• We specialize in sailing!  As a 35 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 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 sail, adventures on St. John: customized, dive gear, private charters for groups, honeymoon, newlyweds, kids
  • 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 wedding at sea or tropical beach
  • Experience the romance of a spiritual wedding ceremony or renewal of wedding vows with Rev. Phil Chalker, an ordained minister


 (includes beer, soda, water)
 Adults  Children
 (under 10)
Exclusive/ Private
(1-6 guests)
 Full Day
 Lunch and dessert  $125  $115  $750
 Half Day
9-12 or 1-4
 Snack  $75  $70  $450
 Sunset Sail
 Champagne and hors d'oeuvres      Exclusive only $450

Sunset Wedding $1100
 Jost Van
Caribbean snack

 $125 plus  $45 p/p
customs & lunch

 $125 plus $45 p/p
customs & lunch
 $750 plus $45 p/p
customs & lunch
No Sunday Trips


St John Tour               Charters

Snorkeling & Sailing Charters

  • Sail to neighboring islands on a classic sloop
  • Snorkel at pristine "out of the way" reefs
  • Learn more about the reef with guided snorkeling

With steady trade winds, the Virgin Islands are known for great sailing.  The Wayward Sailor is a classic sloop and a sailors' dream.  The large cockpit offers a comfortable and safe sailing experience.

Snorkeling St. John

St. John is surrounded by many uninhabited cays with fringing reefs that offer excellent snorkeling.  Capt. Phil is a marine naturalist and has studied the local coral reefs extensively.  He offers guided snorkeling, where he identifies the fish and creatures and discusses their behavior.  One of his fortes, is teaching beginners how to snorkel and making sure everyone is comfortable in the water.  For the experienced snorkeler, we offer advanced snorkel sites with great free diving and drift snorkels.

Full Day Sail:
10am - 4pm
Two snorkel stops
Enjoy our homemade lunch and dessert

Half Day Sail:
9am - 12pm or 1pm - 4pm
One snorkel stop
Refreshing Treat

Jost Van Dyke, BVI

Jost Van Dyke, one of the British Virgin Islands, is a very laid back island of only 180 people. Experience a morning snorkel and beautiful sail to Jost Van Dyke where you can visit the famous Foxy's bar for lunch and be entertained by the Fox himself. After lunch, join us for a nature stroll and enjoy the variety of flora and fauna and the charm of this small island.

*Jost Van Dyke: 8:00 - 4:30
~One snorkel stop
~One nature walk
~Lunch at Foxy's
(average cost of $10 pp)
~Caribbean snack

All sails include:   

Personal Service - maximum of six guests
Open Bar - beer, soda, and bottled water
Guided Snorkeling
Top of the line snorkel gear and flotation devices

*Jost Van Dyke is a foreign country and requires proof of U.S. citizenship.:
U.S. passport OR original birth certificate with a photo ID or a certified copy of original birth certificate with a photo ID. NOTE: December 1, 2005 Passports only.
Non-U.S. citizens are okay with a valid passport.

Sunset Sail

Join us for a Caribbean sunset aboard the Wayward Sailor with spectacular views of the Virgin Islands.  Sail, relax and hear all about the local folklore from Capt. Phil during a spectacular sunset.  

St. John, US Virgin Islands Sunset
St. John Sunset

Mike & Rhonda enjoying a St. John sunset.
Mike and Rhonda

While enjoying a leisure sail, we serve champagne and hors d' oeuvres.  All sails include beer, soda, and bottled water.  Departure time varies throughout the year.  Contact us for the time.

About Us

Capt. Phil Chalker (Marine Naturalist) is a 100 ton master licensed captain aboard the Wayward Sailor.  As a licensed captain and marine naturalist, Capt. Phil combines his knowledge of the sea and marine life for an unforgettable sailing and snorkeling experience.  

Join us for the day aboard the Wayward Sailor, a thirty foot classic sloop.  We offer full day, half day, sunset sails, and Jost Van Dyke trips.  Our specialty is guided snorkeling and personal snorkel instruction.

The Wayward Sailor has a maximum of six guests and guarantees personal service.

*Wayward Sailor by definition:  "in search of one's own destiny"

Capt. Phil Chalker

St John Tour               Charters