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



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 15 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"


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

"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) and British Virgin Islands (BVI) charters: Visit Foxy's or Soggy Dollar Bar, White Bay in the BVI, 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