Echoes of a long-ago family charter reverberate in a Florida charter with grandchildren. Maybe it’s genetic.

It was a long time ago—in our family’s history and in the history of chartering boats—when my husband, George, feeling in immediate need of a vacation one August, chartered the only boat available in the state of Maine. It was our first time chartering, first time sailing in Maine, and first time cruising en famille.

We tossed our three kids, veterans of a couple of years of sailing lessons, in the car along with enough provisions to last a month, drove up to Southwest Harbor, on Penobscot Bay, and went to meet our boat. It was a 30-footer with four bunks (the youngest and smallest child was consigned to the cabin sole), a leak down the mast, and an alcohol stove whose fumes made even George seasick; the nav gear consisted of a compass. Fortunately, we had brought our own charts; more fortunately, there were decent winds and no fog all week. The only other amenities supplied were a dinghy and oars, a few pots and pans, and a barbecue on which we cooked everything. The only amenities we brought were sleeping bags and towels, paper plates, a modicum of clothing, and a kerosene lantern that lit and gave a bit of warmth to the tiny cabin.

We went ashore only once, to reprovision and hunt out ice cream in Camden. The two boys stayed below most of the time, playing interminable two-person card games of their own devising; David, the middle child, appeared on deck to take the wheel when the wind rose enough to pique his interest; the kids caught a shark using scraps of leftover steak as bait. Other than some interpersonal crises, a wonderful time was had by all.

We learned a few things too: Three’s a crowd. Growing boys eat a lot more when exposed to sea air. Our children much preferred the exoticness of life on a boat to tromping around towns. Rules are useful for keeping some semblance of order.

That was then, and last April’s charter in Florida was almost thirty years later. Many things about chartering boats have changed, and many things about family cruising have not.

I arrived at Miami Beach Marina, home of Florida Yacht Charters, with the entire contents of a Publix supermarket, armed for a week of cruising with George, David, and David’s sons Jack, 11, and Max, 9, and went to the dock to meet our boat. Sunset, a Jeanneau Sun Odyssey 40.3 sloop, would easily accommodate the five of us—mattresses for everyone—in her three cabins. Her nav gear consists of everything electronic, the fridge is capacious, there were many sheets and towels, and there was so much stowage space we needed a map. The galley has enough space for a chef and a sous chef. And, we were told, the 54-foot, 6-inch mast would fit under the bridges we might want to go under (check tide!); importantly, Sunset draws around 5 feet.

Months in advance we adults consulted cruising guides, a chart book, info from FYC, and notes from friends on places we shouldn’t miss. From those sources we decided we’d do a one-way cruise from Miami to Key West and consider the delivery fee to be money well spent on not having to rush or retrace our route. It wasn’t exactly a hard sell, especially when Jack and Max learned not only that they would miss a week of school, but that they might get to snorkel the entire 150 miles, half of that with dolphins.

We also decided that, despite curiosity about the ICW—much read about, never experienced—we’d sail the Hawk Channel, which runs east and south of the keys and would allow us to snorkel the reefs that mark its outer bounds. In the channel we could expect greater depths (though not entirely without shallow and/or hard spots), some abatement of the seas by the reef, and widely spaced markers. Should we change our minds, there would be a limited number of crossover points that would take our draft and mast height. I noted from a Web site: “Plan to spend a lot of time and energy navigating.” It sounded perfect for George, who would rather navigate than swim.

Forewarned is forearmed, and there’s no shortage of information about cruising any part of Florida; on our own, we had an uncomfortable combination of too much extraneous information and too little local knowledge. Enter Rick Jones and his excellent boat and chart briefing. We told him what we were thinking about and received in return a list of his favorite anchorages; recommended marinas and restaurants, if necessary; sights to see along the way; and where along the 100 miles of coral reef that constitute the Florida Keys National Marine Sanctuary would make the best stops for us adults and the two water rats. “And don’t forget,” he concluded, “that brown water is bad.” Brown waters obviously do not run deep.

We left on a Sunday morning with what seemed like reasonably loose plans for arriving in Key West on Thursday afternoon so we’d have time to scope out the town, enjoy David’s treat—a fishing charter—on Friday, and be ready to hand over the boat and catch our flight home early Saturday morning. A lovely trade wind of 20 knots or more stayed with us all the way to Key West. We followed Rick’s exiting instructions to the letter: crossed Government Cut, passed the Tinker Toy cranes of the Port of Miami, left ICW green mark 57 to port, passed red and gave green a wide berth, and continued on to the narrow channel along Brickle Bay. This channel is very shallow, he told us, so we should be sure to continuously look behind us to make sure we were still in it. We did.

