Built in 1863 in Norwalk, CT, the Alice S. Wentworth was originally named the Lizzie A. Tolles. In 1863 she was sold to Charles and Arthur Stevens of Maine, where she freighted coal, lumber and salt. After they rebuilt her in 1904, her owners rechristened her the Alice S. Wentworth after a niece.

Zeb spotted her in 1906 in Portland, and quickly fell in love. He sold his ship the Wilfred J. Fuller and signed on as Captain. Here is the description Polly Burroughs wrote of the Wentworth in her book Zeb: Celebrated Schooner Captain of Martha's Vineyard:
"...Seventy-three feet long with a sharp sheer and broad beam-she was a bricker-built to carry 5500 brick on deck. She drew only 5-1/2 feet of water when light and 7-1/2 when fully loaded with a hundred tons. With the centerboard down, she drew seven feet more..."

Zeb had the opportunity to purchase the Wentworth in 1921 and remained as Captain until 1942 when vision problems forced him to retire, temporarily. The Wentworth then went to Maine as a cargo vessel for 10 years, when it was sold several more times and sailed as a windjammer cruise ship. In 1965 she was purchased by Anthony Athanas of Anthony's Pier 4 Restaurant in Boston. Athanas moored her alongside his restaurant until it was destroyed by a storm in 1974. She was 111 years old.