"Hope." Every boater on every outing, no matter how mellow or epic, is hopeful — for fun on the water, happy companions, a safe journey. Aboard the Grand Banks 42, First Light, on a trip up the East Coast from Florida to Rhode Island, the word took on special meaning. It's the simple, concise state motto of so-nicknamed "Little Rhody," emblazoned on its official flag, one of which was mounted on the bow of our trawler as we slowly, steadily cruised up the Intracoastal Waterway and into Chesapeake Bay.

From our elevated perch on the flybridge, as we motored through a fascinating American panoply of towns, cities, islands, and wilderness, the little, triangular white burgee flapping in the breeze was the one constant, never-changing visual. Hour after hour. Mile after mile. It eventually dawned on me that it couldn't have provided a more positive, pleasing watchword. "Hope" was quite literally leading our way.

For First Light's skipper, the seasoned marine author Dan Spurr, the voyage north was the realization of a long-held dream. Some three decades earlier, aboard a compact 32-foot sailboat with his wife, Andra, he'd made the journey in reverse: from the salty, seaside Rhode Island city of Newport to the Sunshine State, a trek that left both lasting impressions and a desire to do it again sometime, but in a rangier, more comfortable vessel. Work and family, so often the case, put those plans on indefinite hold.

But now, semi-retired and with an ideal cruising boat, the window of opportunity had again opened, and Dan had seized it. My longtime pal, one-time colleague, and frequent shipmate had recruited a posse of friends to crew on separate legs, and when he asked if I'd be available for the roughly 450-mile stretch from Southport, North Carolina, to Annapolis, Maryland, he didn't have to query twice. "I'm in," I said, in seconds flat.

First Light had successfully traversed the waters from her Floridian homeport of Longboat Key, through the Okeechobee Canal, and up the coast through Georgia and the Carolinas when I caught up with the boat at the Southport Safe Harbor Marina across from Oak Island at Mile 310 on the Intracoastal Waterway. There, I was joined by our third crewmember for the leg to Portsmouth, Virginia: Dan's friend Ken Green. My lasting memory of the place was watching a big sportfishing boat taking on diesel ($6.99/gallon) at the adjacent fuel dock. Glug glug, cha-ching! Some 555 gallons and $3,800 later, the fishermen were good to go. And I was once again reminded why I've always owned sailboats.

The next morning, we slipped onto the Cape Fear River, bound for a snug anchorage called Mile Hammock Bay at Mile 244. Bucking a solid 2-knot current, our first semi-obstacle was the Wrightsville Beach Bridge, where the helpful bridgetender informed us that the clearance was officially 19 feet but there were a couple of feet to spare. Since our "air draft" — height above the water, counting overhead bimini — was 20 feet, we could continue unimpeded without having to wait for the next scheduled bridge opening. Which we did. Though I must confess to held breath as we squeezed beneath the span.

North of the bridge, we were greeted by row after row of stately, palatial homes, a notably different look from the sparse barrier islands, empty beaches, and lovely marshes we'd left astern. As the day unfolded, there was so much to look at and contemplate: a big dog wading out to his neck off a beachfront, then just standing there, literally and figuratively soaking it all up. A pair of curious birds in a comfy nest atop a mile marker, facing the boat traffic, checking it all out. A couple of wrecked sailboats — high, dry, and abandoned — their service days over, shattered testaments to dashed dreams. Kids galloping across a sandbar, hooting and hollering, their trim Boston Whaler nudged up against the shallows. And, of course, boats, boats, and more boats, of every size and dimension, darting hither and yon, which were quite the contrast to the slow, soft parade of cruising vessels like ours, heading north in a pack, abundant time on our side.

The taut anchorage at Mile Hammock Bay, which we shared with a half-dozen other boats, did have one unsettling feature: the distant report of spent artillery. A glance at the chart unraveled the mystery: We were more or less parked adjacent to Marine Corps Base Camp Lejeune, with nearby training exercises clearly underway. Happily, the firing ceased in concert with the setting sun.

The next morning, thanks to an anchor fouled on what we believe was an unmarked undersea cable, it was more dramatic leaving the bay than arriving. And while we did manage to ultimately break the hook free, the resulting bent stainless-steel bow roller was an annoying souvenir of the entire unfortunate episode. Still, we had it all sorted in time to make the 0800 opening of the Onslow Beach Bridge, and were once again a going concern.

We were now firmly ensconced in "the Ditch," so named for the ICW canals originally built and still maintained by the Army Corps of Engineers. My own boating career, as noted, has been mostly under sail, and I've seen plenty of blue water, competed in most of the major ocean races, rounded Cape Horn, negotiated the Northwest Passage, and so on. But I'd never seen anything quite like the Ditch, such an engineering marvel, such a beautiful, wet, inland highway. It was tops. Churning through those tantric waters, the blue sky above, the lush green foliage framing our very defined borders, was pretty as a painting, but one in fluid motion. It was so new to me. So remote. I absolutely loved it.

A small-craft advisory with attendant thunderstorms had been issued for the Neuse River, and a big southwest breeze kicked in just as we entered. It was perfect for a downwind spinnaker run, and I told Dan I was ready to send it. With a raised eyebrow, he helpfully pointed out we had neither a mast nor sails and suggested I settle down. Spoilsport. We careened into the marina in Oriental, North Carolina (Mile 181), and were snug in our slip mere moments before the weather turned really sporty. Lucky.

