Affordable Sailing & Snorkeling

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Coming to the Caribbean on vacation? St. John is the USVI’s best kept secret so why not enjoy a St. John’s best kept secret activity: a classic day sail option compared to all the other commercial tours and excursions. Singing Dog Sailing is the parent company and leader in the local charter market for quality charters and sailing excursions.  We also offer affordable monohull sailing excursion options for something to do on the water while vacationing in St. John. Please consider our second boat in our fleet –  Salty Dog Day Sails – which is described as the best kept secret and best value for an affordable boat trip while vacationing in St. John, according to our guests. Salty Dog Day Sails of St. John, USVI, a division of Singing Dog Sailing, offers comfortable and affordable US Virgin Islands and British Virgin Islands, USVI & BVI, sailing and snorkeling charters aboard our classic cutter rigged sailing mono-hull.  S/V SELKIE is fitted with traditional tanbark sails and all the expected refinements of a mighty Yar Yacht! Come explore St. John USVI and nearby Jost van Dyke, BVI’s for a memorable day on the water!

“Salty Dog” is nautical slang for an experienced sailor who has spent much of his life aboard a ship at sea. A salty dog is often given increased credibility by ship mates in matters pertaining to ship-board life and duties. Also known as an “old salt.” (Wiki-pedia)

Adjective – Yar (comparativeyarer, superlativeyarest)

  1. (nautical, of a vessel, especially sailboat) Quick and agile; easy to hand, reef and steer.

1940My, she was yar…It means, uh…easy to handle, quick to the helm, fast, right. Everything a boat should be.The Philadelphia Story written by Philip Barry; 1993Arr, here be a fine vessel: the yarest river-going boat there be. – Captain McAllister The Simpsons ep. 1F06


selkie sailing Tayana 37 monohull USVI sailing

Classic & Affordable Day Sail Option from St. John USVI

You do not have to travel far to get into the sailing spirit. Salty Dog Day Sails offers dynamic, fun and affordable trip itineraries within the US Virgin Islands. A full day on the water is a dynamic balance between exhilarating sailing and delightful snorkeling. On all our excursions we visit the best snorkel locations, often not the same bays and reefs listed in the guidebooks which are no longer in healthy condition. US waters trips with Salty Dog Day Sails include off the beaten track sites that are often places you cannot get to by car like some of St. Thomas and St. John’s idyllic neighboring cays like Lovongo, Congo, Henley & Whistling Cays or the marine preserve at Greater St. James called Christmas Cove. We also explore the Us Virgin Islands National Park, snorkel at Waterlemon Cay in Leinster Bay, St. John. Have you heard about the abundance of starfish that live there?


Marine Biologist holding Starfish at US Virgin Islands National Park

We also know all the secret spots for world-class snorkeling where the coral reef is well-preserved and colorful as well as abundant marine life in the variety and quantity of tropical fish with aquarium like conditions. Maho and Hawksnest Bays are known for turtle sightings. Let us take you to swim with the turtles. Often you will spot a Hawksbill sea turtle cascading over the reef whereas Green sea turtles munch on turtle grasses that grow on the sandy, flat bottoms of idyllic bays and are relatively unaffected by your presence.

Hawksbill Turtle

Hawksbill Turtle at Waterlemon Cay

OR–Do you want to get a stamp in your passport by visiting another country only 6 miles away in the nearby British Virgin Islands or BVI’s? Salty Dog Day Sails also offers a day trip to Jost van Dyke, , also known as Jost or JVD, which is one of the more well-known British Virgin Islands mainly due to the renown of Foxy, aka Foxy Callwood, who is the namesake of Foxy’s Bar and Foxy’s Taboo. Foxy was knighted by the British Royal Family for doing so much to promote BVI tourism and put the sleepy little island of Jost van Dyke, which only got electricity in 1995, on the tourism map. Another iconic legendary beach bar on the itinerary of our typical JVD day sail is the Soggy Dollar Bar located in the idyllic White Bay on Jost van Dyke. Yes, that is the establishment responsible for inventing the famous Caribbean cocktail:  the PAINKILLER. You can probably see Soggy Dollar Bar listed as one of the world’s top 10 beach bars and White Bay as one of the top ten beaches on several travel forums like Conde Naste, Caribbean Travel & Leisure, to name a few! Of course this trip includes some world-class snorkeling too and maybe even a chance dolphin or whale sighting while sailing over to the BVI’s. Take a bit of that Caribbean flavor home with you!

White Bay JVD

White Bay – Jost van Dyke – BVI’s

About our boat and your comfort–we are not your typical ‘Clorox bottle’ style monohull sailboat offering day tours. our sailboat is pristine and has classic lines and character for a traditional sailing feel.  We only host small groups of 1 to 6 passengers in your party. We are also not a commercial boat with striped down amenities. Our sailboat boasts plenty of shade and cushioned seating. Our full keel sailboat offers stable, comfortable yet fast sailing, even compared to larger boats. Not only is it comfortable, it is a classic. Our monohull sloop is a traditional double-ended hull design with classic wooden spars (mast) and tanbark sails. It has the look and feel of a traditional boat from the days of merchant ships and pirates—something from legend and history. One trip with us and you will note the superior maintenance and cleanliness that is not the normal experience on a charter boat.  The owners of this boat put years of their lives and several hundred thousand dollars of resources into the detailed restoration of this classic sailboat and have instilled a level of pride and commitment to excellence in their captains and crew for its impeccable upkeep and cleanliness.  You may see or sail on similarly priced monohull boats and sailing charters, but you will not benefit from the same level of experience or cleanliness.  These are NOT STOCK photos like some of the images from other charter websites. Guests beware…at he most basic level–you do not have to WORRY about using a marine toilet on THIS boat!

We have been hosting trips for more than 14 years and take ultimate pride in giving our guests the same level of service and experience we would wish for ourselves. This is what Singing Dog Sailing is so highly regarded on (Salty Dog Day Sails just recently added a review age so please help us and fill out reviews to help get the word out that we have two boats in our fleet).

St. John sailing below decks

Comfortable amenities – NOT the typical day sail boat!

Imagine yourself sailing the same waters as Blackbeard the pirate! Imagine yourself HERE for the day with us—living the dream & sailing on the great blue Caribbean Sea!

St. John affordable sailing charter