Love Letters to Our Favorite Cruising Regions
Date Posted: February 26, 2025
Source: Waterway Guide Media Staff

Some waterways are more than just routes on a chart—they become part of who we are. They challenge us, reward us, and call us back, time and again. Whether it's the thrill of an open-water passage, the quiet of a secluded anchorage, or the steady rhythm of a well-traveled migration, these waters shape our journeys and our stories.

These are our love letters to the places that have carried us, tested us, and welcomed us home.

To the Great Lakes —

You are both a challenge and a gift—an endless stretch of freshwater shaped by time and the elements. Cruising your expanse is an adventure that demands preparation, patience, and respect. In return, you offer unmatched beauty and an ever-changing horizon.

Your seasons are fleeting, and we cherish each one, knowing that from June to September, your harbors and anchorages will welcome us with long days and golden sunsets. Civilization and wilderness exist side by side, from the towering skyline of Chicago to the untouched beauty of the North Channel's granite shores.

But you are never to be taken lightly. Your storms roll in without warning, building waves that rival the open ocean. Your fog obscures the horizon, and your infamous seiches remind boaters that water levels can shift in an instant. Yet for those who embrace your unpredictability, the rewards are boundless—quiet anchorages, breathtaking vistas, and the undeniable thrill of navigating waters steeped in history.


To the Chesapeake Bay —

You are a waterway meant to be savored, like a slow-moving country road that winds past quiet coves, working waterfronts, and timeless towns. You invite boaters to take their time—drifting between sleepy fishing villages and bustling harbors, discovering the rhythms of your tides, and settling into anchorages that feel like well-kept secrets.

There is a charm in your variety. One moment, the skyline of Baltimore or Norfolk rises in the distance, and the next, the only sounds are the lapping of water against a hull and the call of an osprey overhead. Your creeks and rivers stretch deep into the land, offering miles of protected water where mariners can lose themselves among marsh grasses and crab shacks unchanged by time.

You offer both comfort and complexity, rewarding those who know how to read your moods. Your shallows can stir up a steep chop, and your crab pots keep helmsmen ever watchful. You can be sweltering in the summer, with windless days that beg for a dip over the side—but that same warmth lingers late into the fall, extending the season for those who wish to stay just a little longer.

For the boater who embraces your pace, you offer something rare: a journey measured not in miles, but in moments. A quiet anchorage tucked into a winding creek. A seafood feast fresh from the water. The deep satisfaction of finding a place that feels like it was waiting just for you.


To New England's Waters —

Your shores are timeless, and your harbors are nothing short of legendary. Your best-known ports grow busier each season, yet for those who venture beyond the usual routes, hidden anchorages still offer quiet refuge.

You are as unpredictable as you are unforgettable. One moment, your waters welcome a smooth passage beneath clear skies; the next, they challenge even the most seasoned captains with shifting currents, dense fog, and winds that refuse to settle.

Your sounds and bays test our skill and reward our persistence. The chop of Buzzards Bay can wear us down, but its harbors are among the most picturesque on the coast. Rhode Island Sound and Nantucket Sound are vast, restless, and ever-changing, rewarding those who respect their moods. A clear morning can give way to rolling seas by afternoon, but beyond the chop lie quiet harbors, windswept beaches, and anchorages that feel untouched by time.

And yet, for all your challenges, we are always drawn back. There is no thrill quite like raising sail past Newport's storied cliffs, no quiet as humbling as a morning fog rolling off the Elizabeth Islands. You are where tradition meets tide, where every port tells a tale, and where each crossing—no matter how many times we've made it—feels like the first.


To The Bahamas —

You lure us with the clarity of your waters—blues so vibrant they feel otherworldly, depths so transparent they defy logic. You invite us to drift over shallow banks, to slip between cays where the tide whispers through narrow cuts, to anchor in solitude beneath skies untouched by city lights. And yet, you demand patience, preparation, and respect.