The next few days, connecting the chartplotter dots of channel markers and waypoints (easy-peasy navigation), unfolded seamlessly and beautifully: a dash across Pamlico River to a stunning anchorage just past Tuckahoe Point on the Alligator River (Mile 105). A mellow trip through Albemarle Sound with a welcome easy breeze to a cool dock space adjacent to a fine restaurant in Coinjock (Mile 50). And finally, as the chill scenery suddenly morphed into busy and industrial, a passage through the Great Bridge Lock (and the "Welcome to Virginia" sign), and into the seaway of Navy ships, cranes, and freighters, in the bustling cities of Norfolk and Portsmouth (Mile 0), just in time for Memorial Day.

Once tied up, the highlight, if you want to call it that, was having a ringside seat to a Carnival cruise ship with a strong resemblance to a tiered wedding cake (and just slightly smaller than the Grand Canyon), doing a pirouette in the main channel with a DJ blaring incomprehensible music on the top deck, which was packed full of swaying vacationers. You could not have gotten me aboard that bloody monstrosity at gunpoint. It was there that Ken bid us adieu, and I'm not sure it was a coincidence. Wide and mighty Chesapeake Bay now stretched out before us. Part two of my leg of the delivery. This would be a completely different encounter than the ICW we'd left in our wake. But no less terrific.

Dan had charted a route up the bay's Eastern Shore with a first stop in the charming little village of Cape Charles, a 35-mile run from Norfolk during which we weaved through a massive fleet of nearly two-dozen anchored tankers parked between the Chesapeake's eastbound and westbound shipping lines, the dreaded consumer "supply chain" temporarily on hold. A posse of dolphins bodysurfing in our quarter wave offered prettier sightseeing. We eased into our slip in the friendly environs of the Cape Charles Town Harbor and Marina, a short walk from the pretty downtown shops and eateries and the white-sand beach at the end of the street. Highly recommended!

So, too, was our next destination, the wholly unique and idiosyncratic Tangier Island, another 40 miles up the track. It was a scorcher of a day, the flat blue water and cloudless blue sky unified and inseparable, eliminating the horizon between the two (though a welcome following current notched our boat speed up to a trip-best 11-plus knots according to the GPS). Nearly everyone who visits Tangier says the same thing, so I will as well: The place is like stepping back decades in time.

A mile long, 3 miles wide, smack-dab in the middle of the Chesapeake, it's home to some 500 or 600 hearty souls, all of whom — literally and figuratively — are connected to the water. We were the only pleasure boat in the rustic Parks Marina, from which we wandered up to the only open restaurant (Lorraine's: tasty!) and then a stroll down the historic streets, many featuring the tombs of deceased relatives in the front yards of the tidy homes, a feature that amazed Dan to no end.

The "severe thunderstorm watch" on the 60-odd-mile sprint to Tilghman Island provided our first real bit of nasty weather since the passing front on the Neuse River, and we plowed through plenty of whitecaps before securing the docklines at the Knapps Narrows Marina and Inn just as the first raindrops plonked down (still lucky). Tilghman is also alluring and stark, but after Tangier it felt like midtown Manhattan. The good son of a friend of Dan's, Kaeo Clarke, is an intern at the Chesapeake Bay Maritime Museum at nearby St. Michaels, and he was generous enough to collect us in his pickup for a wonderful personalized tour of the facilities, yet another milestone in a journey with tons of them.

After a lay day (first of the trip), we made our way through bustling Kent Island Narrows — its many restaurants and drinking holes with adjacent docking, rocking on a Saturday afternoon — and into a secluded anchorage at Queenstown Creek. We had a swim, launched the dinghy and paddleboard, and got some good photos of First Light in the day's last light — the ideal spot to enjoy the final evening of the voyage. The next morning, up came the anchor and we made our way up the Patapsco River to the fine facilities at Oak Harbor Marina above Annapolis in Pasadena. And with that, all too soon, it was time for me to catch a flight home.

It had been more than fantastic to hang with my great old mate, who'd been a mentor to me as both a sailor and writer since we'd first met in the offices of Cruising World magazine more than four decades ago. He'd just sailed his 28-foot sailboat from the Great Lakes to Newport to take a position as senior editor; I was, ahem, the receptionist, my first real job out of college, and considered him just about the coolest cat I'd ever met. He took me under his wing, and fast friends we became. Now, no longer the raffish dudes we then aspired to be, over the years, as everyone does, we'd endured our share of life's nicks and bruises. But there on First Light, with the blessed luxury of unmarked time, we'd swigged wine, downed tasty chow, explored every topic under the sun, and solved all the world's problems. We'd reconnected in the best way possible, with the blessed common denominator that forged our friendship in the first place. On a boat.

In a broader sense, looking back at our two-week adventure, for a lad from blue-state New England, it was fascinating traversing through a part of the country hued red. But I have to admit, even I got a chuckle in Coinjock from the message emblazoned across the T-shirt of a chap on a go-fast boat called Ship Happens: "I Identify As Non-Bidenary." Politically, though we had a friendly, quick chat, we may not have tread on much common ground. But we were boaters. We sure as hell shared common waters. They always have been, and remain, one of life's great equalizers.

On the several long cross-country drives I've taken, I've often thought that every five years, every American should be mandated to make the same trip. To see and witness what an amazing, diverse, drop-dead beautiful country this really is. To hear all the distinctive regional accents and see all the unique local sights. To embrace the differences, not shun them. I now feel the same way about the serpentine ICW and brilliant Chesapeake Bay. Everybody should experience them. Everyone. What places they are. They left me, it must be said, full of hope.