Joshua Leffingwell, a native of Hartford, Connecticut, seems to have enjoyed wintering in a warmer climate. Leffingwell was an architect and builder in Hartford. According to the Leffingwell Record (a genealogy published in 1897), Joshua and his brother, John, built a number of buildings, including the Hartford Bank, Center Church, and the Old State House.
When not involved in the large projects, Joshua Leffingwell constructed houses, disassembled them, and shipped them to Trinidad. He then spent the winter reassembling them on that sunny, warm, Caribbean island. Sounds great!
There are several mentions of this enterprise in Leffingwell’s diary and account book. In the image below, Leffingwell has detailed his travel back to Connecticut from Trinidad. The journey, he notes on the bottom of the page, took 32 days.

Joshua Leffingwell diary and account book, 1805-1808, Ms 73124. Connecticut Historical Society, Hartford, CT
Later in the volume, Leffingwell recorded his labor as a house carpenter during the winter months. John Munro, who is listed as the debtor, was his employer, and is mentioned many times throughout the volume.

Joshua Leffingwell diary and account book, 1805-1808, Ms 73124. Connecticut Historical Society, Hartford, CT
Numerous recipes and household remedies have been entered in the volume. Some are directly written in, others are sewn or pinned in. Most are handwritten, though others are from newspapers. Among the various entries are a “receipt to make a beautiful and lasting white-wash,” a remedy for curing an inflamed cow, recipes for seasoning sausages, Washington Cake, and keeping meat in warm weather. The recipes shown below are for Queens Cake and Potato Pudding.

Joshua Leffingwell diary and account book, 1805-1808, Ms 73124. Connecticut Historical Society, Hartford CT
As always, this volume is available for research. Come visit!
Sounds like a intersting person. Ron Leffingwell