Sail with the Wayward Sailor


Tarn, Captain Phil and Allison

Best Day Sail on St John
Best Charter Boat on St John
Best Activity in the Virgin Islands


 Sail
 Hours
 Amenities
 (includes beer, soda, water)
 Adults
 Children
 (under 10)
Exclusive/private
(1-6 guests)
 Full Day
10-4
 Lunch and dessert
 $105
 $95
$630
 Half Day
9-12 or 1-4
 Snack
 $65
 $60
$390
 Sunset Sail
5:15-7:15
(summer)
4:30-6:30
(winter)
 Champagne and hors d'oeuvres
 $65
 $60
$390
 Jost Van
 Dyke
8-4:30
Caribbean Snack

 $115 plus customs
 $20 p/p. Trip not available on Sunday.

 $115 plus customs
 $20 p/p. Trip not available on Sunday.
$690
plus $20 / guest
for customs fees
plus lunch


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. 

Capt. Phil 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.


Wayward Sailor has a 2 person minimum and a 6 person maximum.
We offer exclusive sails and can customize any of our trips.
Personal service is guaranteed and we can accommodate most special requests.

Give a friend or loved one a gift they will remember for a lifetime, a day on Wayward Sailor.
Gift Certificates are available for all Wayward Sailor trips, just contact us for details.


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.


Wedding Ceremonies

Includes: Pre-wedding meeting and customized Wedding Ceremony
Locations: St. John Beaches, Villas, Resorts or on board Wayward Sailor
Price: $250

Newlywed Sail

Leisurely romantic private sail (typically a sunset sail)
Hors d'oeuvres - fruit and cheese platter
Open Bar - champagne, beer, soda, and water
Wedding Cake baked exclusively for Wayward Sailor wedding sails
Bouquet professionally done by our local flower shop, Today's Flowers

Sail with
ceremony, bouquet and cake
Sail without
ceremony, bouquet, or cake
2 (Bride & Groom) ~ $850 2 (Bride & Groom - Exclusive) ~ $350
4 (Bride & Groom + 2 Guests) ~ $950 4 (Bride & Groom + 2 Guests) ~ $400
6 (Bride & Groom + 4 Guests) ~ $1050 6 (Bride & Groom + 4 Guests) ~ $500


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
Email Captain Phil

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