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Adventures On The Sea

Private Sailing Charters on Long Island Sound & Small-Group Adventures Worldwide

⚓ Woman-Owned Since 2004

⚓ USCG Master Captain

⚓ Private Charters

⚓ Up to 6 Guests

⚓ Multiple areas to relax, including bow deck chairs and a spacious cockpit

Who We Are:

Captain Joy turned her passion for sailing into a business almost 20 years ago. Her mission is to give her customers a peaceful, joyful and harmonious experience with the sea and each other―always with safety in mind. 

Sailing trips, open spots, and stories—straight to you.

Private Sailing Charters on Long Island Sound

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Step aboard Pure Joy and be sailing on Long Island Sound in less than five minutes. Relax in the spacious cockpit or stretch out in comfortable bow deck chairs while enjoying the beauty of Long Island Sound.

Whether you're celebrating a birthday, anniversary, retirement, marriage proposal, family gathering, or simply looking for a relaxing day on the water, each private sail is tailored to your occasion.

✓ On Long Island Sound in less than 5 minutes

✓ Sail with Captain Joy Sherman, USCG Master Captain and owner since 2004

✓ Private charters for up to 6 guests

✓ Multiple areas to relax, including bow deck chairs and a spacious cockpit

✓ Shade available in the cockpit

✓ Woman-owned and operated since 2004

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Sailing Lessons

Private, group, new boat owners, first mate, docking, and others looking for experience.

Worldwide Adventures

International Charter

NEW DATES:  October 24-31 2026

Limited cabins remaining

Sail the Greek Islands

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Croatia! The Dalmatian Islands 

September 19-26 2026

A long tail boat on the island
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Sail Thailand's Andaman Sea

November-4-11 2026

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Guadeloupe, West Indies

February 3-11, 2027
 

Cloudy Day

Hebrides, Scottish Voyage

April 13-19 2027

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Reviews From Our Travelers

Joy came through for us!  Would highly recommend her for your delivery. She also provided instruction underway which was invaluable.

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Book a cabin on a fully crewed yacht.

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Book solo with us, enjoy the safety and structure of group travel. Meet a bunch of new BFFs along the way.

Join Us at Our Next Meetup

Stay informed about our global charters and lessons

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© 2025 Joyride Charters. All rights reserved.

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