Wayward Sailor, voted the Best of the USVI an embarrassing number of times - We provide Daysails, snorkeling and sailing charters and also perform weddings on St. John, US Virgin Islands
Come Sail Onboard Wayward Sailor!
Voted Best On St. John for 16 years running by
the readers of the Virgin Islands Daily News!

Come Sail and Snorkel with us for the BEST day of your vacation!

"the ultimate in personal service"

Fair Winds and Following Seas Capt. Phil!!!

Capt. Philip George Chalker, age 82, passed Sept. 17, 2021, in a hospice home in Atlanta. He was born Dec. 9, 1938, in Lansing, Mich., to George and Margaret (Walker) Chalker, the youngest of three children.

He is survived by his sisters, Marlene Paul and Sally Smith; his life partner, Allison Smith; step-daughter, Angie “Sunshine” Smith; five grandchildren; and one great-granddaughter. He also leaves behind his island tribe and WSF (Wayward Sailor Family).

Between Phil’s outgoing personality and insatiable drive for life, he was ever drawn to the water. His intrigue with diving began as a young man in Michigan where his entrepreneurial spirit could be found diving shipwrecks off Lake Michigan. Eventually, Phil would buy a boat unseen and move to Florida where he would begin his charter business as a dive boat captain upon the Reef Roamer.

He spent many years in Florida, 15 years in the Bahamas, and even a few in Haiti. Later, he would trade engines for sails and transition to snorkel tours. During his last three decades of life, Capt. Phil could be found hosting St. John charter guests aboard the famous crisp little burgundy and white sailing vessel, the Wayward Sailor, with his shipmate, Tarn Hildreth, who worked alongside him for 18 years. He was a USCG-licensed charter captain for more than 50 years.

Phil was a vivid storyteller, and could often be found around town recounting the adventures of his younger years. When Phil wished one day that he could compile his memories into a book, a close friend began collecting his stories through recordings and interviews over a period of several years, eventually threading together a written narrative that would become the book of which he was very proud, “Adventures at Sea with Captain Phil Chalker.”

Capt. Phil was still booking charters right up until his last year of life. When asked by friends when he might consider retiring, Phil would simply respond, “I don’t want to retire until I get old.” Phil never really did get old. He passed of complications from a neurological disorder caused by COVID-19. His spirit is ever-present in St John and his memory will live on in the hearts of many for years to come.

Due to government restrictions of gathering size, a private service of remembrance will be held and shared via social media. Donations may be made in Phil’s memory to the St. John Animal Care Center, Kids and the Sea, or the Island Health and Wellness Center.

Proceeds from the book will also go to benefit these three St. John nonprofit organizations in his memory.
 

Adventures at Sea with Captain Phil Chalker  
Hot off the press!!!

This book is a collection of stories from memories and events that took place over the course of Phil's lifetime. It begins in his early life as a boy from Michigan and explains how he came to spend most of his adult life living among the sea. The book ends with how he ended up here, in St. John.

For those who dream of bigger things, like chasing the horizon and riding the wind to new places, Adventures at Sea with Captain Phil Chalker is meant to inspire and encourage those navigating the ever-changing seas of life. From dynamite to DEA deals, from the Tonton Macoute to Voodoo religious services, one will never expect the twists and turns that comprise the breadth of Captain Phil's journey.

Click here to purchase



 


Featured in the following publications:

Wayward Sailor, voted the Best of the USVI an embarrassing number of times - We provide Daysails, snorkeling and sailing charters and also perform weddings on St. John, US Virgin Islands

The Wayward Sailor on The Vacation Rental Show



"A day sail on the Wayward Sailor and snorkeling with Capt. Phil Chalker, a marine naturalist, is a must".

Stars Love Going to St. John by Lindsey Hunter
OK Magazine, December 2007

Other than the awards, why should you sail with Wayward Sailor?


  • We specialize in sailing!  As a 30 plus year Caribbean sailor, we only run the engine when we have to
  • U.S. Virgin Islands (USVI) charters: Visit the US Virgin Islands National Park (VINP), St. John
  • Natural adventure and environmental education for your family: children friendly
  • All inclusive full day and half day sails, sunset sails, adventures on St. John, or the Soggy Dollar Bar or White Bay. Customized private charters available for groups, honeymoons, newlyweds, kids. Snorkel gear available.
  • Experience the Caribbean environment on our sailboat trip: eco tour from Cruz Bay, St. John- best activity in the USVI with our charter boat
  • Guided snorkeling and snorkel lessons for all levels: beginner snorkelers to advanced free divers. Capt. Phil joins you in the water to teach and assist!
  • Personal and professional service: Capt. Phil is a licensed, insured captain and marine naturalist of St. John, Virgin Islands
  • Marriage and vow renewal ceremonies: romantic weddings at sea or on a tropical beach
  • Experience the romance of a spiritual wedding ceremony or renewal of wedding vows with Rev. Phil Chalker, an ordained minister



Wayward Sailor, voted the Best of the USVI an embarrassing number of times - We provide Daysails, snorkeling and sailing charters and also perform weddings on St. John, US Virgin Islands.
United States Virgin Islands
  Wayward Sailor, voted the Best of the USVI an embarrassing number of times - We provide Daysails, snorkeling and sailing charters and also perform weddings on St. John, US Virgin Islands.
Virgin Islands Charter Yacht League
  Wayward Sailor, voted the Best of the USVI an embarrassing number of times - We provide Daysails, snorkeling and sailing charters and also perform weddings on St. John, US Virgin Islands.
www.St-John.com