About Us! - Wayward Sailor Crew
On every Wayward Sailor charter, a female crew member is on board for your comfort and safety. She prepares all the meals on board (from scratch!), serves beverages and assists you in every way to be sure your charter is a great experience . . . sometimes even joining you in the water!

Tarn, Capt. Phil and Allison

Tarn Hildreth joined the Wayward Sailor crew in July, 2003, moving to St. John from Massachusetts. She says that "the whole point of being here is to enjoy the water!"

By the way, her name means "small mountain lake"!

Allison Smith: Computer and marketing assistant (former first mate and now onboard crew occasionally!)

Allison is also proud to be a mom and a grandmother of six . . . shown here with two of her grandsons. Her family lives on St. John.


The first mate also handles the sails and anchor and socializes with guests.

Tarn Hildreth: First Mate, Senior Crew and a 50 ton Licensed U.S. Coast Guard Captain

"The best thing about working on the Wayward Sailor is meeting the wonderful guests from all over the world and being out on the water". Tarn is a world traveler herself, who use to organize trips to the Galapagos and annually took school kids to the Amazon.

In addition to being a terrific first mate, she is also a licensed U.S. Coast Guard Captain, works at La Tapa and is co-owner of World Class Anglers, a great St. John sportsfishing business.

A St. Johnian since 1987, Allison is a lifelong sailor who sailed her own boat to the Caribbean from Florida. She joined the Wayward Sailor crew in August, 2003, alternating sailing days with her private practice as the "Island Shrink" (she has a Ph.D. in psychology), free lance writing, her businesses Rejuvenation Vacations and Viva! Villas, director of the non-profit organization, the People Moving Forward Foundation and raising goats in Coral Bay.

Allison was instrumental in making the business what it is today and is still my advisor and confidant and soulmate.


Capt. Phil Chalker
PO Box 37
St. John, VI 00831-0037
(340) 473-9705
Email Capt. Phil