It was Captain John Smith, of Pocahontas fame, who first called these the Calendar Islands, since he imagined that there was one for every day of the year. While there are a good deal fewer than 365, there are easily that many stories and legends, from the Fountain of Youth on Cousins Island to the buried treasure of Captain Kidd said to be hidden somewhere on Jewell.

Six of the islands—Cliff, Great Chebeague, Great Diamond, Little Diamond, Long, and Peaks—are served by ferries from Portland or Yarmouth and host thousands of summer visitors in addition to the year-round residents; others, like Hope—with a private tavern and a chapel for its one resident family—seem like independent countries. Between these extremes is a wide range of island types, including several that are operated as state parks, places where anyone so inclined can inhabit a Maine island absolutely free of charge.

After a while, Joe did manage to catch a proper wind current, and instead of plunging into the Atlantic, our balloon—called the Skybox—floated pleasantly north along the Downeast coast. From our wicker basket, we waved at local turnip farmers before finally coming to rest in a field near Falmouth. To mark the occasion of our landing, we all drank champagne, Strauss waltzes playing on a boom box, as local residents came by to marvel at our unexpected arrival.

Later that day, I saw another side of Casco Bay from a lobster boat piloted by Captain Tommy Martin and his sternwoman, Jenn Doe. Lobstering is the central industry in Casco Bay, and Captain Martin's boat, the Lucky Catch, takes tourists like me out on lobster runs; if you trap anything, you can buy it wholesale and have it prepared at a restaurant onshore.

The Lucky Catch sailed south along some of the most beautiful coastline in the country—past Portland's still thriving Old Port; Fort Gorges, a Civil War–era fortress; Cushing's Island, with its imposing Indian Head rock formation gazing out to sea; and finally classic, picturesque Portland Head Light, which has to be one of the most recognizable silhouettes in the United States, after Britney Spears's.

The eight traps Captain Martin checked on this run yielded three lobsters, several dozen Jonah crabs, and something called a raven fish, a hideous creature covered with barbels, which sternwoman Jenn insisted we all kiss for good luck. I'd never smooched a fish before, let alone one this ugly, but knowing I'd need all the luck I could get if I intended to find the Fountain of Youth, I puckered up and kissed the awful-looking raven fish, an experience I can only describe as . . . salty.

Then it was off to Peaks, the most populated and easily accessible of the Casco Bay islands, on the 2:15 p.m. ferry. It was only a fifteen-minute ride across the bay, and another five up the hill from the ferry landing to my hotel, the Inn on Peaks Island. The inn's rooms are all named after Casco Bay islands, and mine, the Great Diamond Island Suite, was large and airy, with a cathedral ceiling, a great canopy bed, and a porch that overlooks the ocean.