The two essential ingredients of a truly great vacation are time and money. If you’re awash in both, you might consider piping aboard the Great Loop, arguably the most epic leisure activity afloat.

At its barnacled bottom, the Great Loop is a nautical circumnavigation of the Eastern United States. Up on deck, it’s a self-guided grand tour of some of the country’s most lovely, most colorful, and most historic waterscapes. While growing in popularity as increasing numbers of Baby Boomers clock out for the last time and start casting around for something fun to do that will also give “meaning” to their comfortable retirements, the Loop is still largely the province of a small fleet of amateur mariners described among themselves as “Loopers.” To understand why most Loopers don’t have jobs, consider their itinerary.

The typical Looper casts off from the port city of Stuart on Florida’s balmy Treasure Coast. They’re typically in command of a 30-foot trawler, a shallow-draft vessel affording reasonably comfortable personal accommodations, generous fuel capacity and a relatively low profile. They set sail in springtime, calculating that northern latitudes will have gentled before they get there.

Steaming north along the Intracoastal Waterway past Georgia and the Carolinas, they enter the mighty Chesapeake and keep going until they run out of bay, then sidle east through the Chesapeake & Delaware Canal to rejoin the Intracoastal Waterway for a sheltered cruise up to New Jersey. Daring a brief 30-mile stretch of open Atlantic, they dart into the Hudson River at the Big Apple and follow that historic corridor to the even more historic Erie Canal, which dumps them out into Lake Erie.

With summer in full bloom, most Loopers will putz around the Great Lakes for a few months, enjoying the region’s temporary temperance and allowing hurricane season to blow itself out before they head south. About the time kids are going back to school, Loopers are converging on Chicago and the Calumet Sag, a channel linking the Windy City’s busy ports to the southbound Illinois River. It’s on “the Sag” that the humble trawler stands tall. A single bridge over that waterway giving just 19 feet of clearance presents a considerable inconvenience to sailboats and pleasure craft of statelier silhouette.

Following a long drift down the Illinois and a good stretch of the upper Mississippi, the thoughtful Looper hangs a left at the Ohio River and follows it up to the Tennessee River, which leads to one of the Great Loop’s most notable features, the Tennessee-Tombigbee Waterway. Reaching 234 miles to the Gulf of Mexico, the “Tenn-Tom” took the Army Corps of Engineers twelve years and nearly $2 billion to dig. Completed in 1984 – two years ahead of schedule, in fact – that magnificent ditch remains the largest earth-moving project ever undertaken by the hand of Man, requiring the dislocation of about 310 million cubic yards of dirt, which would be ample to fill in the Panama Canal entirely with several million cubic yards left over for landscaping.

Sailing back into salt water at Mobile, the Great Loop rejoins the Intracoastal Waterway on an easterly course. Once offshore of the Sunshine State, the Looping set has the choice of either zipping across the panhandle direct to Stuart via the Okeechobee Waterway, or getting there the long way around the Keys. In either case, the typical Looper will have covered something like 5,000 miles, consumed 10 months, give or take, and parted company with maybe $60,000, boat not included.

On the subject of boats, a decent pre-owned, Loop-worthy trawler will set you back about $50,000, although Loopers have undertaken the voyage in everything from sea kayaks to 70-foot yachts. Dockage expenses can run anywhere from $10,000 to $30,000, since harbors charge by the foot and the careful shopper can often find free berths in unlikely places. Fuel costs vary widely, from less than $4,000 for a small sail-assisted vessel to well-over $40,000 for a mid-sized trawler with an ambitious navigator at the helm. And, for the ambitious, the Great Loop offers endless tempting opportunities for non-typical variation. A serious Looper with the sea in his blood can easily burn 7,500 miles, $150,000 and more than a year of his time.

A hop up the Potomac for a shipboard gander at Washington, D.C., for example, might add a couple of days and a couple hundred miles to the tally. Some Loopers like to extend their adventure by entering the Gulf through New Orleans, although the Lower Mississippi is a daunting avenue filled with tricky currents, precious few services available to the small-time mariner, and lots of really big moving obstacles to steer clear of. For a truly spectacular digression, bypassing the Hudson to enter the Great Lakes by way of the Saint Lawrence Seaway can be a truly memorable 1,500-mile side trip.

Some Loopers take the route in bite-sized pieces, parking their vessel each autumn in whatever marina they find themselves and nibbling away at the Great Loop over the course of three or four years. Many have sold everything they own and live aboard their trawlers, wintering in the Bahamas and undertaking another full circuit with every turn of the calendar. The record currently stands at nine complete revolutions.

These days there are about 300 boats traveling the Great Loop in any given season, up from less than a hundred 20 years ago. This is known because Loopers, like everybody else, have their own advocacy group. Founded in 1999, America’s Great Loop Cruisers’ Organization (AGLCO) provides information and practical support to folks getting ready to Sail America, and works hard to keep track of their comings and goings. AGLCO even sponsors a pair of well-attended annual “reunions” that give Loopers a chance to drop anchor and boast about their endless equipment failures, terrifying weather-related misadventures, and frequent and expensive groundings.

So who’s Looping? Lots of retirees, yes, but also a handful of working people, hard-working citizens who spend years saving up for a once-in-a-lifetime chance to cast off their cares and taste the free air aboard ship. There are even families who Loop, parents home-schooling their children underway, kids learning both long division and how to unclog a balky fuel pump in the dark with a pasta fork.

Of time and money there are rarely enough. But should you ever find yourself uncomfortably burdened by either, you’ll find instant relief – and high adventure – on the Great Loop.