Offering day, half-day, sunset sails, private charters, motor excursions, weddings-on-board and a variety of other water activities for guests of Caneel Bay Resort and the entire St John community.





     Day Sail: We leave Caneel Bay dock at 9:30 AM, and sail north-east into British waters. We then tack to the north shore of St John where we anchor for a snorkel or swim from the boat.  A sit-down lunch prepared on board is provided along with a choice of water, soft drinks, beer, wine or rum concoctions. We then sail back to Caneel Bay and discharge our guests at 3:30 PM. Guests need to bring towels, camera, snorkel gear, sunglasses, hat, cover-up, sunscreen, and maybe a good book. We provide the rest. Passports are not required for this trip. Offered everyday.
      Half-Day Sail: Leaves Caneel Bay dock at 9:00 AM and returns at 12:00 PM for the morning sail and leaves again at 1:00 PM to return at 4:00 PM for the afternoon sail. Typically, we sail north-east towards the BVIs and then change course back to an anchorage in US waters for an optional snorkel stop. Water, soft drinks, beer and rum concoctions are served. There is no food served but the guests are welcome to bring their own snacks. Guests need to bring towels, camera, snorkel gear, sunglasses, hat, cover-up, sunscreen, and a good book. We provide the rest. Passports are not required for this trip. Offered everyday.

      Sunset Sail: Leaves the Caneel Bay dock between 4:30 and 5:30 PM (depending on the time of sunset) and returns 1½ hours later. Appetizers, along with guest’s choice of water, soft drinks, beer, white wine or rum concoctions are served. Guests should dress casual and bring cameras. Offered only as public sails on Wednesday, Friday and Saturdays - private sails everyday.

      Combination Half-day with Sunset Sail: Leaves the Caneel Bay dock between 1:30 and 2:30 PM (depending on the time of sunset) and returns 4 1/2 hours later. Long sail from Caneel with a stop for snorkeling. Appetizers, along with guest's choice of water, soft drinks, beer, white wine or rum concoctions are served on the return sail to Caneel through sunset. Offered only as a private sail for up to six guests. Everyday.

Weddings and Renewal of Vows:

Captains Greg (Spitfire) and Charles (Sea Smoke), are registered with the Territorial Court of the Virgin Islands to perform weddings in the territory. Please call for further information.

Please call for pricing and availability:

Sail Caneel Bay is the official sailing concession of Caneel Bay Resort and an Authorized and licensed Virgin Islands National Park concession


A few words about Virgin Island weather...

Many of our guests will check or some other weather service to see what their week in paradise has in store for them. Well, a forecast of "30% chance of rain and scatter showers" has a very different meaning in the upper 48 States than it does here in the Islands. In the States you would expect grey skies and wet, sloppy weather, generally the type of weather you would like to escape from. However, that same forecast for the Islands means blue skies with puffy white clouds and trade wind breezes, with a chance of a passing (refreshing) rain, just the type of weather you would like to escape to. Rainouts in paradise are unusual and are generally described as "60% (or more) chance of rain and numerous showers". In any case, if you get a little wet, the brilliant sun will dry you quickly.


Note: All of our sailing yachts are now "Green", each with solar panels and wind generators.

SPITFIRE: Built in 1981 by John Alden, Spitfire has been extensively sailed throughout the Caribbean, Bahamas, Bermuda, and the East coast of the United States. She has been continually updated and refitted. Spitfire is extremely comfortable and offers wide, spacious decks and a large shaded cockpit. There is a marine toilet (head) on board.

LOA: 51’-0"    Beam: 14’-2"    Draft: 7’-6"

Designed by Kaufmann & Ladd

SPITFIRE appears on the cover and inside of the December 2007 issue of Travel & Leisure magazine.

SPITFIRE has also been used in photo shoots for and a 2008 Target catalog.



     SPITFIRE’s captain, Greg Freitas, is from Cape Cod, where he was an engineer in the oceanographic field. As captain of the 80-foot schooner ADIRONDACK, he has set the course record and twice won the Mayor’s Cup in Manhattan. He has also appeared on "Regis and Kelly Live" show. He has been sailing since 1969, has had a U.S. Coast Guard Master's License since 1988 and has logged over well over 70,000 miles under sail. He has visited over 36 countries during his career.

