Wayward Sailor


view of boat in harbor

Captain Phil Chalker has 25 years of experience sailing these Caribbean waters, including many years as captain of the Calypso Queen, a glass bottomed boat that gave narrated tours of the reefs of St John. He now sails the Wayward Sailor, a 30 foot sloop that departs from Cruz Bay with 2 - 6 passengers. Captain Phil is a very patient captain and snorkeling instructor and takes great pleasure in introducing the wonders of the reef to beginners.

Full Day Sail (10am - 4pm). The full day sail consists of a morning and afternoon snorkel over two beautiful reefs, both of which are off the beaten track on uninhabited cays. After the first snorkel a great lunch such as a seafood sandwich with salad, fruit and chips is served. Coolers of cold beer and soda are always on board. After a relaxing sail to a second snorkeling adventure, you are homeward bound in time to have sunset cocktails around your pool.

Hours: 10am - 4pm
Adults: $85 each
Kids: $75 each (under age 10)
Exclusives: 2 people = $340/day, 4 people = $510/day
on the boat




Half Day Sail. For those with less time, Capt Phil offers a short sail to one of his many beautiful reefs for snorkeling. On the sail home a delicious platter of cheese and crackers or a fruit plate is served. Coolers of cold beer and soda are always on board.
Hours: 9am - noon and 1pm - 4pm
Adults: $50 each
Kids: $45 each (under age 10)
Exclusives: 2 people = $200/day, 4 people = $300/day
on the boat




Sunset Sail. Leaves Cruz bay in the late afternoon to capture the beautiful tropical sun falling into a purple sea. With clouds of red and orange highlighting the western sky, these are truly magnificent moments. Champagne and hors d'oeuveres complete this totally stressless sail.

Hours: 4:30pm - 6:30pm(winter); 5:15pm - 7:15pm(summer)
Adults: $50 each
Kids: $45 each (under age 10)
Exclusives: 2 people = $200/day, 4 people = $300/day



Jost Van Dyke.* This is an hour and a half sail to a very laid back island of only 450 people who are famous for their hospitality and charm. This is where you can visit the famous Foxy's Bar and be entertained by the Fox himself. Sandcastle's Soggy Dollar Bar and beautiful white sand beach is also just moments away. Snorkeling a beautiful reef completes this memorable day, and of course, coolers of cold beer and soda are always on board. U.S. citizens only: Passport or Birth Certificate with a raised seal and a picture ID.

Hours: 8:00am - 4:00pm
Cost: $100 per person
Exclusives: $500/day for 2-4 people
Note: In addition to the rate there is a $20 customs fee.

*This trip is not available on Sundays
visiting a beach




Caribbean Villas View: Captain Phil has been introducing people to the wonders of the Caribbean for more than 25 years. He genuinely loves his work and it shows. Our guests have nothing but praise for Captain Phil; he's patient, entertaining and an expert sailor and snorkeler who loves sharing his knowledge of the Caribbean and the undersea world. Whether for sailing, snorkeling, island hopping or even a wedding or a honeymoon sail, our guests always enjoy the time they spend aboard the Wayward Sailor.
Form of payment - Cash or traveler's checks
Snorkel gear - yes, but you may want to bring your own
Floats - yes
Showers - no
Fishing - yes
Shade - yes
T-Shirts and hats - yes
another view of the boat


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Caribbean Villas & Resorts. P.O. Box 458. Islandia Building, 3rd Floor. St. John, USVI 00830
Phone (800) 338-0987 | Fax (207) 510-6308 | E-mail: caribvilla@newtonline.com



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Caribbean Villas & Resorts. P.O. Box 458. St. John, USVI 00830
Phone (800) 338-0987 | Fax (207) 510-6308 | E-mail: caribvilla@aol.com


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