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      You’ve found the most popular sailing charter company in Connecticut, with the friendliest crew.

Meet #scuppertheboatdog

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Being held by the lovely Mel.
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Scupper the Boat Dog

Read about our sail to Cuba in November 2016.

**Sail Cuba Now – November 4-11 2017**

One boat full! Taking reservations for the monohull.
We now have three boats!
Come and sail with fellow sailors from across the USA.

“For Love and Money” Good Old Boat article

Watch Joy Ride Charters on NBC30 with Jason Hawkins

Connecticut and Caribbean Sailing Charters

Welcome to Joy Ride Charters. We are celebrating our 11th year of business! If you’re looking for a unique and exceptionally fun sailing charter, you’ve found the right place. Offering sailing adventures on Long Island Sound, the Caribbean and beyond.

Pure Joy is located in Westbrook, Connecticut. We’re available for hourly, half and full day charters. Whether it’s a small family gathering, a romantic sunset sail, birthday, therapeutic sail, lessons or memorial at sea, Joy Ride Charters is here to make it possible. We’re committed to making your sailing experience a memorable one. Do something different this vacation. Sit back and relax or learn how to sail with sailing lessons.

There’s no wifi onboard, but we promise you’ll find a better connection!

  • Patti

    "It is always a pleasure sailing with Joy. She is one if the best captains on the LI Sound."  Patti H.
  • If you are looking

    "If you are looking to learn, you can't find a better teacher than Joy. She has a steady, confidence that can put anyone at ease. She listens, and doesn't judge, and she knows when to challenge you. I've seen her with young children out for the first time and skippers with their new boats, she puts them all at ease. If you have a partner she's the one who will make you a sailing team. I never turn down an opportunity to sail with Joy!" - Cathy E.
  • It’s your own adventure

    "It's your own adventure, with the wind in your hair and Joy or yourself at the helm. Joy listens, and doesn't judge, and she knows when to challenge you."
  • Loved the relaxing

    "Loved the relaxing, beautiful afternoon on Hado and really appreciated Captain Joy making us so welcome!"
  • A Joyride charter

    "A Joyride charter is a fun filled experience and educational too. Joy handles Hado with the utmost professionalism yet with a playful spirit!"
  • Such a peaceful

    "Such a peaceful & meditative way to spend an evening; enjoying and appreciating the splendor that is Long Island Sound."
  • Sit back and relax

    "Sit back and relax or take an active role, either way you can't go wrong, you'll have a good time!"
  • Joy was a knowledgeable

    "Joy was a knowledgeable, patient and excellent teacher who quickly brought me to a point where I now feel comfortable sailing with my family and handling the boat efficiently and, most importantly, safely!"
  • Hado Boat

    "Hado is a beautiful boat and Joy is not only a good teacher and captain but also good company."