Sailing the Great American Loop: CruisinCasa's Story
Community
Feb 14, 2026
We bought a sailboat had no clue we were going to do Americas Great Loop!
This life isn’t easy, but it beats sitting in a house wondering “what if?”
Meet Josh and Haley. They’re currently sailing in the Florida Keys, heading up to Stuart, Florida, to finish the Great American Loop. After completing the Great Loop, they’ll set sail for the Bahamas, where they plan to cruise through July.
Their story is one many people dream about: quitting the traditional lifestyle, learning as they go, working remotely from a boat, and turning a big dream into a real plan!
Josh & Haley’s Story
Josh grew up sailing in Southern California with his grandparents. That’s where the love for sailing started, and it never went away. He always said that one day, they would live on a boat.
Haley grew up in the mountains and had only been on fishing boats along the Oregon Coast. Sailing, or living on a sailboat, was never something she imagined for herself.
In 2023, they drove their renovated 1993 Toyota Dolphin camper across the country. When they reached Florida, they found themselves constantly watching the sailboats.
Instead of Josh teaching Haley, they decided to take sailing lessons together. They completed ASA 101, 102, and 104, and Haley fell in love with sailing immediately. They worked really well together, and it felt right.
Not long after, they bought their first sailboat Slacker, a 33 Nauticat.
How long does it take to sail Great American Loop?
One year: 153 Great Loop logbook entries in SeaPeople and counting.
Josh and Haley have officially been sailing the Great American Loop for a full year, documenting every mile of their Great Loop route with detailed trip tracking and real-time logbook updates. Their journey began on February 13 in Jensen Beach, Florida, marking the start of their liveaboard sailing adventure.
Since then, they’ve navigated hundreds of miles along the Great Loop waterway system, cruising through marinas, anchorages, locks, and coastal passages. Most recently, they completed Great Loop Leg #138, sailing from Marathon, Florida to Hawks Cay Resort in the Florida Keys.
Best Parts of the Great American Loop Route
Their most unforgettable adventure on the Great Loop so far has been the Trent Severn Waterway in Canada. Taking an ocean-going sailboat through narrow canals, surrounded by jet skis, pontoons, and cottage country summer vibes, was unreal.
But also their first overnight passage from Cape May, New Jersey to New York City. That's when they knew this was it. That sail gave them confidence in themselves and in their boat. Sailing into New York Harbor at sunrise, they were emotional and incredibly proud of the life they had created.
Sailing the Great Loop Full-Time
Working full-time remote from the boat has been more challenging than expected and requires planning and focus, especially on the water. But they make it work.
If they could give one tip:
Turn dreams into realistic goals. Break them into bite-sized pieces and go before you’re ready, because no one ever really is. This life isn’t easy, but it’s better than sitting in a house wondering “what if.”
And yes, they would do it all over again. One hundred percent.