Captain Greg has been featured in Time-Out New York magazine  and in numerous newspapers articles including one in The New York Times. Captain Greg was given a Citation of Honor by the United Seamen's Service (New York City), a Certificate of Appreciation from the Humane Society of New York and was awarded a Citation and the Transportation 9-11 medal by the Coast Guard and the Department of Transportation for his work during the 9/11 evacuation and relief effort in New York City. Greg was also interviewed on The History Channel’s documentary, "The Day the Towers Fell".

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

Captain Barbara Emerson spent her early years as an avid equestrian, competing successfully in Florida. However, when she discovered sailing, she traded in her riding boots for a pair of flip-flops. Barbara graduated from Florida State University in 1979, practiced public accounting as a CPA, went body surfing, taught aerobic dancing, and would cruise the Bahamas on her vacations. In 1989, she decided to take a one-year sailing sabbatical to the Caribbean and has never considered returning. She has held her U.S.C.G. Master's license since 1993 and has over twenty years sailing experience. Barbara enjoys traveling, snorkeling, swimming, dancing and hiking. She is an avid reader, loves music, and enjoys entertaining.


LOA: 50’-8" Beam: 14’-9" Draft: 7’-8"



       SEA SMOKE: Also a Morgan Yacht, Sea Smoke was designed for Caribbean charter sailing. Fun, fast, beamy (wide) and stable, Sea Smoke has a roomy and shaded cockpit as well as flush decks that are great for sunbathing. The transom ladder provides easy access in and out of the water, and along with a fresh water rinse, makes Sea Smoke an ideal boat to snorkel and swim from.

LOA: 50’-8" Beam: 14’-9" Draft: 7’-8"

Designed by Nelson Merek


Charles Swaim and Leslie Jones are the captain and crew of Sea Smoke and have been living aboard for ten years.  Together they have sailed over 30,000 sea miles.

Charles' early interest in cooking and an opportunity to apprentice to an excellent continental chef set into motion a lifelong love of cooking and cuisine. A gypsy at heart, Charles was educated in Texas and received a degree in comparative philosophy. Taking early retirement from an administrative position at the University of Oklahoma allowed the pursuit of a dream to live and sail in the Caribbean. Charles holds a US Coast Guard 100 ton masters license.

The operation of Sea Smoke is shared by Leslie Jones. Leslie's first home is central Oklahoma where she was born and received a degree in Business Administration. She left her job at an international lettering arts magazine to go with Charles to the Caribbean.  She loves animals, nature and the sea and would be delighted to share what she has learned about the wildlife of the Caribbean.

    M/Y SATISFACTION - Built in 2006, SATISFACTION is a Neptunus 55 Cabrio, powered by twin 800HP turbo diesels and designed to be the cat's meow of power yachts. Let the captain and crew whisk you away for a day adventure to the British Virgin Islands or pick you up at Little Dix Bay for a transfer to Caneel (or the reverse trip). It will be a day you will remember for a long time.


What our guests are writing about us.

This has been one of our most enjoyable and memorable days, especially aboard Spitfire.
- Amy & Roberto

A really perfect sail… we wish it could have lasted forever…
- Jo Ann & Charlie

Thank you, thank you, and thank you for an amazing, beautiful day!
- Deanne family

We couldn't have made a better decision - great day, wonderful boat, great crew.
- Phil

Thank you for an unforgettable trip around St. John. There are many reasons to return, but this is definitely the most compelling one.
- Paige & Al

What a special day! Terrific sail, lovely snorkel, delicious lunch, great captain and crew.
- Collins family

Heaven on earth! This by far has been the highlight of our trip!
- Anne & Ryan

The best birthday and anniversary gift I can think of for my wife and me. All was beautiful (and killer rum cake).
- Jeff & Krispin

Reservations may be made by contacting:

Sail Caneel Bay / Sail St. John

P.O. Box 37
St. John, VI 00831