(340) 998-2904 capt@sailcaneelbay.com


SPITFIRE: Sail Caneel Bay’s flagship is a John Alden Skye 51. Designed by Kauffman & Ladd and built in 1981, she has been sailed extensively throughout the Caribbean, the Bahamas, Bermuda, and the East Coast of the United States. Spitfire has been continually updated and refitted. She is extremely comfortable and offers wide, spacious decks and a large and shaded cockpit. There is a marine toilet (head) onboard for guest use.

True to the meaning of her name, Spitfire is a high-spirited lady (and fast yacht). She has appeared on the cover and inside of the December 2007 issue of Travel & Leisure magazine, as well in photo-shoots for Macys, a Target 2008 catalog, and an Anne Cole bathing suit photo-shoot in 2016. Her vital statistics are LOA 51’-0”, Beam 14’-2”, and Draft 7’-6”. As of 2016, we have logged over 62,000 sailing miles since we purchased her in 1999.

Captain Greg Freitas

captain greg freitas

Capt. Greg Freitas

Spitfire’s owner and captain, Greg Freitas, grew up in New Bedford, Massachusetts and lived and worked on Cape Cod as an Electrical Engineer in the Oceanographic field. He moved to St John in 1990 to work as a charter captain on his Hinckley Bermuda 40 yawl, DESTINY, out of Caneel Bay Resort. In the Spring of 1995, Greg, and co-captain/first mate, Barbara, left paradise and sailed DESTINY to New England (via the Spanish Virgin Islands, Turks and Caicos, and the Bahamas) to see if they were “missing something”. They bought a 165 year old farm house, two cars, opened a boat shop and ran a factory. mattapoisettCommon sense and deep snow made their decision to move back to St John a very easy one. In the Fall of 1998, they sold their stuff (house, cars, business and DESTINY), bought SPITFIRE, spent the next year refitting her to their standards, and sailed her to St John. There, they ran day sails and term charters. In 2003, Greg and Barbara started Sail Caneel Bay and acquired Caneel Bay Resort’s day sail program from Proper Yachts. Captain Greg Freitas has held his United States Coast Guard Master License (100GT) since 1988 and has logged well over 100,000 miles under sail. He has visited over 36 different countries during his career.

In an issue of “International Yacht Vacations & Charters” magazine, author Scott Rose wrote, “Charter yachtsman simply do not come any finer than Captain Greg Freitas”.

Learn more about Captain Greg Freitas

The Manhattan Years

adirondack-2Greg would take the summers of 2000 through 2003 “off”, and captain the 80-foot schooners, ADIRONDACK, in Manhattan, and ADIRONDACK II, in Newport, RI. In 2000, Greg and his crew of six, set the course speed record and won the Mayor’s Cup in Manhattan. In 2001, they set another speed record in New London, CT. He and his ADIRONDACK crew appeared on the Regis and Kelly show. On the morning of September 11, Captain Greg and his friend, Captain Sean Kennedy, drove Kennedy’s boat, CHELSEA SCREAMER, into Hell and were among the first boats providing evacuation from lower Manhattan to New Jersey by water. They returned over and over. Captain Greg spent the next eight days on site creating and running “The General Store”. Captains Greg and Sean received a Citation of Honor from the United Seaman’s Service (New York City), were given a Certificate of Appreciation from the Humane Society of New York and were awarded a Citation and the Transportation 9-11 medals from the U. S. Coast Guard and Department of Transportation. Captain Greg was subject of articles in The New York Times and Time Out New York and appears in the History Channel’s documentary “The Days the Towers Fell”. In 2002, Greg and his ADIRONDACK crew won the Mayor’s Cup for a second time. A recent documentary, Boatlift, features video taken from the CHELSEA SCREAMER during the morning of September 11, 2001.

Captain Barbara Emerson

Capt. Barbara Emerson

Capt. Barbara Emerson

Captain Barbara Emerson was born in North Carolina and spent her early years living in San Diego, Hawaii and Florida. An avid equestrian, she competed successfully in Florida and took home the Blue Ribbon on many occasion. After graduating from Florida State University where she studied accounting, she discovered the pleasures of sailing and traded her riding boots for a pair of flip-flops. She sat for the CPA exam, worked in a small accounting firm in Vero Beach, FL, and took “April 16 until the money ran out” vacations to the Bahamas on her boat, HORIZON II. After ten years of practicing accounting, she started a “one year sabbatical”, now in its 26th year, to the Virgin Islands. Barbara started to work for Proper Yachts on St John and met Greg on a sunset sail out of Caneel Bay Resort. Captain Barbara has held her United States Coast Guard Master License (100GT) since 1993. Her hobbies include cooking, dining and wine tasting, traveling, swimming and snorkeling, dancing and taking long walks. She is an avid reader and enjoys live music. Together with Greg, they built a kitchen, with two bedrooms suites attached, surrounded by 10 acres of forest in the mountains of western North Carolina.