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Two days later, in New York, Madison wrote to his brother that “Mr. Jefferson is here and we shall set out in a day or two. The extent of our joint tour will depend on circumstances.” Jefferson checked into Mrs. Ellsworth’s boardinghouse on Maiden Lane with Freneau and with his fellow Virginians Madison and John Beckley, clerk of the House of Representatives. The question of whether they were actively carrying out political activities in New York City has long intrigued historians, but reports that they were came almost exclusively from Hamilton’s faction. Hamilton’s confidant George Beckwith, the unofficial envoy of Britain to the United States, wrote to the foreign minister in London, that “the Secretary of State, together with Mr. Madison, are now gone to the Eastern States, there to proselyte as far as they are able a commercial war with Britain.” And Alexander Hamilton’s son John flatly asserted that the Virginians were meeting secretly in New York City with the newly elected U.S. senator Aaron Burr, Hamilton’s enemy, before going on to huddle with Gov. George Clinton, a leading anti-Federalist, in Albany. Burr had just unseated Hamilton’s father-in-law, Philip Schuyler.

If Jefferson and Madison were merely on vacation, they had no reason either to conceal or to record visits to New York politicians on their way north. But if they were engaged, as John Adams’s son John Quincy later wrote, in “double dealing,” they had obvious cause for silence.

INTRIGUES ASIDE, THE FIRST THING Jefferson did when he reached a large town along the road was buy books. Then he sent out his servant James Hemings to get fresh fruit and vegetables for the journey. In Paris Jefferson had placed Hemings in the kitchen of a prince to learn French cooking; he was said to be the half-brother of Jefferson’s wife, and Jefferson eventually would set him free. Jefferson was becoming convinced, as he wrote to the African-American mathematician Benjamin Banneker, that “nature has given to our black brethren talents equal to those of the other colors of men.”

As Jefferson and Madison set out on their tour, Jefferson gave Hemings his loaded carriage and enough travel money to go ahead on the post road to Poughkeepsie, where they would rendezvous. For all their obvious and numerous presence, slaves are almost invisible in most early American history: Jefferson’s expense records offer a rare glimpse of Hemings’s duties on the trip: “James for expenses to Poughkeepsie 6 (dollars).”

After Jefferson had cleared his hotel bill and, for the second time in three days, visited a barber, the two tourists bade their friends good-bye and boarded the fast sloop of Capt. John Cooper. While they were sailing north, Jefferson brought up-to-date his three-column record of each day’s expenses and mileage, spreading out the expense sheets on the laptop desk he brought along. As the sloop slid past the dark, brooding Palisades, Jefferson made no notes about the scenery, but at the overnight stop at Conklin’s Tavern he not only wrote down the price of breakfast but also began to rate the inns along the route. A nondescript one got no comment; a good one, a plus mark or star; a bad one, a minus. (Conklin’s got no comment.) Jefferson kept such records to pass on to family and friends. When, thirty-five years later, his granddaughter went to New England on her honeymoon, he provided her with a set of his notes and travel recommendations from this vacation.

In the morning they went back aboard Captain Cooper’s sloop, and Jefferson began to keep yet another journal, a botanist’s account of the tour: “May 22. Conklin’s in the highlands. Found here the Thuya Occidentalis, called White cedar, and Silverfir, called hemlock. .. . Also the Candleberry myrtle.” Botany was the cutting-edge science of the age, and Jefferson had been keeping scrupulous garden records at Monticello for nearly twenty years, but here he was keeping a detailed traveling botanist’s record book for the first time.

AFTER THREE DAYS ABOARD SHIP Jefferson and Madison were ready for the comforts of a first-rate inn. At Hendrickson’s, in Poughkeepsie, they spent more for dinner and the night’s stay than the entire ship’s fare for the passage up the Hudson. But Jefferson always appreciated good roadside inns. “I do not seek for the good things which it has not,” he once wrote, “but those which it has. A traveler retired at night to his chamber in an inn, all his effects contained in a single trunk, all his cares circumscribed by the walls of his apartment, unknown to all, unheeded and undisturbed, writes, reads, thinks, sleeps, just in the moments when nature and the movements of his body and mind require. Charmed with the tranquillity of his little cell, he finds how few are his real wants, how cheap a thing is happiness.”

Paying his $7.23 bill, Jefferson awarded the place his first star. Leaving Poughkeepsie, he took up his pen and continued his record of plants and trees he had never seen farther south—white pine, pitch pine, and juniper, with “berries used for infusing gin.” He and Madison went sixteen miles before breakfast; in all, they rode thirty-seven miles that first exhilarating day on horseback, while James Hemings drove the carriage behind them, and Jefferson awarded their next stopover, Lasher’s Inn, in Claverack, another star.