Meet Your Virgin Islands Boat Charter Captain & Crew

Virgin Islands Boat Charter Captain & Crew

Your Salty Dog Day Sails Charter experience is led by the best Virgin Islands boat charter captain and crew teams the USVI has to offer.  Our sailing boat charter crew members representing Salty Dog Day Sails are a collective group of  the best Virgin Islands boat charter captain and crew teams all of whom are fun, licensed professionals with years of local USVI and BVI knowledge and experience, sharing a collective passion for sailing and hospitality.  Your Virgin Islands boat charter on either of the Salty Dog Day Sails charter boats will be enriched by their intuitive service and delightful attitudes.  A memorable day on the water awaits. Remember to book a trip with the best Virgin Islands boat charter captain and crew teams in the USVI: Licensed, Competent, Professional, Knowledgeable & Fun.

Book Sailing Charter Now!

Meet Your Crew


Best St. John Boat Captain Salty Dog Day Sails Justin Holt

Virgin Islands Boat Charter Captain Justin

Captain Justin is ranked as one of the best St. John charter boat captains for sailing charters in the USVI. Justin hails from landlocked Mid-west, but that only served as motivation to seek out life’s opportunities. An early student of all things transportation, Justin first obtained his pilot’s license following in his father’s footsteps. Sailing, another family passion, quickly became a vocation as well. From weekly flights and sailing trips while growing up, Justin embraces the lifestyle of movement in all forms. A patient teacher, Justin has been an invaluable mentor to crew seeking experience and training. Captain Justin has worked with Captain Stephen as charter boat co-workers for 16 years. Justin is an easy-going ‘salt’ with a passion for sharing the dream with others.

Best St. John Boat Boat Crew Swab Pepper Salty Dog Day Sails

Virgin Islands Boat Charter Swab Pepper

Pepper hails from Richmond, Virginia, and moved down to the US Virgin Islands to live a life on the sea. Pepper has spent his years on St. John hiking all over the island, exploring its hidden coves and sailing its waters. He one of the most enthusiastic people you’ll ever snorkel with and would love to show you the underwater sights. If you want to identify a fish you’ve seen underwater, take an unforgettable hike or plan a memorable post-sailing adventure, Swab Pepper will steer you in the right direction. Ask for Pepper when booking your St. John Boat charter.

Susan Another Best Boat Captain USVI Salty Dog Day Sails

Captain Susan

After 20 years in dentistry, Susan sold everything to follow her dream of becoming a pirate in the Caribbean. She sailed from Charleston and spent time in the Bahamas before making the Virgin Islands her home. She has sailed most of the Caribbean islands and also spent a season in the Mediterranean after doing her first transatlantic voyage. The past several years, Susan has been doing day charters and she’s looking forward to sharing all of the beauty of the place she now calls home.

Admiral Jake Singing Dog Sailing and Salty Dog Day Sails

Virgin Islands Boat Charter Dog Admiral Jake

Although he is not the best Virgin Islands boat charter captain, he is most certainly the most affectionately respected Admiral in the USVI. Admiral Jake joined our St. John sailing charters crew in 2005. As the Admiral he chooses which charter boat in our fleet to command daily. He has led this ragtag bunch for thousands of sea miles in both the Atlantic and Caribbean Seas, visiting a multitude of countries and territories. His reputation as the bow-riding singing dinghy dog is known in the far reaches of outlying islands from the Chesapeake shores to the Keys in Florida, Bahamian Cays, Turks & Caicos Islands, Harbors of the Dominican Republic, Anchorages of Puerto Rico & his homeport of the Virgin Islands! The Coconut telegraph whispers his name often. Join the St. John sailing charter crew for a fun day with Salty Dog Day Sails or Singing Dog Sailing and Admiral Jake! Check out his own Instagram account under his handle: @admiral_jake

Sailor Sandy crew of Salty Dog Day Sails St. John Boat Charter

St. John Boat Charter Dog Sailor Sandy

Sailor Sandy is the newest member of our crew! Therefore Sailor Sandy gets neither the praise of being the best Virgin Islands boat charter captain or any special title, as she is only ranked as a ‘sailor.’ She joined up in 2015 and has counted on Jake to show her the ropes onboard Salty Dog Days Sails & Singing Dog Sailing. Sandy originally hails from Florida but earned her sea legs during Singing Dog Sailing’s 2016 journey from St. John all the way to Maine, a journey of 4,500+ nautical miles. Sandy loves a good dinghy ride, exploring a new beach and chasing her toy Lambchop all over the boat. She is also available as a snuggle buddy for naps. Sailor Sandy, still in training, accompanies Admiral Jake on his chosen charter for the day.  They make the rounds between Salty Dog Day Sails and Singing Dog Sailing.  Check out Sandy’s Instagram here: @sailor.sandy

Captain Kelly Quinn St. John USVI

Virgin Islands Boat Charter Captain Kelly

You will want to see Salty Dog Day Sails and Singing Dog Sailing’s Captain Kelly shine. She offers the best of guest relations!

Captain Kelly, another best Virgin Islands boat charter captain favorite in the USVI, went on a fateful vacation more than 16 years ago and found inspiration in the example of a lust for life that was so palpable it was the proverbial “it” of happiness she was seeking. Leaving the business world of Organizational Psychology and pursuits of a Ph.D. behind, she ventured toward a life on the water. She became a PADI scuba instructor leading more than 5000 Discover Scuba divers during more than 1,700 dives per season while obtaining seatime toward her captain’s license qualifications which she obtained in 2002. She holds the same qualifications as Captain Stephen and Captain Justin (actually taking several Captains courses with both) and has skippered 30′ to 80′ vessels for private and commercial ventures. Trip Advisor is showered with praise about Captain Kelly in St John! Kelly also keeps our Twitter followers and Facebook Page fans pleased with fun photos, posts and tweets. Check out Salty Dog Day Sails accounts at:  @SaltyDogSail on Twitter and Salty Dog Day Sails on Facebook.  Check out Singing Dog Sailing accounts: @SingingDogSail on Twitter and Singing Dog Sailing on Facebook

Swab Stephen Captain Stephen Sloan St. John USVI

Virgin Islands Boat Charter Swab (Captain) Stephen

Captain Stephen is the true founder of this rabble, Singing Dog Sailing and Salty Dog Day Sails. He has been living aboard a boat since the mid-80’s. Graduating Texas A&M in Marine Biology, he took off sailing in his 20’s, single handling a 24′ C&C from the Texas coast to Nova Scotia and has been sailing the waters of the US Atlantic coast and the Caribbean Sea ever since. He holds a 100 ton US Coast Guard Master’s License with Aux Sail & Towing endorsements as well as STCW compliance for international voyages. He is a PADI Dive Master and holds current TWIC & First Aid/CPR certifications. He has skippered deliveries across the Atlantic to Bermuda and day charters on 30′ dive boats to 100′ wooden schooners. He is a natural sailor & a darn good guitar player too! Catch him after sunset at St. John’s best venues!

Back to Top