1. Affordable Boats Open the Door

In the early 2000s, cruising boats—especially those under 36 feet—became significantly more affordable. Baby boomers were entering retirement ages right as larger used mono-hulls, and the first generation of used catamarans, were entering the aftermarkets in large numbers. They were armed with the cash, and the timing, to drive a market for 40ft+ boats, and leave a plethora of unwanted, well-built, boats from the 70s and 80s. These vessel saw steep price drops. Online marketplaces like YachtWorld made it easier than ever to find these boats at a bargain, turning the dream of full-time sailing into an attainable reality for more people than ever before.

2. Economic Shifts and Changing Priorities

The 2008 financial crisis forced a reevaluation of traditional career paths and homeownership. Many who had grown up believing in the “safe” path—buy a house, work a 9-to-5, retire at 65—saw firsthand how fragile that system could be. As a result, alternative lifestyles, including long-term cruising, started gaining appeal. With inexpensive boats available, some took the opportunity to step away from the conventional workforce, using their savings or freelancing to support a life afloat.

3. The Rise of Remote Work

The next big shift came with the rise of remote work. Even before the global pandemic, companies were reducing office space, leveraging digital tools, and allowing employees to work from anywhere. But in 2020, with the arrival and subsequent lockdowns from COVID-19, when businesses were forced to embrace remote work at scale, a new reality emerged: you didn’t have to be tied to a physical office at all.

For many, this was the ultimate game-changer. The long-standing barrier of needing to be in one location for work was gone. If you had a reliable internet connection, you could take your career offshore—literally.

4. Starlink Changes Everything

For years, connectivity was one of the biggest challenges for remote workers wanting to live on a boat. While cell service and mobile hotspots helped in coastal areas, coverage was unreliable, expensive, and limited when venturing further offshore. Enter Starlink.

With high-speed satellite internet that works in most anchorages and even underway, Starlink has made working from a boat as seamless as working from a land-based home. Whether you’re in the Bahamas, French Polynesia, or a secluded cove in the Pacific Northwest, you can now take Zoom calls, upload large files, and stay connected without the stress of searching for WiFi.