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Still weak, the men half walked, half limped from office to office until, finally, a local prefect granted them the permission they sought, after accepting a bribe of two gold coins. The contract allowed the men to start selling ice immediately. Satisfied, they set sail again, this time for Jamaica.

This stretch of the trip went almost as poorly as the last. They were on a different ship, and this ship's captain was deep in his cups by ten each morning, rarely leaving his cabin after the first drink. This left the duties of steering the ship to the first mate, who was largely unfamiliar with the ship's mechanics and nearly capsized the vessel twice. Everyone agreed to dock in Santo Domingo to search for a new captain to lead them on. It was an unplanned stop, but since they were there anyway, William and James figured they'd apply for permission to sell ice. The local government granted their request, but that was the end of their good luck. French soldiers occupying the Dominican Republic prevented them from traveling to any other island. They managed to find passage on a Danish schooner bound for Jamaica, but a privateer stopped them just outside Port Royal and took William's favorite pistols. When they were finally permitted to proceed to port, they stayed for several weeks just to avoid having to get back on a ship. "A seaman's life is a dog's life," James later wrote in his diary.

The men eventually sailed back to Boston, getting lost along the way for nearly twenty-seven days. When they finally arrived, a flustered and annoyed Frederic met them at the harbor, showing little sympathy for their bad luck. To his mind, they'd spent way too much money and had accomplished little. "The advantages derived from their part of the expedition," he wrote in his diary, "were not equal to the expense of it, which was near $2,000." When he calmed down, he explained how busy he'd been while they were gone, ginning up interest among investors (who, in actuality, had either said no outright or pledged to talk again after Frederic proved his plan could be successful) and mortgaging the Tudor family's South Boston land to cover the rest of the capital. This would be the first of many poor business decisions.

He'd also been working on a plan to keep ice cold while at sea. Frederic had noticed that ice in the family icehouse melted fastest in open air or when sitting in its own meltwater—the runoff from melting ice. He drew up blueprints for a cargo hold that would keep the ice elevated and as sealed off from air as possible. He'd even bought his own ship, the Favorite. This would be the second of many poor business decisions. Traders rarely owned their own vessels in Frederic's day. Instead, they purchased space on cargo ships that sailed their preferred trade routes. The ship alone cost $4,750 ($120,000 today), and reconstructing the cargo hold cost more.

William and James responded to all this by vowing never to sail again (though they did). Still, celebration was in order. As far as the men were concerned, the hardest parts of the plan were complete. They had permissions to sell ice. They had their ship. Plans were underway to begin harvesting Rockwood Pond as soon as temperatures were cold enough to freeze the lake. What could go wrong?

The next challenge wouldn't be the considerable labor of extracting and shipping ice. What none of them had considered was how they would actually sell the ice, a substance people in the tropics had rarely—if ever—seen.

* * *

Even as their plan came together, no one seemed to have any faith in what the men were doing—not even Judge Tudor, who told his son that no one in their right mind would pay money to buy ice when they could get it for free. (The judge rarely traveled outside Massachusetts.)

"People only laugh and belittle me when I tell them I am going to carry ice to the West Indies," wrote Frederic in his diary. "Let those laugh who win."

As the shipment day grew closer, Frederic had more to worry about than ridicule from family and friends. There existed the real possibility that he wouldn't get the ice harvested in time. This had been one of the warmest winters on record, with ice thinner than it had ever been in Frederic's lifetime. Not until two weeks before the February shipment date did Rockwood Pond freeze deep enough to harvest thick blocks that could survive, at least in theory, the weeks-long journey to Martinique.

Frederic hired dozens of men—more than the Tudors had ever employed at one time—to carve up the lake and haul the ice blocks to the harbor, where they were hoisted into the Favorite's newly constructed cargo hold. When the ship was full, Frederic strode aboard and walked to the bow. As the ship nosed its way toward the open sea, he would have looked out at a cold, hazy horizon. Whatever came next, he was about to be the first person on earth to bring ice to the tropics. And, he thought to himself, he was about to make a fortune.

Meanwhile, the press back in Massachusetts was having a field day. "No JOKE," reported the Boston Gazette. "A Vessel has cleared at the Custom House for Martinique with a cargo of ice. We hope this will not prove a slippery  speculation." (Emphasis added.)

On March 5, 1806, the Favorite arrived at the island. Much to Frederic's delight, the carefully constructed cargo hold had prevented two-thirds of the ice from melting. The bad news was that there was no place on the island to store it. Only now did Frederic appreciate just how difficult this trading scheme was going to be. To sell ice in the Caribbean in 1806 was somewhat akin to selling television sets to Americans before the 1950s: Few broadcasting stations existed in the early twentieth century because few people owned TVs. But few people owned TVs because there were so few stations. Worse, TVs didn't become puddles if they languished unsold. To succeed at selling ice, Frederic was going to have to build both interest and an infrastructure to support it.