We are not your average charter company! Join us for a luxury Virgin Islands charter on our classic sailing yacht for an incredible day of sailing, snorkeling and relaxation!

Our full day charter includes a well stocked open bar customized to your preference! For lunch we serve our famous "Lowcountry Boil" - a delicious, down-home feast done right with local Caribbean lobster!

And if that wasn't enough, sailing with Happy Island Charters also means you get to spend the day hanging out with our famous, furry and fun first mate, Pedro the Pirate Dog!

If you have questions about what it is like to spend a day with Happy Island Charters, please give us a call! We are happy to talk.  Our number is 340-514-7705 

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welcome to happy island

We are a St. Thomas, US Virgin Islands
yacht charter company. 
We offer private

all-inclusive day charters on our classic 50' sailing yacht. 

Sail with us and see why we are a local favorite! 

sea level south side st thomas.JPG


  • private charter ON A 50' CLASSIC YACHT, our durbeck ketch s/y "sea level"

    • you get the entire yacht to yourself!

  • professional captain and crew to serve you!

    • captain fancy is a us coast guard 100ton master captain with 15 years of experience sailing  th​e virgin islands

    • our trained crew provide full service hospitality and delicious drinks from our well stocked open bar

  • all-inclusive charter includes our famous home cooked lunch

    • our down-home "low Country Boil" feast includes local caribbean lobster!

  • custom personalized, premium open bar

    • we stock the bar with your personal favorite liquors, wines & beers!​

    • try our tropical happy island cocktail: "Pedro's Pirate-Killer" 

  • dog friendly boat

    • our pirate dog, pedro, always sails with us!

    • traveling with you pup? contact us about bringing your dog along on a charter!

  • all charters also include:

    • premium snorkel gear

    • large floating raft and other water toys

    • luxury 100% turkish cotton towels

    • reef safe sunscreen 

    • premium bean bag seating on our spacious foredeck

    • shaded cockpit

    • fresh-water head (toilet) is air-conditioned & spacious for changing clothes 

    • spacious, air-conditioned main salon is a perfect place for children to nap and to safely stow bags & purses  



Pedro the Pirate Dog is our famous first mate!

He joins us on all our sailing adventures!

Pedro loves going sailing, swimming with sea turtles

 and snuggling up in the sun for an afternoon nap!


Pedro also loves having canine company on the boat. Contact us about bringing your pup or service dog
along with you on your charter!

Follow Pedro on Instagram:


  • Instagram
Pirate shark doo doo doooo dooooo _#pirateshark #nextbighit ☠️_☠️_☠️_☠️_☠️_☠️_#pedro #pedr


We offer full day, half day, and sunset sail 

charters on our classic sailing yacht.  

Email, call or text us at 340-514-7705 to

begin planning your adventure now!

Standard Charter Rates:

Half Day Sail $149

Sunset Sail $199

Full Day Sail $299

(Rates are per person, four person minimum charge.)