Since sailing down Biscayne Bay didn’t pose any remarkable challenges, we pulled out the jib and had a nice ride down to Angelfish Creek, a tricky, windy channel wide enough for 1.5 sailboats, which led us into Card Sound for the night and out to the ocean side and Hawk Channel the next morning. Pumpkin Key, recommended by all our sources, was indeed a nice anchorage, so the boys got out their gear—fishing rods, snorkel masks, rashguard shirts—and plunged into those very clear waters.

Rule 1 for sailing with kids: You may go up on deck while we’re under way, but most of your limbs must be inside the lifelines. Rule 2: Rule 1 is void if water is coming over the bow. Rule 3: Nine- and 11-year-olds are perfectly capable of spotting channel markers instead of horsing around. Rule 4: No swimming unless an adult is present.

The wind was up to 25 the next morning, with 2-to-4-foot seas, as we came back out Angelfish Creek to the ocean side and Hawk Channel. We were making 7.5 knots sailing toward the reef when, noticing that the boys were looking greenish, we opted to cut the sail short and head for the closest place, North Dry Rocks. This was the first of many changes of plan made on the fly; most of them involved where we would anchor for the night since the wind was strong enough to make some of our first choices—the ones marked “Good Fishing” on the chart—untenable. Sometimes we couldn’t let out enough scope without swinging aground; other times it was simply too lumpy. Rule 5: Bonine for breakfast (agreed).

Clearly, lumpy is in the eye (or inner ear) of the beholder. Hen and Chickens Reef, where there was plenty of chop, was Max’s favorite because it was there that he saw what he described as more, bigger, and better fish—barracuda, tuna, and grunts. That was the afternoon we bolted into the ICW in search of a pretty much guaranteed quiet night in Jewfish Hole (“Good Fishing”) off Fiesta Key. Getting there involved following Channel Five under a fixed bridge; it was hard to believe we had more than 6 inches clearance under the keel or above the mast.

It was clear from the start that we weren’t going to drum up any interest in exploring on shore. The boys were perfectly content on the boat and in the water, trolling (unsuccessfully) when we were sailing and fishing when not swimming at anchor. But about halfway to Key West, we’d run out of some essentials and were forced to spend a couple of hours on land—one hour hunting for supplies and one having lunch in a restaurant. Rule 6: It is a cardinal sin to eat all the cookies at once, and even worse not to share them. Rule 7: It is not child abuse to require kids to set the table and dry the dishes.

Evening boat entertainment usually consists of reading and playing cards, but we had another arrow in our quiver of boat toys: A GPS-powered SkyScout, on loan from Celestron. While we initially identified the masthead light as a new supernova, Max quickly figured out how to use it to identify and characterize any of the visible stars in that bright, light-pollution-free sky. It sure beats watching TV.

We arrived in Key West on Thursday afternoon, having done a lot of sailing, thanks to big distances between anchorages and numerous trips to and from the offshore reefs. Highly praised Looe Key had been my ultimate goal, and we had it to ourselves that morning. The fact that we passed three Portuguese men-of-war (my greatest fear, greater even than hungry sharks) on the way out gave snorkeling there a certain edge.

David’s fishing charter the next day, the gilding on the lily, took us out beyond the reef and provided not one but three hungry (small) sharks (caught and released) and a couple of snappers. We took them to Hogfish Bar and Grill, on Stock Island, where Florida Yacht Charters’s marina is located, where they were perfectly cooked. All’s well that ends well, especially when all has been well all along.

Cruise Notes

Why Go: Florida is a perfect spring destination—not too hot, not too cold, reliable wind, beautiful water of unbeatable color and clarity. If you go, be sure there’s at least one experienced navigator in your crew.

Florida Yacht Chaters: The company has bases in Miami Beach, Key West, St. Petersburg, and Abaco, Bahamas. www.floridayacht.com; 800-537-0050

Cruising Guides:Cruising the Florida Keys by Claiborne S. Young and Morgan Stinemetz; Cruising Guide to the Florida Keys, by Frank Papy; Diving and Snorkeling the Florida Keyes, by Bill Harrigan (Lonely Planet); Florida Keyes and Evergaldes Cruising Guides, by Capt. Freya Rauscher.