Your passages are not for the complacent. The Gulf Stream crossing is a rite of passage, a transition from the familiar to the unknown. Your open-water jumps between island groups rival that first crossing—uncharted inlets, shifting sandbars, and ocean cuts that can turn from tranquil to treacherous in a single tide cycle. Your currents pull hard, your storms form fast, and your provisioning is never taken for granted. Here, a boat is not just a vessel; it is self-sufficiency, lifeline, and home.

But, oh, the rewards. To sail from the bustling docks of Nassau into the quiet embrace of the Exumas, where the anchor finds purchase in powder-white sand. To chase the setting sun along Eleuthera's western shores, where pink sand beaches and sheltered coves glow in the fading light. To wake in the Berrys, where time slows and each day is dictated not by a schedule, but by the rhythm of wind and tide.

No two journeys are alike, no two crews experience you the same way. Some race through, eager to see it all, while others linger, losing themselves in your rhythm. But all of us, no matter the pace, leave forever marked by the memory of your waters and the pull to return.


To the Atlantic ICW—

You are the thread that ties together a thousand ports, a route both familiar and ever-changing. From the marshy bends of the Carolinas to the palm-lined inlets of Florida, your waters carry us through landscapes that shift with the tide, revealing the quiet beauty of the coast mile by mile.

You demand patience and attentiveness. Your shoals shift with the seasons, your bridges dictate the day, and your currents remind us that timing is everything. You are not a route to be rushed but one to be understood, where slow passes through quiet towns and glassy morning waters are as much a part of the experience as the miles themselves.

We follow your path without urgency, knowing that the journey itself is the reward. Your bridges rise for us, your markers guide us, and your hidden anchorages become our temporary homes. You are a rhythm, a season, a migration—the link between old ports and new adventures, between past voyages and those still waiting on the horizon.


To the Gulf Coast—

Your shores are a mosaic of cultures and currents, where the flavors of the South meet the rhythms of the sea. From the sugar-white beaches of the Florida Panhandle to Louisiana's working waterfronts and Texas' sprawling coast, you are a passage of contrasts—untamed and industrious, serene and relentless.

Your waters offer refuge from the open Gulf, weaving through bayous, barrier islands, and quiet stretches where time seems to stand still. But solitude is never guaranteed. You are shared with tugs and barges—giants that move with purpose, demanding respect and patience. The fog of the Mississippi Delta rolls in thick, and the long, open reaches test endurance when Gulf winds sweep across the shallows. Yet those who time their crossings, heed the VHF chatter, and embrace the demands of the journey find a waterway rich with character and challenge.

And yet, for all your demands, you offer rewards that can't be found elsewhere. We follow your winding channels, past shrimp boats and skiffs, knowing that every inlet holds a story, and every mile brings a new discovery.


What Waters Have Captured Your Heart?

Every boater has a place that feels like home. A place where the wind carries familiar whispers, where the water welcomes us back like an old friend. Which cruising region has stolen your heart? Tell us your love letter in the comments or share your favorite memories with us.


Comment Submitted by Brad - February 27, 2025
Wonderfully written! We've been lucky to also sail these same sailing grounds!! But, the one thing I would add is all the great people you meet along the way, especially the Bahamians. People near water just seem to have better attitudes and outlooks on life. We feel truly blessed to have met many of the outstanding folks that we encountered along the way and look forward to continuing the encounters!
Comment Submitted by Orita - February 26, 2025
What a wonderful and well written piece! It rings the bell of sleepiness and awakens your yearning for travel! The desire to experience every place mentioned in it rises deep from inside me and impacientes my curiosity to start the voyage we've been planning. True, I've done Bahamas and Caribbean on a sailboat, quite some time ago, for 2 years. But the thirst to do it again and to navigate through to new horizons has always been with me! So, thanks for this wonderful article that only made my desire more intense to explore our beautiful country and our beautiful world! Orita
Comment Submitted by Bob S - February 26, 2025
Lovely article! The Chesapeake is home, but we've spent time in both NE, the Bahamas and the ICW. All have their charms, but I am most fond of the Chesapeake for all it has to offer.
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