this one was purposely built heavier—just under 40,000 lbs—making her exceptionally solid, stable, and confident in heavy seas. That extra weight translates into a smoother, safer, and more enjoyable ride whether you're running offshore or navigating inland waters.

The boat was specifically set up for America's Great Loop, with comfort, reliability, and safety in mind. She has been meticulously maintained over the years, and most importantly, she has been serviced consistently by a Volvo-certified team. Both the service manager and lead technician have been working on this vessel for years. They know her inside and out and recently went through every system, engine, and component from bow to stern to ensure she runs like new.

The current owner, who has enjoyed countless adventures aboard, made one request before offering her for sale: make sure everything is in the best possible condition so the next owner can step aboard and continue the journey without hesitation. From mechanical systems to overall cosmetics, this boat has been inspected and cared for with that goal in mind.

If you've been searching for a dependable, proven, and uniquely capable cruiser to take on the Loop or simply enjoy extended cruising, this Island Pilot 395 deserves your attention. With her upgraded construction, one-owner history, and professional maintenance pedigree, she is truly a standout opportunity.