633 Boston Post Rd, Westbrook, CT

Adventures on the sea

Private sailing charters on Long Island Sound & small-group adventures worldwide

Helping guests create memorable days on the water since 2004.

Joyride Charters sailboat at anchor, seen from above
Woman-owned since2004

Who we are

Meet Captain Joy

Captain Joy turned her passion for sailing into a business almost 22 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.

USCGMaster Captain
Up to 6Guests per charter
WorldwideSmall-group trips
Read Joy's story

Ways to sail

How would you like to sail?

A private afternoon on the Sound, a week in the islands, or a single cabin on a crewed yacht.

Sailing trips, open spots, and stories. Straight to you.

What our guests are saying
4.7
★★★★★
on Google
4.9
★★★★★
on TripAdvisor
96%
★★★★★
recommend on Facebook

International charters

Sail the world with Joy

Small groups, crewed yachts, and cabins you can book on your own.

Harbor in Croatia at sunset with yachts at the quay
September 19–26, 2026

Croatia! The Dalmatian Islands

Sail Croatia
Three catamarans anchored in clear turquoise water in Greece
October 24–31, 2026Full

Sail the Greek Islands

Missed this one? Our May 2027 Greece sailing has cabins open.

Explore Greece

Reviews from our travelers

Joy came through for us! Would highly recommend her for your delivery. She also provided instruction underway which was invaluable.
Delivery client
Two guests on a paddleboard near an anchored catamaran

Crewed yacht

By the Cabin

Book a cabin on a fully crewed yacht.

See cabin trips
Guest relaxing on deck over blue water

Travel on your own

Solo Traveler

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

Sail solo
Free guideWhat to pack on a sailing charter Download PDF

Join us at our next meetup

Stay informed about our global charters and lessons.

Learn more

@joyridecharters

Life on board

Follow on Instagram
Guest relaxing on the foredeck Group of women on the sailboat at the dock Couple lying on deck on Long Island Sound Vintage car and dog at the Westbrook dock View from under the bimini top Four guests in captain hats